We’re all a product of our lifelong experience. I have 18 years of experience in the advertising and marketing industry. I still consider myself in that field even in my current role as CEO, because so much of what we do here at Second City Works is focused on marketing and storytelling.

Fast Facts

Location Chicago, Illinois
Time at Second City Works 13 years
Previous experiences • Senior Marketing Executive at 3COM and Sears • Vice President in the advertising firms Hal Riney & Partners, Ogilvy & Mather and Grey
Interesting fact Tom is co-author of "Yes, And"...How Improvisation Reverses "No, But" Thinking and Improves Creativity, Communication and Collaboration
Leader you admire Joe Maddon, manager for the Cubs. He's at the top of his game, yet he's an eager learner and a creative thinker.

Questions & Answers

How has your experience shaped you to be the leader you are today?

We’re all a product of our lifelong experience. I have 18 years of experience in the advertising and marketing industry. I still consider myself in that field even in my current role as CEO, because so much of what we do here at Second City Works is focused on marketing and storytelling.

I’ve been lucky to have worked in so many industries, because that breadth of experience helps me connect with the clients we have today. Lastly, I’ve learned that business is an act of improvisation and people with an interest in comedy-improv like me can thrive in today’s economy.

What are you doing now to ensure you’re growing and developing as a leader?

We work with so many different kinds of clients across all different sectors; that helps me grow and develop as a leader. Second, this place is a school; together we’re taking improv classes as a team to help develop our communication skills. Third, I’m a voracious reader. I would suggest everyone be as much of a student of the world as possible.

What do you think is the biggest challenge leaders face today?

A new model of leadership is emerging. Top-down leadership is out of vogue, and collaborative leadership — the kind we mean when we say “follow the follower” at Second City—is on the rise. In a world where teams form and disband quickly, where one day you’re the subject matter expert and the next you’re a learner, a more fluid approach to leadership and ensemble-building can make you more nimble, adaptive and innovative. Leaders who cling to command-and-control models are increasingly frustrated by the fluid nature of decision-making today.

What is one of the toughest lessons that you’ve learned?

We tend to judge ourselves by our intentions, but others judge us by our actions. We all try to be self-aware, but sometimes we fall short. It’s difficult as a boss because your words carry more weight than you think. Sometimes your off-hand comments can really impact the people around you, even when you never intended them to. Because of that, it’s important as a leader to seek feedback, and to check in with those around you to make sure you have a good read on the state of the business and the people you lead.

What type of people do you prefer to work with?

I look for curious people who ask smart questions because it means they’re inquisitive about life, and chances are they’ll be lifelong learners. It’s important that I hire people who are interested in personal growth and will continue to expand their skillset. I’m not interested in someone who thinks they’ve already arrived. I want people who can read a room and who will bring curiosity into a meeting or into the workplace.

I’ve also found that people who know how to ask great questions are usually the best listeners. I’ve really come to value listening. Through my work at Second City, I’ve learned that the best improvisers are supremely good listeners.

What is your advice for finding a mentor?

You need to seek out both a few formal mentors and a lot of informal mentors. Sometimes if you ask someone directly, “Will you be my mentor?” it sounds like a burden, even if it’s well intended. It is important to go into conversations without any strings attached. Be authentic and allow mentorship to happen wherever and however it’s offered.

What advice would you give to aspiring leaders?

Talk to good leaders, and find a way to spend time with them. It is important to study being a leader, as you would study a technical aspect of your job. Don’t assume that you’ll automatically become one; you have to work on it. However, you can move it along a lot quicker if you’re being intentional about it and you establish relationships with people who have been there.

Leadership is humbling because you win and lose at it. You’re great for a while, and then you’re lousy again. You don’t arrive at being a leader; you keep getting better and better as you evolve within your role and as a person.

Interviewed by Renata Sandor and Lindsey Pellegrini.