There's an old saying that doing the same thing over and over and expecting a different result is the definition of insanity.

Research by Kaplan and Norton found that 90 percent of organizations fail to execute their strategies successfully. Harvard Business Review reports that 67 percent of well-formulated strategies fail due to poor execution. Most leaders have lived those numbers. And yet the approach to execution rarely changes.

The strategy is set. The kickoff went really well. But a few months later, the leader has moved on to the next thing, and the team is left navigating execution largely on their own.

A leader's job doesn't end when the strategy is handed off. It shifts. The planning phase requires strategic thinking. The execution phase requires coaching, which is the active, ongoing work of keeping teams focused, motivated, and moving forward as reality unfolds.

The more something seems to benefit you, the less risky it seems overall. Your brain doesn't evaluate benefit and risk as separate questions, it bundles them together. So when you're genuinely excited about an idea, the risks get diminished in your brain. The reverse is also true. When you're skeptical of something, the benefits get harder to see.

Want never goes away.

The people who actually follow through aren't more disciplined than the rest of us. They just planned for the moment when want would tempt them away from should. Everyone else assumed future-them would handle it. Future-them rarely does.

Every strategy is a essentially a list of shoulds. We should enter this new market. We should fix our customer experience. We should build this capability. And when the plan gets built, it looks completely achievable.

I'm writing this from New Orleans JazzFest. One of my favorite places on earth.

Yesterday, between sets, I just sat. No phone. No podcast. No plan. Just the hum of the crowd thinning out and the distant sound of someone's soundcheck bleeding across the fairgrounds. And somewhere in that quiet, my brain did something it rarely gets to do anymore: it wandered.

Thoughts I hadn't made time for started surfacing. Nothing particularly urgent—just loose, unfinished ideas I'd been carrying around without realizing it. It felt like the mental equivalent of a good stretch.

Picture a leadership meeting that seems to be going well. You’re engaged, laying out the plan, asking questions. The team is nodding. Nobody pushes back. Everyone leaves aligned.

That much agreement is worth examining.

When a room full of capable people stops challenging ideas, stops flagging risks, stops asking hard questions, something is suppressing their instinct to do so. Usually it’s self-protection, not apathy.

Your team made hundreds—maybe thousands—of decisions today without you. What to prioritize when two things are due at once. Whether to push back on a customer or accommodate. Which features to fix first. How much to spend before asking for approval. What "good enough" looks like on a deliverable you'll never see.

You weren't in the room for most of them. You never will be.

That's not a problem…unless those people don't have what they need to decide well.

Michael Basch put it plainly in Customer Culture: "People change, not because managers direct them to change, but because they find themselves in a culture where personal change is in their best interest."

Restaurateur Danny Meyer said something similar, from a different angle: “Culture is the sum of all the wanted behaviors you celebrate, minus the unwanted behaviors you tolerate.”

Two definitions. One conclusion: culture is built—or eroded—through daily behavior.

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 context. I shared my why behind 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.

Silence creates more work than bad decisions.

When leadership communication slows down, people start filling in the blanks. You’ll hear questions like: Is this still a priority? Did something change? Should I move forward, or wait?

Most people don’t want to make the wrong call. So they slow down. They check with others or wait for direction.

I call this the interpretation tax.

Some of the worst strategic decisions happen in the smoothest meetings.

You’ve been in these meetings. Everyone gets along, the conversation is easy, and the discussion feels productive. The meeting ends with nods around the table and a sense of direction.

But agreement isn’t alignment.

The hardest part of communicating anything isn’t deciding what to say. It’s deciding what not to say.

Clear communication is a discipline. It means resisting the urge to add, even when adding feels helpful. It means stripping the message down to the parts that actually guide action and letting the rest go.

Alignment isn’t everyone nodding in agreement. You can’t determine alignment with a yes or no question. Alignment runs too deep for that.

True alignment is when everyone making the same decision when you’re not in the room.

When alignment isn’t real, the cracks show up fast.

Did you know the placebo effect is active in your brain every single day, not just in hospitals or clinical trials? 

Psychologists call it Expectancy Theory, and it shows that the reality we experience is driven by our expectations.

Nice is a trap. Kind is a catalyst.

At first glance, nice and kind sound like synonyms. But when coaching a team through execution, they couldn’t be further apart.

When you’re accountable for the outcome, letting go of the “how” feels risky.

If the team takes a wrong turn or misses a date, you’ll be the one explaining.

Still, trying to own every move will burn you out, disenfranchise your team, and likely leave better solutions undiscovered. Instead, define the destination; they determine the path to get there.

With (American) football season right around the corner, I’ve been revisiting some of my highlights from former 49ers coach Bill Walsh’s excellent book, The Score Takes Care of Itself. It’s packed with leadership insights that reach well beyond the field.

One section in particular stands out, especially for those of us thinking about how to build and lead effective teams. It’s called Establishing Your Standard of Performance, and the rules are pretty darn good:

There’s a mismatch in many organizations that leads to frustration, inefficiency, and that nagging “why can’t we get anything done around here?” feeling.

It’s the disconnect between Authority and Accountability.

In just the past few weeks, I’ve heard the phrase pop up in three separate conversations:

“We need to celebrate failure.”

I understand the intent. It’s about reducing fear and encouraging risk-taking. A noble goal. But I think it’s the wrong message—especially right now.

For many people, fear isn’t some abstract concept that sits quietly in the back of their minds. It’s real. It’s watching a respected colleague get laid off and wondering if your name’s next on the list. In environments like that, “celebrating failure” doesn’t feel like a courageous rallying cry. It feels disconnected. Even reckless.

And let’s be honest, nobody wants to fail.

Do you remember The Dress controversy?

Back in 2015 a washed-out photo of a striped dress split the web: half the planet saw blue-black, the rest swore it was white-gold.

I recently came across an article that explained why so many of us conclusively saw something so different. Scientists found two key drivers: (1) the photo was low quality, forcing our brain’s visual system to “repair” missing data, and (2) people’s repairs depended on the light they were used to. Regular daylight dwellers mentally subtracted bluish light and perceived white-gold; night owls tended to discount yellowish bulbs and landed on blue-black. The real split was experience-driven guesswork by the predictive brain, which constantly fills gaps with prior knowledge to keep perception running smoothly. 

That same shortcut shows up whenever leaders drop a half-lit strategy note.