The Message Your Decision Sends

Leadership decisions are rarely just about the decision itself. They are about the message that decision sends. Consider a few common scenarios. An employee asks to upgrade an already generous snack bar. Another suggests increasing the catered lunch budget. A group proposes expanding an already generous vacation policy. Individually, none of these requests are catastrophic.…

When Helping Becomes Expensive

Most teams champion helpfulness. We encourage people to ask questions, foster collaboration, and make sure no one struggles in silence. These values are essential for a healthy work environment. But a subtle yet important reality often goes unexamined: helping has a cost.And when we ignore that cost, we can unintentionally create the very inefficiencies we’re…

Why Customer Feedback Shouldn’t Drive Your Roadmap Alone

“Listen to your customers” is some of the most repeated advice in product management, and for good reason. Customer feedback is a vital compass, helping you understand what’s working, what’s not, and where there may be new opportunities to add value. But like any powerful tool, feedback needs thoughtful handling. Building your product roadmap by…

Scale Is a Distraction When You Don’t Have Customers

“Is this scalable?” It’s one of the most common and misunderstood questions in modern business. I hear it freuently from founders, executives, and product leaders who are nowhere near the kind of growth that makes scalability a real constraint. Yet, entire strategies are shaped around this single question. Conversations that should be about customer needs…

Handling Complaints Without Fueling Drama

I’m sure you’ve been there. An employee shows up at your door, or, perhaps more likely, in your Slack message, with a familiar story. They start venting about another person or department, a surefire way to make things worse for everyone, especially for the person complaining. Maybe it’s a frustrated team member complaining that “Laurie…

The energy audit: what to stop, start, and continue

Leadership isn’t just about the decisions you make or the vision you set. It’s also about how you manage your most finite resource: your energy. On any given day, my energy can easily scatter across 30+ Slack threads, an inbox that restocks itself hourly, a to-do list in my notes, and open mental tabs. In…

Losing well: How honest reflection turns defeat into a growth

“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,…

Why leaders waste time (and how AI might be able to fix that)

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,…

Not all feedback is created equal

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…

The bias for action when certainty is out of reach

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,…

Why Leah Williamson Is the Leader Every Team Deserves

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…

9 powerful ways legal, finance, and HR can use AI

When you think of AI at work, it’s easy to picture marketers drafting blog posts or crafting social media content. But AI’s possibilities go beyond marketing. In fact, some of the most revolutionary uses of AI are happening in traditionally less front-facing roles such as legal, finance, and HR. These departments are the backbone of…

Search AI and SMBs: How to Evolve with Conversational Search

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…

Get better results from AI with prompt layering

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…

Speaking up: How to share feedback with leadership thoughtfully and effectively

For most of us, giving feedback “up the chain” can feel intimidating. Whether it’s your team lead, your VP, or the CEO, it’s easy to second-guess yourself: “Is this worth bringing up?”,“What if I sound like I’m complaining?”, “Will this actually change anything?” I venture to say that most leaders want and appreciate your feedback…

Are AI notetakers helping or hurting your meetings?

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,…

Thank you for your (current) shortcomings, AI

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…

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