Dropping various objects off of buildings as high as the sky is tall just might be the very definition of stupid. But it's so much fun, too. Ever witnessed a melon explode into a million pieces, dropped onto the concrete sidewalk from a balcony several stories above ground? The sound is spectacular. Unique even. Like Johnny Cash's singing. Or Prince Charles' ears. But the mushroom cloud of red and green watermelon bits -- interspersed by speckled black seeds -- that creates a radial symmetry of organic beauty is something only Van Gogh or Picasso could dream up. It's perhaps the first real example of sidewalk art. letterman_oprahDavid Letterman taught me that. I know, most of you might think it's an immature, disrespectful and utterly foolish act to drop items off of a roof or balcony, solely for entertainment purposes.

And you're probably right. In hindsight, it is rather dumb.

And that's how many of you will remember David Letterman. He was Late Night's buffoon. He was "that guy" who used to drop buckets of paint, oversized rocks or televisions off various New York building roofs to see what might happen. He adorned a velcro suit, hurled himself onto a wall to see if he might stick. He terrorized patrons at fast food restaurant drive-thrus just to make fun of their orders. You thought he was obnoxious. "What an idiot," you may have muttered when hearing of his antics. You vouched never to watch him again. He was "that guy" who might otherwise have been coined a curmudgeon. Cantankerous, perhaps. You had heard of the way he interacted and interviewed some of his guests. "Why is he so mad," you asked a friend. Dave had an edge, for certain. In fact, it was his sharp, intense and at times pointed questioning and conversations that also sent you fleeing for the remote control. Just ask Paris Hilton. "I like the other guy," you exclaimed to your spouse. "You know, the friendlier one with the big chin." He was "that guy" who rather famously -- or should it be infamously -- started off the 1995 Oscars telecast with the Oprah-Uma joke. I found it hilarious, but they didn't. But "that guy" -- in his final week as a late night television host -- deserves more than your scorn and scrapheap castoff. I'm here to say "Thank You, David Letterman." I'm here to illustrate that there are leadership lessons to learn from television's last remaining true broadcaster. More importantly perhaps, I want you (David Letterman) to know how much I've personally learned from you over the many years of watching your late night zaniness. 1. Self-Deprecation Over the course of 6,028 shows and interviews with some 19,932 guests, you never once made it about "David Letterman." In fact, the most enduring and endearing characteristic was an unending swarm of self-deprecation. Whether for the show itself, or your own self-described foibles and idiosyncrasies, the predominant portion of guests were put at ease by your goof-ball, aw shucks, I'm an idiot demeanor. This sort of behaviour puts people at ease. I've learned to use a self-deprecating style in many of my interactions, most notably as a leader of people. 2. Honesty There's a certain element to being a late night television talk show host where honesty is expected. It's not as though you could have lied about attending the Department of Radio and Television at Ball State University. But when you opened up to a live audience (and millions of viewers on television) about extortion attempts and acts of infidelity, well...that's about as honest as things can get. In the same vein, you never faked your way through an interview or comedy bit. If the guest wasn't the sharpest knife in the drawer -- hello Justin Bieber -- you wouldn't mince words, nor play down to their lack of intelligence. You were honest, you remained you, and that's how I learned to remain comfortable in my own skin. 3. Public Love Although I'm 25 years younger than you, we had our first child at the same time. You're a late night television talk show host. I'm not. But that didn't stop you from demonstrating how proud you were -- how much love you had developed -- when your son, Harry, was born. Subsequently, Harry's name, pictures and even appearances on the show surfaced over the years. It was PDAs (public displays of affection) non-stop. The best? Publicly quizzing your guests on parenthood tips, so you could become a better parent. (At least that's how you masked the questions.) The public affection you showed for your precious mother was also infectious. As a result, I've learned not to be afraid to say in public, "I love my kids and wife and family." 4. Involving Others I feel as though you might have been a part of the "math club" or some other high school team that often (and inappropriately) gets made fun of during the teenage years. Your penchant for involving others -- particularly the regular people of society -- was first-class. Stagehands like Biff, Pat, Kenny, Tony and Harold always had a role to play on your shows. In the neighbouring community, you'd involve "normal" citizens like Rupert, Mujibur or Sirajul as part of the show. I learned that community is important, and much like in sports it's the crest on the front not the name on the back that we all play for. 5. Sincerity You ran a comedy show. That didn't stop you from being sincere. You presented flowers for Julie Roberts and other guests. You showed deep concern for peace when discussing political and worldly issues with former or current presidents and elected officials. After 9/11 -- arguably your sincerest shows ever -- you were the capstone of emotional unity. When you returned from quintuple bypass heart surgery, you invited the doctors and nurses that both saved your life, and took care of your recovery. You taught me to never forget those that assist you in life. I'm 43 years old, and am blessed to have "married up," now co-parenting a 12, 10 and 8 year old. I met you -- David Letterman -- well before I ever met my infinitely better half. I've known you for more than half of my life, and through this one-sided relationship, I've learned to laugh, love, loathe, lead and live. We'll never meet. But I wanted you to know that although I was only one of the millions of people who learned from your zaniness and your love of life, it has meant a great deal to many of us. Thank you, David Letterman. Your only leadership mistake? You really should have dropped Howard Stern off of those buildings instead of the melons. In fact, you picked the wrong melon.  


Find out if you’re currently blooming, budding, stunted or in need of renewal through the Work-Life Bloom Personal Assessment.



  • Dan is a conference organizer’s ideal speaker. Not only did he inspire and energize our group, but he also masterfully adapted his content so it resonated with the audience and our conference theme. As a bonus, Dan is able to nimbly navigate to adjust to a reduced time slot when other speakers went over time without sacrificing the impact of his session.

    Director and General Counsel
  • Dan accomplished what we set out to do, which was not only to be inspirational, but also to leave everyone with tools and food for thought / self-reflection to improve their personal and professional lives.

    Hermann Handa, FCT
  • Dan challenged us to have clarity of purpose, both as individuals and as an organization. He related inspiring stories drawing on his experience in business, technology and academia. As he said, ‘There is no ownership without belonging.’

    Christian Pantel, D2L
  • Dan Pontefract suggests leaders must be transformational and transactional, collaborative and considerate, daring and decisive, inclusive and insistent, playful and formal, harmonious, and humble, encouraging and results-driven. In a word, Flat.

    Robert Morris
    “How to strengthen engagement, empowerment, and execution, then leverage them for a decisive competitive advantage”

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