Celebrating Milestones Doesn’t Kill Your Ambition. I Realized This Too Late To Enjoy Many Of Them.

One of My Liabilities as a Leader Was Not Acknowledging the Wins Along The Way

“I don’t want praise, I want to know what I could have done better.” For years this was my default response to even the smallest of positive feedback. Forget the PROS, I just want the CONS.

There were a variety of reasons for this posture: a strong conviction in the value of lessons learned, a desire to learn from those I respected. But if you really pushed on it, there were layers of fear and insecurity on the other side of the self-confidence cookie. The things which didn’t doom me this time might catch me next go round, so let’s get on top of them. And an intense concern about complacency, as if any satisfaction in my work (or my life?) would cause me to stop seeking excellence, remove the chip on my shoulder, dull the edge, or whatever your metaphor of choice.

I’d heard the sayings, in print, from colleagues. In this world raised nails get pounded down. Compliments are arrows from the mediocre, meant to reduce your ambition. And with a 20something/30something’s amount of testosterone, I didn’t want to be pounded down. Didn’t want to be mediocre.

When I think about my career during those years there’s always a recognition that perhaps hearing some praise wouldn’t have killed me. These days I’m able to smile more and try to bring the ‘how lucky are we to be doing this work’ mentality to those around me. So present day Hunter is better.

That doesn’t make up for the way I treated my teams and colleagues though. I was the quintessential “don’t stop and smell the roses, do you know how much more there is to do until we win? Be happy then!” manager. Urging people forward towards a set of goalposts that would never get any closer.

Sounds like a recipe for burnout, feeling under-appreciated, and like I’d never be satisfied, right? Well, I’m sure some people experienced me that way and for that I’m sorry. I like to think the care for them came through in other ways but in hindsight, there was a level I never reached in terms of empathetic leadership.

Colleagues of mine, some in the product org, some outside of it, were much more attuned to these needs, and for that I’m really thankful. They knew when a happy hour, or t-shirt, or ‘send this email out to the team’ was needed and were able to extend our culture in ways I fell short.

So why write this? Because I work with a lot of CEOs where I recognize some of the same traits. They do care about their teams deeply as human beings but work to find their own balance of “let’s celebrate” and “push harder!” And as individuals there’s often the same desire to critique themselves without pausing to take a breath. In my experience it’s not about first time vs repeat entrepreneurs. Men vs women. Old or young. It’s not universal but it’s prevalent. And so I’m just hoping that my own reflections help set some of them at ease with their own struggles.