#27: Improv your way to more sales, with Kelly Leonard
On this episode, Kelly Leonard is going to tell you how to use comedy – and some of the skills comedians use – to become better at what you do and get more sales.
“Improv your way to more sales” is not so much an invitation to hit the road as a stand-up comedian as it is a different take on doing business. When it comes to applying comedy skills to business, Kelly Leonard is helping lead the way. Kelly is executive director of insights and applied improvisation at Second City Works, which is a new offshoot of The Second City theater in Chicago.
Kelly co-wrote the book Yes, And with the CEO of Second City Works, Tom Yorton, to share some of the principles of improvisation and how they can be applied to businesses and relationship-building. Kelly had a nearly 30-year career at the theater as producer, creative director and executive vice president, where he helped develop the programs to teach people all about the magic of comedy.

That’s important, because when you make people laugh, you earn a bit of trust and build bonds.
[powerpress]
SHOW NOTES:
5:10 Kelly talks about how improv can help businesses.
7:00 One of the primary tenets of improv is a “Yes, and” mindset – to keep the dialogue moving and more interesting. That’s also important in a business environment.
8:05 In business, one of the most powerful illustrations of the “Yes, and” mindset is in brainstorming sessions.
12:30 The insurance industry is fairly conservative and full of compliance. As a result, some people think you can’t use humor and improv while also being “compliant” – but that’s not the case.
15:05 Humor is a great way to engage people at a different level – and it lowers their barriers.
18:30 In his book, Kelly talks about some essentials of comedy. Here, he outlines some essentials that could help businesses be funnier.
20:10 It’s been said that fear of failure is the enemy of improv. With that in mind, how can we all learn to “fail well?”
22:25 As for strategies to reduce your fear of failure, Kelly says you literally have to practice.
25:50 Kelly talks about the importance of building an ensemble, not a team.
27:20 Kelly also extends that thinking to the hiring process. As he says, to hire well is to hire different.
28:50 Kelly is quick to point out that listening is a vital skill for improv – and it’s also a muscle you can develop through practice.


#26: Turning no into yes, with Tom Hopkins
#28: Make Insurance Cool Again, with Patrick Bet-David
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