In an earlier post, “Re-considering the No,” I reflected on how easily we default to no, especially in moments that require change, risk, or vulnerability. That post was about the internal calculus we make when faced with the unknown, and how saying yes, even if it’s a tentative, nervous yes, can open doors to creativity, connection, and possibility.
But what happens after the yes? If “Re-considering the No” was about cracking the door open, today’s reflection is about what it takes to actually step through it. That next step requires cultivating something I’ve been hearing more and more in recent conversations: a bias for action.
The hidden cost of overthinking
In my experience, we tend to reward intellectual rigor. We value planning, stakeholder input, and alignment, and rightfully so. But sometimes, those very strengths can often morph into stagnation. We get caught in analysis loops and hypothetical what-ifs. We seek consensus when what’s needed is the courage to make a move. We become so focused on getting it “right” that we end up not doing anything at all.
A bias for action counters that by asking: What if starting imperfectly is actually the most strategic move I can make?
And here’s the truth most of us know deep down: clarity tends to come from action, not the other way around. The project plan doesn’t reveal the sticking points but the first iteration does. The meeting doesn’t uncover misalignment, but the actual collaboration does.
Motion as a catalyst for learning
I may be stating the obvious: A bias for action doesn’t mean acting without thinking. It just means that we’re using motion as a mechanism for discovery. This can happen in many different ways. For example, you might spin up a prototype for something that’s not on the roadmap yet, ship an early version of a new feature and let usage data influence the next iteration, or put yourself on the hook for a webinar before you’ve done all the research needed.
Do these actions carry risk? Of course. But they can also be the most effective way to uncover the next step.
As Amelia Earhart once said, “The most difficult thing is the decision to act. The rest is merely tenacity.”
This simple truth reminds us that the first move, however small, is often the hardest. But once momentum is on your side, everything changes.
Leading through action
As a leader, modeling a bias for action is one of the most powerful ways to build agility and resilience within your team. When your team sees you moving forward, and making adjustments when needed, they feel permission to do the same.
I’ve watched more than once how action can spawn energy. One draft inspires another, one customer outreach reveals a new opportunity, one slightly awkward team experiment can be the origin of a new practice or services offering. These moments don’t happen because the idea was perfect but because someone had the courage to move.
Leadership often requires creating conditions in which movement and action is encouraged and even expected, even if you don’t always have all of the answers.
As a Cy Wakeman fan, I like to remind myself of this quote: “Stop arguing with reality, and start leading what’s next.” It reframes change from something to fear into something to harness.
Reconnecting to “Re-considering the No”
In “Re-considering the No,” I wrote about how saying no too soon can rob us of growth. But now I’ll add this: Saying yes and then not acting is just a slower version of the same problem.
We tell ourselves we’re on board, give a thumbs up in Slack, nod in meetings, or add to an idea. But if those ideas never get acted on, if the yes never becomes movement, then we’ve only postponed the no. A yes without action is like planting a seed and never watering it. A bias for action is what turns that yes into progress.
Don’t get me wrong. I need to listen to my own advice more frequently and ask myself “Is there something I’ve said yes to but haven’t moved on?” or “What’s a small step I can take immediately to build momentum?”.
When in doubt, move
Action is not about busyness or bravado, but about building momentum, no matter how big or small. It’s about trusting that movement and direction will teach you more than inaction or delay. So next time you find yourself nodding at a new idea, agreeing with a bold suggestion, or sensing that yes rising in your throat, commit to taking the next step, and then take it.
What about you? How do you practice bias for action?
I’ve been a massive soccer fan all my life, and have always wanted to do a leadership spotlight in the world of soccer. Leah Williamson was an easy choice, as there are many lessons to be learned from her leadership approach, even for seasoned leaders, and certainly for me.
Leadership isn’t always about being the loudest voice in the room. Sometimes, it’s about thoughtful action, quiet confidence, and a deep sense of purpose. Leah Williamson, captain of the England women’s national team and a cornerstone for Arsenal, where she’s played since she was a kid, shows what modern leadership truly looks like. Her influence extends far beyond the football pitch, offering a powerful lesson in leading with intelligence, empathy, and authenticity.
Leads through intelligence, not impulse
Williamson’s leadership begins with the way she plays. As a defender, her greatest strength is her ability to read the game. She anticipates attacking moves before they happen, positioning herself and organizing her teammates to neutralize threats with calm efficiency. You won’t often see her making desperate, last-ditch tackles because her football intelligence means she’s usually already a step ahead. Although you can count on her to be your last line of defense any time.
This composure under pressure is a hallmark of her captaincy. She leads with a steady hand, providing a sense of control and stability that resonates throughout the team. Yet, when the moment requires decisive action, she has the courage and skill to step in. This blend of calm anticipation and assertive action defines her on-field presence.
Elevates everyone around her
A great leader makes others shine brighter. Williamson consistently elevates her teammates through clear communication, constant encouragement, and leading by example. Players often speak of the confidence she instills in them, creating a secure and organized backline where everyone feels empowered to perform at their best.
This supportive leadership was instrumental during England’s historic Euro 2022 victory. Thrust into the captaincy just months before the tournament, she fostered a resilient and united squad. Her focus was never on her own performance but on building a collective strength that could withstand the pressure of a major final. This year, Williamson made history again by leading England to their second consecutive Euros win, a first for the team and a testament to her exceptional ability to inspire and unite those around her.
Champions the team over self
Humility is a rare but powerful leadership trait. After lifting the Euro 2022 trophy, Williamson immediately shifted the focus to her teammates, the coaching staff, and the fans. Her words highlighted the shared effort and belief that brought the team to victory. For her, the captain’s armband is not a symbol of status but a responsibility to serve the group. This team-first mentality builds trust and creates a culture where every member feels valued.
Uses her platform for good
Off the pitch, Leah Williamson is a dedicated advocate for causes she believes in. She uses her influential platform to speak out on gender equality in sport, mental health awareness, and the importance of inclusivity. She approaches these complex conversations with the same thoughtfulness and conviction she brings to the game.
She speaks not as a celebrity seeking attention, but as a person committed to making a positive impact. Her willingness to be vulnerable and authentic makes her advocacy powerful and relatable, inspiring a new generation of athletes and fans to stand up for what is right.
Proves introverts can lead powerfully
Leah Williamson is living proof that you don’t need to be extroverted to be an outstanding leader. She is often described as quiet and thoughtful (“I’m not very social,” she once said about herself), preferring to listen and observe before stepping in. Yet, this reflective approach allows her to connect deeply with her teammates and understand what the group needs.
Leah recognizes the importance of genuine connection, even in the smallest moments. For example, she started drinking tea simply to spend more time with her teammates, using those shared breaks to build trust and camaraderie. Her willingness to step outside her comfort zone for the good of the group shows true adaptability and emotional intelligence. Through these everyday acts, Leah demonstrates that leadership is about creating bonds and making others feel seen. Sometimes, a cup of tea and a listening ear can be just as powerful as a rousing speech.
She is also known for being exceptionally well spoken and well mannered, traits that shine through in press conferences. Leah consistently greets each reporter who asks her a question and always thanks them after she responds. These small gestures reflect her respect for others and highlight yet another way she leads through kindness, humility, and professionalism.
What makes Leah even more relatable and authentic as a leader is her willingness to laugh at herself and openly admit her own quirks and weaknesses. She’s not afraid to share that she’s actually terrible at riding a bike or that she only eats plain foods, lighthearted confessions that endear her to fans and teammates alike. By being open about these little things, she breaks down barriers and shows that you don’t have to be flawless or larger-than-life to be respected. This self-deprecating humor and honesty make her approachable and reinforce the trust she builds within her teams.
Understands the value of balance
While Leah gives absolutely everything on the pitch, as evidenced by the many injuries she’s battled throughout her career, she also recognizes the importance of being well-rounded beyond football. Off the field, she’s found meaningful ways to recharge and grow. Leah is an accomplished children’s book author, sharing stories that inspire young readers. During the COVID lockdowns, she took on an entirely new challenge: learning to play the piano. Her dedication paid off in a truly remarkable way, leading to a performance with the BBC Concert Orchestra. These pursuits show that, even for someone at the height of their sport, cultivating interests outside of football is vital. Leah’s commitment to growth, both as an athlete and as a person, sets a powerful example for anyone striving to be their best self.
Redefines modern leadership
Leah Williamson represents a new model of leadership, one that values empathy over ego and intelligence over intimidation. She proves that quiet confidence, thoughtful action, and a genuine connection with others are incredibly powerful tools. Her style is a masterclass in leading with heart and purpose, demonstrating that true strength lies in authenticity.
Her influence reminds us that leadership is not about command, but about inspiration. By leading with her values, Williamson doesn’t just guide her team to victory. She shows us all a better way to lead.
What about you? Which athlete’s leadership style do you admire and learn from?
How customers find your products, services, and expertise is changing fast. The days of typing stiff keyword strings into a search bar are giving way to natural, conversational, intent-driven queries powered by search AI. For small and mid-sized businesses (SMBs), this shift fundamentally changes how you attract, convert, and keep customers online. If you adapt now, you stay visible and competitive. If you don’t, you risk fading from the results your customers actually see.
Let’s walk through how AI is reshaping search, and what you can do to thrive.
What is Search AI and why does it matter for SMBs?
Search AI blends artificial intelligence, natural language processing, and machine learning to understand what people mean, not just what they type. Instead of matching keywords, it interprets context, intent, and nuance.
So when someone asks, “What’s the best local bakery that delivers gluten-free cupcakes today?”, AI doesn’t just scan for “bakery” or “cupcakes.” It looks for businesses with clear, structured, up-to-date, trustworthy info that matches that exact intent. If your website doesn’t provide that context clearly, including hours, offers, inventory, delivery windows, and reviews, you can disappear from view, even if old-school SEO once worked.
How Search AI is changing the customer experience
AI-powered search has raised the bar. People expect fast, friendly, and personalized answers right where they’re searching. Here’s how that affects your presence.
Personalized, contextual results
Results are tailored by location, behavior, and intent. If someone searches “eco-friendly cleaning services near me,” you’ll show up only if your local data, service pages, and reviews consistently reinforce that positioning. Keywords still matter, but context matters more.
Voice search and conversational queries
With Alexa, Google Assistant, and Siri, natural questions are the norm. People ask, “Who’s the top-rated landscaper open this weekend?”, not “landscaper weekend hours.” To be found, write your site copy and FAQs in a conversational Q&A format that mirrors how customers actually speak.
Zero-click searches and featured answers
Search engines increasingly surface instant answers on the results page. Yes, that can reduce clicks. But if your content powers those featured snippets, you gain credibility and mindshare. The new SEO goal isn’t just ranking, but providing the answer.
The good news is that you don’t need a huge budget. You do need smart structure, clear messaging, and consistent updates. Here’s how to get started.
How SMBs can adapt and win with Search AI
Optimize content for questions and intent
Shift from “ranking for keywords” to “answering customer questions.” That makes your content more useful to both people and AI.
• Create FAQ-style content: Dedicated pages that directly cover pricing, turnaround times, delivery areas, policies, and service details. • Use natural language: Write like you talk to customers, in a clear, concise, and helpful manner. • Keep content fresh: Outdated hours, menus, inventory, or policies erode trust and visibility. Review and update regularly.
Leverage structured data (schema)
Schema markup is code that helps search engines interpret your content precisely. Think of it as labeling your information so AI can deliver it confidently.
• Add relevant schema: LocalBusiness, Product, Service, and FAQPage are common winners. • Complete your Google Business Profile: Keep it fully filled out with accurate info, posts, photos, and timely updates. • Ensure NAP consistency: Your name, address, and phone must match across your site, maps, and directories. Reliability matters more than you might think.
Prioritize mobile and accessibility
Most AI-driven searches happen on phones. A smooth mobile experience is what your audience expects and deserves.
• Design mobile-first: Fast load times, legible text, simple thumb-friendly navigation. • Follow accessibility best practices: Proper headings, alt text, good color contrast. This improves user experience and helps AI parse your site. • Improve speed: Slow pages get demoted. Audit performance and fix bottlenecks.
Build topical and local authority
AI rewards expertise and consistency. Show you’re a trusted pro in your niche and community.
• Create pillar pages: Comprehensive guides like “Complete Guide to HVAC Maintenance” or “Everything You Need to Know About Maintaining a Salt Water Pool.” • Publish valuable content: How-tos, checklists, comparisons, and original insights that demonstrate know-how. • Earn reviews and testimonials: Fresh, positive reviews are powerful trust signals for people and algorithms alike.
The bottom line
AI-driven search has changed the rules and opened new opportunities for SMBs that adapt. Your future customers aren’t typing stiff keywords; they’re asking real questions. And search AI is deciding who gets to answer.
By aligning content to intent, implementing structured data, keeping business info accurate, and delivering a fast, accessible mobile experience, you keep your brand discoverable and trusted. Don’t wait for traffic to slip. The businesses that prepare now will be the ones AI chooses tomorrow.
What about you? Have you started optimizing your site for Search AI?
When people first start using AI tools like ChatGPT, they usually ask questions in one shot and hope for the best. Sometimes that works, but oftentimes, the output is not as wonderful as expected. Too generic, too long, or missing the mark entirely. And then they give up, which is one of the biggest mistakes you can make with AI.
Getting great results from AI isn’t about asking the perfect question. It’s about layering prompts strategically to build toward exactly what you need without going down a rabbit hole of endless rewrites.
Many professionals spend hours tweaking massive prompts or repeatedly starting over because their initial request didn’t capture their vision. This approach wastes time and often leads to frustration. There’s a better way.
Prompt layering transforms your AI interactions from guesswork into a more systematic process. It’s a method that helps you guide AI tools step by step, refining output incrementally rather than hoping for perfection on the first try.
What is prompt layering?
Think of prompt layering as having a conversation with your AI tool rather than issuing a single command. Instead of trying to cram every detail into one mega-prompt, you stack smaller, purposeful instructions.
Each layer refines the output by narrowing focus, improving clarity, or adjusting style until you arrive at something polished and usable.
It’s a bit like cooking:
The first layer is getting all your ingredients lined up.
The second is preparing them.
The third is seasoning to taste.
By the end, you’ve created a meal instead of tossing everything into the pot at once.
This approach recognizes that AI tools work best when given clear, sequential guidance rather than complex, multi-faceted instructions all at once. Treat AI like a new team member! You wouldn’t expect a new person to give you the perfect deliverable on the first try, right?
Why it works
Clarity compounds: Breaking a complex request into layers gives the AI room to think step by step, which typically produces sharper results. Each layer builds on the previos one, thus creating a clearer picture of what you want.
Faster iteration: Instead of rewriting long prompts from scratch, you tweak in small steps. This saves time and avoids the frustration of losing perfectly good elements when making changes (we’ve all been there!).
Creative control: Layering lets you guide the AI output more like an editor than a passive recipient. You maintain control over the direction while optimizing AI’s capabilities.
Reduced cognitive load: Rather than trying to anticipate every requirement upfront, you can respond to what you see and adjust accordingly. This mirrors how humans naturally work through complex solutions and is also reminiscent of the agile developement approach.
The 3 core layers
Here’s a simple framework you can apply to almost any task:
1. Rough draft
Start broad. Give the AI a clear but simple request.
Example: “Write a blog intro about why personalization matters in higher ed websites.”
This gets something on the page quickly. Don’t worry about perfection here. You’re establishing the foundation and giving yourself material to work with.
The key is to be specific enough that the AI understands the topic but general enough that you’re not overwhelming it with requirements.
2. Refinement
Now you add precision. Tell the AI what’s missing, what tone to use, or what format you need.
Example: “Make it more conversational and add a quick metaphor that compares personalization to a campus tour guide.”
This is where you shape the content closer to your voice and vision. You’re working with existing material, which is much more efficient than starting over.
Focus on one or two key improvements per refinement layer. This keeps the AI focused and prevents confusion.
3. Optimization
Finally, you polish for your specific purpose. Ask for variations, summaries, or format adjustments.
Example: “Shorten this to under 150 words and include the phrase ‘higher education marketing.'”
This last step makes the output immediately usable for your specific context and requirements.
As Antoine de Saint-Exupéry once said, “Perfection is achieved not when there is nothing more to add, but when there is nothing left to take away.” That’s exactly what the optimization layer is about: removing the excess and sharpening what matters until the result is clear, concise, and ready to use.
Advanced strategies
Shifting perspective: After getting your initial output, ask the AI to rewrite from a different perspective or for a different audience. This often reveals new angles you hadn’t considered.
Flipping the format: Take your content and ask for it in different formats such as bullet points, numbered lists, or narrative form. This helps you find the most effective presentation.
Stacking speficity: Start general, then get increasingly specific with each layer. This helps you maintain the big picture while drilling down into details.
