May 2025: What If Your Best Idea Is the One Holding You Back?
this is newsletter issue #75
A few conversations this month made me pause. Not because of what people were doing, but because of how tightly they were holding onto the frame around it.
This month's selections are all, in one way or another, about stepping outside the usual lens; whether that's how you lead, what you measure, or how you define a good day's work.
The Opposite Test
"Have you thought about doing the opposite of whatever you're doing or considering?"
DHH's team spent two decades without full-time managers, then hired some just to test their assumptions. They went back to the original approach, but the experiment wasn't wasted. It was intellectual insurance. The real insight? We get so comfortable with what works that we forget to question whether it still works.
The science: Thinking, Fast and Slow by Daniel Kahneman
Why Timing Beats Intensity in Leadership
"When leaders expressed positivity during the preseason, team members felt more highly respected and desired to maintain that respect throughout the year."
Research tracking 9,968 consultants found that when you express positivity matters more than how much you express. Leaders who showed genuine enthusiasm early, then delivered tough love at the midpoint, got the best performance. People work harder to maintain respect they've already earned than to gain respect they've never had.
The playbook: Multipliers by Liz Wiseman
The Mourinho Method for Difficult Talent
"You are not going to teach Ronaldo how to take a free kick... You are going to teach them how to play football in that team."
A data science manager's breakthrough with a brilliant but difficult team member came from José Mourinho's approach: you don't teach elite performers their craft, you teach them how to apply their craft within your system. High performers often resist feedback because they interpret it as criticism rather than optimization guidance.
The framework: Radical Candor by Kim Scott
Hard Work Is Energy Management
"Hard work isn't a personality trait. It's energy management. It's not about discipline or hustling or some deep moral virtue, it's about what your system reinforces."
Hiten Shah destroys the myth that you can inspire laziness out of people with the right pep talk. He's seen the same person look lazy on one team and become unstoppable on another. The lesson: You don't fix underperformance with speeches. You fix the system.
The research: Drive by Daniel Pink
Why Your Best People Become Bad Managers
"In a hierarchy, everyone rises to their level of incompetence."
Three forces turn your workplace into a slow-moving disaster: work expands to fill available time, promotions reward skill until people reach roles they can't handle, and bureaucracy exists to waste your time. The Peter Principle particularly stings because your best salesperson becomes a terrible sales manager, and your best engineer becomes a miserable CTO.
The classic: High Output Management by Andy Grove
The Metrics Trap: When Measuring More Delivers Less
"You can't measure the right things unless you understand what you are truly trying to accomplish."
Most companies are optimizing for the wrong things—counting clicks and tracking hours while missing whether any of it actually matters. When Amazon shifted from "ship faster" (output) to "make waiting obsolete" (outcome), everything changed. Your team doesn't need more tasks to check off; they need clarity on what actually moves the needle.
The method: Measure What Matters by John Doerr
The 3-Hour Difference Between Fulfilled and Fried
"Hour by hour, how we spend our time adds up to how we spend our lives—and for many of us, the sum can feel unsatisfying."
MIT researchers discovered that people satisfied with their lives spend just 1.5 more hours daily on high-value activities and 1.5 hours less on low-value ones. Their JAM framework (Joy, Achievement, Meaningfulness) shows that small changes compound massively, and fulfilling time outside work actually makes you better at work.
The practice: Digital Minimalism by Cal Newport
Andy Grove's Survival Lessons
"If we got kicked out and the board brought in a new CEO, what would he do?"
Intel's founder survived Nazi occupation and helped invent Silicon Valley's most enduring management playbook. His sharpest tool? Brutal hypotheticals that cut through personal attachment to the status quo. When Japanese manufacturers threatened Intel, this thought experiment helped him abandon the very business that built the company.
The source: Only the Paranoid Survive by Andy Grove
The Tyranny of Efficiency
"Efficiency without morality is a form of tyranny."
When GM closed the Lordstown plant, it wasn't cruel—a spreadsheet simply showed each car cost more to build there than in Mexico. Our retreat from moral frameworks has left us defenseless against pure optimization. AI is just the endgame: a world streamlined to run without us.
The foundation: The Righteous Mind by Jonathan Haidt
I've been hearing from more of you lately: how you're using these ideas, sharing them, or challenging them in your own teams. That makes this a better conversation. Thank you.
In Case You Missed It
These are the weekly essays I published this month:
You're in the Room: Stop Justifying, Start Leading - Someone wanted you there. You're already here. The energy spent explaining your presence is energy not spent leading.
The Five Dimensions of Strategic Career Choices - Your next move isn't about the job title. It's about alignment across work, people, game, package, and life impact that most professionals overlook.
The Question That Cuts Through Every Explanation - Skip the guesswork about motivations and follow the benefits. Who actually wins when the dust settles?
Whenever You're Ready
Here are ways we can work together:
Facilitation — I can help your team think and work better together—whether in strategy sessions, planning meetings, or team development. Thoughtful facilitation that brings out your collective best thinking.
Leadership Coaching — One-on-one conversations to sharpen your leadership instincts, think strategically about your next steps, and work through challenges with clarity and focus. I'm taking new clients.
If you'd like to discuss how any of these might fit your current situation, reply to this email. I'm always happy to chat.