Stephen Tobolowsky: “Improvisation works because it’s about the leap and not about the landing.”

tobolowsky-author-photo-credit-jim-britt_vert-e6433ea80411ec55f6815fe07d04f84dcdf58b38-s6-c30Stephen Tobolowsky is one of the leading character actors in film and TV today. USA Today listed Stephen as the 9th most frequently seen actor in movies; he has appeared over 200 movies and television shows. He is best known for playing Ned Ryerson in Groundhog Day, Sammy Jankis in Memento, Werner Brandes in Sneakers, Happy Chapman in Garfield, and Mr. Bates in Freaky Friday.  On television, he played Tor Ekland on Seinfeld, Hugo Jarry on Deadwood, Bob Bishop on Heroes, Sandy Ryerson on Glee and Stu Beggs on Californication.
Stephen is also a writer (of the excellent The Dangerous Animals Club—a series of funny and touching life stories), a popular podcaster and radio talk-show guest, and a longtime acting teacher who specializes in improv. (His website link.)
I interviewed him in 2013 as part of my research for A More Beautiful Question, partly because I’d come across an old quote from him about curiosity. It had to do with the idea that what people think is important is opening the door to get the answer because the answer is on the other side of the door. Stephen said that what he thought really matters is the curiosity that makes you go to that door or keep going through that door.
Stephen had only a hazy memory of that quote, but turned out to have lots of great thoughts about how asking questions helps you get to the truth of any situation and the importance of improv training for real life. I was only able to use a couple of quotes from our interesting conversation in the book, so am happy to present Stephen Tobolowsky’s thoughts at much fuller length here on the AMBQ blog. Let me know what you think, in the comments.
Warren: One of the things I talk about in my book is about how to question things that you wouldn’t ordinarily question, that ability to step back and see things with the beginner’s mind or the idea that you’re seeing it the way you’re not used to seeing it but the way you should see it. Have you found any ways to get better at that kind of seeing?
Stephen: Yes! I’ve been teaching improv for about the last 7 years and I began to notice a trend in all my students. And my students are not actors. Maybe 25% of them are actors. The other 75% come from all walks of life; they’re therapists, lawyers, policemen, landscapers, contractors.
The first day in class, I do something on questions. I have found a universal thread in all my students and that is it takes 3 attacks at a question to get to a real answer. For example: one question I’ll ask someone is: Who is the first person you fell in love with?
The person will be sitting on the stage saying, “Oh, some girl in junior high school.” I’ll say, “Well, what was the girl’s name?” And they’ll say, “Jenny Dobson.” Suddenly their face will flush red and I’ll say, “Well, what was it about Jenny Dobson that really did it for you?” And then they’ll say, “I remember I was sitting in English class and the teacher had scolded me for not bringing my homework. Jenny Dobson was sitting beside me and she gave me a piece of gum. She sent me a piece of gum and then she smiled at me after the teacher yelled at me. From that point on, she walked with me…” Suddenly this torrent comes out.
It’s so different than “some girl in junior high school.” The first answer was correct but it had no real truth in it.

I noticed it takes 3 levels of questions, 3 assaults on the fortress, to get to something really useful and specific as an actor. 

I find I have to do that to myself when I work on a part. If I have the part of a doctor, one question I always try to ask myself as an actor is “am I good at what I do?” Generally I’ll say, “Yeah.” Then I’ll say, “Well, what am I really good at and what am I not so good at as a doctor?”
Then I go to a deeper level of questioning. “Well, I’m good at working with patients but I’m terrible at handling the vials.” Then I go even lower. “Well, what made me want to become a doctor in the first place?” Finally I get down to questions that are reusable as an actor and playable as an actor.
Warren: Have you ever heard of the 5 whys? It’s an idea that comes out of the business world. The Japanese developed a system where, when they found a problem like a defective part or something like that, you were supposed to ask why 5 times in succession. So if you said, “Okay, why is the piece wrong?” “Well, the guy on the assembly line put the wrong thing on this end.” “Why did he put the wrong thing on this end?” Etcetera. They found that if you work backwards with 5 whys you would get to the real source of the problem.
Stephen: I love that. I’ve never heard that but that sounds true. As an actor, what I’m talking about is usually just levels of human existence that are almost like the shelves of electrons around a nucleus. They always tend to go to the shelves of lowest energy and you have to really hit energy into them to move those electrons to a shelf that’s further away from the nucleus. It takes energy continually going into it to keep them out of that far orbit before they shed that energy and come back to the lowest possible energy level they can exist at.
People do the least amount of work – this is true in casting. If you’re a casting director, do you want to call 20 different agencies to get actors or do you want to call 2? Well, they want to call 2 so they end up calling William Morris or CAA, and then that’s the “answer” to the question: Why don’t you get any auditions unless you’re with a huge agency? Because the casting directors don’t want to do the work calling 20 different people.
Warren: What I’m discovering about questioning is that a lot of the reasons we don’t question are based on routine and comfort. Questioning is really about getting out of your routine or looking outside of it. It’s very interesting the natural resistance we have to it.
Stephen: There’s something I’ve talked about in terms of my podcast or my stories and my teaching: Usually you don’t have a lot of time to get an answer. And so you need to find the questions that work most efficiently in getting to the heart of things.