Quick tips for better prompt layering
Start simple. Don’t over-engineer the first layer. Give yourself plenty of room to build.
Give feedback like a coach. Instead of “this is bad,” say “make it punchier” or “add examples.” Constructive direction works better than criticism.
Reuse winning layers. Save your favorite refinements as templates for future projects. If “make it more conversational” consistently improves your content, use it regularly.
Know when to stop. If the output is good enough for your purpose, move on. Perfect is the enemy of done, and over-layering can sometimes muddy clear content.
Document your process. Keep track of layer combinations that work well for different types of content. This builds your personal prompt library.
Common pitfalls
Layer overload: Adding too many layers can confuse the AI and dilute your message. Three to four layers usually provide the sweet spot.
Contradictory instructions: Make sure each layer builds on rather than conflicts with previous ones.
Impatience: Give each layer a chance to work before moving to the next one. Sometimes the AI needs a moment to process complex refinements.
Prompt layering turns AI from a one-shot experiment into a repeatable process. It’s faster, more flexible, and far less frustrating than hoping for a perfect response on the first try.
The beauty of this approach is its adaptability. Whether you’re writing marketing copy, creating presentation outlines, or generating creative ideas, the same three-layer framework applies. You’re getting better results while developing a skill that improves with practice.
Next time you sit down with ChatGPT or any other AI tool, remember: don’t just ask once. Layer your way to better results. The better of a partnership you develop with your tool, the better the outcome.
It feels like every other week a new AI tool pops up, promising to “make meetings effortless, saving you hundreds of hours.” One of the hottest right now is AI notetakers. Tools that join your Zoom, Teams, or Google Meet, quietly record the call, and then generate a transcript and summary for you.
In theory, it sounds amazing. No more frantic typing. No more “Wait. What did they say about that deadline/that feature request?” You can actually sit back and be present.
I was a rabid fan when I started using them. But, like most shiny new AI helpers, it’s not all upside.
The positives
You’ll never miss a detail again Having a transcript is great if someone misses a meeting or if you just want to check back on who agreed to what. From an accountability standpoint, that is a huge plus.
Freedom to actually listen Instead of scribbling notes, you can make eye contact the entire time and really focus on the conversation, knowing the AI will capture it all.
Great for remote teams When your teammates are spread across time zones, having a neat summary waiting in Slack or email can keep everyone aligned without another meeting.
So far so good.
Where it gets messy
People clam up The moment you tell a customer, “By the way, we’re recording this,” the tone often changes. They’re less likely to be brutally honest about what isn’t working. That’s obviously a problem if you actually want the truth.
Things become performative The opposite can also happen: instead of clamming up, people sometimes go into “stage mode” when they know they’re being recorded. They perform instead of just talking, which makes the whole meeting feel less authentic.
You stop taking your own notes There’s something about writing things down that makes your brain hold onto them better. If you just rely on AI, you’re outsourcing not just the notes but your memory. I can certainly attest to that. I remember more details from meetings I had pre-notetaker compared to the ones where I had it running.
You over-rely on other people’s discussions If you care about delivering the right products and services to your customers, you can’t just lurk in transcripts of meetings you weren’t in. You need to talk to customers yourself frequently (here’s more on the subject). You know best what insights you want, and you’ll never get the same clarity secondhand.
Coaching gets robotic It’s tempting to let AI summaries or call insights do the work of coaching sales reps and customer success managers. But AI can’t detect subtle hesitations, awkward silences, or emotional tones that matter in human relationships. Leaders still need to guide and mentor, especially since AI doesn’t have the same context as you when it comes to organizational history, challenges, or your relationship with a customer.
AI can’t read the room Yes, it knows what was said. But it has no clue how it was said. That subtle sarcasm? Gone. The change in tone? Undetected. The tension you felt when someone crossed their arms? Can’t be found in the notes.
Not every meeting needs a transcript Sometimes it’s overkill. Recording everything can make people feel like they’re under surveillance. And honestly, it can be a massive distraction. Plus, it’s a time sink when people start digging through meetings they weren’t even in just out of curiosity.
Privacy risks are real You’re storing transcripts of strategy calls, customer complaints, even HR issues. Those are sensitive topics, and they need to be treated with care, or it could come back to bite you.
Is there a middle ground?
To be clear, I’m not anti-AI notetaker. They can be lifesavers in the right situation. But like most tools, the value depends on how you use them.
Ask yourself:
Do we really need this meeting recorded?
Will it make people less likely to share openly?
Am I letting AI make me lazy?
If the answer to any of those is “yes,” maybe leave the bot out of it.
AI notetakers are like that super-organized friend who always remembers the details. They’re great to have around, but you don’t want to rely on them so much that you stop paying attention yourself.
Meetings are, at their core, about humans connecting problem-solving, and helping each other . Let’s not lose that just because a bot can spit out bullet points.
What about you? Do you find that AI-notetakers help or hurt your meetings?
Most people see constraints as obstacles to overcome. But what if your biggest limitations might actually be your greatest opportunities for breakthrough thinking and meaningful progress?
When resources are scarce, deadlines are tight, and options feel limited, our natural instinct is to focus on what we can’t do. We get stuck in frustration mode, wishing we had more time, more budget, more resources, or more freedom. But this mindset misses a fundamental truth: constraints don’t just limit us. They can actually be liberating.
Hear me out.
Don’t underestimate the power of limitations
Constraints force us to think differently. They strip away the paralysis of infinite options and demand focus on what truly matters. When you can’t do everything, you’re forced to do the right things really well.
Consider the most innovative solutions you’ve encountered. Chances are, many emerged not in spite of constraints, but because of them. Look at all the innovations and pivots that happened during COVID!
Take Georgia State University, for example. When in-person orientation was canceled during COVID lockdowns, they didn’t try to replicate the traditional experience with clunky Zoom calls. Instead, they launched a gamified digital orientation that used mobile apps, behavioral nudges, and personalized messaging to walk students through everything from class registration to financial aid. Not only did engagement increase, but the infrastructure they built continues to support hybrid orientation year-round. The constraint became a springboard for deeper personalization and better outcomes.
Or look at Little Sesame, a Mediterranean fast-casual restaurant in Washington, D.C. When they had to shut their doors, they could’ve waited it out. But instead, they pivoted to launch “Hummus at Home” meal kits, a creative way to bring their brand into customers’ homes. They paired that with a community initiative called “Feed the People,” delivering free meals to frontline workers and local families. In the process, they built a new revenue stream, expanded their customer base, and deepened their brand’s emotional resonance.
These are perfect examples of how constraints can channel creative energy into focused, high-impact solutions. When limitations demand better thinking, organizations often uncover approaches they wouldn’t have considered in times of abundance.
How constraints may foster better thinking
When facing unlimited options, we often freeze. Research shows that too many choices can lead to decision fatigue and decreased satisfaction. Constraints narrow our focus to what’s actually possible and important.
With limited resources, you can’t pursue every good idea. Instead, you must identify what matters most. This forced prioritization often reveals insights that would remain hidden in environments with excess.
Constraints make us more creative with what we have. When the usual solutions aren’t available, we’re pushed to find novel approaches, repurpose existing resources, or discover efficiencies we never knew existed.
Shifting Your Constraint Mindset
The key to leveraging constraints isn’t to pretend they don’t exist or to simply “think positive.” It’s to fundamentally shift how you relate to them.
“I Can’t” -> “How Might I?”
Instead of focusing on what constraints prevent, ask what they make possible. What new approaches do they open up? What assumptions do they force you to challenge?
Problem -> Parameter
Treat constraints as design parameters rather than problems to solve. If you’re building a house, the lot size isn’t a problem—it’s a boundary that shapes your design. Apply the same thinking to your professional limitations.
Scarcity -> Focus
Reframe limited resources as focused resources. When you can’t do everything, you get the rare chance to do the right things exceptionally well.
How you talk about constraints matters.
In my post “Venting: The Not-So-Silent Culture Killer”, I explored how habitual complaining creates a ripple effect of powerlessness. When we vent about constraints without reframing them, we reinforce the idea that we’re stuck. But when we treat constraints as catalysts, we reclaim the narrative and the power.
Getting started
Embrace “good enough”:Perfectionism and constraints rarely coexist. Often, a good-enough solution delivered on time and within budget is far more valuable than a perfect one that’s too expensive or too late.
Look for unconventional resources:When traditional resources are limited, think creatively. Can you partner with another team? Leverage user-generated content? Build a minimum viable version first? Let your constraint spark resourcefulness.
Question assumptions:Constraints surface hidden assumptions. Use them as prompts to challenge standard approaches and uncover new paths.
Use and build on what you have: Inventory what’s already working. Often, progress comes not from acquiring more, but from better using what you already have.
Even in the most constrained situations, you retain control over your response. You can’t always change your circumstances, but you can change how you approach them.
As noted in “Developing Resilience in the Face of Adversity”, focusing on your locus of control is essential to both personal effectiveness and professional impact. When you shift from lamenting constraints to leveraging them, you unlock a form of agency that’s deeply energizing.
When a constraint shows up, pause before defaulting to frustration. Ask:
What does this limitation force me to focus on?
What creative solutions does this constraint make necessary?
How might this restriction lead to a better outcome?
Keep a record of times when limitations actually led to better solutions. This helps build confidence that the next constraint could be a new opportunity.
And when you see colleagues struggling with limitations, share your own constraint-to-clarity stories. This builds a culture that sees possibility where others see barriers.
What about you? When have you benefitted from a constraint?
When someone asks us “how are you?,” the common answer is “busy”. Yes, we’re all busy and never seem to have enough time. Over the last year, I’ve discovered that one of the best time-saving tools isn’t a scheduling app or productivity hack, but ChatGPT.
While most people know ChatGPT can write emails and summarize documents, some of the most powerful time-saving benefits come from more unexpected, creative uses. Here are some ways I’ve used ChatGPT to get more done faster.
Parse notes into action items
I love using Attention as my AI-powered notetaker, but sometimes I skip it. People can be more open when they’re not being recorded, and I still enjoy manual note-taking for retention.
Still, I often end up with messy shorthand in my Remarkable or Notes app. I’ll paste the text into ChatGPT and ask it to turn it into an action plan with tasks, deadlines, and priorities.
Example prompt: “Here are my notes from today’s team meeting. Can you create a prioritized task list with deadlines and owners?”
Brainstorm faster
“I write because I don’t know what I think until I read what I say” is a quote by Flannery O’Connor that I can relate to. Whether it’s working on a new feature or product idea, piece of content or song, or I am looking for new initiatives for the company, I start jotting down anything that comes to mind without internal censorship. When you’re stuck in idea limbo, whether it’s for marketing copy or an outside-of-the-box solution to a problem, ChatGPT can jumpstart your brainstorming. Just give it context and ask for 10 ideas to kick it off, which can help you avoid the dreaded blank page and gets your creative juices flowing faster.
Example prompt: “I’m launching a new feature for higher ed web teams. What are 10 creative blog post titles that balance approachability and professionalism?”
Simplify complex concepts for yourself and others
Whether you’re learning something new or explaining a technical concept to someone less familiar, ChatGPT can help summarize jargon-heavy material in plain English. For example, if someone asks what a specific section in a legal contract means or looking to understand a highly technical concept, you can ask the tool to break it down in simpler terms. In fact, ChatGPT is usually pretty good at coming up with relatable analogies. I recommend being as specific as possible in defining who the intended audience is.
Example prompt: “Explain this section of a SaaS contract in plain English for someone with no technical or legal background.”
Create first drafts
From RFP answers to project requirements, the first draft is often the most time-consuming. I use ChatGPT to write a rough outline or narrative based on key points. Editing from a starting point is so much faster than starting cold. For things like Statements of Work, you can even create your own custom ChatGPT by teaching it about what you’re looking for and uploading existing SOWs (minus the customer name) to use as guidelines.
Example prompt: “Based on these bullets, draft the first two paragraphs of proposal for an implementation project.”
Prepare for conversations
Before heading into a call with a potential partner or customer, consider asking ChatGPT to help prep questions, review context, or suggest talking points based on previous interactions or public info. It saves me from digging through inboxes or LinkedIn for background, although, admittedly, sometimes I can’t help it.
Example prompt: “Help me prepare for a call with [customer/partner] interested in [topic]. Summarize the top 3 news stories from the past 6 months about [Customer Name] and highlight anything relevant to digital transformation or leadership changes.”
Create new templates or formats
One of the most underestimated time-saving superpowers of ChatGPT is its ability to build custom frameworks, templates, and models on the fly, which is especially helpful when you’re tackling something ambiguous or complex.
Whether you’re evaluating vendors, planning a new campaign, scoping a project, or making a strategic decision, having the right framework helps you move faster and with more clarity. But instead of spending hours on the internet for one that almostfits your needs, ChatGPT can help you create one that’s tailored to your situation. The trick is to not settle for the first answer the tool gives you, but to keep asking for refinements until you have something that is a great starting-off point.
Example prompts:
“Build a scoring matrix for whether or not to RFPs based on fit, scope, risk, and competitive positioning.”
“Create a content planning template based on the awareness, consideration, and decision stages of the buyer journey.”
“Develop a Standard Operating Procedure template for customer onboarding.”
Develop learning plans
This is one of my favorite use cases. When I want to sharpen my skills and acquire more knowledge about a certain area, I ask ChatGPT for learning plans based on my time frame and availability.
Example prompt:
“I want to learn more about GDPR and how it affects web content and web personalization. Create a two week crash course for me with relevant resources like articles, videos, and podcasts. I can spend 15 minutes a day on this”
Use it as a sounding board
Sometimes you just need a gut check on tone, clarity, or how something might resonate better with your audience. ChatGPT is great for quick, low-stakes feedback that helps you keep moving. Whether I’m drafting an email that needs to be direct but diplomatic, or tweaking a copy that just doesn’t seem to hit the note I’m aiming for, I’ll often paste it in and ask for suggestions or a tone check. It’s like having a neutral second set of eyes without needing to bug a colleague.
That said, I draw a line when the context is deeply emotional, politically sensitive, or calls for real empathy. In those cases, I still rely on my own judgment or talk it through with someone I trust. For me, ChatGPT is less about replacing human insight and more about accelerating the mechanical parts, so I have more time and mental space for the conversations that actually require the human touch.
Example prompt: “Does this message sound too unempathetic? I want it to be clear and firm, but still respectful.”
What about you? What are some ways in which you’re using ChatGPT to save time?
Saying no can be liberating. It’s a word that leaders, product managers, and founders often use as their shield against scope creep, burnout, and loss of focus. Yet, I wonder if the real art isn’t about defaulting to a firm no. It’s about knowing why you’re saying no, understanding the impact, and being open to other paths when possible. What if we can shift from knee-jerk rejections to meaningful, strategic decisions that serve both our business and our customers.
Why revisiting our no matters
It’s been years since I explored why we shouldn’t shy away from saying no to projects, features, or deals that don’t align with our vision. But time and experience have shown me that “no” is not a free pass out of tough conversations. Nor does it automatically mean you’re operating in the best interests of your team or users. The nuance lies in the decision-making process and the honesty behind it.
With over a billion results for “saying no to a feature request,” the topic is far from new. Yet, many teams still struggle to move beyond a templated refusal, missing out on growth, innovation, and customer goodwill in the process.
Identify the real reason behind your no
Be honest with yourself
Before saying no, dig deeper. Is your answer rooted in what’s truly best for your product and customers? Or are you being swayed by something less objective, like risk averseness, internal bandwidth issues, or personal bias? Sometimes, a quick refusal feels safer than challenging assumptions or pushing your team outside their comfort zone.
Tracking your decisions helps. Document every no and, more importantly, the reason behind it. This reflection gives you valuable data, helping you spot patterns like resisting new ideas, underestimating team capacity, or playing it too safe. You might discover that your “no” is occasionally more about your own limits than your customers’ needs.
Separate product needs from personal preferences
Maybe a feature request sounds wrong simply because it’s not what you’d want as a user. Or maybe a contract term feels risky, but you haven’t weighed the potential upside. By being transparent, you open up space for objective analysis.
Here’s an idea.Start an internal “no log.” When you turn down a request, capture what was asked, why you’re declining, and the true business reason. After a quarter, review for trends or missed opportunities.
No doesn’t always mean never
Consider no, but add “but”
The word no doesn’t have to be a conversation-ender. Sometimes, a flat rejection is appropriate. More often, a “no, but…” unlocks better dialogue and creative alternatives.
Contract terms: Maybe you can’t agree to everything the partner asks, but could you offer a concession elsewhere?
Feature requests: If a proposed feature isn’t feasible, could an integration with another tool help your customer achieve the same outcome?
Project proposals: Resource-constrained? Suggest a partnership with a trusted contractor instead of rejecting the project outright.
