Where Do You Learn How to Lead?
I’ve been having a quiet debate with myself for a while now: where should we teach leadership skills?
Is it in an academic setting, where there’s room to experiment and take risks but without the real-world context to recognize the consequences?
Or is it in the professional workplace, where the impact is real and often observable but the appetite for risk is understandably lower?
Lately, I’ve found myself leaning toward the former because behaviors we’re seeing in the workplace today didn’t start there, they just show up there.
Bad habits get developed in the classroom, long before anyone gets their first job: The reluctance to speak up. The tendency to overcommit and underdeliver. The disregard for accountability. The hesitancy to disagree. The fear of conflict.
These aren’t workplace problems—they’re human ones that simply go unaddressed for too long. But once they calcify, they’re harder to shift.
This is why organizations such as the Constructive Dialogue Institute advocate for change that starts in the classroom. CDI focuses on higher education as a sort of ground-zero for developing dialogue skill but with an eye towards their infinite durability in the world of work. In their words:
“Employers consistently rank communication, teamwork, and critical thinking among the most important career readiness skills. Increasingly, they also emphasize the ability to navigate disagreement—especially across political, generational, and cultural differences—without disrupting collaboration. Yet many students and early-career professionals enter the workplace without structured experience handling these moments.” (1)
This is why I believe it’s never too early to introduce foundational leadership skills, before the habits harden and while there’s still space to experiment. Academic environments offer something rare in this regard: a relatively safe place to try, to fail, to recalibrate. To say the wrong thing and figure out how to repair it. To step into leadership before anyone is officially “in charge.” To do all this by learning to lead oneself before leading others.
I recently had the opportunity to conduct an experiment with the entire first-year class of graduate students at the Yale School of Architecture. They were at a pivotal moment in their program—working together on a long-standing, immersive project (2) that spans more than an entire semester and asks them to collaborate under pressure in order to produce something real together. In other words: the perfect leadership lab.
But even when programs like these exist, academia can only take things so far. At some point, employers have to pick up the baton because the most significant post-graduate transition - moving from individual contributor to a frontline manager role - is where these skills become non-negotiable. Too often that transition happens without the support that people need.
If you’re in charge of leadership development in your organization, you know that time and budget are real constraints. So, where have you chosen to direct those limited resources? Do your investments address dialogue, collaboration, and critical thinking? AI cannot and will not replace these competencies
In my recent session at Yale I had four hours to work with and a room of 60 semi-skeptical students. Not the ideal conditions, but good enough to run an experiment.
I’ll let you know how I used that time in my next dispatch.
(1) Webinar: From Campus to Career: Building Dialogue Skills for the Workplace
(2) Every year since 1967, graduate students have designed and constructed a building for a community-based client during the Spring-Summer of their first year.