One question which an acting teacher taught me that I have found is the most effective for getting to the heart of the matter the quickest, is, when you read the part, you ask, “What is my greatest hope? What is my greatest fear?”

The answer to those 2 questions creates a tightrope in which every other question hangs off of when you’re acting, when you’re directing, when you’re writing. If you know those 2 things, you can play anything from Romeo to Juliet.
Warren: Do you think those are useful questions in a larger context?
Stephen: It’s absolutely useful for the most important thing in the world—and that is assessing other people you come in contact with. People rarely are able to hide what their greatest hope and what their greatest fear is. I mean, there’s a paraphrase of an Emerson quote that I use all the time because I love it so much which is,“What you are, thunders so loud I cannot hear what you say.” The questions – what is your greatest hope and what is your greatest fear – are what you are. You can’t hide it. It is all over you.
It comes out of the cracks and when you’re dealing with interpersonal relationships, if you’re talking about an employer seeking employees, you may find that you do well to hire someone who’s greatest fear is that they will be looked at as inefficient or ineffective as a worker because it’s primal for them to show that they really do a good job.
Warren: In terms of someone embracing that question, what do you think that can do for an individual? I’m gathering these quotes that really resonate with people for my book. One I came across recently was using the question what would you try if you knew you couldn’t fail. But I want to go back to yours, the greatest hope and the greatest fear.
Stephen: I think a lot of times in our lives we go back to “Why am I fat?” or “I want to lose weight. How do I lose weight?”—those questions. We try to deal with our personalities and our lives on the micro management level but the macro level is adjusted by what is my greatest hope and what is my greatest fear.
If I look at the big picture and say, “What a minute. My greatest fear is not that I’ll fail as a manager or not get a part. My greatest fear is that I will not do my best and that I will let myself down,” suddenly I find my whole attitude towards my work, towards auditioning, towards other people changes.
I find that my attitude towards my work environment changes; that I want to give myself the best opportunity to do the best work I can. I want to prepare for my audition, give myself enough time to prepare for an audition not because I want them to think well of me or to get the part but I want to give myself the opportunity to do my best and not shoot myself in the foot.
Warren: So with a really tough question, it gets back what you were talking about earlier, where you might have to take a number of passes at it before you’re going to come up with an answer.
Stephen: And you have to be specific with an answer. The majority of people answering that question about fear—80% of them might say “My greatest fear is that I’m not enough.” You have to be able to say, “Okay, what the hell does that mean? What could those words mean?” We say a lot of words as answers that we think we know what they mean but we don’t know what they mean. What does it mean to say that I won’t be enough? Enough to myself? Enough to my potential? That I won’t be viewed as enough by other people?
You have to go to that next level of questioning and say, “What the hell am I saying?”
When you eventually get to where you know you squeezed out all the jargon and all the hyperbole like a sponge, then you can go, “I know what the truth is.” 
But I don’t give a damn whether somebody says, “whether I did this is good or not good.” I really don’t. In fact, when they’ve given me bad reviews I go, “To hell with that,” and I move on.

