Why Everyone Needs A Dave Kelly In Their Career

There I was, up later than usual, shoving a pierogi in my mouth, and it was one of the best things I ever did for my career.

Everyone asks about finding a mentor: how to approach someone at work, how to pick the right one, how to cold-call or "shoot your shot" for someone you don't know at all but aspire to be like, etc. But no one tells you that sometimes the mentor you need is the one that may just appear, and all you need to do is be smart enough to lean in. Dave Kelly was that mentor to me, and I am beyond thankful that he welcomed my leaning in. Let me explain why and how to keep your eyes peeled for yours.

I said something similar in the article I wrote about why Michael Guth was the best boss I ever had; I have had the privilege of working alongside many super-intelligent, kind-hearted, and exceptionally fascinating people (for all kinds of reasons) over the years. I learned a ton from them, including who I wanted to become and did not want to become. With all due respect and love to everyone I ever called a friend or anyone I learned anything from, Dave Kelly was the mentor I needed.

I have had a pretty rigid routine over the past 10 years, and there were a few reasons I would even contemplate deviating from it, especially during stressful times at work. I remember having a conversation with a guy named Doug (who will get his own article in time about being the best HR partner ever), and he was trying to explain something to me called "Kelly Tours". I remember Doug describing "feeling more alive" as a result of going on one of these "tours" more than the tour itself and what the hell it actually was.

"You're at these places you probably wouldn't go otherwise, eating stuff you wouldn't usually eat, you probably have one more drink than you usually would, and you're out later than you'd like to be, but it just feels terrific, especially for guys like us that keep to a pretty strict routine," Doug told me one day in my office as we were catching up on a handful or work and non-work topics. Doug and I were very similar. Introverts, by nature, obsessive-compulsive with exercising and nutrition, and would be the first ones to leave at a cocktail hour or bow out when others headed out.

Dave Kelly and I were not very similar until I saw that we were.

Dave has known our business since its inception and is one of the main reasons the MVPD advertising industry looks the way it does. This is not only because of how smart he is but also because of the talent he can pull together, the relationships he fosters, and how everyone wins when he is in the mix. Dave is also not an introvert and not obsessive-compulsive like Doug and I were and still are.

In an effort to make the most of living in New York as a super-commuter, Dave started something called "Kelly Tours," which were well-polished walking, eating, and drinking tours with a hyperlocal theme that would find the best and most interesting in New York while also having some history or story within it.

Historic dive bar followed by an impossible to get into hidden speakeasy, followed by a perfectly timed, on-theme dinner, followed by a stop or two more, all within walking distance of each other. That was a "Kelly's Tour". They hit neighborhoods like the East Village, Two Bridges, Carroll Gardens, Inwood, Chelsea, Hoboken, and so on; the list was extensive. Each tour had a 5ish person limit, and the invites were exclusive and evasive.

Somehow, my name got on the list to not only participate but help orchestrate one in my neighborhood of Carroll Gardens, Brooklyn. I hung out with colleagues I had never spent that kind of time with, got to share a part of my world I kept relatively private, and was able to let some of my own personal branding shine through by suggesting the dinner stop and getting us a private tour of my favorite brewery on the planet that just happens to be around the block from me, Other Half Brewing.

At Other Half, Dave tried to buy my wife a potted plant as a kind gesture to the family and a sign of "we are all in this together". The potted plant he had his eye on was not for sale; it just happened to be a plant behind the bar with an Other Half sticker on it. As Dave haggled with the bartender a bit, I Irish exited. It was one of the boldest I had ever pulled off, and I've pulled off a ton of them. I went from mid-conversation a foot away from him to out the door in the time it took him to turn around and say, "There is no way I can't buy that plant from you," in a kind but salesperson style that had both the barkeep and I perplexed.

I thought I would get blackballed from Kelly Tours, but it was quite the opposite. He appreciated my commitment to being my true self and leaned in more as the brilliant, savvy veteran who could teach a person like me a thing or two.

Shortly after my first tour, he was kind enough to set up one just for me, my wife, and her friend, who did everything Doug said it would do. I was out later than I wanted, ate more than I should have, and probably had that one extra sip I didn't need, but I kind of did after being so strict with myself for so long. And there I was, up later than usual, shoving a pierogi in my mouth, and it was one of the best things I ever did for my career.

After that night he helped me think through and survive one of the darkest periods in my career. He helped me wrap my head around that I was not getting the SVP role I so desperately wanted in early 2020. He would always save me a seat at offsites and help me push my boundaries but never push me so hard that I didn't see him as a safe place to go to with anything I needed help with or perspective on.

So, let's call this list "10 of the things Dave Kelly gave me that everyone should keep an eye out for and why everyone needs a Dave Kelly kind of mentor in their career."

1. Someone who works on a completely different side of the business from you probably sees the entire picture and can size you up in a second

2. Someone who can see your strengths, weaknesses, current challenges, and challenges yet to be faced simply because of their tenure and intelligence

3. Someone who you might be lucky enough to sense that they genuinely care about your career and personal life in a unique way that makes it feel genuine and uplifting

4. Someone may teach you things passively, just by observing them, like presentation skills, managing up, and self-awareness

5. Someone who may not be shy to close the door to your workspace and tell you what you need to hear, not what you hoped or wanted to hear

6. Someone who will make sure you have eyes wide open to all current challenges with the business and opportunities at the company without it ever coming across as them trying to push on you all the answers

7. Someone who can get along with anyone, and everyone wants to spend time with them too

8. Someone who can always contextualize what was happening in the industry and why it was happening in simple ways that you could use to help make better decisions on your end too

9. Someone who sees the best in others and inserts positive energy into a conversation or situation without trying to command it

10. Someone who can lead in different ways and might even be able to make people around them feel a bit more alive and connected to what truly matters

If you can find even a few of those things in someone around you and their door is open to you in any way, make the most of it. Everyone should be so lucky to find a Dave Kelly in their career.

Dave and his lovely wife, Marnie, came out to Carroll Gardens just before July 4th and was the first former co-worker I spent time with after leaving that building for the last time on June 20th. It was the perfect view from the other side of the table. His wisdom, friendship, and perspective are why I am where I am now. He was and will always be the mentor I never traditionally sought out but needed most in my career. Not to mention that he helped me live a little more along the way, too.