AI dominates today’s business conversations. Companies are pouring billions into tools that write, analyze, and automate. But the leaders who thrive aren’t those who blindly outsource to machines. They’re the ones who recognize AI’s limits and lean into the distinctly human strengths that technology can’t touch, at least not yet.
As leadership expert Cy Wakeman reminds us, “Your circumstances aren’t the reason you can’t succeed. They’re the reality in which you must succeed.” AI isn’t the obstacle. It’s the reality. Your edge as a leader comes from doubling down on what AI can’t do.
1. Context over data
AI is fantastic at processing information, but it doesn’t live in your organization. It can’t read the silence in a tense meeting, recall the project that failed (but succeeded to traumatize your team members) two years ago, or understand that one employee’s informal influence outweighs their job title.
Satya Nadella has described AI as a “copilot, not an autopilot.” That distinction matters. Leaders who know their company’s culture, history, and unwritten rules can make calls no algorithm could ever justify in a spreadsheet.
2. Inspiration instead of automation
AI can generate motivational text on command. But true inspiration isn’t written. It’s experienced. It comes from leaders who rally a team through uncertainty, or who celebrate a small breakthrough that carries months of weight.
Empathy requires sensing what’s said and what’s left unsaid. It means taking a struggling employee out for coffee, or lowering the temperature in a tense room. Those moments build culture and commitment. As Wakeman teaches, great leaders skip the drama and connect people back to reality and purpose.
3. Values-based judgment
AI will show you probabilities. It won’t show you principles. Leaders make decisions where the “optimal” answer isn’t the right one, where cutting costs might please the board but result in burnout on your team.
Google’s Sundar Pichai has called AI “more profound than fire or electricity.” If that’s true, then leaders need to be the firebreak: using judgment, ethics, and values to ensure the power of AI serves people, not the other way around.
4. Trust through humanity
Trust doesn’t live in dashboards or reports. It grows in hallway conversations, after hours crisis calls, and moments where leaders admit they don’t have the answer.
Consistency, vulnerability, and care build psychological safety. Can this be automated? Not now, at least. AI can give your team information faster, but only you can make them feel safe enough to share the truth.
5. Vision beyond the data
AI predicts the future by analyzing the past. But breakthrough innovation requires imagination. Leaders must see possibilities no dataset can show. Think of the iPhone before the iPhone, or the electric car before it was mainstream.
In Contact, when scientist Ellie Arroway witnesses a cosmic spectacle too beautiful for words, she says: “They should have sent a poet.” Even with all our technology, some things require human awe, artistry, and vision. (Fittingly, OpenAI is currently hiring poets: it turns out machines still need us to make sense of wonder.)
The leadership advantage
Understanding AI’s limits reveals where leaders should focus: contextual intelligence, emotional intelligence, values, trust, and vision. AI offers speed and scale, while humans offer meaning and direction.
Organizations that integrate both (using AI as a copilot while leaders lean into uniquely human strengths) will outperform those that rely too heavily on either side alone. The gift isn’t what AI can do. The gift is what it can’t, and the space it leaves for leaders to show up more fully human.
What about you? Which shortcomings of AI do you see not as flaws, but as your opportunity to lead differently?
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?
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?
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