I looked back to the other side of the crosswalk I’d just rushed through. The rest of our group was still on the other side. Their faces reflected annoyance, impatience, and disappointment. I knew I had been pushing it to rush across the wide South Chicago intersection, and I thought others would be willing to do the same. I was a college sophomore in an urban immersion experience. In that intersection, I experienced a defining leadership moment.

One of our two guides yelled to me from across the street, “Christin! Lead for the group.”

Lead for the group – go at their pace. Get better at sensing when to push and when to create a safe space. Don’t be selfish. That four-word admonishment still echoes in my mind today.

That month-long immersion experience many years ago was transforming. Not only did I confront cultural and socioeconomic issues I’d never had to face before, I was directly challenged and pushed as a leader.

At Kairos, we’ve always been excited about this kind of inside-out leadership maturation. Recently we heard the term “vertical development” used to describe this process. [ Check out the Center for Creative Leadership’s fantastic white papers (part one and part two) to learn about the differences between vertical development (more expansive and complex thinking approaches) and horizontal development (improved skills and competencies). ]

Three ingredients contributed to my own growth in Chicago:

1.  Learning was connected to a real experience. No theory. No classrooms. A mixed cohort regularly debriefed lessons learned and struggles from days of individual work in the neighborhood.

2.  I was forced to confront perspectives and beliefs that collided with my own and eventually pushed me to think at new levels.

3.  Mentors helped the group members make sense of this wonderful mix of challenging experiences and colliding perspectives. They called us out—sometimes by yelling across Chicago intersections, sometimes in more subtle ways– like 1-on-1 over coffee and donuts. They helped the group wrestle with uncomfortable ideas. They pushed us out of our comfort zone. They connected us to resources. Without this sense-making element, the first two elements would not have been enough to truly create a transformational experience.

I’d love to hear about defining moments in your leadership development.  I’ll bet they didn’t happen in a classroom.



  1. My defining moments have *never* happened in a classroom. As I think about it, every quantum leap in my own leadership has had all three of those ingredients. Sometimes the perspective that collided with mine was welcome and appreciated, and sometimes I initially rejected the otherness of the perspective. But I needed both.

    • Christin (Author)

      Interesting, Chip. Any key lessons that come to mind?

    • Here are 2 moments that helped define me. The first was painful, and the second was mercifully pain-free.

      Lesson 1: Own up to your embarrassing mistakes.
      When I was a young Marine officer, I borrowed another officer’s tank. I broke the bustle rack (think a luggage rack made out of 1-inch rebar steel) and didn’t tell him. I caught hell, and deservedly so. I sacrificed my integrity to save face. Never again (God willing and the crick don’t rise).

      Lesson 2: Never abuse your authority.
      I needed a ride after school when I was in middle school. My dad was thinking about how to solve the problem, and he mentioned asking someone senior to him in his organization if she could give me a ride. I said, “Why not Mary? She lives close to us.” He said, “Mary works for me. I can’t ask her, because she can’t say no.”

  2. Great piece, Christin.

    I’ve learned the most about leadership from being a Husband and Father. The defining moment that comes to mind is the birth of our daughter.

    That moment started a learning process for me to lead selflessly. I like to think I carry that into the workplace well.