Whenever you deliver a “no,” challenge yourself to also offer a workaround, a timeline for revisiting, or a different way forward. You’ll build trust and demonstrate that you’re listening.
Weigh the consequences of saying no
Balance ROI with opportunity cost
Rejecting a new idea or feature is rarely risk-free. Of course you should ask, “What will this bring us?” But you must also flip the question: “What could we lose by turning this down?” Each no closes a door, possibly for good.
Could refusing a feature be the difference between keeping and losing key customers?
Is turning down a contract leaving money and future partnerships on the table?
Will a pattern of no responses become a reputation risk over time?
For example, a SaaS platform might skip a small feature to focus on core improvements. But if that feature is critical to a cluster of customers in a lucrative segment, the opportunity cost could outweigh the savings.
With every major no, write a short post-mortem. Review both the intended gains and potential losses, and discuss as a team before finalizing.
Stay flexible as context changes
Adapt your no to the times
Business climates evolve. That means your “no’s” should, too. Maybe last year you avoided broad integrations because of limited resources, but now, economic shifts or new partnerships demand a more open approach.
Are current market or global trends changing customer expectations?
Has a new law or regulation made your earlier decision irrelevant?
Could tighter budgets mean you revisit previously shelved ideas that now look more viable?
As leaders, we need to widen our lens to include industry shifts, economic downturns, and even global crises. What was a hard no yesterday might be a qualified yes, a “maybe” with caveats, or a “no, but” today.
Regularly revisit your default responses. At your quarterly strategy review, ask, “Is our no still the right answer given what’s changed?”
Align the best for customer and company
There’s nothing weak about turning down a customer, a feature, or a contract term. What matters is that your decision aligns with long-term goals for both your company and the people you serve. These interests are not opposing forces. The sweet spot is where they overlap.
Make decisions with transparency.
Communicate your reasoning.
Demonstrate that you’ve weighed impacts on all sides.
When your team and your customers see that your no’s are principled instead of arbitrary or reactionary, they’re far more likely to stick with you.
Let’s rethink our relationship with “no.” The next time you’re asked for a feature, project, or partnership, pause before defaulting to a refusal.
Track and analyze your decisions for hidden patterns.
Look for “no, but” opportunities wherever possible.
Evaluate both the costs and opportunities of every no.
Stay alert to shifts, from market sentiment to legislative changes.
Be transparent with your reasoning, building credibility inside and out.
Saying no is an essential leadership tool. But it’s a scalpel, not a sledgehammer. Use it to cut out what’s unnecessary, not to block growth, innovation, or trust.
What about you? How have your views on saying no changed as your context has evolved?
I’ve been thinking about higher ed a lot (even more than usual) these days, as it’s facing some challenging times, so I’ll be posting a bit more higher-ed focused content on here.
It’s safe to say that higher education has finally embraced the art of personalized marketing. From campus tours tailored to prospective students’ interests to website content that dynamically highlights programs based on a visitor’s search history, personalization has helped colleges and universities drive up engagement and enrollment
But what happens after the acceptance letter? All too often, and sadly, that’s where the personalization stops, and in its place comes a generic approach for incoming students.
For a generation as diverse and digitally savvy as Gen Z, this is more than just a missed opportunity. It’s a potential risk to engagement, retention, and student satisfaction. And given the demographic enrollment cliff, the last thing we want is to do anything to jeopardize retention.
Let’s examine why personalization after enrollment is critical to success and offering actionable steps to help your institution get it right.
The captive audience myth
Once a student has enrolled, it may feel like the hard part is over. They’ve chosen your institution, which should mean the relationship is secure. But we all know that this is not quite the case. Melt and student attrition are huge risks.
Today’s students, especially Gen Z, expect seamless, meaningful digital experiences at every stage of their relationship with your institution, including after they’ve enrolled.
Throughout their time at your college or university, they navigate many challenges, including
Outdated or disjointed systemsfor course registration, housing selection, and tuition payment that require navigating multiple logins and interfaces
Major life transitions like newfound independence, mental health challenges, or creating a sense of belonging
Decision fatigue from having to make constant academic, social, and financial choices with long-term impact
Information overload from emails, text alerts, portal updates, and social media notifications that can blur priorities
Fear of failure or imposter syndrome, especially among first-generation or nontraditional students
Navigating complex identities such as being an international student, transfer student, student parent, or part of an underrepresented group
Balancing academics with internships, jobs, or caregiving responsibilities, which can lead to burnout
Personalization post-enrollment is about ensuring they feel supported, understood, and part of a community during some of the most pivotal years of their lives.
Make no mistake about it: they notice when the effort stops.
Why personalization after enrollment matters
For students, personalization is a clear signal that your institution recognizes their unique needs and cares about their success. Post-enrollment personalization creates opportunities to support students in ways that drive engagement, improve retention, and foster a sense of belonging.
Here are some opportunities to implement personalization that makes a meaningful difference:
Orientation and onboarding
Not all students are the same, and their onboarding experiences shouldn’t be either. Customize orientation content for first-generation, transfer, or international students to address the unique challenges these groups face. Whether it’s helping first-gen students understand financial aid or offering international students local resources, targeted onboarding ensures every student has an experience that fits their needs.
Academic milestones
For students still deciding on their path or contemplating a switch, personalized recommendations for majors, clubs, or support services can have a huge impact. For example, data such as campaign sources or form submissions can help you suggest the right programs at the right time.
Mental health and well-being
With the rise in mental health concerns among college students, institutions must adopt a proactive approach. Behavioral cues such as frequent visits to counseling services pages can trigger non-intrusive content like mental health resources or check-ins that show students you’re paying attention to their well-being without being overbearing.
Resource and event reminders
Generic emails about campus resources like tutoring centers or libraries can often get ignored. Instead, personalize outreach based on factors like a student’s major or course load. For instance, a reminder about the tutoring center might be much more impactful during peak exam seasons.
Avoiding pitfalls in post-enrollment personalization
While personalization is key, not all approaches are created equal. One common mistake is overloading students with content that feels less personal and more transactional.
Students crave connection, not just information. To ensure your personalization efforts hit the mark, consider the following tips:
Make it a conversation
Instead of sending static, one-way messages, create opportunities for students to share their preferences, needs, and feedback. Use tools like surveys, opt-in content, and micro-interactions to build a dialogue and foster engagement.
Focus on relevance
Personalization should feel intentional, not overwhelming. Prioritize relevant, actionable content that aligns with a student’s current needs over a bombardment of generalized announcements.
Keep it human
Digital tools can be powerful, but personalization should still have a human touch. Ensure your messaging feels supportive and empathetic, not purely algorithm-driven.
Building a post-enrollment personalization strategy
If your institution is ready to take its personalization efforts beyond the acceptance letter, here’s how to design a strategy that truly supports students.
Segment by experience
Go beyond demographic segmentation by grouping students based on their behaviors, form responses, or specific needs. For example, categorize students based on interests like academic goals, extracurricular activities, or career aspirations.
Use the right tools
Leverage AI-driven platforms like Clive to simplify the process of identifying student needs and sending targeted messaging. These tools can provide insights on student behaviors and initiate the right content delivery at just the right moment.
Build a feedback loop
Direct communication with students fosters transparency and trust. Create straightforward feedback systems that allow students to share whether your efforts are working and what could be improved. Use this input to iterate and enhance your strategy.
Keep student needs front and center
Every piece of personalized content should answer one key question. What does the student need right now? A focus on their well-being and growth will reinforce their trust in your institution.
Creating long-lasting connections
Enrollment is not the end of the student experience. It’s the beginning of a critical relationship driven by growth, trust, and shared purpose. When you personalize digital experiences post-enrollment, you’re showing students that they’re more than just a number.
You’re telling them, “We see you.”
This effort drives better retention rates and can help build deeper, more meaningful connections that set the foundation for long-term success for both the student and the college.
What about you? What are your ideas for personalizing the experience for enrolled students?
Accessibility isn’t a nice-to-have, not just for higher education. It’s a legal requirement, a moral imperative, and a core part of serving your full audience. As digital content continues to multiply across websites, accessibility can feel like a moving target, especially for teams that are already stretched thin.
Once again, many are looking at AI for help. With generative tools, automated checkers, and language models promising efficiency and scale, many web teams are wondering: can AI finally help us get ahead of accessibility?
The answer is: yes and no.
Let’s take a look at where AI can offer real support and where human oversight still reigns supreme.
Where AI can help with accessibility
1. Captioning and transcription
AI tools like Otter.ai or Whisper can automatically generate transcripts and captions for videos and podcasts. This is a big win for speed and coverage.
Pro tip: Always review auto-generated captions. Even small misinterpretations can alter meaning (especially in academic content).
2. Alternative text suggestions
Some platforms can suggest alt text for images using object recognition or contextual inference. This can save time, especially when uploading dozens of images at once.
However, these suggestions often lack nuance. “Two people at a table” doesn’t convey the same information as “Admissions counselor advising a first-year student in the student center.”
Pro Tip: Try Cascade CMS’s AI-driven suggestions for alt-text.
3. Accessibility checks
AI-powered platforms can crawl entire websites and flag potential accessibility violations such as contrast issues, missing form labels, improper heading structures, etc.
You canuse it for triaging large sites and identifying systemic problems.
Where AI falls short
1. Contextual meaning
AI can’t determine whether your content actually communicates what it needs to. It might pass a technical scan but still confuse a screen reader user.
Example: A button that says “Click here” might be perfectly marked up. But it doesn’t tell the user what they’re clicking for.
2. Tone, empathy, and inclusivity
AI lacks emotional intelligence. It won’t know if your language is unintentionally biased, confusing, or exclusionary. That requires lived experience, human testing, and editorial review.
3. Compliance vs. experience
Passing a checklist doesn’t mean your site is usable for people with disabilities. Real accessibility is about experience, not just validation.
How should you use AI?
Here’s a simple framework:
Task Type
AI Role
Human Role
Captioning & transcription
Generate draft
Edit and verify
Alt text
Suggest based on image
Add context and intent
Site scans
Identify patterns
Prioritize and implement fixes
Content writing
Flag complex phrases
Simplify and personalize
Use AI to amplify, not replace. Let it surface patterns, automate the repetitive, and help you work faster. But remember: accessibility is ultimately about people. That means it always requires human care.
Aim higher than just compliance
AI can help you meet accessibility guidelines, but it can’t replace empathy. The most inclusive digital experiences come from teams who deeply understand their audiences and are committed to making everyone feel welcome, respected, and supported.
Once again, AI can free up time for the human work that really matters.
What about you? Have you used AI to help with accessibility?
I’ve been thinking about higher ed a lot (even more than usual) these days, as it’s facing some challenging times, so I’ll be posting a bit more higher-ed focused content on here.
Personalization is no longer a luxury or “great opportunity” for higher education websites. It is now a necessity for connecting with your varied audiences in a meaningful way. Even more drastically, in the face of the demographic enrollment cliff, it’s becoming a survival tool. But how can colleges and universities deliver impactful, relevant experiences at scale, especially with limited teams and tight budgets? One way is to use smarter AI prompts to drive web personalization.
Here are a few strategies and AI prompts for creating personalized content that resonates with prospective students, parents, alumni, faculty, employers, the media, and more. Let’s take a look at how you could scale your personalization efforts and enrich user journeys a bit more quickly.
Personalization and higher education
Every university website speaks to a diverse set of audiences, each with unique questions, goals, and backgrounds. A high school senior may want campus tour dates. Parents are searching for support resources and information on campus safety. Alumni might be ready to give back but want to see their impact first, or want to make sure that their donation is going towards a specific area they care about, such as research, scholarships, or athletics.
Generic, one-size-fits-all content risks leaving these users disconnected or overwhelmed. Web personalization bridges this gap by meeting users where they are in their higher ed journey, boosting engagement and conversion (such as more applications, completed forms, or donations), and demonstrating genuine care and understanding of individual needs
But as you can imagine, creating custom content for every segment can be challenging. This is where AI, particularly tools like ChatGPT, can help scale personalized experiences.
Understanding your audiences
Before crafting personalized content, map your university’s key audiences, such as
Prospective students (domestic, international, transfer, etc.)
Parents
Current students
Alumni and donors
Faculty and staff
Members of the media
Employers
Local communities
Next, identify things that you might want to base your personalization on, including:
Geolocation (where the visitor is browsing from)
Referral source (a scholarship Google ad, a campaign landing page)
Behavior (pages viewed, search terms used, frequency of visits)
With these segments documented, your content creators can use structured AI prompts to quickly produce first drafts or ideas tailored messaging. Of course, you know your audience best, so AI becomes even more powerful when paired with your insights.
Getting started with AI prompts
The best AI prompts are precise, set context, specify the audience, and request the tone or outcome you want.
Prompt best practices
Supply audience background and the desired outcome (application submitted, donation made, RFI sent, interview requested)
Specify the content type (welcome message, CTA, paragraph, FAQ).
Define tone (friendly, professional, mission-driven, inspirational).
For example, “Write a welcoming headline and brief paragraph for a sophomore biochemistry major from California visiting the programs page. Focus on hands-on learning and student stories.”
For prospective students
Geolocation-based welcome
Prompt:
“Write a friendly greeting for a prospective student from Texas visiting the undergraduate admissions page.”
AI output example:“Welcome, future Longhorn from Texas! Explore how our campus blends big city opportunities with a tight-knit academic community. From Texas-sized ambitions to unforgettable adventures, your next chapter starts here.”
Program interest spotlight
Prompt:
“Create homepage content for a high school senior interested in computer science. Highlight related majors, career prospects, and student stories.”
AI output example:“Step into a future powered by technology! Our Computer Science program opens doors to AI research, global internships, and start-up careers. Meet Maria, who turned her campus coding passion into a role with Google. Find your path here.”
Note: I’m stating the obvious here, but make sure to replace the fictitious Maria with a story of an actual student.
Multilingual content
Prompt: “Translate this welcome message into Spanish for a prospective international student from Colombia. Use a friendly and encouraging tone.”
AI output example:“¡Bienvenido! Explora nuestro campus conectado globalmente, donde te esperan tus sueños académicos y nuevas amistades. Descubre programas, apoyo y una comunidad lista para ayudarte a triunfar.”
Follow-up after download
Prompt:
Generate a follow-up email for a student who downloaded the financial aid guide. Keep the tone helpful and accessible.
AI output example:“Hi [Student’s Name], glad you found our financial aid guide helpful! If questions pop up or you want to chat about scholarships, our team is always here. Your dreams should never be out of reach. See you at our virtual info session next week!”
For parents
Parents play a major role in the college decision process. Speak directly to their needs and concerns.
Parent-specific messaging
Prompt:
“Write a welcoming message for a first-time parent visiting the orientation page.”
AI output example:“As your student begins their college adventure, we’re here every step of the way. Explore schedules, support resources, and tips from families who have been in your shoes. Welcome to our campus community!”
Campus safety FAQ
Prompt:
“Create a list of questions for a short FAQ for parents about campus safety, including emergency alerts and student support services.”
AI Output Example: “How will my student be alerted during an emergency? Are there evening safety resources? What wellness services are available?”
Support resource overview
Prompt:
“List five key university support services parents would want to know about and write a brief intro for a landing page.”
AI output example: “Supporting your student’s success takes a village. Discover:
Academic Advising
Financial Aid Assistance
Health & Wellness Services
Career Planning
Student Life and Engagement
Explore these resources and see how we partner with families for a seamless transition.”
For alumni and donors
You can nurture relationships and drive engagement by tailoring content for alumni and donors based on graduation year, past involvement, or area of study.
Affinity-based personalization for donor campaigns
Prompt:
“Provide personalized donation messaging based on past campus involvement.”
AI output example:
Former Student-Athletes: “You trained hard, played with heart, and left it all on the field. Now, help the next generation of athletes compete with pride. Your gift to Athletics supports scholarships, equipment, and team travel.”
Student Government Alumni: “As a campus leader, you helped shape policy and progress. Today, your donation can fuel leadership development programs and civic engagement training for current students.”
Arts Program Alumni: “Whether you performed on stage or behind the scenes, your creativity enriched campus life. Support student artists by donating to the School of Arts Fund.”
Content suggestions by alumni stage
Prompt:
“Generate tailored content suggestions for a university website homepage that will appeal to three different alumni segments.”
AI Output Example:
Recent Graduates (0–5 years):
Headline: “Your Journey’s Just Begun – Stay Connected!”
Content Block: Career services spotlight, young alumni events, networking mixers
CTA: “Join the Young Alumni Network”
Donation Ask: “Give $10 to help new graduates succeed”
Mid-Career Alumni (6–15 years):
Headline: “Lead, Mentor, Inspire – You’re the Difference”
Content Block: “Mentorship opportunities and Braves game watch party this month”
CTA Button: “Get Involved Locally”
For faculty and staff
Recruitment and onboarding are high-impact yet often overlooked opportunities for personalization.
