Second City and Life Lessons

Improvisation is a key component to living in the real world. The head honchos at The Second City make the case for developing improvisational skills in everyday life to get ahead at work and also to better relate with those around you. We sit down with Kelly Leonard, executive vice president of The Second City, and Second City Works CEO Tom Yorton, to discuss their new book, Yes, And.

Here’s an idea to try. What if instead of responding to a challenging idea by saying “no, but” you instead responded “yes, and”? Saying “yes” to your collaborator’s ideas is one of the core principles of improv at The Second City theater, and it’s the idea behind the new book Yes, And by Kelly Leonard and Tom Yorton. The two have spent years working at The Second City and have seen how the concepts applied onstage can be effective offstage.

Thanks to our sponsors:

View all sponsors

The book discusses the key elements of improv and comedy, the ways in which we can fail constructively, and the value of co-creation. The authors describe Yes, And not as a step-by-step guide down the path of success, but as a way to help people become better collaborators and communicators.

Watch a book trailer and read an excerpt.


The Lansdowne Conference Center in Leesburg, Virginia, is a fine place to hold a business meeting, but located in the D.C. area wine country, with a hotel-style glass-and-brick facade and two championship golf courses, nobody would ever confuse it with a mecca for comedy. Yet every January for the past thirteen years, Lansdowne has rocked with laughter brought on by actors from The Second City who come to Virginia for an unlikely reason: to help about a hundred Major League Baseball rookies adapt to the unusual challenges of life in The Bigs.

These challenges are wide ranging and quite foreign to mere mortals who can’t throw or hit a 95 mph fastball: how to deal effectively with veterans in the clubhouse and the rapacious media hordes, how to manage a newfound fortune when you grew up poor, how to find work-life balance when there is none, and how to navigate the perils of performance-enhancing drugs, aggressive autograph seekers, and the influence of organized crime in sports. Typical stuff for professional athletes, but not the typical fodder of comedy.

But Major League Baseball and the Major League Baseball Players Association know their audience (mostly guys around twenty years old, brimming with swag and testosterone) and because they know them well, they know that lectures and classroom finger wagging aren’t effective ways to teach the vital life skills that will allow the rookies to have long and productive careers on the field. So they made the unlikely choice to bring in Second City talent who, over the course of four days, perform custom-written comedy vignettes based on real-world baseball situations, facilitate productive conversations around those vignettes (with Second City alum and clinical psychologist Dr. Kate Porterfield), teach improv-based communications skills, and in general, win over a tough audience of ballplayers who will be better equipped to protect their careers because of the time they’ve spent with a bunch of comedians and improv instructors.

While our work at this conference is fun and funny, we’re not brought in for mere entertainment. We’re called on to bring serious topics to life through comedy, to get young athletes engaged, and to give them some important communications skills that will help them cope with circumstances few of us could ever truly understand. They do this because what The Second City knows, and what Major League Baseball has learned, is that the individual who is armed with an improvisational tool kit has an instantaneous advantage in dealing with all manner of difficult situations that naturally arise in the course of one’s career. When, for instance, a long-lost third cousin once removed comes calling for a loan to start a deli/vinyl record shop, the young ballplayer will have learned improv skills to both disarm and deflect the advance—the same set of tools we’ll give you to turn around difficult employees and disgruntled customers. Improvisation, at its most basic level, lets you respond more quickly in real time—and when practiced, also allows you to use comic relief to ease a potentially awkward confrontation.

Kelly Leonard

Make ’em laugh. Make ’em think. A winning formula not only for baseball rookies, but for education reformers, cruise line directors, and the millions of other professionals whom Second City has reached over the past three decades by reformulating venerable theatre teaching methods into cutting-edge business training programs for the twenty-first century. We’re not merely offering an improved communication tool, either. We’ve introduced a whole new skill set for invention and innovation that has been proven to unlock the creative forces of individuals and teams and make it easier for them to test those creative ideas and launch them in the marketplace.

