My favorite way to spend a day? Helping leadership teams transform from a group of individuals into a powerful collective. Rather than teach skills, my job is to create a container for connection. It’s a facilitated experience focused on greasing the system to reduce friction and increase their ability to work together. Individual concerns give way to the larger collective. They begin to see what they can achieve together. They learn to be open, and how to navigate tricky conversations all while deepening their relationships. They recognize their differences and their shared mission. It's a beautiful transformation to watch.
I love that you can’t script this experience. When facilitating, I never know exactly where it will go. There’s always a chance for conflict and awkwardness. People say surprising things, disagree with each other, and get off-topic. There will be a rich conversation and deeper connections, but otherwise it’s different every time. I walk into the experience ready to be in the moment and expect the unexpected. I love it.
Here's the funny thing.
If you told twenty-something me that I'd grow to love facilitating events with groups of leaders I would have responded, "Absolutely not. You have the wrong person."
Back then, I often froze in conversation when it took a turn I wasn't expecting. I worried about getting it wrong, saying something dumb, or looking uninformed. Only hours later would I have a response — too late. I froze in one-on-one conversations and meetings. It was debilitating. I worried it would limit my career. When I shared my concerns with a colleague, he told me an improv class helped him. He suggested I look into it. Living in Chicago at the time, finding improv classes was easy. I picked The Player's Workshop (whose alumni include folks like Bill Murray, Bob Odenkirk, Harold Ramis, and Amy Sedaris).
I took a class. In the first exercise, we had to throw a ball to a person while looking at someone else. Most of us got a ball in the face, teaching us to be in the moment, rather than anticipate. In the next exercise, another participant took the scene in a wild and unpredictable direction. Instead of going with him, I denied his reality resulting in an awkward dynamic. I was (rightfully) scolded for not being a good scene partner. (This improv principle known as "yes, and" fosters cooperation.) I went home feeling uncomfortable but exhilarated. That one class turned into a yearlong improv program culminating in a final live improv performance with my troop.
Improv was a fantastic experience that changed my career trajectory. It freed me up, teaching me how to be in the moment. Instead of striving for perfection, I allowed myself to be flawed, imperfect. The skills I gained are invaluable in my work as a facilitator, coach, and tech leader — a career I never would have dreamed of. My skills allow me to stay present, open, and focused on others and the interactions rather than focusing only on my contribution. In short, improv taught me to be a better partner and team member.
I became obsessed with improv, taking any opportunity to see shows. My favorite was The Harold, a challenging long-form style of improv. Developed by Del Close the co-founder of Improv Olympic in the 1960s, Improv Wiki describes it as: "A collage of scenes inspired by a single suggestion which are interwoven and connected.”
To guide performers, Del Close had 11 rules for the Harold:
You are all supporting actors.
Always check your impulses.
Never enter a scene unless you are needed.
Save your fellow actor, don't worry about the piece.
Your prime responsibility is to support.
Work at the top of your brains at all times.
Never underestimate or condescend to the audience.
No jokes.
Trust. Trust your fellow actors to support you; trust them to come through if you lay something heavy on them; trust yourself.
Avoid judging what is going down except in terms of whether it needs help, what can best follow, or how you can support it imaginatively if your support is called for.
LISTEN.
Principles for leadership teams
When I became a COO, I realized that leadership teams have a lot in common with improv groups. They both work in dynamic, constantly changing environments that require an ability to adapt, to work collaboratively, and that success depends on all parts of the system working well together. In a way, organizational leadership is a kind of performance art — although one with real consequences.
Here’s how I interpret these principles for leadership teams:
Team first, you second. Leave your ego at the door. (#1)
Manage your emotions, especially under pressure. (#2)
Yes, goals are important but we get there faster when we do it together rather than making heroic efforts on our own. (#4)
Focus on supporting rather than advancing your own goals. That’s how we win together. (#5)
Take good care of yourself so you can be your best (#6).
Be mindful in communicating with the team, treat them as partners, and don’t talk down to them. (#7)
Prioritize relationships rather than making yourself the star of the show. (#8)
Trust is the foundation of everything. Bake this into the leadership team straight away. It might take time, but well worth the effort. (#9).
Judging might feel good at the moment but doesn’t lead to better choices or outcomes. Focus on support or improvement. (#10)
Rather than worrying about what you're going to say or do, listen first. Seek to understand, then to be understood (#11).
You might notice that I skipped #3 — Never enter a scene unless you are needed. This was intentional. Be careful with this one. Creating an effective organization requires leaders from across the entity. While more people can add chaos, it also brings a more well-rounded perspective. Creating an inclusive decision-making process also discourages an us vs. them mentality. For those worried about going slower, intentionally designed decision-making structures can counter this.
In other words…
Be in the moment.
Less ego, more interdependence.
Be a good partner (not just a good solo performer).
Remember, we operate in a system — we’re better together.
The guidelines Del Close set out all those years ago to help Harold performers are relevant for senior leaders today. In my experience, teams that recognize and optimize for their interdependence are more cohesive, tend to perform better, and have less strife.
Want to learn more about how a Leadership Archetypes Experience can help your team? Grab a spot on my calendar or read more about it.