Recruitment page prompt
Prompt:
Write a landing page welcome for prospective College of Education faculty. Highlight research, inclusive culture, and relocation support.
AI output example: “Join a community of scholars who believe education transforms lives. We support innovative research, value DEI, and help every new faculty member feel at home with tailored relocation support. Shape the future here.”
Onboarding checklist
Prompt:
“Create an onboarding checklist for new Registrar’s Office staff. Make it conversational and actionable.”
AI output example: “Welcome to the Registrar’s Office!
Meet your buddy for a campus tour
Set up your university email
Review key policies with HR
Attend your department’s welcome lunch
Login to the student records system
Reach out anytime. We’re excited to have you!”
For campaigns and content testing
CTA tone variation
Want to A/B test different styles for your call to action? Use an AI prompt like:
Rewrite this CTA ‘Apply Now’ in five different tones: professional, casual, excited, inclusive, and urgent.
AI Output Example:
Professional: Start your application today.
Casual: Ready to apply? Let’s go!
Excited: Your journey begins here—apply now!
Inclusive: Wherever you’re from, your future starts here. Apply today.
Urgent: Applications close soon—don’t miss your chance!
Content mapping for user personas
Prompt:
“Create a content mapping table that shows homepage content for these personas: high school senior, parent, transfer student, alum, faculty candidate. Include headlines, CTAs, and featured resources.”
AI Output Example:
This can help you visualize your main audience journeys and keeps your homepage dynamic and relevant to all.
A personalized higher ed website starts with clear audience segments. But the magic is in using repeatable, structured AI prompts to take the heavy lifting out of content creation. This approach enables consistent messaging across channels and journeys, rapid scaling without burning out your team, the freedom to A/B test and refine continuously.
Ready to start personalizing?
If you’re interested in web personalization and are looking to implement a tool like Clive or you just need some guidance on how to get started, drop me a message.
What about you? Have you used AI to get started with personalization?
AI tools are evolving rapidly, but the real revolution isn’t just in smarter algorithms. It’s in how we prompt, guide, and collaborate with these systems. If the prompts of 2023 were “write my blog post” or “summarize this article,” the prompts of 2026 will reshape what it means to think, decide, and work.
Let’s look at some next generation AI prompts, why they matter, and how you can build this power skill to stay ahead.
The shift from simple commands to strategic collaboration
Ask anyone who used ChatGPT or other LLM-powered tools in 2023, and you’ll hear the same story. AI made everything a little bit easier and a lot faster. With one command, you can have AI write an email or social post, create a checklist or edit your content.
But as AI becomes central to every knowledge worker’s toolkit, prompts will become less about one-off tasks and more about nuanced collaboration. Your AI assistant is moving beyond “do this” to “think with me.”
This shift is significant,because in the coming years, those who master strategic prompting will set the standards for efficiency, insight, and impact in the workplace. It’s a difference as fundamental as learning Google search in the 2000s or project management basics in the 2010s.
What makes a next generation AI prompting different
Great prompts in 2026 won’t just be clear and specific. They’ll embody a new kind of leadership:
Context-rich and goal-oriented
The best prompts give the AI backstory, constraints, and a desired end result.
Intellectual integration
You’ll blend expert opinions, critique decisions, and ask AI to serve as a challenger or thinking partner and not just a content generator.
Multi-format and multi-step
Modern prompts will expect the AI to analyze, summarize, synthesize, and output results for different stakeholders and channels at once.
Bias-awareness and inclusivity
Instead of simply generating content, top prompts instruct AI to screen for accessibility, conscientious language, and systemic impacts.
Consequential foresight
The leading edge of prompts will model downstream effects and surface scenarios leaders need to plan for.
Prompt engineering will be a core skill
Prompting is no longer about getting decent results out of a clunky tool. It has become a core operating skill for strategists, analysts, marketers, product leaders, and executives. Those who learn the new prompt language will get more out of their AI partners and spend less time bridging gaps between what they want and what AI delivers.
Next generation AI prompt examples
Here are examples and use cases that showcase what prompting mastery will look like by 2026. Adapt and experiment with these to boost your own workflows.
Rethink decision-making with a strategic partner
Prompt:
Act as my strategic thinking partner. Here’s what I’m stuck on…
Use case example: “Act as my strategic partner. I’m trying to decide whether to invest more in international student recruitment or in expanding adult learner programs. Here’s what I know so far…”
AI is no longer a passive assistant. By inviting it in as a strategic partner, you unlock cross-checks, scenario planning, and perspective-broadening dialogue. This is especially powerful in complex decisions where human bias or bandwidth might limit analysis.
Synthesize leading thinkers and frameworks
Prompt:
Combine the perspectives of [Author A] and [Author B] to critique this idea.
Use case example: “Evaluate our plan to restructure team check-ins from weekly all-hands to asynchronous updates, using the leadership frameworks of Cy Wakeman and Simon Sinek. What strengths, risks, and cultural impacts should we anticipate?”
This prompt pits efficiency and accountability (Wakeman) against connection and inspiration (Sinek), which is a common tension in remote and hybrid leadership. It forces AI to weigh emotional truth vs. emotional management, and productivity vs. purpose.
Engineer persuasive content with behavioral insight
Prompt:
Analyze this content for psychological triggers, then rewrite it to resonate with [audience persona].
Use case example: “Review this alumni donation page. What psychological levers are being used? How could this better resonate with first-gen students from rural areas?”
Personalized, high-impact content becomes standard, not a luxury reserved for big brands. The best prompts look beyond surface-level edits to shape content for real emotional effect.
Summarize, reformat, and distribute
Prompt:
Turn this 2-hour meeting transcript into 5 action items, 3 questions for leadership, and a Slack post summary.
Use case example: “Here’s a Zoom transcript of our design sprint. Give me a TLDR, stakeholder-specific summaries, and a timeline.”
Why it matters:
AI becomes the go-to tool for knowledge distribution. You get actionable summaries and communication-ready outputs in minutes, saving leaders and teams hours each week.
Personalize communication at scale
Prompt:
Create multiple message variants based on this user’s behavioral data and communication style.
Use case example: “Using Clive campaign data, generate 3 re-engagement email variants that match a warm but efficient tone. Target parents who clicked the financial aid link but didn’t convert.”
AI-powered personalization shifts from nice-to-have to standard operating procedure, equipping teams to address micro-segments and individuals with far greater relevance.
Audit for values, ethics, and inclusion
Prompt:
Audit this content for accessibility, inclusivity, and ethical phrasing.
Use case example: “Scan this chatbot script for bias, stereotype triggers, and readability below a 9th-grade level.”
With increasing regulatory pressure and cultural expectations, prompts that screen content for bias, accessibility, and inclusive language become non-negotiable. These help protect brands and empower more equitable engagement.
Anticipate outcomes and design responsibly
Prompt:
Help me think through the downstream consequences of this product feature.
Use case example: “We’re launching an AI-powered tutor to help students with writing assignments. What are the second- and third-order effects? What should we prepare for?”
The skill of prompt engineering extends into systemic thinking. You’ll use AI to challenge your vision, anticipate unintended effects, and identify risks early.
Benefits of next-level prompting
Adopting these advanced prompting techniques leads to:
Faster, more relevant decision cycles: Actionable insights and summaries delivered in the moment.
Consistency and inclusivity: Communication that meets ethical standards and resonates with diverse audiences.
Personalization at scale: Content and outreach that meet users where they are.
Operational efficiency: Multi-step summaries, reformats, and distribution handled in minutes.
Foresight and risk management: Better anticipation of systemic impacts and ethical considerations.
Prompt engineering can be the key to more intentional, resilient, and creative teams.
Leading in the age of AI-native work
Prompting is no longer about wringing results out of black boxes. It’s about leading strategic, creative, and responsible collaboration between human and machine.
If your prompts still sound like “write an email,” now is the time to level up. The future belongs to those who know how to ask better questions, challenge assumptions, and guide AI as a true thinking partner. Start practicing these prompts today, and position yourself (and your organization) to stand out in the next AI-powered chapter of work.
What about you? What are your best examples of next-gen prompts?
Higher education is entering a new chapter. Yes, enrollment is shifting, budgets are tightening, and student expectations are evolving faster than ever, but these challenges also open the door to innovation. One of the most exciting tools at the center of this transformation is AI, as it is a real opportunity to enhance efficiency, personalize experiences, and amplify your team’s impact. You don’t need to be a tech whiz to take advantage of it, but you do need a clear understanding of what AI can do today, where it’s already making a difference in higher ed, and how to lead the way.
Let’s take a look.
What AI is and isn’t
Before we even think about strategy, we need to understand what AI is and isn’t. It’s not a replacement for your human team, nor is it a silver bullet that will help save struggling departments or instantly cut your workload in half. It’s more like an always-on assistant (I often call it your bionic arm), that can help in a number of ways, such as
Drafting emails and reports so much faster than you can
Summarizing complex meeting transcripts or documents
Analyzing enrollment or marketing trends
Generating different versions of content for different audiences
But someone still needs to set the direction, provide the context, and review outputs for alignment with your unique mission.
Higher ed‘s current use of AI
Many colleges and universities are no longer wondering if they should use AI. They’re already refining how they use it strategically. For example,
Marketing and Communications
Segment emails for prospective students, alumni, and donors
Draft event invites and newsletters tailored for different audiences
Audit communications for tone, consistency, and inclusive language
Summarize content performance or campaign reach
Example: Marketing teams use AI tools to generate multiple email or invitation drafts, which frees up time for higher-level planning.
Enrollment Management
Personalize interest-based content at scale for different types of students
Identify signals of student interest or drop-off through identifying patterns
Summarize notes from hundreds of student interactions to detect themes
For instance, by using AI to analyze application essays or email interactions, institutions can detect trends in applicant concerns, then address them directly in targeted outreach.
Advancement and Alumni Relations
Draft donor letters and campaign communications customized for audience segments
Summarize long board reports into digestible briefs
Generate recognition copy for milestones or giving anniversaries
AI can save many hours by helping staff convert board updates into concise leadership emails that keep everyone informed quickly.
Student Success and Advising
Automate regular nudges for key milestones to boost student retention
Personalize messages to students who might be at risk or need support
Translate complex policy language into plain English tips or FAQs
For examples, advisers may use AI-powered platforms to proactive reach out to students ahead of registration deadlines.
Internal Operations and Administration
Summarize transcripts or documentation from meetings and committee sessions
Draft and edit job descriptions
Quickly create executive summaries from sprawling reports
HR and operations teams rely on AI to condense meeting notes into checklists and action items, which makes follow-through easier across teams.
What Higher Ed VPs need to focus on
With AI already integrated into so many aspects of campus operations, here are a few ares that VPs should focus on:
Strategic structure
The real magic happens when you move past occasional, one-off uses (“write this newsletter”) and start structuring AI into ongoing workflows that learn and improve. AI is about compounding value. For example, once you have a playbook for drafting segmented campaigns or summarizing meeting notes, you can refine it over time, increasing quality while saving more staff time with each cycle.
Strategy guides the tools
AI’s strength is in scale and speed, and definitely not in institutional memory, culture, or nuanced judgment. This means no matter how powerful the tool, your strategy always leads the way. You know what resonates with your alumni better than any AI tool ever could.
Focus on real-world problems
Ask practical questions such as
Where are staff bogged down by repetitive or time-consuming tasks?
What processes cause delays or burn valuable staff hours?
Which areas could benefit from faster, more personalized communication?
Start by solving the real bottlenecks your teams talk about every month. That’s where AI delivers the biggest, most immediate ROI in higher education.
Questions every higher ed leader should ask
If you want AI to be a multiplier instead of a distraction, start with these questions:
Where are we using AI already and who is governing it?
Chances are, faculty or staff are already using tools like ChatGPT, Grammarly, or other writing aids. You may already have AI-features in your Content Management System. Map out where these tools are deployed and who is making operational or ethical choices about them.
Do we have shared guidelines?
Establish simple, clear principles for responsible AI use:
What counts as acceptable use?
Are outputs fact-checked for accuracy and tone?
Does the use align with your brand and values?
How will you ensure accessibility for all users?
Are there any other legal ramifications that we need to be aware of?
What type of training is needed?
Staff anxiety about “messing things up with AI” is real. Leaders can speed up adoption and prevent misuse by offering guides, practice sessions, and safe spaces to experiment and become more proficient.
What higher ed VPs shouldn’t worry about
Here’s what you do not have to do:
Learn prompt engineering from scratch. Use, adapt, and share prompts that have already proven effective (see these prompt examples).
Approve every single AI use case. Trust frontline teams with clear parameters and encourage smart experimentation.
Invest heavily on day one. Most effective AI solutions start at departmental or pilot scale. Scale up tools only when you have evidence of need and success.
The shifting role of higher ed leadership in the AI era
The institutions that succeed won’t necessarily have the flashiest tech stack. Neither will they be the ones who cling to old ways of thinking. Instead, those that thrive will be led by VPs and executives who align AI adoption with mission and culture, set clear expectations and boundaries, encourage cross-team sharing and learning, and stay committed to ethical, accessible, and transparent practices.
What about you? What would you add to the list of things that higher ed VPs should know about AI?
I’ve been thinking about higher ed a lot (even more than usual) these days, as it’s facing some challenging times, so I’ll be posting a bit more higher-ed focused content on here.
AI isn’t just another way to save a few minutes on your next campaign. For marketers in higher ed, it offers a lot more. In fact, if used wisely, it can become a system that makes every piece of work more efficient, more insightful, and more effective the more you use it. It’s often referred to as the AI Flywheel.
Let’s take a look at how higher ed marketing teams can move beyond one-off AI prompts and quick fixes, and start building systems that get smarter, faster, and more valuable with each cycle. If you’re spending too much time feeling like every enrollment or giving campaign is a new lift (like planning Welcome Week for the third time in six months), this approach will help you shift from reinvention to momentum.
Why AI in higher ed is not just about faster emails
Higher ed marketers operate in a world defined by big challenges and limited resources. Budgets are tight, teams are lean, and institutional expectations keep growing. And yes, you’re still somehow expected to write like a copywriter, strategize like a VP, and test like a CRO, all before lunch.
Think about it like this: You don’t want a robot that spits out a decent subject line when you ask. Instead, you want to me more ambitious and develop a process that helps your marketing team get sharper, learn from every email sent, and make the next campaign even more relevant, personalized, and achieve better results.
What is the AI Flywheel?
The AI Flywheel is a feedback loop with the intention to compound value. Instead of approaching tasks in isolation, the AI Flywheel connects every prompt, every campaign, and every data point so that the next round is always easier and more effective.
For example:
Ask AI to draft initial content for anything from an email to an event invitation.
Refine the output, shaping the tone and content to match your institution’s brand, tone, and values.
Reuse the structure or logic behind successful outputs for new use cases or audiences.
Analyze the response data. Did students click more? Did parents open less? What seemed to resonate?
Feed those insights right back into the next prompt, so that each turn becomes faster and smarter.
Instead of improving by accident, you develop a plan. Your systems, prompts, and institutional knowledge compound, which can make each campaign more agile and aligned.
How to build an AI Flywheel in higher ed marketing
Here’s how your marketing team can get started:
1. Design prompts for systems, not just single results
Don’t just ask AI to “write a welcome email for new students.” Instead, break the campaign down and think in terms of building blocks you and your team can reuse across future projects.
For a student welcome series, your AI prompt structure might include:
A general template with modular sections (intro, campus highlight, quick next steps, CTA)
Whenever possible, capture not only the result but also the reusable logic and variants. This way, your initial prompt seeds a content system rather than a one-and-done piece.
2. Create a living context file
AI is only as good as the context you give it. Feed your key institutional inputs into your AI companion or prompt library:
Brand voice and tone (welcoming, inclusive, aspirational, empathetic)
Personas (prospective students, parents, alumni, faculty, donors, employers)
Differentiators (small class sizes, experiential learning, first-year programs)
“Using our brand voice, draft a headline and subhead for our rural-first-gen scholarship landing page.”
Your context doc becomes a shared institutional brain, without needing to Slack a coworker for that one tagline she wrote back in 2019.
3. Turn every output into a future input
Every campaign, message, or landing page is a learning opportunity. Once you send an email with great open rates or a text message that parents forward widely, don’t just celebrate and move on. Feed that result back into your AI system.
For instance, prompt your tool with:
This open house email had a 52% open rate and strong parent engagement. Use it as a model to draft a campaign for our admitted student event.
This way, you’re building institutional intelligence that compounds, turning AI into a digital team member who remembers what worked (and what fell flat) last semester, last year, and beyond.
