Improv and the Art of Conversation

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Unlike many everyday conversations with our social contacts, often when engaging in business conversations, we have an agenda. It might be to pitch an idea, get someone’s opinion, or learn something new. As such we have a sense of direction where the conversation may want to go. Some people even plan out the conversation in their head ahead of time.

As the poet Robert Burns famously reflected, things go oft awry. A slightly more modern version is from Field Marshal Helmuth Carl Bernard von Moltke which is summarized as “no plan survives contact with the enemy. (A quote often mis-attributed to Eisenhower, and also famously rephrased by Mike Tyson.) If plans are unpredictable in and of themselves, adding someone else to the mix can often make them more so. What’s a conversationalist to do?

Enter improv comedy. The first rule of improv is “yes, and . . .” Whatever my scene partner says is true, I must accept it as true. This holds no matter how absurd the premise. Of course, absurdity is the point of improv comedy. Also implied is that I must continue the scene with this new reality. If I was thinking we were at a movie theater and my scene partner says we’re in a carwash, I can’t say, “No, you’re wrong we’re in a movie theater.” That kills the scene. I have to accept that we’re in a carwash. If I really needed to get us to a movie theater, I would have to start from us being a car wash and then find a way to organically move us into a movie theater later in the scene.

The same holds true in our conversations. I may want to talk about one topic, or a particular aspect of that topic. You, however, may have a different idea. With close friends and longtime contacts, we can say, “wait, I want to talk about something else;” but with most people, especially less familiar business contacts, we can’t.

It can feel frustrating to talk about something other than what I hoped to get from this conversation (especially if I have limited time with you). What matters is that I must “yes, and . . .” the conversation. I need to accept that the topic or aspect of it you have chosen was chosen by you for a reason. It may be important to you. It may be you misunderstanding what I was hoping to talk about. It may be something you wanted to discuss with me. Whatever the reason, I need to take it as true that you want to talk about it and not simply brush it aside. Doing so dismisses your opinion and kills the conversation the same way it kills the improv scene.

This is where the “and” comes in. I now need to organically move the conversation to where I want it to go. Again, I can’t rush it or I’m dismissing your contributions to the conversation and that will make you want to leave the conversation.

Just like with actual improv comedy, it takes a lot of practice, so don’t give up if this feels challenging at first. You can practice by having a conversation with a friend and then, in your head, pick a new topic, and try to shift to that topic organically, not abruptly. Don’t force it. Don’t tell your friend you’re doing this, or it might not be a true practice session. Over time (months if not years) you’ll get more comfortable creating conversation transition paths in real time.

Most of us at one time or another have kicked ourselves after a conversation, thinking, “why didn’t I get to the question I wanted to talk about.” It’s not always easy (and in extreme cases the other party may not want to talk about it at all). But like many challenging things, it can get easier with practice. We can take a page from improv comedy and learn to guide our conversations to get more out of them.