The role of improv in embracing failure and picking up and moving on

Warren: Improv has been identified as something helping people get better at idea generation. People are looking for ways to get better at it and faster at it and more off the wall and out there. Improv seems good for this. Is it?
Stephen: It could be a good idea. It depends how it’s used. Sometimes I find that people use it as a vehicle to try to be clever and they use it to recycle old gags. They try to be clever as opposed to really being in the moment.
I know people sometimes use improv as a tool of discovery in rehearsal. As an actor, they’ll say let’s just pretend we’re at a party and put your character Tom from the Glass Menagerie with the gentleman caller and you’re all at the party and let’s just talk and see what you’re doing.
Sometimes you’re able to develop behavior from that and some real good behaviors come out of that so long as you’re not just trying to be up there and be cute. You’re intention has to be good.
Warren: I guess the aspect of building on things with improv is good, the idea that you build on whatever you started with?
Stephen: In Curb Your Enthusiasm, that show is done completely through improvisation. You are not allowed to rehearse. You’re not allowed to speak while they set up cameras. You go through the scene with Larry David and you’re just allowed to go blah, blah, blah. Then they say, Okay, I want you to have a political argument with Larry David about something – get involved in some political argument with him. They go, “action,” and you do it. Then the director comes running out and says, “That’s good. Let’s keep this and this and this and keep that as part of the argument. Do it again.”
And then you do it again and the things that you’re keeping become a bit of a framework and then you start adding new things. So this is one way they built that show completely on improvisation. When you shoot comedy, like when I’m on Glee or on Californication – Californication in particular – there’s a lot of improvisation that they want to capture by camera. That leads to good things, but the guide for the improvisation always has to be what is your greatest hope and what is your greatest fear so that you’re in character with improvisation.
Warren: What do you think the improvisation does that’s good? Why does it work?
Stephen: I think improvisation works because it’s about the leap and not about the landing.
It says, “It doesn’t matter where you land. You could succeed and fail and that’s not the issue. The issue is that you take the leap.” When you take the leap, it allows instincts to take over. I think it’s the difference between pitching and throwing in baseball where they say somebody is trying to control the ball. It isn’t as effective as when the batter up there and suddenly their instincts take over and their body self corrects in such ways to throw a strike. That’s when the pitcher’s really on.
So I think that’s what improv does; it frees you in that way. It says it’s okay to have instincts and okay to fail. It’s a free place to fail.
Warren: And to really just try stuff.
Stephen: And to experiment. When I work with different improv groups, some of them would have a fail safe in there of, “Well, we know this works. So what we’ll do is we’ll do our improv thing but then when somebody starts doing a tutu with a feather boa we know that it’s coming to an end and we’ll do the big joke that we know will always work.” But that isn’t what I teach.
Warren: You teach improv in terms of auditions and parts. Could you imagine that someone could come to the class and get skills that go beyond auditions?
Stephen: Yes, completely. I’m a big fan of Aristotle. Aristotle believed that there’s this thing called techne, from which we get the word technique, that happens in your brain. There is a burst of pleasure in your brain – I’m restating it in my own words there – when you hear the truth. We have a sense of wholeness or completion. I try to use improv to allow people to have permission to reach things in their lives that are true rather than reach things in their life that are clever.
When you’re doing an audition with producers, when you hit that techne moment where you hit something that’s true, the producers will start laughing. Not that what you said is a joke or funny but because they recognize it’s true and the techne connection that’s made in your brain. I found this to be a really important tool in acting and in storytelling and in improv. If you tell the truth or the truth as far as you know it as opposed to trying to craft or a clever truth, you will make your story more universal and appeal to more people. When you start fudging and trying to make your story clever, the audience sniffs that you’re lying and it kills techne.
Warren: Do you see improv as a way of life? Can a person live their life in an improv way and should they?
Stephen: We all do. The idea that we don’t is a fiction and in the category that you could say is either illusion or delusion. Whether you have your life guided by science, whether you have your life guided by art, whether you have your life guided by religion, these are 3 big filters that different people use to guide their lives. At the bottom line of all 3 of those is the unknown. Whether you’re talking about the uncertainty principle in science – that you can never know anything; that as the closer you get to the truth the more incorrect your findings are.
Of course, religion is based on complete uncertainty and a view of a series of propositions that are improvable. And art is saying that all we really have to understand the world is metaphor and the accuracy or the depth of the art is only how true the metaphor is. It’s blind man’s bluff. So whatever of these things you’re using to guide you’re way through life, you’re in the dark. You are improvising. And anything else you do could be described as artful willfulness. Anything else that you do is what people call, “Well, I’m stuck in my ways,” or “I know what I like and I like what I know.” Whatever else it is, it’s you dealing with your limitations.
Warren: And the teaching of improvisation will have the effect of helping you embrace that uncertainty?
Stephen: It also widens your horizon. I think all of life is like you’re on a frozen lake and you’re trying to get to shore. Usually when people are on a frozen lake they are terrified and they take one little step around them and they move in slow, concentric circles trying to find where the ice is sturdiest.
Improvisation is one of those tools that helps you have ever-widening circles on the frozen lake.
It gives you permission to take a wider stance, a wider circle until you’re able to get to shore. That’s all improv does; it helps you observe more; it helps you trust more; it helps you believe more to where your circles are bigger and bigger than you thought they could be.

From time to time on this blog I post my conversations (edited for length) with interesting thinkers on the topics of questioning and leading a fuller life. Click on “Interview” in the Tags below to see more conversations (with more of them to come).

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About the Author

Innovation expert and questionologist Warren Berger has studied hundreds of the world’s foremost innovators, entrepreneurs, and creative thinkers to learn how they ask questions, generate original ideas, and solve problems. He is the author or co-author of 12 books, including his three books about the power of questioning: BEAUTIFUL QUESTIONS IN THE CLASSROOM: Transforming Classrooms Into Cultures of Curiosity and Inquiry, THE BOOK OF BEAUTIFUL QUESTIONS: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead, and A MORE BEAUTIFUL QUESTION: The Power of Inquiry to Spark Breakthrough Ideas. Warren’s writing appears regularly in Psychology Today, Fast CompanyHarvard Business Review, and The New York Times. He lives in New York. Follow him on Twitter at @GlimmerGuy and subscribe to his blog posts.

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