4. Systematize with a prompt library
Organize your prompts and templates so you’re never starting from scratch. Think of this as your team’s living playbook, where you collect and annotate things like
Outreach plan evaluations
Donor message variants based on giving history
Career-focused homepage copy
Accessibility and language audits
Infographic summaries
This living library becomes more valuable with each project, which can help make every new campaign both faster and more targeted.
Benefits of the AI Flywheel for higher ed teams
Scalable personalization: AI enables you to deliver tailored messaging, but the flywheel structure prevents your small team from reinventing the wheel with every campaign.
Consistent messaging: Centralized inputs, living prompt libraries, and reusable assets mean that your voice, values, and strategy show up seamlessly wherever your audience is.
Smarter and faster decision-making: Data feeds back into your system after every initiative, enabling rapid learning and focused improvements instead of guesswork.
Sustainable marketing systems: Even with staff changes or shifting priorities, your documented systems make it easy for new team members to ramp up and keep improving what’s working best.
How to get started
You don’t need a large team or a massive investment to begin. Start small and intentionally:
Save your three most-used prompts and tweak them with every cycle
Keep a shared doc with core messaging, personas, and brand guidelines
Make a habit of reviewing results and adding insights back into your system
Over time, your flywheel will pick up speed, giving your institution compound returns and marketing agility.
What about you? Have you started working on your AI Flywheel?
You know AI can help you get more done faster. But too often, it feels like one more tool to manage rather than a true productivity partner. The missing piece: Clear, structured prompts that make AI do the heavy lifting.
Here are some ideas to get started with 20 ready-to-use AI prompts that distill tasks into fast, repeatable wins. Whether you handle operations, marketing, hiring, analytics, or content creation, I hope these examples will save time and deliver consistent results.
Good prompts matter
Before jumping into specific prompts, it is essential to understand what separates a quick win from wasted time.
A strong prompt should:
Include relevant context so the AI understands your goal
Request a defined outcome (such as a checklist or email)
Specify the structure or tone you expect in the answer
Clear, intentional prompting transforms AI from a novelty into a practical tool for day-to-day efficiency.
Prompts for business owners and operators
Target operations tasks with precise instructions to introduce structure and speed up repetitive processes.
1. Build a Standard Operating Procedure (SOP)
Prompt:
Write a clear, step-by-step SOP for how we [task: onboard new clients into our product]. Use short, numbered steps and include any tools we need to use.
How it works: You receive a process document organized for new or existing employees, reducing onboarding time and errors.
2. Conduct a process improvement audit
Prompt:
Here is our current process for handling inbound leads: [paste process]. Suggest improvements using automation or AI, and explain how each change saves time.
What to expect: Actionable recommendations with time-saving calculations to fuel continuous improvement strategies.
3. Use the Eisenhower matrix for prioritization
Prompt:
Here are 10 tasks I need to get done this week. Help me prioritize them using the Eisenhower Matrix. Tasks: [list].
Result: AI provides a clear task matrix, allowing decision-makers to focus on what is urgent and important.
High-impact prompts for marketers
AI can shortcut ideation, optimization, and content repurposing processes. Structure is fundamental for valuable outputs.
4. Generate campaign ideas
Prompt:
Give me 5 creative campaign ideas for promoting our [product/service] to [target audience] with a budget of [enter budget range].
Benefit: AI offers campaign concepts tailored to real constraints, shortening planning cycles.
5. Generate ideas for blog posts
Prompt:
Analyze the content on [URL] and give me 10 blog post topic ideas optimized for the keyword ‘[keyword]’. For each, include a suggested title and a meta description.
Why it’s useful: This prompt helps you generate content ideas that are both strategically aligned with your existing site and optimized for SEO.You’ll walk away with not just broad topic direction (macro) but also ready-to-use titles and descriptions (micro) , accelerating your drafting process and boosting your search performance.
6. Repurpose Content for Social Media
Prompt:
Take this blog post: [paste blog text] and create 3 LinkedIn posts and 2 Instagram captions using a friendly, helpful tone.
Time saving: Redistribute long-form content into bite-size marketing assets in minutes, not hours.
7. Draft an engaging promotional email
Prompt:
Write a concise, engaging promotional email for [offer] that encourages [action]. Keep it under 150 words and include a strong CTA.
Outcome: A ready-to-edit email draft, consistent in style and focused on driving immediate action.
Prompts for content creators and educators
Use AI to streamline educational and creative production, focusing on clarity and engagement.
8. Build an agenda for a webinar
Prompt:
Build a 30-minute webinar agenda on [topic]. Include 3 key talking points, 2 interactive moments, and 1 call to action.
Practicality: Provides a structured, audience-focused plan for live events.
9. Turn documents into slide summaries
Prompt:
Here’s a long document: [paste or describe]. Create a 5-slide summary presentation with slide titles and bullet points.
Efficiency: Turns dense materials into high-level summaries viewers can process quickly.
10. Simplify complex topics for beginners
Prompt:
Explain [complex concept] in simple terms suitable for beginners. Use analogies and bullet points.
Value: Makes knowledge accessible, supporting onboarding and learning initiatives.
Streamlining hiring and HR with AI
Automate writing and talent screening with prompts configured for quality and inclusion. Check out my detailed post with more prompts here.
11. Craft compelling job descriptions
Prompt:
Write a compelling, inclusive job description for a [role] at a [type of company]. Include responsibilities, qualifications, and company culture highlights.
Advantage: Ensures roles are marketed attractively and inclusively, saving time on rewrites.
12. Generate interview questions
Prompt:
Give me 10 behavioral interview questions to assess a candidate’s problem-solving skills for a [job title] role.
How it helps: Builds precise question sets that test relevant competencies.
13. Onboarding checklist creation
Prompt:
Create a 2-week onboarding checklist for a new [role], with tasks broken down by day and links to relevant resources.
Desired outcome: Smooth onboarding processes mean faster time-to-productivity and less manager oversight.
Prompts for analysts and administrative efficiency
Extract insights and move from raw data to actionable summaries without manual labor.
14. Summarize spreadsheet data
Prompt:
Summarize this spreadsheet data: [paste table or describe data]. Highlight key trends and anomalies.
Value: Convert messy sheets into insights for focused, strategic reviews.
15. Summarize Meeting Notes
Prompt:
Summarize the key decisions, action items, and next steps from this meeting transcript: [paste notes].
ROI: Ensures important discussions result in tangible next actions.
16. Suggest useful dashboard charts
Prompt:
Suggest the most useful charts to include on a dashboard for tracking [goal, e.g., website conversions]. Explain why each is valuable.
Performance Tracking: Prioritizes metrics that matter, enabling smarter dashboard design.
General productivity hacks
Use AI to design repeatable frameworks, triage communications, and enforce strategic time allocation.
17. Create templates that save time
Prompt:
Create a reusable template for writing weekly status updates to my team. Include sections like ‘Highlights’, ‘Blockers’, and ‘Next Steps’.
Standardization: Fosters clarity and unity in reporting, saving time weekly.
18. Triage Slack messages
Prompt:
Here are 10 recent Slack messages I received across different channels. Help me classify each as Needs my action, FYI, or can be ignored. Messages: [paste messages].
Why it’s useful: This prompt helps you cut through the noise in team communication tools like Slack, Teams, or Discord. By instantly identifying what needs your attention versus what doesn’t, you can reclaim your focus and stop letting pings and notifications derail your deep work.
19. Design a weekly planning grid
Prompt:
Help me plan my week. I want to spend 60% of my time on deep work, 30% on meetings, and 10% on admin. I work Monday–Friday, 9–5.
Desired outcome: Enables intentional time management with built-in deep work prioritization.
20. Encourage personal reflection
Prompt:
Guide me through a weekly reflection. Ask me 5 questions about what went well, what I learned, and what to improve next week.
Continuous improvement: Promotes regular self-review, building resilience and alignment.
Combine prompts
When real transformation is the goal, don’t just use standalone prompts. Combine them into workflows. For example:
Craft a compelling job description (#11) Start by generating an inclusive, well-written job listing that attracts the right candidates.
Create an onboarding checklist (#13) Once the role is filled, immediately build a 2-week onboarding checklist so you’re ready to hit the ground running.
Turn onboarding docs into a slide summary (#9) Transform lengthy onboarding materials into a 5-slide overview presentation for your new hire’s first day.
By stacking these prompts, you move from role definition → hiring → onboarding with minimal lift. You reduce context-switching, create consistency across hiring assets, and make the employee experience smoother, all in under an hour of focused AI-assisted work.
Stacking prompts leverages compounding time savings, multiplying your impact across every phase of a project.
Wrap-up
Great AI prompts are not shortcuts but disciplined processes encoded into accessible language. They allow you to automate what’s repetitive, delegate without confusion, and direct your best effort where it counts.
Bring intentionality and structure to every AI interaction, and you will transition from spending time on busywork to delivering meaningful, strategic outcomes.
What about you? What are your favorite time-saving AI prompts?
There’s a moment every morning that quietly determines how the rest of your day will go. It’s not when you open your inbox. It’s not your first meeting. It’s that moment, before the noise sets in, when you decide what kind of day you’re going to have. That’s why I’m a firm believer in starting the day with a realistic, intentional plan and in posting that plan right when your day begins, not hours into it. This isn’t about reporting in or logging hours. It’s about leading your own day with clarity, honesty, and purpose.
This post is about the power of being proactive and about starting on purpose rather than drifting into reaction mode.
Surface blockers and competing priorities in real time
Create small moments of accountability that compound over time
And here’s the key: they only work if they happen at the beginning of your day. Not mid-morning or after your meetings. If your update isn’t shaping your day, it’s just commentary. Not a tool.
If live stand-ups aren’t possible, the next best thing is this:
Have everyone post a short, focused update in Slack as soon as they start working.
Why it has to happen first
When you wait until later in the day to plan, your day’s already been hijacked. The meetings, messages, and fire drills have already dictated your focus.
Posting a morning update before you dive in forces intentionality, puts you in the driver’s seat, and signals to you team where you’re focused and where you may need support.
Plan with honesty and realism
Let’s be blunt: you’re not going to accomplish 20 meaningful things in one day. So don’t write your update as if you will.
Your daily plan isn’t about documenting everything you could do. It’s about identifying what really matters today. The 2–5 high-impact priorities that deserve your time, attention, and energy.
Being honest with yourself matters here:
Is this task truly important or just easy to check off?
Is this list realistic given the meetings and energy you actually have?
Am I setting myself up to succeed or to feel behind?
As Greg McKeown puts it in Essentialism: “You can do anything, but not everything.”
The value of daily planning isn’t in ambition. It’s in alignment.
What a good update looks like
Your update should be written by you, in plain English, and at the start of your day. Not by a tool. Not copied from a ticketing system. Not written in project-speak or tech jargon.
It should answer:
What did I plan to do yesterday? Did I follow through? If not, why not?
What am I focusing on today, and why does it matter?
Is anything blocking me or shifting my focus?
Tools don’t think, but you do
Most of us use project management systems that populate our tasks automatically. And while those are helpful for visibility, they’re not your plan.
If you let a tool dictate your priorities, you’ll end up reacting to deadlines instead of leading with intention.
Writing your own update forces you to pause, prioritize, and communicate clearly, not just to others, but to yourself.
Reflect honestly and learn from the patterns
At the end of the day (or the next morning), check in with yourself:
Did you stick to your plan?
If not, what got in the way? Were your priorities realistic?
Did you let urgency overtake importance?
Honest reflection is what turns this from a routine into a leadership tool. When you regularly notice what’s working and what isn’t, you get better at planning, better at staying in your lane and better at protecting time for what matters.
This isn’t about micromanagement or checking boxes. It’s about building a habit of purposeful work, starting with a plan, crafted by you, in your own words, at the very beginning of your day.
And it only works if you’re honest with yourself. If you know you’re not going to get to 20 things today, don’t write down 20 things. Start early and in a truthful way.
Because real momentum doesn’t come from doing more, it comes from doing what matters, on purpose.
Onboarding and continuous learning are critical to building a strong, capable workforce, but they can also be time-consuming and inconsistent. New hires often feel overwhelmed due to information overload. At the same time, managers are stretched thin trying to provide personalized support. Therefore, it’s no surprise that companies are starting to explore ways in which AI can help provide a scalable and accessible way to enhance the onboarding and training experience. This isn’t about replacing human interaction, but about making important information more consistent, approachable, and available on demand. For the purpose of this post, we will focus on ChatGPT.
Instant and personalized knowledge bases
ChatGPT can act as an always-available assistant for new hires, answering common questions about processes, policies, tools, and culture. Instead of waiting hours or days for a manager’s reply, a new team member can ask simple questions such as “How do I submit a PTO request?”, “How do I request help from IT?”, “Who needs to approve external communications before they’re published?” or “What branding guidelines should I follow when creating social media posts?”. Note that it’s easy to train custom versions of ChatGPT by feeding it internal documentation like your handbook and communication playbook, to deliver answers specifically for your company.
Role-specific learning paths
Managers and HR teams can use ChatGPT to quickly create customized onboarding checklists or learning plans for different roles. For example, you can use a prompt like “Create a 30-day onboarding plan for a new Customer Success Manager for a SaaS company/[your company]”. You can even take it a step further by asking for key success metrics or for further details about a specific objective, for a daily planner that includes recurring meetings like stand-ups, or for a table indicating which tasks involve other team members and which ones are self-guided.
This approach ensures that every new hire has a thoughtful, structured experience without requiring managers to reinvent the wheel every time.
Practicing scenarios and soft skills
ChatGPT can simulate real-world conversations, giving new hires a chance to practice soft skills in a safe environment. For example:
Handling a difficult customer interaction
Conducting a feedback conversation with a colleague
Asking questions during a discovery call
Conducting a Quarterly Business Review (QBR)
Managing a customer who missed key onboarding deadlines.
Just provide ChatGPT with instructions like “Act as a customer who…” or “Simulate a situation where…”, or “Pretend to be a user who”. These role-playing exercises help employees build confidence and prepare for real-world challenges before they encounter them.
Reinforce ongoing training
Of course, training doesn’t stop after the first 90 days. ChatGPT can also serve as an ongoing resource for you when it comes to things like
Quizzing employees on company values, product knowledge, security protocols, or value proposition
Scenario testing, where employees can walk through different case studies and challenges.
Microlearning sessions, allowing employees to engage in bite-sized learning at their own convenience.
Here are some examples:
After a new product release, Customer Success Managers could quiz themselves on the new features by using prompts such as “Give me 5 multiple-choice questions about [product]’s new feature rollout.” Or an Account Executive could ask ChatGPT to act as a specific buyer persona and provide feedback on how well the AE explained the value of a specific feature set. You can also use the tool to help prepare for potentially uncomfortable internal conversations. For example, you can ask ChatGPT to “Act as a teammate to whom I need to give critical feedback about their time management skills.”. Examples of microlearning opportunities are a CSM quickly refreshing their knowledge on upcoming feature names before a call with a customer, or a Support Engineer getting a summary of the last 3 releases to help explain to a customer why they should upgrade to the latest version of the product.
Fostering a culture of continuous learning is not just beneficial for everyone, but it can also be fun. Consider creating a Slack channel where team members discuss creative uses of AI that help them in their roles.
Support managers and team leads
ChatGPT isn’t just for new hires, but it can also be a valuable tool for the people supporting them. Managers and trainers can use AI to:
Get suggestions on how to improve existing training materials
Provide ideas for mini-”homework” assignments for each role on the team to continue to sharpen their skills (“Explain our newest feature like you’re talking to a non-technical customer”)
Help team members hone their communication skills (for instance, have ChatGPT generate an email from a customer who is frustrated with something specific and then assign the team member the task to respond to it)
Reinforce knowledge of new product features, internal tools, or SOPs by having team members quiz themselves (“Summarize the top 2 use cases for marketers and for developers when interacting with X”).
By using ChatGPT, managers can make professional growth feel more continuous and accessible, help employees practice in a safe space, and foster a culture of curiosity, all without adding heavy training costs. It also frees up time spent on repetitive tasks and frees managers up to focus more on mentorship.
These are just a few ideas on how to use ChatGPT to help with onboarding and continuous learning, making it more consistent, accessible, and effective, while allowing managers and team leads to have more time for individual coaching. By combining the best of human guidance with the capabilities of AI, organizations can create a better experience for everyone involved.
What about you? What are your ideas for using ChatGPT for onboarding and ongoing training?
We’ve all had them, those weeks that knock the wind out of you. A missed opportunity, an unexpected client loss, a launch gone sideways, a painful conflict. Whatever the cause, there are times when work feels heavier than usual. In those weeks, the pressure to spin positivity is real. I try not to.
Not because I believe in wallowing, or in dragging the team down by being a Debbie Downer. But because honesty is far more valuable and powerful than pretending things are better than they are.
