The best AI skill is older than you think
How clarity unlocks everything in your team, your AI, and your thinking
The most valuable AI prompting skill right now has been around longer than the internet, smartphones, and AI combined.
This week we’re also taking a field trip to a company running itself democratically, learning how to lead through a crisis from someone who’s been in plenty of them, and taking a long look back at history to remember that humans are remarkably good at getting through hard times. Plus, a little people watching to send you off with a smile.
Cheers,
Kevin
FEATURED MUSING
The skill that separates great AI users from average ones is the same skill that separates great leaders from average ones. It has nothing to do with technology.
I had an idea the other day I wanted to develop, and I went to Claude and said, essentially, “I think there’s something here. Help me figure out what it is.”
But I didn’t just give it a task. I gave it a context. I shared my why—what I was trying to accomplish. I shared my uncertainty that I wasn’t sure exactly where it would land. And I asked it to help me get there rather than just telling it what to produce.
We had a genuinely good conversation. It pushed back. It asked clarifying questions. It helped me find the sharpest version of the idea. The output was better than anything I would have gotten if I had just said “write me a post about…”
What struck me afterward was that what I did with AI wasn’t a prompting technique. It was a leadership technique.
MIT researchers recently confirmed what a lot of us are discovering the hard way—that half the performance gap between AI users has nothing to do with the model. It comes from how users communicate with it. The people getting the best results weren’t better technologists. They were better communicators.
It turns out a psychologist named Robert Rosenthal documented the exact same dynamic sixty years ago.
In 1965, Rosenthal ran an experiment at a California elementary school. He gave students a fictitious IQ test and told teachers that certain, randomly selected students had scored exceptionally high and were poised to bloom academically.
A year later, the “bloomers” significantly outperformed their peers.
Nothing about the students had changed. What changed was how their teachers engaged with them. They gave those students more specific feedback. They were more patient with their mistakes. They communicated higher expectations, and the students rose to meet them.
Rosenthal’s conclusion reached well beyond the classroom. The same factors, he said, operate with bosses and employees, with therapists and clients, with parents and children. (And now, humans and AI.) The more clearly and warmly you communicate your expectations, the better the person receiving them will perform.
Same basic finding, sixty years apart. One with humans. One with AI.
We invest heavily in capability — we hire talented people, we adopt powerful AI — and then we underinvest in the communication that unlocks it. And when we don’t get what we wanted, we look outward. We blame the hire. We blame the model. When the bottleneck was almost always the same place.
It’s us.
It’s the clarity we didn’t invest in. The why we assumed was obvious. The expected outcome we never actually defined.
The Fix:
So what does better look like?
Three things, whether you’re directing a person or prompting an AI:
Start with why. Context is the difference between a capable collaborator and a confused one. Tell them what you’re trying to accomplish and why it matters.
Define done. Vague requests produce vague results. The clearer your picture of the destination, the better the path your collaborator will find to get there.
Invite, don’t just instruct. The best output often comes when you share what you’re uncertain about and let the other party contribute to shaping the answer.
The skill is the same. The discipline is the same. And the return—whether from your team or your AI—depends entirely on how much clarity you’re willing to invest upfront.
ORGANIZATIONAL CULTURE
What Happens When the Founder Has to Win Over the Room
My friend Shilo Jones has always been an innovator, and his latest experiment might be his most ambitious: running his company democratically. Not as a feel-good exercise, but as a genuine governance model where employees vote on strategic direction, capital allocation, and company policy. What really struck me was how familiar the requirements sounded. To earn a real vote, leaders have to communicate clearly, build genuine buy-in, define decisions well, and close the loop. Every element Shilo describes as necessary to make democracy work is an essential element of great execution. The vote is just the forcing function that makes cutting corners impossible. If you want your idea to win, you have to do the work of the Six Cs System. Turns out, democracy and great strategy have more in common than you’d think.
DECISION-MAKING
Commit First. Perform Better. Every Time.
Crises happen. How we lead through them makes all the difference. In this candid and practical piece, Dan Mcginn draws on 40 years of crisis management experience—and a recent personal health scare—to share what actually works when everything feels uncertain. His advice covers finding wisdom over smarts, avoiding advisors who predict outcomes, and never losing sight of the objective. But the insight that hit hardest for me is the simplest: just decide. The paralysis of indecision delays the path forward. Once you commit to a course anxiety declines, clarity sharpens, and performance improves. The decision doesn’t have to be perfect. It just has to be made.
QUOTE OF THE WEEK
“The quality of your expectations determines the quality of your action.”
— often attributed to French industrialist and social philosopher Jean-Baptiste André Godin
INTERESTING
A Century of Chaos, and They Survived It Too
We’re living through a lot of chaos and turmoil right now, and it’s easy to feel like this moment is uniquely overwhelming. This Instagram post offers a healthy dose of perspective by walking through the life of someone born in 1900: two World Wars, the Spanish Flu, the Great Depression, the Korean War, the Cuban Missile Crisis, and Vietnam, all before their 75th birthday. Not to minimize what we’re facing today, but as a reminder that humans have navigated extraordinary disruption before and come out the other side. In the history of the world, there has never been a storm that lasted forever. Perspective is a powerful thing.
😀 AND NOW… YOUR MOMENT OF HAPPINESS. 😀
Just doing a bit of people watching.
My book, The Strategy Trap: Why Companies Fail at Execution and How to Get It Right, is now available!
If you’ve ever struggled to turn team agreement into consistent action, the book goes deep on how to fix that — with practical tools, real-world stories, and a framework for turning strategy into results.
I love the parallel between prompting AI and directing people!
Context, a clear definition of done and genuine invitation to push back produce better output whether the collaborator is human or not.
The uncomfortable corollary is that most managers who complain about poor output from their team are describing their own communication, not their team’s capability.
AI just makes the feedback loop faster, so the gap becomes harder to ignore.