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What Great Comedians Taught Me About Selling

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Sales Takes Guts and Humor

I just got back from a few days in Jamestown, New York. The birthplace of Lucille Ball and home of the National Comedy Center. My wife Linda and I toured the Lucille Ball Desi Arnaz Museum, caught a book signing, watched Jerry Seinfeld live, and walked away with a lot more than souvenirs. I kept seeing the same lessons I teach in sales show up again and again in comedy.

🔷 Guts and Humor

David Sandler used to say, "Sales takes guts and humor." It takes guts to put yourself out there, take risks, hear "no," and keep going. It takes humor to not take yourself too seriously when things don't go exactly as planned.

Comedy works the same way.

Danny Wood standing beside Lucy Ball StatueLucille Ball left Jamestown as a teenager to study acting in New York City. She was told she didn't have what it took to succeed in show business. Fortunately, she didn't listen. Through grit, focus, persistence, and an incredible willingness to keep learning, she became one of the most recognizable entertainers in the world and a groundbreaking businesswoman.

That's not so different from sales. You must be willing to bomb once in a while, learn from it, make adjustments, and get back out there. Professional comedians don't just show up and wing it, although the great ones make it look like they do.

🔷 Preparation Beats Improvisation

At the National Comedy Center, I learned that Joan Rivers kept a card catalog of more than 70,000 jokes, organized by category. She even prepared one-liners to handle hecklers. She was ready for wherever the conversation might go.

That's a Sandler lesson in disguise: don't put all your eggs in one basket.

Ever go into a sales call expecting it to go one way, only to have the buyer take it in a completely different direction?

Preparation gives you the ability to pivot, stay flexible, and respond in the moment without sounding rehearsed. It's why Sandler pre-call planning asks questions like:

  • What is my goal for this conversation?
  • What questions do I need to ask?
  • What might the buyer ask me?
  • How will I respond?

The best salespeople, like the best comedians, make preparation look spontaneous.

Another highlight of the trip was a book signing with Carol Leifer, comedian and writer for Seinfeld and Curb Your Enthusiasm. She shared something that stuck with me. When pitching ideas, she'd rather hear a fast "no" than get a vague, wishy-washy response that leaves her wondering where she stands.

🔷 Go for the No

Which brings me to my favorite Sandlerism from the whole trip: go for the no!

A clear no gives you information. It lets you move forward, adjust, or move on. Sometimes a quick no is far more valuable than a long maybe.

To top off the trip, we got to see Jerry Seinfeld perform. He was amazing. Watching him work reminded me of something I learned years ago studying Bob Pike's Creative Training Techniques: adults are just children in bigger bodies.

We still like to laugh. We still like to have fun. And when people are relaxed and engaged, they learn and retain more.

That's always been part of how I train. If you've attended one of my sessions, you already know we like to have some fun along the way. Just ask my rubber chickens.

If you haven't attended one of my classes, you're always welcome to crash a class.

🔷 Guts. Humor. Preparation. Persistence.

It turns out great comedians and great salespeople have a lot in common!

► Learn more on Pre-Call Planning and download the tool.

Sandler Pre-Call Planner