Lessons are hiding in the hard weeks
Hard weeks don’t just hurt, they can also be learning opportunities. They illuminate blind spots, reveal what’s not working, and force clarity around what matters most, but only if we’re willing to face them directly.
As leadership expert Brené Brown puts it: “Clear is kind. Unclear is unkind.” – Brené Brown, Dare to Lead
Being honest about a loss or a failure isn’t a weakness. It’s a commitment to learning. It’s saying: This didn’t go as planned. Let’s understand why so we can do better next time.
Simon Sinek reminds us: “The most effective leaders are the ones who can tell the truth, even when it’s hard, because that truth clears a path to progress.”
Lead with honesty and resilience
Being honest doesn’t mean being dramatic or dwelling in negativity. It means acknowledging what’s hard, owning the impact, and offering a way forward.
You can say: “This was a really tough week. We didn’t hit the mark. But here’s what I’m doing to get us back on track and here’s how you can help.”
That kind of leadership invites ownership and builds a sense of safety. It tells your team that we can handle this together.Learning how to develop resilience in the face of adversity is one of the best gifts you can give your team and yourself. It also helps us focus on the most important things rather than engaging in discussions or activities that are not moving the needle.
Trust your team to rise to the occasion
Your team doesn’t need you to be endlessly upbeat. They need you to be transparent. When people understand what’s at stake, most will step up if they’re given the chance. But if they’re led to believe everything is fine, they’ll either be caught off guard later or continue under false assumptions.
That’s not just inefficient, but downright unfair.
Don’t hide the hard stuff, but instead be clear, candid, and real. Not just because it’s the right thing to do, but because it builds a culture of trust, growth, and accountability.
Some weeks are tough. Losses are tough. But they’re not the end if you don’t let them be wasted. They’re often the beginning of the next chapter if we let them teach us.
What about you? How do handle communication when it’s been a rough week or two?
If there’s one thing I’ve been saying at nauseam in internal conversations: There’s no such thing as over- communicating when it comes to your customers.
We’ve all experienced first hand how some organizations treat customer communication like a one-lane road, owned and operated solely by the customer success or support team. But the truth is, our customers don’t experience our companies in silos at all, so why shouldn’t operate that way? When you open up communication across teams and create visibility into what customers are experiencing and sharing, you can build a culture that’s not just customer-friendly, but customer-obsessed, which is a much better place to be in.
Here’s why I think it matters, and how you can start fostering a that culture.
Create a dedicated Slack channel
Nobody wants more meetings, so you can start with a cross-functional Slack channel for customer insights. This can be your internal hub for things like:
Good news: big wins, unsolicited praise, successful launches
Red flags: early signs of dissatisfaction, usage drops, missed expectations
Complaints: even if they’re tough to hear. You need to share what’s really going on without sugarcoating.
Challenges and blockers: recurring issues, misalignments, confusing parts of your product
Aha moments: when a customer uses your product in a brilliant, creative, or unexpected way
Don’t restrict access to the channel. Invite Sales, Product, Services, Marketing, and Leadership, and really anyone who touches or impacts the customer experience. You might be surprised by the insights that come from someone who isn’t a Customer Success Manager. A marketer may have seen a trend. A developer might immediately understand the root cause of an issue that the customer is reporting. An account executive might chime in with helpful background from the buying journey. If you’re worried about overloading your team with messages, just make it clear that not everything requires an acknowledgement, let alone a response.
Make customers a part of the weekly conversation
Sharing updates in Slack is a good start, but not everyone looks at those updates all the time, and you don’t want to miss the opportunity to drive change. Make some space in your weekly company updates or all-hands meetings for a quick customer snapshot. It doesn’t need to be a full write-up or polished presentation, just a few minutes to surface recurring themes, such as
Are multiple customers asking for the same functionality?
Did a recent update excite users or confuse them?
Are there usage patterns indicating onboarding gaps?
Were customers not aware of a newly implemented feature or a service that you offer?
These patterns should inform roadmap conversations, onboarding optimization, and sometimes even hiring.
In addition, encourage your team to stay informed and curious about what’s going on in your customers’ world that may not have anything to do with your product or service. We share at least three articles about our customers every week in our weekly updates, because it makes us appreciate everything that our customers do and how they make the world a better place.
Break down the walls between roles
One of the most impactful things you can do is give everyone the opportunity to interact with customers, especially when they can add unique value. For example, let your engineers sit in on customer success calls. Encourage your marketers to attend quarterly business reviews. Invite your product leaders to join customer onboarding calls. Empower your sales reps to loop in implementation developers earlier in the sales process (if they have the bandwidth, of course).
The point is not to flood your customers with too many touchpoints, but to bring more clarity, more empathy, and more value to every interaction. When customer knowledge lives in silos, things tend to fall through the cracks, issues get repeated, feedback loops can break down, and your teams make assumptions based on partial or outdated information.
But when customer communication is shared, celebrated, and acted on:
Product decisions feel less speculative
Marketing becomes more relevant
Support becomes more proactive
The team starts speaking the customer’s language
Empathy grows
You can create alignment not just on what you’re building, but who you’re building it for. Make everyone listen to your customers. Because when your whole company becomes part of the customer conversation, you build stronger relationships, better products, and a clearer sense of purpose.
What about you? How much communication about your customers is too much?
Most of us follow an unspoken (or sometimes very much spoken!) rule in the workplace: stay politically neutral. Don’t stir the pot, don’t alienate, and simply don’t “go there.” In a professional setting, neutrality often feels like the most respectful and inclusive choice. After all, we’re here to do the work, not debate federal or state policies or political philosophies. But when politics and policies start directly impacting your employees, your customers, or your ability to do business, silence can feel less like neutrality and more like avoidance. So how can you mitigate the tension?
Here are a few thoughts:
Neutrality doesn’t mean numbness or ignorance
Being politically neutral in a professional setting doesn’t mean we stop caring. It doesn’t mean we avoid hard topics or pretend they don’t exist. It means we don’t turn our platforms into partisan battlegrounds. But we can, and should, acknowledge reality, especially when it’s affecting the people we work with or serve.
If your team is impacted by immigration policy changes, if your clients are in a state where access to education or healthcare is shifting, or if legislation affects your ability to hire talent, you don’t need to pick a party to speak up. You just need to focus on your people.
When deciding whether to address something political, ask yourself: Does this issue intersect with your mission, your team members, or your work in a real way? If the answer is yes, you know that it’s a business issue, not a political one. And treating it like one doesn’t make you biased. It makes you responsible. You’re not weighing in for the sake of commentary, but you’re staying aligned with our values and helping the people who make your work possible.
Example: Higher ed and shifting immigration policies
As someone who works closely with colleges and universities, I’ve seen firsthand how federal or state-level policies directly affect our clients’ ability to do their jobs. Take international student enrollment, for example. When visa rules change or when public discourse creates a perception that international students aren’t welcome, institutions are put in a tough spot. Their budgets are affected. Their student services teams are strained. Their reputation may even take a hit. And, perhaps most importantly, they’re trying to support students who might feel unsure, unsafe, or unwanted.
If we, as a partner, ignore that or stay silent out of fear of “being political”, we’re missing the point. It’s not about politics. It’s about people. And it’s about understanding the real-world context in which our customers operate, so we can better serve and support them.
Clear and careful communication
Let’s say you decide to speak up about a certain issue or development. Keep in mind that it is not a performance or getting on a soapbox. It’s about being clear, sincere, and grounded in real impact.
You don’t need a press release or chime in on every headline. But if a policy or political shift is directly affecting your team or your clients, say so. Be specific. For example, if new visa restrictions are making it harder for your university clients to support international students, acknowledge that and share helpful resources. You don’t have to issue sweeping statements, and you’re definitely not expected to solve the issue. But you can acknowledge it, share how it impacts your company, and outline what you’re doing in response.
Not everything requires a response
There’s a big difference between being silent and being thoughtful about when and how you engage. And it is perfectly fine to take some time for reflection or to refrain from jumping into the discourse every chance you get. You don’t have to issue grand statements, and you don’t have to take sides.
What you do need to do is stay informed about what is going on in the world and develop a deep understanding of how it affects your company and your customers, so that you can lead with intention.
Always keep in mind that it’s not about taking sides, but about being focused on your team members and your clients.
What about you? How do you navigate situations when politics impact your company?
Let’s talk about time savers, but not in the way you might expect. If you’re here for color-coded calendars, Pomodoro hacks, or a list of “5 productivity tools that changed my life,” this post is probably not for you. I’m not anti-time management. I’m just not a fan of spending too much time managing time.
I’ve found that for me, trying to optimize every minute of the day can be exhausting, and ironically, a massive time suck. I’d rather make quick decisions (though, of course, that is not always feasible or advisable), knock out an unenjoyable task, act with intention, and trust that if we get something wrong, we can course-correct. It’s not about being reckless. It’s about being efficiently decisive.
A few of my favorite counterintuitive time savers:
Say yes to the 30-minute meeting (sometimes)
If a meeting has clear outcomes, I’d rather attend than spend 30 minutes crafting messages in an attempt to get out of it.. “Can we do this asynchronously in Slack?” Sure, sometimes. But if the meeting will unblock a project, move a decision forward, or allow for rapid alignment, let’s just get in and get it done.
Do the quick thing now
If something takes two minutes (or even ten), I’ll usually just knock it out. The mental energy of tracking it, rescheduling it, or “prioritizing it later” often takes more time than simply doing the task.
Good enough is sometimes perfect
Not everything needs to be optimized, reworked, or run through another round of revisions. Perfectionism masquerades as productivity, but it rarely delivers the same results. I’ll take ‘done’ over perfect most of the time.
Block off time, and then honor it
While I don’t spend hours planning my schedule, I do block off chunks of time for heads-down work. No meetings, no pings, just focused progress. It helps me protect my energy and avoid the context-switching tax that can eat up a day. Confession: this is still an area that I need to improve in.
Don’t overcomplicate the system
Fancy task apps, automated workflows, and time-blocking templates are great if they work for you. But if you’re spending more time tweaking the system than using it, it’s time to simplify. A plain old checklist and calendar might just do the trick
Know what actually matters
Time management shouldn’t be a full-time job. For me, it’s about clarity: What do I actually want to get done today? What’s the real priority? I’d rather spend five minutes answering that than fifty minutes rearranging my to-do list.
In the end, the best time savers aren’t about tricks or hacks. They’re about doing what works for you, and in my case, I’d rather use my time than manage it.
I’d love to hear your take. What time savers feel surprisingly right for you, even if they go against the usual advice?”
Net Revenue Retention (NRR) has been a key indicator of business health in SaaS for a long time, and for good reasons. It tells you how well you’re expanding within your existing customer base. But while NRR is a highly valuable metric, it can also be misleading, because it may mask challenges, especially when it comes to acquiring new customers. That’s why you may consider shifting your focus to something more fundamental: the number of (good-fit) customers.
Don’t over-rely on NRR as the main indicator of success
A high NRR can make a company look successful on paper, but if customer acquisition is stagnant, focusing too much on NRR might make you ignore signs of trouble. In addition, relying too heavily on expansion revenue within an existing customer base creates a ceiling on growth. Eventually, there’s only so much revenue you can farm from our current customers, no matter how much value you add.
While retaining and expanding within your customer base remains important (Hannon Hill‘s retention rate in the last two years exceeded 97%!), sustainable long-term growth depends on consistently bringing in new customers. By prioritizing customer count as a key metric, you ensure that your business remains viable and competitive.
Why customer count helps paint a truer picture
Of course, it’s not all about customer count, and we all know that getting a new customer signed just for the count without considering if they fit into your ideal customer profile is a flawed approach. However, let’s look at some of the benefits of identifying the number of customers as a key metric.
Driving new business and competitiveness Expanding your customer base means actively selling your product to new organizations. This not only generates new revenue streams but also reinforces the value and relevance of your offering in the market.
Building a more expansive customer community More customers mean a broader range of success stories, testimonials, and case studies. A thriving customer community adds credibility, strengthens brand advocacy, and enhances your ability to attract even more customers.
Enabling better product decisions with diverse feedback A growing customer base provides a more diverse set of perspectives, use cases, and challenges. This variety helps you make more informed product decisions, ensuring your platform evolves in a way that benefits a wide range of users.
Ensuring long-term sustainability A business that prioritizes new customer acquisition (again, only if the customer is a fit – don’t pursue bad fits, as this is a lose-lose scenario) is better positioned for long-term success. Over-relying on upsells and expansions can create an illusion of growth, but without a steady influx of new customers, churn and market saturation will eventually limit progress.
Of course, retention still matters – a lot
This shift in focus doesn’t mean retention no longer matters. Keeping existing customers happy is still critical. However, retention should support, rather than overshadow, the primary goal of increasing your customer count. A balanced approach ensures that you continue to provide value to your current customers while also expanding your reach.
At the end of the day…
Ultimately, long-term success in SaaS isn’t just about getting more revenue from your existing base by providing more value, but it’s about continuously bringing new organizations into your ecosystem. By making customer count a core metric, you may better position yourself for sustainable, scalable growth.
Is there ever a virtual meeting where the sentence “You’re on mute” isn’t uttered at least once? This is then typically followed by a joke (“Every single time!”, “What, you can’t read my lips?”) or an apology. Does that completely derail the conversation? No. But it’s an unnecessary disruption. Being on “mute” has become the default for many people, but should it be?
By defaulting to the “mute” button, we create an unintentional barrier to natural interaction. If you were in an in-person meeting with a group, you wouldn’t tape your mouth shut. Embracing open audio channels can foster more authentic conversations, where participants feel connected and engaged, almost as if they’re in the same room. It encourages active listening, quicker responses, and a more fluid exchange of ideas, making meetings feel collaborative rather than isolated. It also makes the immediate feedback loop tighter and more authentic. Whether it’s a laugh, a “wow”, or even a gasp or other expressive sound, the feedback is valuable. You simply don’t get this when everyone is muted and meetings feel more like webinars.
What about background noise, you may ask? Yes, there may be an occasion where an unexpected loud noise would be a distraction. For example, if the landscapers blow leaves right in front of your window. In those cases, if you can’t relocate to another room, by all means, hit the mute button. But minor imperfections, such as a cough or a sneeze are part of human life, and you would certainly hear them in an in-person meeting. Why not bring a little humanity back to our virtual workspaces. Now, if uncontrollable noise constantly interferes, that’s a broader issue to address.
Similarly, keep your camera on if the other participants have theirs turned on. You wouldn’t hide under the table in an in-person meeting, right? Show your co-workers, partners, or customers that they have your undivided attention. And give them your undivided attention. It’s easy to tell when someone is clearly working on other things, and it can often feel disrespectful or even demoralizing when someone is engaged in something else. I realize that there are different opinions on this particular subject, but personally I am not a fan of exercising, driving (please don’t!), cooking, playing the piano or doing other things while in a meeting.
Let’s prioritize genuine communication over pristine silence. The next time you hop on a call, consider leaving that mute button off (and turning the camera on).
We’ve all been there. We experience frustration with a certain situation, or we simply disagree with a decision. Oh, how tempting it is to find a sympathetic ear and vent “to get it out”! Naturally, as we vent, our stories become colored with assumptions and are less focused on problem-solving. But that is just one of the many downsides of venting, which don’t just negatively affect you, but often your team and the company culture. Let’s take a deeper look at why we vent, why it’s bad for us, and how we can transition to a better approach.
Why we vent and let others vent
Venting makes you feel closer to the person that you’re venting to, says Ethan Cross in his article in EdWeek. When we are frustrated with something or someone, we look for allies and seek validation of our righteous indignation. In a post-pandemic world, a rather strange economic and quite divisive social climate, we crave a sense of support. Bonding over a perceived shared grievance seems to be an easy solution. We vent or we indulge someone else’s venting. For example, a new manager who wants to ingratiate themselves with their direct reports might not just listen to them complain, but actually fan the flames because it creates a sense of bonding. A team member who has been feeling disconnected might engage in venting with a colleague to feel a sense of camaraderie.
Venting causes energy-levels to go up. A disengaged employee will feel energized, albeit in a negative and counter-productive way when complaining to a team member about a perceived injustice, unwanted behavior or decision. After all, the spurt of energy feels better than indifference or disengagement.
Another reason why we vent is rooted in the misconception that it will make you feel better, which has been perpetuated for decades. It is often our go-to strategy. Even if we don’t vent in the workplace, we may go home and unleash our frustrations and the stories we’ve told ourselves on our spouses and partners, who may or may not be equipped to redirect the conversation into something more productive.
