On Not Knowing

On Not Knowing
April 9, 2019 Summit Coffee
In Blog, Fashion

There’s some perception in leadership, rooted probably in hubris or entitlement or, perhaps just inexperience, that the more you accomplish the more you also need to know. That somehow promotions and new jobs, raises and bonuses, are equal to a spike in intelligence, or knowhow, and that as you head down this path there also is less room to throw your hands in the air and say, “I don’t know!”

If you’re familiar asking a boss or a mentor or a parent for an answer, and all of a sudden you’re the boss or mentor or parent, it’s as if you have to make this parallel shift from question asker to question answerer. Yet, this approach is all wrong. Chances are, you got a promotion or a new job, a raise or a bonus, because you asked great questions. Questions lead to answers, and in the working world we’re constantly looking for the best of those.

It’s a bit chicken-or-the-egg, on how to attack this troubling perception. Because this increase in title or prominence (note: NOT importance) also gives the impression to friends, customers, observers, that you know more than you did, say, 20 minutes ago before your promotion or new job, a raise or a bonus. So not only are you no longer the question asker, you’re suddenly more of an expert with more answers and more intelligence and more clue what the heck is going on.

But chances are, you don’t know anything more. It’s not like becoming a boss or mentor or parent unlocks a secret box of answers. Frankly, when you open that secret box all that’s in there are more questions than before, more responsibility, more expectation. It’s part privilege, part opportunity, part increase in anxiety.

I’m a bit of an odd case, since I am a self-appointed CEO. Turns out, if you own the company no one can argue with what title you grant yourself. But as I have said in previous entries, it’s lonely sometimes at the top. And never does that feel more true than when you’re expected to know answers, lead others, be infallible when sometimes you really want to throw your hands in the air and say, “I don’t know!”

Through 8+ years running Summit, and 3 years this week as its majority owner and CEO, I’ve learned two key things I want to share on this topic:

1) It’s ok not to know. 

2) It’s ok to remain the question asker.

Respect and admiration and loyalty and trust, from friends or coworkers or observers, don’t come from knowing the answers. That’s what Wikipedia is for. No, respect and admiration and loyalty and trust come from humility. The author Ralph Waldo Emerson wrote, “A great man is always willing to be little.”

I am a young (though heading in the wrong direction, again, this week) leader who doesn’t always know. I don’t know how to market a pop-up cafe in Boston this weekend. I don’t know how to sell the #1 coffee in El Salvador that we bought last week. I don’t know how to negotiate a distribution contract for our new cold brew cans coming out this month. There’s so much I don’t know!

I have an advisory team of people all younger than me, and guess what guys, you also don’t always know. When I handed the financial reins to Andrew 3 years ago this week and asked him to rebuild our financial system, he didn’t know how to do it! When I asked Tyler to design the Outpost in 2013, she’d never designed a cafe before! When I asked Courtney to host truly remarkable beer dinners, she didn’t know where to turn. When I asked Evan to roast coffee, he’d never touched a machine before.

To the staff that looks up to us, for answers and guidance and solutions: we don’t always know! Guess what? You don’t either. And how cool is that?

If you take away only one thing from this blog, let it be the beauty of not knowing. In not knowing, there exists opportunity to learn, opportunity to showcase humility and vulnerability, opportunity to find new answers, not just regurgitate existing ones.

I implore you, today, reading this: think of something you don’t know but really feel like you should. Now tell that to someone. It could be the person next to you, the person you’re texting, your coworker or partner or friend. Or in my case, a squirmy three-year-old son who’s 5 hours into this 10-hour flight from Rome back home.

If you go so far as to ask for help, good for you. If you just blurt it out and aren’t looking for a response, that’s good too. Let’s all start throwing our hands in the air and saying, “I don’t know!” Then we’re all on the same page, one that replaces hubris with humility. And that’s a better place to start.

Comments (2)

  1. Joey Schnople 2 weeks ago

    Great thoughts, and great honesty. It’s hard to keep asking questions when you feel like it makes you vulnerable.

    Patty McCord, one of the Netflix founders, has a really good book called “Powerful” – it addresses, among other things, how to create a culture around openness and questioning.

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