Leading Other Leaders
I often tell my students that college is the best time to build skills. Four in particular line up closely with entrepreneurial success and making money: selling, designing, hunting, and building.
Most entrepreneurs are sellers. They sell their product to customers, their idea to investors, their vision to recruits, and their credibility to partners. Great entrepreneurs are almost always great at selling.
Then you have the designers like Steve Jobs. Design is an agent for change. Great designers don’t accept the status quo; they see what could be and pull the rest of us toward it. Design often comes down to taste, which makes it hard to teach.
Next are the hunters like Warren Buffett. He’s made his fortune on just a dozen big investments. Hunters don’t chase every deal. They wait, watch, and strike when the odds are stacked in their favor.
Finally, the builders. Elon Musk. Jeff Bezos. Jensen Huang. Builders fascinate me most. It’s inspiring to see where they start, then watch what they turn those fragile beginnings into. That’s also what I love about teaching.
Being around smart, passionate builders at the earliest stage keeps me energized. One of my students, Jack, runs a YouTube channel called More Than Mise where he interviews chefs. No crew, no editors, just him, and the quality is TV-level. Another student, Cole, is building a platform called Phenom that connects youth sports programs with top creatives for video, photography, and design. And Ava is developing a 3D-printed modular shoe and is already pursuing a patent. Watching them build reminds me why I do this work and pushes me to keep building myself.
Teaching and managing people means I get asked a lot of questions. Most I can answer on the spot. But the best ones force me to stop, think, and write my way through them. A friend recently asked me this:
“I’ve been the general sales manager for a dealership for a year and a half. We’re one of the best in the region, but I’m noticing weaknesses that could hurt us. I’ve earned respect as the leader, but my managers don’t have that same respect from their teams. They don’t always hold staff accountable or lead in ways that inspire people to do the small things. How did you handle this dynamic with your NCOs in the military?”
One of my favorite leadership quotes is from President Eisenhower:
“Leadership is the art of getting someone else to do something you want done because he wants to do it.”
That’s not manipulation. It’s art. And the art gets even harder when you’re leading leaders.
As a new military officer, your first job is leading a platoon. That means working with a Platoon Sergeant and multiple Squad Leaders, all of them seasoned NCOs. They had more leadership experience than I did, but I was still the boss. It’s tough to replicate that kind of pressure early in a career, but it teaches you fast. Here are a few lessons I carried forward:
Do the small things
Everyone’s watching. Culture is built on the behaviors leaders show and tolerate. If you want punctuality, don’t show up late. If you want discipline, don’t cut corners. Hypocrisy kills morale. Credibility comes from consistency.
Include your leaders in decisions
Accountability sticks when leaders help define what they’re accountable for. That’s why offsites matter: time to align on values, priorities, and execution. Dictating works for compliance. Co-creating builds commitment.
Reward and coach
Once values are set, reinforce them constantly. Praise the right behaviors. Confront the wrong ones quickly, before they calcify. Growth requires discomfort, for the person giving feedback and the one receiving it. Avoiding tough conversations builds losing teams. I often say everything you want is on the other side of sacrifice. That sacrifice is usually your comfort.
Model restraint in authority
The temptation to grab the wheel is strong, especially when progress stalls. Resist it. If you keep stepping in, you’ll suffocate initiative. Let your leaders run their lanes, even if they trip. Step in when the mission is at risk, not when your patience is.
Build a chain of trust
Titles can demand obedience, but only trust inspires loyalty. Back your leaders in public, coach them in private. That’s how you create a team that fights with you, not just for you. Influence often matters more than authority, especially in business where you need support from people who don’t report to you. Influence comes from credibility and from showing you’re serving a mission bigger than yourself.
None of this is easy. Leadership never is. Sometimes it means realizing someone on your team isn’t aligned with the culture and having the courage to let them go. Firing is brutal, but sometimes it’s the right move for the organization and for the individual.
What inspires me most are the people willing to try. Whether they’re building companies or building teams, their effort pushes me to be a better leader. Often, leadership isn’t about learning something new. It’s about being reminded of what you already know, and doing it anyway.
When I think back on my students’ projects, or my friend navigating his leadership challenge, I’m reminded that building, whether it’s a startup, a team, or yourself, is never finished. What matters most is the willingness to keep going.
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