It’s Funny

“Comedy depends upon the audience not having any expectations…if you’re up here thinking of the funny thing you’re going to say, you’re not listening. You’re not being present and paying attention to what’s happening in real time in the scene or context that you’re in.” If you read this and thought, This insight is as relevant to the sales world as it is to improvisational comedy, you’re too late. Shawn Westfall’s already made the connection.

After announcing I was going to write a blog about humor in the world of sales and then realizing how woefully underbaked my vision was, I reached out to Shawn, an improv performer and teacher. (Ask me how I know him.)

Shawn is uniquely qualified to have opinions on this topic because, in addition to living in the world of Improv the Art Form, he works in the world of Improv the Corporate Asset. “What I do is I go on-site to organizations (at their invitation) and, using the principles of improv, which you’ve experienced firsthand, I teach them to be more collaborative, more creative, to listen to each other…” It’s true, what he says. I may have taken a class of his, and another, and another. They were creative and intellectually stimulating and let me pretend I was an actor. That is how I know him.

For years, Shawn split his time between performing/teaching comedy and working in advertising and communications. Now, when he walks into a large office building, it’s usually to train other organizations through his consultancy, Westfall Partners.

When companies “conclude that there’s a challenge or issue in their culture, something that needs to be sort of met…they go, ‘Oh, people aren’t having fun,’ or ‘People aren’t communicating clearly,’ or ‘The team isn’t aligned,’ or something like that, and so they call me up and say, ‘What can you do about that?’ And I go, ‘Have I got something for you.’”

Other situations that may conjure Westfall Partners’ presence are the merging of two organizations (and, consequently, their cultures), change management, leadership shifts, and remote-to-in-office transitions. “I’m the guy that has to come in and say, ‘That person you’ve been looking at on a screen for the past couple of years is actually a human being.’”

And this is where things get hyper-relevant to sales.

PLEASE VERIFY THAT YOU ARE NOT A ROBOT

Given the sales world’s emphasis on pre-meeting preparation, I asked Shawn whether prep and the more improvisational goals of a meeting are at odds.

Nope. “I completely get when there’s a high-stakes meeting or when the pitch is high stakes, and there’s a lot of money that could potentially change hands, to feel that pressure naturally.” But acknowledging mistakes doesn’t mean losing your personality to them. Customers “want to know that they’re dealing with a human being and going off script and communicating in such a way that the potential customer…isn’t dealing with an automaton of some sort that just spits out an answer. I think that’s where the connections come. And there are plenty of more sophisticated sales theorists who are a bit more high-minded about it, who can explain that transaction a little better than I can…” I didn’t feel the need to consult with the theorists, because with connections, Shawn had invoked a piece of advice we hear again and again from sales professionals we talk to: be real.

Will Fuentes (founder and managing partner of Maestro Group) used that same word when I talked to him. “Anything that you do that allows people to connect with you at that human level, I’m always going to recommend in sales.” Will has also found it useful to lean on humor during oops moments. When he worked at Best Buy, he said, “I was really bad—like really bad—at using the technology. Really, really bad.” He decided to level with customers and just lean in. “I would be like, ‘Hey, I work here. And I’m gonna try and do this.’” He’d let them watch him fail, “showing them the ineptitude that I have.” Then he would say, “I work here. Imagine your mom coming over, babysitting your kids…” He’d paint a picture of “your mom losing her mind, who’s babysitting your kids, because you can’t put the movie on for them versus a simple button.” Often, it worked.

WELCOME TO THE FAMILY

“Humor is contextual,” said Shawn, “which is why it’s hard to explain inside jokes, which is why ‘you had to be there’ is a catchphrase, and the only way you can be inside a context is to commit to it.”

Will agrees. He talked to me about listening, about being “invited” into other people’s private jokes. “ ‘Oh, Tom’s always late. He’s always grabbing a sandwich; I guarantee you he’s gonna come with a sandwich,’ right? And Tom has a sandwich in the next call. You show up with a sandwich, people are like: ‘Oh, he gets it. He’s one of us.’” All of a sudden, humor becomes another tool to show the folks on the other end of the line that you pay attention to the details of their lives.

One of the things Shawn often says at the beginning of an improv course is: don’t try to be funny. The context begets the humor. The relationship begets the humor. Tom plus his sandwiches plus his coworkers talking about his sandwiches plus you and the sandwich on the next sales-alignment meeting begets the humor. “I don’t know what it takes to be funny outside [he actually kind of does, though?], but I do know that it has a lot to do with listening. I do know it has a lot to do with reading the room quickly. I do know it has a lot to do with being present for other people.”

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