Why venting is bad for us
Contrary to popular belief, venting does not have the healing effects that we often attribute to it. Jill Suttie outlines the dark sides of venting in her article on Greater Good Magazine. “emotional venting likely doesn’t soothe anger as much as augment it. That’s because encouraging people to act out their anger makes them relive it in their bodies, strengthening the neural pathways for anger and making it easier to get angry the next time around”. So as we are venting, we don’t release our frustrations and grievances, but we’re making ourselves go through them again, often augmenting them, thus releasing higher cortisol levels into our bodies, which can result in a higher heart rate and even higher blood pressure, the long-term effects of which can’t be underestimated.
Anna Maravelas’ book “Creating a Drama-Free Workplace” dedicates an entire section to the perils of venting. She points out the adverse impact on our health as well as the effects on our professional standing and credibility, and our company culture. When we’re in a venting mindset, she says, we’re “flooded”, which greatly impairs our ability to problem-solve. She also points out that venting can damage your relationships with your colleagues, who might know that if you speak ill of someone else, you likely speak ill of them as well. We could also be considered hypocritical. For example, if Bob unloads on John a litany of why Jane is unqualified, lazy, and just doesn’t care about the team and then acts delighted when interacting with Jane, John might consider Bob a hypocrite and assume that Bob will have no qualms talking poorly about him. This clearly does not foster a culture of trust. Instead, Bob does what Maravelas calls “bankrolling drama at the expense of seeking solutions.” It can even have a bigger ripple effect. If the venting revolves around the assumption that key players or leadership just “don’t care” why would team members feel that they are part of something great? Why would they continue to be engaged?
The “feel-good” sensation that we experience when venting can be compared to scratching a mosquito bite or rubbing our itchy eyes. It might feel good at the moment, but it doesn’t help. In fact, you irritate your body even more and crave more scratching. Now think about what you’re doing to the person that you’re venting to: you’re essentially scratching them or rubbing their eyes. Does that seem like a good idea?
How to stop it
The good news is that we are capable of change. We just have to learn better techniques once we recognize the negative impact of venting.
In preparation for one of our company meetings, we asked everyone to watch Cy Wakeman’s clip entitled “Why venting is unhealthy and wrong”. The discussion that ensued was wonderful. Many of us acknowledged that we had always thought that venting had a positive effect by getting frustration out of our system. We also admitted that we all vented at times. Looking at it from a new perspective was eye-opening. Awareness is the first step to improvement.
Following Wakeman’s philosophy of reality-based leadership provides a great framework for establishing a culture of accountability and support. Before you go down a downward spiral, ask yourself “What do you know for sure?” For example, you may think that a team member doesn’t care about your department’s success because they missed a deadline. What do you know for sure? They missed a deadline. That’s it. Everything else is an assumption. If we follow the guideline of “the only acceptable assumption is to assume good intentions”, then we could stop our negative thoughts and start determining how we can help the situation and the team member. Similarly, we can help others by redirecting the conversation accordingly. Instead of fanning the flames of Mary’s indignation about Jack’s attitude/lack of respect/know-it-allism, you can make simple suggestions about how Mary can help Jack. This may be frustrating to Mary at first, but in the long term, you are increasing your chances of a better relationship between the two and an elevated company culture. Instead of getting a high from venting, help Mary get a “helper’s high,” as Maravelis calls it.
You may also stress the importance of locus of control, which could be part of your company values. The team members who are most appreciated and most successful focus on things that they can control, not on external factors. They don’t play the blame game, they don’t form alliances against others, but they solve problems. Consider making locus of control part of your check-ins.
Another technique involves talking about your own feelings and the impact on your own solution-finding abilities. How about showing vulnerability by saying “Steven, I want us to have a productive conversation that will be a win-win situation, but the way you’re communicating right now is not allowing me to problem-solve. Could we reconvene later today and focus on facts and how we all can help contribute to a solution?”
Hold yourself and your team members accountable. Stop yourself when you have the itch to vent. Find things to be grateful for, suggests Dr. Firdaus S. Dhabhar, Ph.D., a professor at the University of Miami Miller School of Medicine’s Department of Psychiatry. He also recommends channeling your energy into productive, healthy activities like exercise, spending time in nature, working on your hobbies, listening to music, meditating, or sleeping. Most importantly, “spend time with people you have meaningful connections with and focus on positive things.”
As there is overwhelming evidence about the negative effects of venting, let’s help each other develop healthier and more productive ways to handle frustrations. We’ll be better off as individuals and as a team.
What about you? What are your ideas for eliminating venting and fostering a more cohesive, healthy, and positive company culture?
Adaptability to ever-changing circumstances and the ability to recover quickly from adversity are two characteristics that define resilience, which happens to be one of the most transferable and desirable skills you can foster. As a leader, helping your team members develop resilience doesn’t just increase your chances of success, it can also play an impactful part in their personal and professional development. But of course, we have to start with ourselves and continue to train our resilience muscle, because there’ll always be adversity and unexpected challenges that we need to be able to handle in a much more productive way. Here are some ideas:
Focus on your locus of control
When faced with adversity, our knee-jerk reaction might be to freeze, vent, or capitulate, even though we know perfectly well that none of these behaviors are going to improve the situation. Cy Wakeman, in her reality-based leadership lessons and her No Ego podcast, frequently reminds us “Don’t outsource your happiness and well-being to external circumstances”. It’s a great framework on which to build resilience. Start with separating what happened from you as a human being, as difficult as it may be. Next, try not to go down a rabbit hole of speculating about other people’s intentions (“They only did this to me because they don’t respect me”). Then, focus on what’s in your control. What can you do to work within the parameters of the changed reality? What can you do to take on this challenge and mold it into new opportunities for yourself or your team?
Keep a log of lessons learned
One of the positives of adversity is that it might teach you valuable lessons. As Winston Churchill once stated, “Never let a good crisis go to waste”. How about keeping a log of your lessons learned from situations big and small? What has the adverse situation taught you about your industry, your company, your profession, and about yourself? Were there signs that you ignored? Was the situation avoidable? If so, what are you going to do differently? If not, what are the best strategies for embracing the change? Are your team members struggling with the adverse situation? How can you help them? Whose behavior is worth emulating?
Build a supportive network
Depending on the nature and severity of the adversity you’re facing, you need to pick the size and make-up of your support network. Be sure to surround yourself with people who can lift you up and help you figure out a game plan. Consider keeping a safe distance from anyone who seems to offer a sympathetic ear, but actually stokes negativity. Your network may consist of colleagues, peers in your professional circle, your family, friends, mentors, or even experts in the area in which your adversity occurred. Just don’t isolate yourself.
Practice gratitude
Adversity might cause you to hit the snooze button in the morning and/or to say out loud that you’re “just not feeling it”. We’ve all been there, and we all know that this approach rarely works. How about making yourself start your day by thinking about (and writing down) something that you’re looking forward to and that you’re thankful for? Maybe schedule something that you’d be looking forward to, whether it’s a massage, date night, or a hike. Keeping a gratitude journal and a lessons learned journal can also get you out of a slump when you read it back to yourself.
Train yourself in adaptability
As creatures of habit, change is hard, even if it’s a positive one. Facing adversity, it’s even more challenging. As we’re building up our ability to adapt quickly, even little experiments in breaking our attachment to routines can be useful, such as taking a different route to work or parking in a different spot. In fact, attachment to tangible and intangible things and our vision of the future often impairs our ability to be as resilient as we could be.
There’s no such thing as being “too resilient”. It’s a quality and a skill that can greatly reduce suffering, make you more successful, and even enable you to help others be more resilient in the face of adversity.
What about you? What are your thoughts on developing resilience?
“I have not failed. I’ve just found 10,000 ways that won’t work.” – attributed to Thomas Edison
Let’s be honest: Failure stings and stinks. No matter your role, you’ve probably felt the gut punch of watching a project misfire, losing out on a key client, or realizing efforts missed the mark. When things go sideways, it’s human to want to move on quickly. Many teams bury frustrations and quickly shift their focus, hoping that momentum will heal their wounds. However, pushing past failure without proper reflection seems like a missed opportunity, doesn’t it? When you study teams that adapt and outpace competitors, there’s a noticeable pattern: not fewer failures, but better learning. The best teams aren’t perfect, but they lose exceptionally well.
Let’s take a look at how losing well can fuel lasting progress and smarter innovation and how to transform setbacks into real momentum.
Why we avoid failure and miss the gold
There’s an unspoken pressure to perform flawlessly. Perfection is rewarded and mistakes are typically not celebrated. While striving for excellence isn’t a bad thing, it’s easy for teams to equate imperfection with weakness and to see loss as a threat rather than an asset. But think about this:
Innovation thrives on experimentation
Experimentation guarantees failure along the way
Growth is the result of honest reflection
Avoiding mistakes doesn’t make a team stronger; it quietly erodes resilience. When failures are hidden, teams repeat blind spots and compound small errors into bigger ones. On the flip side, teams that openly reflect on defeats learn faster and recover stronger. Research on psychological safety (Google’s Project Aristotle, 2012–2015) shows that when people feel safe to admit missteps without fear, teams collaborate and outperform peers.
The defeats that teach the most
Not all failures are created equal. Some are careless, driven by lack of process or attention. Others are courageous, rooted in calculated risks or bold experiments. Only the latter have the potential to boost team learning. Celebrate those, and see careless ones as signals for better process.
Lost opportunities
Maybe you spent weeks tailoring a proposal, only to watch the prospect choose a competitor. Rather than shifting blame, dig into the detail:
What signs or signals did you miss?
What did the winning team do better?
What assumptions guided your strategy?
Feature flops
Perhaps you launched a product update with fanfare and high expectation but saw usage plateau or feedback turn sour. Resist the urge to blame the market or end users.
Were you actually solving the right problem?
Did you test enough, and with the right audience?
Were you listening for real user friction, or just echoing internal assumptions?
Team misfires
Maybe communication broke down on a deadline, you missed a key deliverable, or morale slumped. These misfires are often swept aside with generic retrospectives, but there’s so much value in the specific questions:
Where were expectations or roles unclear?
Did feedback dry up at a key moment?
Did anyone flag the issue early, and how did the team react?
Reframing mistakes from shame to strategy
A healthy learning culture meets mistakes with honest inquiry, not finger-pointing. Instead of “Who messed up?”, start with “What do we know now?”. Here’s how resilient teams process loss:
Lead with genuine interest and curiosity
Brené Brown, in Dare to Lead, argues, “Clear is kind. Unclear is unkind.” Openly naming failure removes the shame and creates pathways for learning. Try questions like:
“What do we know now that we didn’t before?”
“What surprised us?”
“Where did we make assumptions?”
This frames loss as valuable and insightful data, not defeat.
Distinguish two types of failure
Avoidable: Slips due to lack of clarity, miscommunication, or skipping process.
Exploratory: Outcomes of smart experiments where risk was expected.
Reward honest reporting of both, but celebrate exploratory failure. True innovation requires teams to risk getting it wrong and report back.
Capture what you learn
Verbal debriefs fade fast. Build a habit of short write ups after every meaningful loss:
What did we try?
What didn’t work?
What signals pointed to the issue?
What will we do differently next time?
This simple practice builds a searchable database of “lessons learned”, turning memory into an asset.
Make space for losing well
Learning from defeat requires deliberate cultural cues. Here’s how to create psychological safety and normalize loss as fuel for growth:
Model learning from the top
When you admit your own misjudgments or openly review a failed project, you give your team permission to do the same.
Try language like:
“This didn’t go as planned. What can we learn from it?”
“The effort matters. The result surprised us, but I’m proud we went for it.”
“This is a data point, not a disaster.”
Make reflection public
Some team insights will be sensitive, but when possible, share mini case studies internally.
What we tried
What didn’t go as planned
What we learned
What we’ll try next time
Public reflection removes stigma and amplifies key lessons.
Recognize learning behaviors
Most organizations reward achievement. Start also rewarding the mindset and actions that drive better outcomes over time:
Spot and recognize when someone calls out risk.
Celebrate quick course corrections after a red flag.
Share wins from teams that pivoted due to lessons learned from prior refusal.
Recognition shifts focus from outcomes alone to continuous improvement.
Turning mistakes into momentum
Turning reflection into forward progress requires more than just good intentions. Here are some quick tips to get started
The 5 Whys
Start with the surface explanation and ask, “Why?” five times.
Example:
Why did we lose the RFP? Because our proposal didn’t clearly address the client’s top priorities.
Why didn’t it address their priorities? Because we misunderstood what mattered most to the selection committee.
Why did we misunderstand? Because we didn’t speak directly with a stakeholder before submitting.
Why didn’t we speak with one? Because we assumed the RFP document provided enough context.
Why did we make that assumption? Because we were focused on meeting the deadline and didn’t want to slow the process with outreach.
You’ll often find the true root is three or four whys deeper.
Hold a (blameless) postmortem
Frame postmortems as system and sequence reviews, not blame sessions.
What happened and in what order?
What were the contributing factors?
Where could the process have caught the problem/error?
Avoid naming and shaming. Focus on gaps in process, communication, or understanding.
Share learning case studies
At the end of a project, write a brief snapshot detailing:
What worked
What didn’t
What you’ll change in future attempts
Give a platform for team members who raised a red flag or pivoted quickly.
Make learning a routine
Consider a Slack channel, Notion board, or short section in team meetings to regularly share “lessons from last week.” Small, honest updates build team memory.
Moving forward
The difference between teams that plateau and those that bounce back higher lies in their willingness to examine what happened, honestly and intentionally.
Effective teams:
Ask better questions about every loss
Make learning public and persistent
Celebrate those who surface insights, not just successes
If you can shift your culture from loss-avoidant to learning-forward, defeats become data, fuel, and even a quiet kind of advantage. Every loss, when analyzed with honesty, is one less blind spot and one more step in the right direction.
Failure is only failure when you refuse to look at it. Otherwise, it’s necessary and invaluable research.
What are your tips for using failure as an opportunity?
Leaders rarely waste time because they are disorganized or unmotivated. They waste time because they operate on outdated assumptions. They find themselves managing drama, re-explaining expectations, reacting to unclear priorities, and drowning in meetings that exist solely to compensate for broken processes. This is a reality-based approach to modern leadership.
As author Cy Wakeman says, “Suffering is optional.” The drama, confusion, and rework that fill your day are not the job. They’re noise around the job. For the first time in decades, we have a powerful way to eliminate that noise: AI. Not as a shiny object or a replacement for real leadership, but as a catalyst for clarity. It’s a way to remove the friction that steals your time, focus, and energy.
Let’s look at some of the biggest time-wasters for leaders, and how we can use AI to turn those chronic stressors into more streamlined workflows, so that we can focus on what matters most.
The five ways leaders waste time
Leadership roles have quietly ballooned into something unsustainable. Leaders are expected to be strategists, therapists, technical experts, project managers, communicators, and culture-shapers, all at once. When we break it down, most of the drains on a leader’s time fall into five patterns.
1. Solving the wrong problems
Many leaders spend their days firefighting symptoms instead of addressing root causes. They fix last-minute crises, rewrite team content, chase missing updates, and build one workaround after another. This might feel productive, but it’s a trap.
The real issue often isn’t the circumstance but how we think about it. Leaders frequently jump into action without first stepping back to ask: What problem actually needs solving here? AI can help you get clean data quickly, summarize what’s going on, and surface the root causes instead of just the symptoms.
2. Reclarifying expectations again and again
This one issue costs teams hundreds of hours every year. You explain a process. Then you explain it again. Then you find yourself explaining it once more in Slack, in meetings, and in follow-up emails. The lack of clear documentation is arguably one of the biggest causes of time wasting.
Ambiguity is a petri dish for drama. Clarity, on the other hand, sanitizes it. When expectations are fuzzy, team members fill in the gaps with their own stories and assumptions, leading to rework and frustration.
3. Managing emotions and drama
Leadership requires a high degree of emotional intelligence. However, there is a difference between productive emotional support and unnecessary emotional labor. Time spent navigating venting, spiraling conversations, and conflict triangulation is time stolen from high-impact work.
Drama is essentially emotional waste. It consists of the stories, assumptions, and narratives that steal focus from reality. While AI cannot fix human emotions, it can reduce the ambiguity and miscommunication that often spark drama in the first place.
4. Meetings that should have been a workflow
A shocking percentage of meetings exist simply to get updates, restate decisions, clarify next steps, or piece together scattered information.
When work is clear and processes are documented, the need for these kinds of meetings shrinks dramatically. Meetings can become what they are meant to be: forums for strategic discussion and collaborative problem-solving, not therapy sessions or complaint centers.
5. Delayed decisions
Leaders sometimes stall important decisions because they feel responsible for having perfect information. This drive for perfection leads to collecting more data, getting more input, or rewriting a message “just one more time.” This pursuit of certainty slows everything and everyone down.
Your circumstances are not the reason you cannot succeed. It’s your thinking about your circumstances. AI can support leaders with drafts, scenarios, and data-driven clarity so they feel confident making decisions sooner.
