What David Letterman Taught Me About Being a Leader

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I have been an avid fan of David Letterman since the age when I was far too young to be watching late night television. My parent’s irresponsible child-rearing is not to blame…it was my friend’s irresponsible child-rearing. A pioneer of binge watching, his dad would tape Late Show all week for a Saturday afternoon marathon session.

When timed right, we could pass by the TV just in time for the VCR tape to be injected. I may not have understood every joke, but who can’t appreciate a stupid pet or human trick? Now, four-ish decades later, David has more than made me laugh; he’s shown me how to be a better leader. So, in the spirit of Late Show, here are the top ten leadership lessons I’ve gleaned from David Letterman.

#10 Be irreverent. While today’s humor relies heavily on irreverence, David was a trendsetter in the 1980s. His less-than-traditional performances were distinctly different from Johnny Carson and all the other hosts of his time. Like David, don’t be a victim of social taboos. Just because something has always been a certain way doesn’t mean you need to replicate it. Learn and make it your own.

#9 Be silly without being a clown. It was ridiculous that David would throw a thousand ping pong balls off the top of a 10-story building. Wonderfully ridiculous. And yet, with all of these , stunts, David never came across as silly. The ability to display absurdity bolsters how others view you and your leadership. You become more approachable, more relatable, and more influential.

I never knew if the stupider things we did or the more traditional things we did would work. I didn’t know if the stupid stuff would alienate people. I didn’t know if the traditional stuff would be more appealing. And then, when I look back on it now, of course the answer is, you want to do the weird thing.

#8 Share the spotlight. On most shows, the host is the only reoccurring personality. However, in taking another swipe at traditional roles, David had regular on-camera dialogue with his stage manager (Biff Henderson), musical director (Paul Shaffer), announcer (Alan Kalter), a local deli owner (Rupert), and his mother. Including others does not dilute your leadership, it makes you appear more confident and an aggregator of talent. Where’s the untapped potential that is already surrounding you?

#7 Remain in control. Some of my favorite moments on the show were when Chris Elliott or Larry “Bud” Melman would show up. They were unpredictable and could throw most people off track. Thankfully, David is no mere mortal; he was entertained by their interruptions but always in charge of the show. Don’t let the impulsive disturbances deter you from maintaining your stoicism.

#6 Be your own worst critic. A former Late Show segment producer once said that David is “such a perfectionist that everything that is not exactly right is like a knife through his soul… He blames himself for everything, when 95% of the time it’s clearly someone else’s fault.” Moving from good to great cannot be accomplished while you are patting yourself on the back. Continue to strive towards enhanced results and hold those on your team to the same high standards.

Why can’t a person be allowed a moment or two of critical assessment? Just show me somebody who’s happy with a mediocre job, who’s pleased with a lame performance!… Sometimes being unable to deliver the goods in that one moment will affect my mood for an hour after the show.

#5 Don’t be fooled by other people’s hype. Most shows try to get the biggest, most popular celebrities. David may not shy away, but it was not a requirement. When asked about this in a 1984 interview he said,

We don’t necessarily want big names. See, I would guess that to most shows the name ‘Howard Stern’ wouldn’t sound like a big catch as a guest. But we had Howard on last night and he has an attitude, he’s ready to go, he gets audience reaction… So we feel that you do not automatically get a better guest by having a bigger star.

It’s easy to go for the surefire win, but everyone else is trying to do the exact same thing. Be the first to discover the unclaimed gems.

#4 Don’t be fooled by your own hype. With all of his success, David has never appeared arrogant or conceited. In fact, he remains self-effacing.

At some point, all of a sudden, people in show business that I never knew before would say to me on the show, ‘Oh, it’s such an honor to be here.’ And I would think, ‘What are you talking about? It’s just a goddamn TV show.’ And then I realized, this is what happens when you get to be older and you’ve been around for a while, people succumb to this artificial reverence.

A win may bring fans, but don’t confuse their adulation with veneration. The former is appreciation for a job well done, while the latter is a ploy to pump your ego. Like David said, it’s artificial reverence.

#3 Show gratitude. After his 2000 heart attack, David brought his entire surgical team onto the show to thank them. It was a grand gesture that we can all duplicate when recognizing those on our team.

If you do good things for people, it will never stop making you feel good about yourself. – David’s graduation advice to an audience member

#2 Recognize how you are perceived. David has often been accused of coming across as cool detachment. However, that’s not how he sees himself.

Inside, I feel like everything’s firing properly. And then when I look at a videotape, I just think, ‘What the hell is Dave [angry] about?’ When in fact I’m not [angry]. We used to do that with my mom. We’d say, ‘Mom, are you all right?’ Because she’d sit there looking dour. And she’d say [shouting], ‘I’m fine!’ It’s the Golden Rule. I try to be nice to people who are nice to me.

Remain cognizant of the transparency illusion, the misbelief that what you feel and intend is clear to others. If it’s not clear, take action to appear the way you would like to be seen.

#1 Continually seek happiness. If you don’t feel fulfilled, do something about it.

I was too unhappy with myself to stay there. If you’re secure with yourself, then regardless of where you are, you’re happy and you lead a productive life, and have kids and go to Rotary meetings and you have, you know, just a great life. But if you’re insecure like me and millions of other young airheads, you move to Los Angeles and entertain drunks in bars. Or try to.

David has clearly had a tremendous impact on my sense of humor and the way I view the world. He’d say that this is scary. I say that I’m grateful.

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