Finding Business Lessons in the World of Improv

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In his book Funny Business, Bill Connolly explores the connection between business and comedy. With interviews from Boston’s powerhouse standup Gary Gulman to the owners of Boston’s Improv Asylum, Connolly explores how his ten comedic principles, if applied, can better any boardroom or office.

For several years Connolly performed at the Improv Asylum in Boston and worked as a marketing analyst. He couldn’t deny the benefit his professional life received from his comedic one, and it inspired him to research the correlation.The result? His book and a new career.

Connolly currently travels for the ad agency iCrossing teaching improv to all its US employees. I caught up with him while he was on the road, and we talked improv, business, and how the concepts of comedy can change everything.

Tell me about Funny Business. What would you like to see written about it that you haven’t yet?

It has been written about a little bit almost as a novelty in the business world.  What I think is particularly interesting about it is the comedy side because I have not seen that written about. What I’ve learned from my research and from experience is that there are a lot of business people who are also comedians.

It’s not just like, “Hey lets take some basic ideas of comedy and make a business.” There are actually people who are working comics outside of the workplace. They have jobs and careers. I think taking a substantial look from the comedy side of it is interesting.

The comedy side is interesting.

Yeah. Not just how comedy can apply to business, which obviously I think that’s important because I do it all the time and it’s really a great thing, but also how business could apply to comedy. That’s interesting and something that is not widely talked about. You know like taking a professional approach to your comedic career.

Many comedians like to take jabs at improv because when it’s bad it’s really bad and it’s almost rare to find truly great improv. In your book you said improv is worth doing even if you’ll never do it perfectly. What’s your take on the two perspectives – don’t do improv if it’s bad or you should do it for the sake of the experience?  

Well, if you come at it from two sides I would say from a performer angle, always do it. You get a lot out of being bad. There’s this weird dichotomy because I’m very much a learning improviser where I could do a show at the PIT with people who are so much more talented than me and I would rise up to their level, and I’m like, “This is it! I’m a comedian.” And in the same week I’ll do a show in a t-shirt shop for five people and I’m terrible. And I’m like, “What am I doing this isn’t my life right now?” Both of those extremes are useful as a performer.

As a performer I think it’s useful to be bad, like really bad. Improv is unique. In standup you have your jokes you know are going to work with most audiences. Maybe not the whole set but you have your jokes that you know are going to work. In improv you really don’t know what the hell is going to happen.

You might have a really bad show but I think that’s good because it’s constructive and keeps you grounded – makes you realize you’re not perfect and have to keep working. It gets you over that fear of constant failure and as improvisers we get over that fear pretty quickly. If I have a really bad show I’m like, “Wow that sucked” and I just move on.

From the audience perspective, of course, I would not want to say that. To say, “Just keep doing terrible improv and putting it in front of audiences” is ridiculous. Watching bad improv is one of the worst things you can do. It’s so cringeworthy and uncomfortable. It’s not something you should strive for but I don’t think it should stop you from pursuing it.

What benefits have you seen in teaching improv to businesses both personally as well as in clients?

I just got done doing the most substantial teaching thing I’ve done. I was just on a seven-city tour teaching improv to a full service ad agency called iCrossing. I taught all of their U.S. offices, which was an interesting experience.

I’ve done workshops and conferences with other companies but I’ll tell you what I get out of it most is seeing people do it for the first time – getting a laugh for the first time – the look on their face when they realize they just did something they didn’t think they could do is personally gratifying. I love that.

I used to assist and teach at Improv Asylum when I was in NXT there and I would do level one instruction with Jeremy and I would say, “Do this exercise” and these people would be so nervous on day one. Then they would do something and get their first laugh and fear washes away from them. I think it’s really really cool. Personally I love seeing that. Watching people do something they didn’t think they could do.

Feedback I’ve gotten, is that people love that feeling as well. They like getting over that inhibition – the fear of looking stupid and the cure for it is to look stupid. Some of the exercise we do or the scene work we do, people will do it and it won’t be that good but they’re like, “Wow that wasn’t that bad. It wasn’t as bad as I thought it would be.”

