By Kelly Leonard – Executive Director, Insights and Applied Improvisation
I became producer of The Second City in 1992 and Stephen Colbert was in the first show I produced, Where’s Your God Now, Charlie Brown at The Second City e.t.c. I was 26 years old and I had worked at the theatre as a dishwasher and host who helped seat the room; I worked in the box office and created the Director of Sales position for the theatre. Second City Owner and CEO Andrew Alexander added me as his assistant in 1991 before I became Associate Producer, following in the footsteps of the legendary Bernie Sahlins and Joyce Sloane. I was less than legendary, to be honest. Andrew took a huge chance on me for which I will be forever grateful. Luckily, with his mentor-ship, I was able to learn, fail, succeed, fail some more, succeed again and then I eventually figured out that good bosses never stop learning.I ended up working with Stephen for 3 years at The Second City. Our connection wasn’t just from work, however. Stephen was roommates with my wife, Anne Libera (who also works at Second City), when they were studying theatre at Northwestern University and Anne directed Stephen in his one man show Describing a Circle. All this to say that Stephen had plenty of time to observe me both in and out of Second City.
The difficult conversation is part of any leader’s day to day responsibility. But I wasn’t given a rulebook for how to have the difficult conversation. Early in my career, I can remember the dread when I had to deliver a bad performance review. It was even worse when I had to let someone go. Apparently, Stephen was doing what artists do – observing with intent – because shortly after he left Second City for New York City to film the Comedy Central series Exit 57, I got a call from him asking if I would be upset if he based a character on me for a scene they were shooting for the series. He said the basic premise of the scene was a boss who can’t fire his secretary, so he makes her fire herself.
One thing you learn quickly at The Second City is to not take things personally – especially when the actors are making fun of you. Frankly, it’s their job. We want them to speak truth to power and when you are in charge, you’re one of the powers that they will be speaking truth to.
More importantly, you get to hear truth, even if it happens be uncomfortable truth.
And many, many leaders never get to hear truth.
When the sketch appeared on TV, I was forced to face the fact that I needed to get better at having those difficult conversations. To be completely frank, I never really nailed that part of the job.
Some bosses don’t want to hear truth, so they create barriers to real conversations; they send clear signals that dissenting opinions are not welcome; and they surround themselves with people who are great at saying yes, but there is not an “and” to be found anywhere.
In the training we offer at Second City Works, we contend that getting to truth is vital for leaders that are looking to foster creativity and to inspire engaged employees. But getting to truth requires environments and actions that lead employees to truth.
Improvisational practice puts individuals in the act of dynamic engagement with others; it purposefully creates environments where people cannot operate only in the mode of high status; it rewards brave conversations and punishes us when we skirt around the important stuff.
While I never got the rule book for having difficult conversations when I became a boss, I learned years later that improvisation provided skills building for just that.