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03 · Essay

Teaching Leadership: What 120 First-Years Taught Me

On building learning communities and teaching what you're still learning

December 2025  ·  4 min read

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The Course

During my MBA at Chicago Booth, I designed and taught a full-credit leadership course to the entire first-year cohort — 120 students. I wasn't a professor. I was a student who believed leadership shouldn't be taught like a typical course, and convinced the school to let me try something different.

What I Learned

I expected to teach leadership. Instead, 120 first-year MBA students taught me what leadership actually is, by showing me how people learn, change, and grow under pressure. The most important lesson: leadership isn't a set of skills you acquire and then practice. It's a practice you develop by staying in discomfort with integrity. It's not comfortable for leaders, and it's not meant to be comfortable for people learning to lead.

What Worked

The course succeeded not because of the content I designed, but because I created space for people to examine themselves and each other honestly. We made vulnerability the norm. We treated failure as data, not shame. We built trust early so people could take intellectual risks later. That's actually the opposite of how most leadership training works. Most programs try to make leadership feel achievable, aspirational, safe. We made it real — which meant uncomfortable.

Teaching As Learning

Teaching leadership to 120 people forced me to keep learning. I couldn't hide behind credentials or experience. I had to keep asking the same questions my students were asking, keep being honest about uncertainty, keep modeling the behavior I was asking them to practice. That's the most important insight from those 120 conversations: if you want to teach something, you have to stay in the learning process yourself. You can't move past the hard questions. You have to live in them.