Inevitable too, people like personally interacting with their coworkers. One of the things I talk about are those can conversations you have at the work place. You know the, “Hey how was your weekend?” “Great. How was your weekend?” “Great.” “Okay, goodbye.” You know you just talk about the same damn stuff all the time that anytime you can enter into a real personal engagement with someone and say, “Hey we’re going to try improv together” that’s pretty personal. That’s deeper than “How was your weekend.”

People have told me that’s one of the things they love most about it is connecting with their coworkers. To the point to when they’re passing each other in the halls or whatever they have a bit of a connection of something they did together that was out of the ordinary that they wouldn’t otherwise have.

What is your process of training? How far do you take company employees that you’re training?  

Well it’s totally different with actors than it is with business people. There’s a level of depth you’re not going to get into. I’ve developed a workshop where I can do it in one day or a couple days. But I also have it at a two-hour level. Like if someone wants me to do a workshop two hours is the minimum. You can’t get into anything substantial without that much time.

What I typically do in the first half hour or so is a presentation on the basic lessons of comedy. It’s tied to my book. The idea of “yes, and,” “knowing your audience,” “maintain perspective,” I run through all of those things that are intrinsic to improvisers that business people could benefit from understand better. I liken it to business for instance people often say, “In business we only hear ‘no’ all of the time.” In improv we say “yes” and that can have a creative benefit for businesses.

If you’ve read my book you know Mike Burke is a case study, he’s an IBM sales guy, and he likened the angry IT guy to a heckler in the audience. He helps people to deal with negaters. Again, stuff that comedians know that you could benefit from as a businessperson.

Then for another half hour we do Eight Count Shake Out and Logical Word Toss. I make points throughout it. For Eight Count Shake Out I’ll say, “We sit all day. Our sedentary lifestyle is not healthy” and I list research on why you shouldn’t sit at your desk all day and then for Logical Word Toss I’ll talk about how it requires listening. Most people don’t listen to what is being said before them because they are thinking about what they are going to say. I teach little lessons there as everyone warms up and getting them on the same page.

Then for the last hour we do real scene work with our audience. Typically the class size is 15 people or so. I’ll go through some “yes, and” themes like you have to say “yes, and” at the start of every sentence. I’ll do Hitchhiker where three people are in a car and when they pick up a hitchhiker they have to mirror or take on the energy of the hitchhiker who gets in the car. That’s really where I start.

It’s fun because people can mess with each other. You see where someone will be like, “Wow I never knew Deborah could do a British accent.” That’s fun to see. I’ll challenge people too. I side coach a little bit. I’ll say, “Hey that guy got in playing an old Chinese man so you need to also play an old Chinese man” and they’ll be like, “I don’t know how to do that” and I say, “Good try it anyway.” I want to push people as much as I can to be outside their comfort zone. They’ll learn more that way.

Typically we end the session with a brainstorm activity. Now that communication is open some companies will be like, “We want to come up with new ideas for content or new project ideas for clients.”

When did you integrate improv into your career path?  

I was doing comedy for two years. I had my day job and then I would go do standup and eventually the Improv Asylum. I would go at night and then during the day I would be at work. I would hold it separate because that’s kind of the way you think of things. It was probably two years in (I’ve been doing this for about five years) when I was like, “Okay, there’s more to this.”

Comedy is the combination of public speaking and rejection in one. It helps you get over those fears in every day exchanges. From there I threw myself into it. I love comedy and started researching it. I researched people who had done it and turns out I found all these people who I had in my book who were comedians (it wasn’t something I came up with) and that lead to the book. I realized I had underestimated the value of the skills I was getting from comedy.

What’s your goal with the book and your profession?

I get the question of what do you want to do a lot. Like do you want to be a CMO or do you want to be a comedian and which path are you going to choose? I don’t have to choose one. That’s the thing. Personally, I want to do both. Whatever comes to me even if it’s deviation from what I thought I was going to do, I’ll do it.

Comedy is not a zero sum game. Most things aren’t. Business isn’t either and people treat it like the most competitive thing in the world. You can succeed in comedy and I can succeed in comedy as well as in business. It’s not like there’s one piece of pie for both of us. Am I going to succeed because I’m the funniest person on stage? No. Never in my life is that going to happen for me. But will I succeed because I work hard at it and I’m willing to put myself out there? Yeah, that’s where opportunities will come from. In the book I quote Mark Twain, “Twenty years from now you’re going to regret the things you didn’t do over the things you did do” and that can be applied to comedy and business alike.