Welcome to Musings—

A space where I cut through the noise and get to the heart of effective leadership and strategy execution. Here, I share hard-earned insights, practical frameworks, and candid reflections to help you navigate the complexities of leading teams and driving change.

Each post is designed to be a quick, impactful read—something you can digest between meetings and apply immediately. Whether you're refining your leadership approach, tackling execution challenges, or seeking to foster a more cohesive team, you'll find valuable takeaways here.

Dive in, reflect, and let's grow together.

Strategy, Execution, Leadership, Culture Kevin Ertell Strategy, Execution, Leadership, Culture Kevin Ertell

Fear Is the Default. Safety Has to Be Built.

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.

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Leadership, Decision-making, Guidelines Kevin Ertell Leadership, Decision-making, Guidelines Kevin Ertell

The Decisions You'll Never See

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.

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Strategy, Execution, Culture, Leadership Kevin Ertell Strategy, Execution, Culture, Leadership Kevin Ertell

The Behaviors You Tolerate

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.

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Strategy, Execution, Communication, Leadership, AI Kevin Ertell Strategy, Execution, Communication, Leadership, AI Kevin Ertell

It Wasn’t a Prompting Technique

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.

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The Interpretation Tax

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.

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The Most Dangerous Phase in Strategy Meetings is “Sounds Good”

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.

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The Illusion of Alignment

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.

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Delegate the How

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.

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Leadership, Culture, Communication, Execution Kevin Ertell Leadership, Culture, Communication, Execution Kevin Ertell

Why Great Teams Win One Play at a Time

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:

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Leadership, Innovation Kevin Ertell Leadership, Innovation Kevin Ertell

Celebrate Failure? Hard Pass.

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.

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Leadership, Strategy, Communication, Execution Kevin Ertell Leadership, Strategy, Communication, Execution Kevin Ertell

The Dress Test for Leadership: Why Vague Strategies Split Teams

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.

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Leadership Kevin Ertell Leadership Kevin Ertell

Why the Best Leaders Start in the Back Row

Steve Jobs. Serena Williams. Yo-Yo Ma.

Different fields, same formula: they all became legends by first being obsessive followers of their craft.

The best leaders I’ve met all started as world-class followers.

"He who cannot be a good follower cannot be a good leader"- Aristotle

Think about it. Great authors read obsessively. Great musicians are fans of other great artists. Great athletes are students of the game, watching tape like it’s their job, because it is. Observing is how mastery begins.

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Leadership, Execution, Strategy, Prioritization Kevin Ertell Leadership, Execution, Strategy, Prioritization Kevin Ertell

The Lie of ‘Priorities’: Why Focus Is a Singular Discipline

Did you know the word priority was only ever used in the singular form for hundreds of years?

It entered the English language in the 1400s and meant the very first thing—the one item that came before all others. And for the next 500 years, that’s how it stayed. Singular. Clear. Undeniable.

Then somewhere in the 20th century, we started saying “priorities.” Plural.

As if by declaring five things “most important,” we could bend time and energy to our will. It’s like claiming there were multiple winners in a race. Everyone gets a trophy, right? But that’s not how performance works. Not in competition. Not in strategy. Real focus doesn’t allow for handing out participation ribbons. It means hard choices. It declares a winner. It says: this comes first.

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Leadership Kevin Ertell Leadership Kevin Ertell

The Leadership Secret Hidden in Plain Sight

It’s tempting to think of “your team” as the people who report to you. That’s where your expertise is. That’s where you feel most accountable. And that’s where the outcomes often show up on paper.

But here’s the shift that separates great managers from great leaders:

Your peer leadership team is your first team. Your function is your second.

This mindset isn’t just for the C-suite. It applies to every level of management. If you lead people, your peer group is your primary team. And the sooner you embrace that, the more your strategy, execution, and trust across the business will improve.

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Problem solving, Communication, Leadership Kevin Ertell Problem solving, Communication, Leadership Kevin Ertell

“What Do You Think?” Might Be the Most Dangerous Question You Can Ask

In theory, “What do you think?” is an open-minded, inclusive, and collaborative question.

In practice, it can be a total disaster.

Over the past few weeks, I’ve been in a handful of meetings where that question completely derailed the conversation. In each case, an idea was shared without any explanation of what problem it was solving or what objective it was trying to achieve.

The responses started rolling in.

They were enthusiastic. They were critical. They were long-winded.

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Communication, Leadership Kevin Ertell Communication, Leadership Kevin Ertell

The Meeting Disease: Why Hacks Fail and Clarity Prevails

We love to hate meetings.

Too many, too long, too little value. It’s the most universal workplace complaint out there. And it’s gotten so bad that “let’s not have another meeting” has practically become a badge of honor. In response, leaders and experts have doubled down on meeting hacks—timers, agendas, “no meeting Wednesdays,” or fancy door signs that declare, “This meeting could’ve been an email.”

But those are band-aids. They treat the symptoms, not the disease.

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