The more The Second City works with folks from the business world, the more we have come to understand that despite all the planning, processes, controls, and governance, business is one big act of improvisation. For anyone who has spent time working in or running a business, you know that a great deal of your time and energy go to dealing with the unplanned and the unexpected, with the curve balls and gray zones that typify corporate life.

This book is for you, to help you build the tool kit you’ll need to deal with that challenging reality.


Maybe we’re not brothers from another mother, but our comedy troupe and the businesses we work with have a lot of the same needs and priorities. We both work in teams that have to adapt to change and new information under high pressure and rapidly changing circumstances. Just as businesses must create and innovate (or die), so must we, every night on the stage. We are both ultimately accountable to the audiences we serve. Like our corporate clients, we must find and develop new talent to make sure our business grows and stays vibrant over time. We face silos separating departments that would benefit greatly from a higher degree of interaction and collaboration. When sales goals aren’t being reached or the competition steals away a client or that new product launch lands like a lead balloon, we are just as likely as others to drop our best practices and work out of fear.

The list goes on, to the surprise of many, though probably to none more so than the founders of The Second City. They could have had no idea that their small cabaret theatre catering to University of Chicago intellectuals and a burgeoning countercultural movement would one day take its radical practices into the same institutions it questioned and challenged in the late ’50s and early ’60s.

When The Second City, housed in a converted Chinese laundry, first opened its doors on a snowy December night in 1959, few attendees would have suspected that they were present at the birth of an institution that would serve as the leading source of cutting-edge comic artistry for the next half century. Today, we take for granted that original comic voices have venues for expression across all manner of stage and screen. But to understand how truly radical The Second City was when it launched, we need to understand the cultural and artistic landscape at the time.

Tom Yorton

“My wife will buy anything marked down. Last year she bought an escalator.” Such was the flavor of popular comedy in the late ’50s. Henny Youngman, Jack Benny, George Burns, Lucille Ball, Jackie Gleason—all very funny, even legendary, comedians, but none of them satirists. Their comedy, rooted in the inherent funniness of relationships and family dynamics, was never vulgar or political. By the late ’50s, however, a new breed of comedians appeared on the scene—Lenny Bruce, Mort Sahl, and Dick Gregory, for example—who would become part of the countercultural movement of the 1960s. Playing clubs such as Mister Kelly’s and The Gaslight Club in Chicago, The Hungry i and North Beach Nightclub in San Francisco, and The Bitter End and The Duplex in New York, these new voices of stand-up represented an entirely different kind of comedy. They talked openly about sex, race, and politics, and, in the case of Lenny Bruce, they got thrown in jail for the profane language they used onstage. Prior to this movement, popular comedy was seen mostly as entertainment or diversion—rarely as part of an artistic movement that promoted social and political change.

The founders of The Second City—Paul Sills, Bernie Sahlins, and Howard Alk, all University of Chicago graduates—approached their work on two important fronts. They created a new form for the comic arts: ensemble based and rooted in the improvisational games that Sills’s mother, Viola Spolin, taught as a social worker for a WPA-sponsored program on Chicago’s South Side, designed to help immigrant children assimilate into their new culture. At the same time, in terms of content, these artists used comedy as a way to challenge the status quo.

They combined both to react directly to the Eisenhower era—which they saw as conformist, intellectually bereft, and morally bankrupt—often shocking audiences in the process. The comedy they were creating was rooted in truth, rather than broad parody or exaggeration; the behavior they portrayed onstage was real and recognizable.

Excerpted from YES, AND: How Improvisation Reverses “No, But” Thinking and Improves Creativity and Collaboration Copyright © 2014 by Kelly Leonard and Tom Yorton.  Excerpted by permission of Harper Business, a division of HarperCollins Publishers. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

Thanks to our sponsors:

View all sponsors

Thanks to our sponsors:

View all sponsors