A Q&A with Kelly Leonard and Tom Yorton

I'm curious to hear about two days for each of you: Your first day of work at The Second City, and the first day you encountered "Yes, And" thinking.

KELLY: October 10, 1988 – I was told to meet a woman named Alison at the front bar of Second City to start my new job – a position I had "earned" when the former owner of Second City, Bernie Sahlins, needed to keep me employed for a few months until I could start working on his newest theatrical venture. Alison took one look at me – sure that I was another spoiled scion of some family with influence – and brought me to the back bar at Second City where I assumed the position of dishwasher. The job itself was terrible. But the fringe benefits were astounding. Each night, after the two act scripted revue, the cast did a free improvisational set. It was during the improv set that I could take a break and watch all manner of invention and brilliance take place on that stage. Various celebrities and alumni would come by to "play." Quite simply, by applying the concept of "Yes, And" these actors made something rather wonderful out of nothing night after night.

TOM:  Jan. 30, 2002—I'd taken a major leap from my marketing career path into a comedy theatre. Big pay cut, big need to make it work. Second City Communications (as we called the group I lead) was in rough shape back then. 9/11 had just happened, my predecessor had been gone for several months, and the business was in the tank. It was just me and a couple staff members from the prior organization. I remember three things about day one: trying to get the heat to work in my beautiful but very vintage office; confusing my new co-workers over lunch with a wild eyed success fantasy vision; locking the offices and shutting off the lights at the end of the day. That simple act...being so tangibly tied to a place...was something I never experienced in big companies, and I knew then that I'd be connected to The Second City in a more profound way than any place I'd worked before.

From an outsider's perspective, it's seems like a no-brainer that improv would be a great tool to help companies with brainstorming and other marketing concerns. How did you first come to realize that it could be used for other aspects of the business world as well?

KELLY: Really, it was our own business successes that provided the realization that our work in improv was essential to driving our own success. We talk in our book about collaboration. Well, we're very, very good at it. Our collaborations with Norwegian Cruise Line, Major League Baseball, Lyric Opera Chicago, Hubbard Street Dance, etc., have all yielded deep and long-term dividends. Innovation and originality are prized commodities. At The Second City, our core competency is developing original content – each year and every year. We do new work. In the theatre world, it's unheard of for commercial theatres to have hit new shows every year for 55 years. But that's what we've done. So, it seemed high time that we explore how we have done this and share the knowledge.

TOM:  I agree with Kelly, but saw it from the perspective of our clients, because I was one. I'd lived in big companies and saw the stiff communication, lack of ensemble play and fun, stultifying attitude toward risk and failure. When I got here and learned that improv actually taught the soft skills you wish you'd learned in B-school, and did it in a fun, cool way, I knew we had to build a business-specific development curriculum. We started small but the market really wanted it, so we've been able to expand to over 400 engagements a year, about half of which are with Fortune 1000 companies.

What is the most surprising business breakthrough you have witnessed in your work with clients?

KELLY: When they re-find their joy. It's simply astounding how many individuals not only don't "love" what they do, but, often, how much they don't "like" what they do. The greatest gift in this work is when a client is able to self-actualize our teaching, apply it directly into their working day, and come out the other end happier. If we accomplished that alone, we've succeeded.

TOM:  We do a lot of presentation storytelling training, and I love watching nervous, fearful execs become powerful and authoritative. We're not prescriptive, meaning we don't preach a "5-step Second City method," because we've found that prescriptive approaches can hurt as much as they help. We are extremely good at helping people find their unique voice and having the confidence to use it when presenting. No fear is greater in business and we get a lot of satisfaction in helping people beat that fear.  

An entire chapter of the book is dedicated to spectacular failures by The Second City team--well done! What kinds of failures have you encountered on the B2B side? Did they change anything about your approach to working with business clients?

KELLY: That list of failures is a tiny excerpt. Every failure can teach you something, it's just that we don't often possess the time or perspective to truly get to the truth of why we failed. We're too bunched up in shame or closing the door on what didn't work so we can get to something new that can work to take stock, analyze, assess and incorporate that failure into our tool kit. Very early in my career at Second City, when I was the Director of Marketing, we dealt with a client that had brought a group to the theatre and had an awful time. She yelled at us six ways to Sunday about how badly they had been treated. We offered her this: let us comp her next group – free drinks, free tickets for as big a group as she wanted – we promised we would make it up to her. She took us up on the offer. She brought a group of 30 to the show; she had a great time; and we had just made a client for life. Something like that teaches you to "use" failure, don't be defeated by it.

TOM:  I head the B2B group, and yes, we've had plenty of screw-ups on my watch. Over my 13 years, our marketing should have been much stronger – we have a great story to tell, but haven't done it nearly well enough. Irony: I'm a career marketing guy. Ugh. On it now.

We've gotten better at staffing, but in earlier days, we were not as disciplined as we needed to be with our hires. We needed to build a better pipeline of qualified people (like we do for our stages) to make sure we weren't scrambling when we had an opening.

In the early days, we were too accommodating to clients...bending over backwards to meet unfair demands. We're still accommodating, within reason. But now, we're not afraid to fire clients who are unreasonable.

KELLY: Great question. One of the genius constructs at The Second City is that we are constantly infused with fresh, new talent out of necessity. At our theatre, we train talent, help hone their comedic skills and POV and then put them on the professional stage to astound audiences, ourselves and – more often than not – themselves. And then...we let them go. We don't try to hang on to the writer/performers we develop. We let them move forward into their careers. So what is the result? We have an alumni list that reads like a who's who of comedy over the last five plus decades – alumni that are more than happy to exclaim the powerful connection to our brand.

And...we've made room for the next generation. We risk that we can do it all over again. That we will find great new comic voices who will thrive within a creative construct that gives them the one two punch of skills and freedom.

TOM:  Nothing to add.  Great answer.