Why leaders need to celebrate their wins

A few weeks ago, I went to another fancy blah blah filled with investors, entrepreneurs, hangers-on, service providers, founders, as well as a really good vintner, who showered us with grapes I have never heard of and cannot afford. But no one says no to something red with alcohol in it.

A pal who I have known for years, who was a big shot at a local, very big tech company, comes up and tells me a story. He is starting a company, and he is surprised at how hard it is. Well, what do you know. The kicker is that for many years, this fellow has been a coach, a mentor, a judge at numerous pitchfests, in other words, he has been giving advice for the past dozen years.

I loved him for his honesty and his candor when he said that actually doing it is a lot different than talking to others about how they should do it. There was a charming humility to his acknowledgement.

Our entrepreneurial ecosystem is bifurcated. There are the founders in the trenches. Then there is the investor class, going to events, claiming to look for these founders, and many are afflicted with “alligator arms” when the question is called.  

For those unfamiliar with that above approbation, alligator arms is an idiom that describes “a person who is cheap, perhaps stingy and doesn’t reach for their wallet.” Often seen at restaurants when the check arrives at the table. Also describes the rara avis species, Venture Capitalist Parsimonious.   

Enough bird-watching, let’s look now at a critical component for effective CEO/executive leadership. When you score, it is important to celebrate the wins, chucklehead.  

You need to stop and blow the horn, ring the bell or give out new polo shirts. Sometimes, in spite of all your actions, things actually begin to go well. Stop the madness and celebrate.  

But the nuance here is to not only call out your team wins, but also your own personal wins.  Lan Nguyen Chaplin, marketing professor at Northwestern, says, “self-celebration is genuinely uncomfortable.” It feels unnatural and even embarrassing.  

You just put out five fires, launched a new product, won a large contract, and you spend less than two minutes in a personal semi-congratulatory mode. Hey, a bit of self-affirmation won’t kill you.  

In fact, Chaplin says that being able to embrace yourself increases creativity and resilience.  (I know you don’t deserve it, it was dumb luck, you only had a minor role in the success and your mother told you to never boast or praise yourself. My custom Armani hairshirt is hanging in the closet.)

Why is it so hard to accept success or approval? My co-founder is a genius, but if I tell him that to his face, he grimaces and explains that there are still 1,238 more things that have to get done before the product will actually be any good.  

This is why a psychotherapist should be on your board of advisers. Chaplin tells executives to navigate “the worthiness gap.” In simple terms, take a break, you earned it, “make your progress visible to yourself.”   

A true story. Recently, our company had a huge moment: The product actually launched, and it worked (within reasonable tolerance). My co-founder had just spent seven months all in, leading a team of 40 to achieve this result. That night I called him. I had only one suggestion. Take a moment and go look in the mirror. Greatness will reflect. He calls me back in a few hours and tells me the mirror broke.

Look, we all know people who are driven and “always on” and under pressure and have never done enough and are chased by internal demons that do not exist. I have faced these mythical demons myself and have spent a lifetime in psychoanalysis learning how to manage.  

I will not play shrink and offer cheap pablum or the obvious platitudes. Do your own work.  But the bottom line, not open to debate: It is critical to your company and to your life to learn to celebrate the wins.  

They are like hors d’oeuvres. When they pass them, you need to take one, even if you’re not hungry. Because you never know, they may not come around again.

Rule No. 808: Tuna tartare on a Parmesan crisp.  

Senturia is a serial entrepreneur who invests in startups. Please email ideas to neil@askturing.ai