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Leading with Truth, Debriefing with Purpose, and Holding the Standard

In this week’s Saturday Blueprint, we explore the inner foundations of sustainable leadership—where truth isn’t avoided, accountability isn’t feared, and curiosity becomes a daily practice of connection and growth.

In this week’s Saturday Blueprint, we explore the inner foundations of sustainable leadership—where truth isn’t avoided, accountability isn’t feared, and curiosity becomes a daily practice of connection and growth.

From military precision to locker rooms and boardrooms, the most impactful leaders don’t lead by impulse—they lead by example. They create cultures where people feel safe enough to speak, valued enough to ask “why,” and held to a standard that doesn’t shift with the scoreboard.

These insights remind us: great leadership isn’t just about what we accomplish. It’s about how we show up, how we decide, and how we invite others to grow alongside us.

Join The Daily Coach for, “A Discussion on Leadership with Coach Tom Crean and Michael Lombardi”, on June 9, 2025 at 6pm EDT. Limited to the first 400 registrants, secure your spot now.

On Biggest Takeaway from West Point:

I learned how important the truth was. Everything there was very black and white. If the answer was “Yes,” it was yes. If it was “No,” they didn’t sugarcoat it. I left there to work in a private country club in the mid-1980s, and there was no black and white. Everything was gray, negotiable, and I struggled in that setting.

Now, as a coach, one of the things I tell my players and when I speak to companies, I tell them this, too. You have one obligation: Always let the people you employ know what went into a decision. They don’t have to like it. They don’t have to agree with it. But they deserve to know what went into it.

I find that very black-and-white approach very helpful. This generation wants to know why, and I bristle at that and often want to say, “Because I said so.” But that doesn’t fly anymore. I have to explain why, and the black-and-white style I learned at West Point is how I do it.

On Debriefs and Accountability: 

A debrief is important whether the mission is successful or not. Part of a debrief is we check rank and ego at the door because we want younger, less-experienced people on the team to feel safe and provide feedback to more experienced members. It’s got to be a safe space where people feel they can provide feedback without blame, without shame. The focus is on learning, development and growth.

I think that debrief is a great accountability tool for any team or organization. We have objectives that we want to achieve. How did we do? What did we do well? What didn’t we do so well? And what are we going to do differently?

When we share the lessons, then we create better teammates, better leaders. It’s about creating a culture focused on continuous improvement, one where we can learn from our failures and mistakes along the way. It’s not easy. It does take a leader to set the example, to set that safe space, to admit mistakes themselves. But debriefs are very critical.

On Winning and Culture

I think we assume if a team is winning, they must have a great culture, that nothing must be going wrong. But I’d say bad cultures win all the time. Bad leaders win all the time. They don’t win over the long run, but they can win for a season, just not five, 10 or 20 seasons.

I found a lot of teams that start to win start avoiding accountability. When people are falling short of the standards, (leaders) don’t want to rock the boat or screw anything up. But those little cracks you ignore… can become massive fractures, and we could’ve just dealt with those a month ago when it wasn’t that big of a deal. Now, it’s a major deal.

The standard always has to be the standard, whether you’re winning or losing. We have to live, and practice, and communicate, and lead the way that we’ve committed to, not just base it on a result.

On Coaching and Curiosity: 

The way I define coaching is behavioral. Can you stay curious a little bit longer? Can you rush to action and advice-giving a little bit more slowly?

Curiosity unlocks insight about the situation and yourself. Curiosity helps people feel seen, understood and encouraged. If you lead with curiosity, it’s a more powerful place to lead from most of the time.

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