How AI fixes the time-wasting problem
It is here to remove friction so humans can lead with clarity, courage, and accountability. Here are some ways in which the right application of AI can transform leadership.
AI creates clean data and decisions
Leaders spend an enormous amount of time cleaning up information. AI can take on this burden by summarizing complex discussions, turning messy notes into clear documentation, and extracting decisions and next steps. It can also outline risks and tradeoffs for you. As clarity goes up, rework goes down. Teams get aligned faster, and leaders stop repeating themselves.
AI as a thinking partner
Every leader needs a sounding board. With AI, you can have one instantly. You can use AI to explore scenarios, challenge your own assumptions, generate strategic options, and refine your messaging. It helps reduce overthinking and analysis paralysis because you no longer start from a blank page. You start from a structured, thoughtful draft.
AI workflow automation shrinks meeting overload
Imagine a world with fewer, better meetings. AI can make that a reality by automating or streamlining weekly updates, agenda creation, post-meeting summaries, onboarding steps, and recurring project tasks. The result is fewer meetings, more momentum, and more breathing room for actual leadership work.
AI strengthens accountability
Accountability often becomes an emotional issue (“Why didn’t this get done?”) instead of an operational one (“Here is what we agreed to, documented clearly”). AI helps leaders create checklists, documentation, clear responsibilities, and action plans. When expectations are documented and transparent, accountability becomes objective, not personal.
AI reduces emotional load
Communicating as a leader can be hard. AI can support you by drafting difficult messages in neutral, factual language. It can help you remove emotional charge, eliminate assumptions, and rewrite escalation messages with clarity and calm. This helps leaders stay grounded and model the emotional neutrality that Reality-Based Leadership encourages.
Seven steps to get started
Ready to see a change? Small shifts can compound quickly. Try this simple plan to integrate AI into your leadership practice.
Day 1: Replace one status meeting with an async update generated by AI. Day 2: Turn one chaotic process into a clear Standard Operating Procedure (SOP) using AI to help you draft it. Day 3: Create your “AI executive assistant” prompt to help manage your schedule, communications, and priorities. Day 4: Identify one recurring leadership task, like drafting a weekly report, and automate it with an AI tool. Day 5: Use AI to draft a difficult or delicate communication, focusing on neutral and factual language. Day 6: Have AI summarize your week’s activities and help you set clear priorities for the week ahead. Day 7: Reflect. Where did drama decrease this week? Where did clarity increase?
Prompts to try
Here are some prompts leaders can use to reduce emotional waste, eliminate friction, and lead with clarity.
Clarifying the problem
“Here’s the situation I’m dealing with: [paste situation]. Help me identify the root cause, not just the symptoms. What problem should I actually be solving?”
“Before I jump into action, break this down into: what’s happening, what I know for sure, what assumptions I might be making, and my next best step.”
Setting clear expectations
“Create a clear, actionable set of expectations based on these goals and responsibilities. Make it concise, specific, and easy to understand: [paste info].”
“Here’s a process I’ve explained verbally multiple times: [paste process]. Turn it into a clean step-by-step SOP with owners, timelines, and success criteria.”
“Turn this Slack thread into a single-source-of-truth summary with decisions, next steps, owners, and deadlines: [paste thread].”
Reducing drama and emotional waste
“Rewrite this message in neutral, factual, drama-free language that removes emotion, judgment, and assumptions: [paste message].”
“Help me respond to this emotional message with calm clarity—compassionate but focused on facts and next steps: [paste message].”
“Create a script that helps redirect someone from venting to problem-solving using Reality-Based Leadership principles.”
Eliminating meetings
“Convert this weekly status meeting agenda into a fully async workflow with templates and update formats so the meeting becomes unnecessary.”
“Summarize this meeting transcript into: decisions, owners, deadlines, risks, and open questions: [paste transcript].”
Accelerating decisions
“I need to make a decision about: [topic]. Give me 3–5 options, the tradeoffs for each, and your recommendation based on the data.”
“Draft a ‘good enough’ version of this message that is clear, concise, and ready to send with minimal edits: [paste draft].”
“Generate a scenario analysis for these choices: [list], including risks, effort, ROI, and what happens if I delay.”
Strengthening accountability
“Turn these notes into a clear agreement with tasks, owners, success criteria, and due dates: [paste notes].”
“Create a RACI-style responsibility breakdown for this project based on the following info: [paste project details].”
“Rewrite this follow-up message so it’s direct, neutral, and grounded in documented expectations: [paste message].”
Reducing overload
“Summarize my week based on these notes and help me identify my top 5 priorities for next week: [paste notes].”
“Help me create a customized ‘AI Executive Assistant’ prompt that supports scheduling, message drafting, priority setting, and weekly reviews. Here’s my role: [describe role].”
“Organize these scattered notes into a clear plan with categories, deadlines, and delegated items: [paste notes].”
Reality-based leadership reminds us that the biggest cost in any organization is emotional waste. AI finally gives leaders the ability to reduce drama, increase clarity, speed up decision-making, and improve accountability. It helps eliminate expensive rework and stop the cycle of babysitting emotions. Let AI do the work that drains your time but does not require your unique talent.
A lot of companies pride themselves in soliciting a continuous stream of feedback from team members. We’ve all seen post after post about the importance of employee engagement surveys. But let’s be honest: not all feedback is created equal, and not all feedback is helpful.
That might sound controversial, but it’s something I’ve come to believe strongly, especially after discovering Cy Wakeman’s Reality-Based Leadership philosophy. It’s a game changer for anyone who’s tired of the drama, the venting, and the endless cycles of “collaboration” or surveys that lead nowhere.
Here’s one of the core ideas that stuck with me: feedback from high-accountability people carries more weight.
Not all feedback deserves equal airtime
Giving all team members forums and opportunities to voice their opinion is absolutely crucial, so I’m not saying we ignore people. However, it may be time to stop putting every opinion on the same level when it comes to making decisions. There’s a big difference between feedback from someone who takes ownership, works through challenges, and stays focused on solutions versus someone who blames, deflects, and resists change.
If someone consistently shows up as a problem-solver and truth-teller, we absolutely want to hear what they think. If someone just wants to vent without taking action, that feedback is more noise that is much less actionable – or should be acted on. So when feedback comes from a high-accountability person, we should lean in. When it’s coming from someone who’s not taking ownership themselves, we need to view it through a different lens. Not to dismiss it, but to weigh it appropriately.
Venting isn’t healthy, but contagious
We’ve heard this take on venting many times: people “just need to get it out.” But most of the time, venting isn’t releasing energy. It’s actually counterproductive and spreading negativity to others, while augmenting your own. (Check out my post about it in a previous post, which you can check out here)
Venting reinforces the idea that our circumstances are more powerful than we are. That we’re victims of bad leadership, annoying teammates, or unfair systems. But what if, instead, we need to ask questions such as “What role did I play in this?”, “What can I do differently next time?”, “What do I know for sure?”, “How can I help?”
High-accountability people tend to vent less and reflect more. Their feedback usually comes with awareness and ideas for action. That’s the kind of input we value most, because it’s grounded in ownership, not offloading.
Be helpful, not judgy
Reality-Based Leadership reminds us that judgment adds nothing but curiosity and support can change everything. If a teammate is struggling, gossiping about their attitude helps no one. But asking, “How can I help you get back on track?” opens a door.
I try (and, admittedly, don’t always succeed) to be less reactive, and more curious. Less certain, more supportive. It’s amazing what shifts when you lead from that space, but it takes work.
And guess who tends to offer that kind of feedback? People who own their impact. High-accountability people. Again, their voice should carry more weight.
Assumptions fuel drama, while questions dismantle it
We’re all wired to make up stories. We fill in the gaps with narratives based on what we would do or how we see the world. But assumptions can often be a fast track to conflict.
When in doubt, ask more questions. “Can you help me understand?” goes a lot further than “Why did you do that?” Drama thrives on assumptions, so we need to use clarity as a way to squash it.
What’s just as powerful as redirecting your own instinct is helping others do the same. Assuming good intentions and focusing on what you know for sure will be empowering for you, but also invaluable to others who you help along the way.
High-accountability people question assumptions and seek clarity. That makes their feedback more trustworthy and actionable, because it’s grounded in curiosity and honesty, not assumptions and blame.
Focus on what you can control
This one’s simple, but not easy. You can’t control how others lead. You can’t control policies, platforms, your competitors, the economy, or personalities. You can control how you respond, how you show up, and how you hold yourself accountable.
When you live in that space, your energy changes. You go from frustrated to focused and from helpless to impactful.
High-accountability feedback always includes an element of self-awareness: “I could’ve communicated this better, but I noticed that…” “I see this challenge, and here’s an idea to address it…”
That kind of feedback is rare and incredibly valuable, and that’s why we should weigh it more heavily.
We all want cultures of accountability, clarity, and trust. But we don’t get there by treating every opinion the same, or by indulging in endless venting sessions. Instead, we get there by showing up with ownership, curiosity, and a clear understanding of what we can control and letting go of what we can’t.
So no, I don’t look at every piece of feedback equally. I pay more attention to those who lead with accountability. Because that’s the kind of culture we want to build.
What about you? Do you take everyone’s feedback equally into account?
Feedback is how you refine your product, shape your messaging, and uncover blind spots. But not all feedback is created equal. The most useful feedback doesn’t just confirm your assumptions or point out flaws, but it reveals intent, context, and patterns that help you make better decisions.
So how do you get that kind of feedback from customers who are busy and prospects who aren’t yet invested?
Let’s take a look.
Ask why
Too many feedback forms and surveys stop at surface-level questions:
“Did you like this feature?”
“Would you recommend us?”
“What didn’t work for you?”
While feedback that comes out of these questions can be useful, you may get even better insights by focusing on the why.
Ask:
What were you trying to accomplish?
Why did this feature help, or fail to help, you do that?
Why did you choose us over other options? Or why didn’t you?
You’ll uncover underlying motivations, not just reactions. And that’s what drives product clarity and positioning.
But a word of caution: how you ask why matters. If it comes off like you’re challenging the validity of someone’s feedback, especially if they’re voicing frustration, they may get defensive. Worse, they might double down on a perception that your product lacks something crucial, even if it’s a misunderstanding or misalignment.
Instead, approach with genuine curiosity and a tone of collaboration. Frame it like, “I want to make sure I fully understand so we can get better at solving that problem.” That keeps the door open to dialogue and positions you as a partner, not a skeptic.
Talk to the extremes
It’s tempting to focus on your “average” customer. But the most valuable insights often come from:
Your biggest fans: They can articulate your differentiators and help you understand your true value.
Your toughest critics: They reveal gaps you’ve ignored or underestimated. Remember Bill Gates’ comment ““Your most unhappy customers are your greatest source of learning.”
Your lost prospects: They tell you where you missed the mark and what mattered most in their decision.
Build regular cadences to talk to all three. Exit interviews with lost deals are especially underrated.
How to get lost prospects to talk to you
Reaching out after a deal is lost can feel awkward, but when handled with the right tone, it can actually build long-term goodwill.
Lead with humility and transparency. Try: “Thanks again for considering us. We know you made the best decision for your team. We’d love to learn how we can improve for the future. Would you be open to a short conversation?”
Offer value in return. For example: “We’re refining our onboarding process and messaging. If you’re open to sharing your thoughts, we’ll send you a preview of what we’ve changed based on customer feedback.”
Keep it low-effort and non-salesy. Clarify upfront: “This isn’t a sales call, just a chance to learn from your experience.”
How to get to the real reasons
Often, the reason prospects give (“pricing,” “missing feature”) is just the surface. To uncover the deeper drivers, use open-ended prompts like:
“Walk me through your decision-making process and what mattered most to your team.”
“Were there any trade-offs you had to make?”
“Was there anything that gave you pause about our product?”
“If you could have changed one thing about our offering, what would it have been?”
Don’t be afraid of a little silence. Often, the most honest feedback comes after the first, more “polite” answer.
Observe behavior
What people say they want and how they actually behave often diverge. This is especially true in SaaS.
Let’s say you launch a new page builder in your CMS. During interviews, both developers and non-technical users express excitement.
But once it’s live, your data shows that power users continue making update right in the HTML, non-technical users still submit help tickets for formatting issues, or bounce rates from the feature documentation are high.
That’s a red flag: behavior doesn’t match enthusiasm. Why? Maybe:
The interface wasn’t intuitive enough.
They weren’t confident using it without training.
It didn’t accommodate the custom components your developers already rely on.
Governance concerns are forcing users back to IT for review anyway.
This kind of insight won’t surface through surveys alone. It shows up in click paths, support logs, and feature adoption data.
So instead of just asking, “Do you find the page builder helpful?”, combine that feedback with behavioral signals:
Are users completing their tasks independently?
Are certain roles ignoring the feature altogether?
Is usage consistent across departments?
In the CMS world, watching how content is actually created, updated, and published is often more revealing than what users say about the tool.
Ask open-ended questions
Instead of asking “What do you like about our product?”, ask:
“Tell me about the last time you used our product to solve a problem.”
“Walk me through how you currently manage [X] and where you get stuck.”
“Walk me through a workaround that you use just to avoid a specific feature.”
“What’s the process like when someone new joins the web team. How easy is it for them to get up to speed?”
“How does the system support (or hinder) collaboration between departments?”
“If your system disappeared tomorrow, what would you miss, and what wouldn’t you?”
“What’s something you wish your system could help you do that it currently can’t?”
“Can you tell me about a moment when using the tool made you look like a hero internally?”
Stories provide context. They help you see how your product fits into real workflows and where it falls short. They also help you uncover language you can use in your own messaging.
Make feedback-giving easy and low-risk
Don’t expect people to write a novel or get on a one hour call with you. Offer simple ways to share:
A single question in a pop-up: “What’s one thing that would have made this page more useful?”
A quick check-in email: “Mind hopping on a 15-minute call to give us some honest feedback?”
Embedded tools like Hotjar or FullStory that let you capture input as users interact.
Also, avoid making feedback feel like a trap. Let people speak freely, anonymously if needed, and make it clear there are no wrong answers.
Quick tip: While I’m generally not against having an AI notetaker on my calls, I try to read the room, and when I feel that I would get more honest feedback if it was just me and the customer “off the record”, I turn it off. You can also just ask if the customer would feel more comfortable without the notetaker.
Separate the signal from the noise
When you start collecting feedback at scale from users, prospects, support tickets, user groups, and internal stakeholders, it can get noisy fast. Everyone has ideas, and everyone has “must-haves.” Obviously, trying to implement everything leads to a bloated product that loses focus.
Imagine you start getting feedback like this from multiple content contributors across departments:
“We need more design flexibility on our pages.” “Users wants more layout options without going through the web team.”
This can quickly trigger alarm bells:
Should we allow drag-and-drop layouts?
Do we need to revamp the entire templating system?
Should non-technical users have full control over design?
But before diving into solutions, pause to ask: What are they actually trying to do?
You conduct a few interviews and review support tickets. This could look like this:
Most users aren’t asking for pixel-perfect design control. They just want to add a call-to-action or rearrange content blocks.
Others are frustrated because they don’t understand how to use existing layout options that are available but maybe not easy to find.
A few are working around limitations by pasting formatted content from Word or Canva, which breaks accessibility standards.
The signal may be “Non-technical users want to feel empowered to make their content look professional, but the current tools are hard to find or unintuitive.” But the noise could be “Requests for total design freedom, when in reality, that would lead to governance chaos.”
This separation will provide more clarity and lets you implement the right set of features and enhancements without overcorrecting or deviating from your product philosophy.
In summary:
Look for patterns: What themes come up repeatedly across roles and industries?
Use jobs-to-be-done thinking: What core problems are people trying to solve?
Prioritize based on impact vs. effort and alignment with your strategy.
Great feedback isn’t just a list of requests but set of clues that need to be interpreted carefully.
Close the loop
The easiest way to encourage feedback? Show people it matters.
Let users know what changed based on their input (these are huge wins for you and them!)
Thank them personally when their insight led to a fix or improvement.
Involve your customers in early access programs and beta testing.
Picture this. A customer filed a support ticket for a use case that your product could not support at the time. Now, months later, you have a new feature that can help the user do what they need to do. You send them a personal message, thanking them for their feedback and informing them that this new feature is now for use in beta. Ask them to test it and let you know how it works dor them. Who knows, this may even result in a user story for your next blog post or webinar as a real world example of how customer feedback drives your roadmap.
Be curious, not defensive
When someone tells you your product didn’t work for them, or that they chose a competitor, it’s tempting to explain or defend. Resist the urge.
Instead, get curious, dig deeper, and ask more questions
The most valuable feedback doesn’t stroke your ego. The best products are built by people who know how to listen with open minds and strategic intent.
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