All My Friends Are Beating Me At Scrabble

I recently went on a girls' trip to Napa that feels like the setup to a bad joke: a sports marketer, a construction project manager, a procurement expert, and an executive search partner get into a minivan…

As a group of word and puzzle people, we all started playing one-on-one games of the New York Times Scrabble-like game, Crossplay. And every single one of my friends is beating me. Every single one of them! Even the one fifteen years younger than me, the one we went there to visit.

I kind of love it, and here’s why.

This group exists because I brought everyone together. Intentionally, not accidentally. I looked at six people from completely different corners of my life and thought, these humans will get each other. They'll travel well, they'll make each other laugh, and give it six months, and they'll be texting without me.

I was right. Seeing who belongs together, who brings out what in whom, that's the thing I'm actually good at. And it turns out it's the same skill that made me good at building teams. I don’t claim to be the smartest person in the room, but I can confidently say I know who belongs on a team and why. 

The best leaders aren't the smartest people in the room either. They're the best at making the room smarter.

When I was a department head at Eataly and later at Dig, I built teams of people who were sharper than me in almost every functional area. Better operators. More creative. Faster with numbers. More technically skilled in the kitchen. And my departments excelled because I hired exceptional people and let them shine. I removed obstacles, I advocated for what they needed, and I got out of the way.

What I was good at was seeing people clearly. Knowing who belonged where, understanding what someone needed to do their best work, and then clearing the path so they could do it.

That’s its own skill set, and I think in leadership it’s a critical one. 

What Being The "Smartest Person In The Room" Can Cost You

Here's what I've noticed about leaders who need to be the smartest person in the room: they build teams that reflect that need. Meaning they hire people who won't outshine them, or they hire people who will and then dull that shine constantly, creating a culture of paranoia and defeat. They answer questions before anyone else can. They say things like "How come I'm the only one who caught this?" which quietly tells the team that the 999 things they did catch don't count. They make decisions alone, because collective input feels like a threat to their authority. Or they allow the team to make a decision and then override it at the last minute. 

And then they wonder why their team isn't more autonomous, more creative, more engaged.

You can't hire people for their strengths and then refuse to let them use them.

One clarification, because someone's probably already thinking it: sometimes you are the most informed person in the room. You've got the years, the reps, the scar tissue. However, the difference is between being smart and needing to be the smartest. Being smart means you bring what you know and stay open to being wrong. Needing to be the smartest means the group can't function unless you're the one who's right. One makes the team better, the other stifles them.

How To Be A Better Team Builder

The leaders I've seen build genuinely great teams share a few habits, and most of them are learnable. Your credibility as a leader comes from creating the conditions where the right answers can surface, not from having all the answers.

Get genuinely curious about what your people know that you don't. Ask questions you don't already know the answer to, and then sit with the answer instead of immediately building on it with your own point. See my post on reflective listening.

A founder I know was frustrated that his bar wasn’t selling enough margaritas. He could have just told the team to ‘push margarita sales,' but instead he asked what was going on, and then got behind the bar and made one himself. It turned out that the recipe had an absurd amount of steps that no one wanted to deal with on a busy night. He worked with the bartender to simplify it, and suddenly the team was happy to sell the thing. 

Redefine your job. Not "makes the calls." More like, it removes the obstacles that keep smart people from doing smart things. If your team keeps hitting the same walls, that's a you-problem, not a them-problem.

Say the words. "I don't know, but I'll find out and get back to you." "I don't know, let's think about it together." These are the kinds of phrases that make it safe for everyone else to say them too. 

Notice who you're not hearing from. In every meeting there's someone who knows something useful and isn't saying it. Your job is to figure out why and fix the conditions (not the person).

At a board meeting recently, a fellow member told me he hates being called on. "If I have something to say, I'll say it." Point taken. Fixing the conditions doesn't mean putting people on the spot. It’s more about learning what's keeping someone from speaking up in the first place, and changing that.

Smart People In Badly Designed Environments

Yves Morieux, a senior partner at BCG, frames it this way: the problem with most organizations isn't that people aren't smart enough. It's that the system doesn't let their intelligence be useful. Smart people in badly designed environments make the same bad decisions as everyone else.

Your job as a leader isn't to be the brightest light in the room. It's to make sure everyone else has room to shine.

The Dumbest One In The Room

The summer before my senior year of high school, I went to the New Jersey Scholars Program. I called my mom on the first day and said, "I'm the dumbest one here."

She probably braced herself because that's not the call a parent wants.

But I was thrilled! Completely thrilled. Because I understood instinctively that being the dumbest one in that room meant I had more to learn than anyone else in it. It felt like an opportunity, not a verdict. Like finding out the pool is deeper than you thought, it’s scary for a second, then exciting.

At the end of the summer, they nominated two people to give the graduation speeches. Me, and the person who was, without question, the smartest one in the room.

I think about that pairing a lot. It turns out there's a job for the sharpest person in the room, and a job for the one who knows how to be in a room full of them. Both got to speak.

If you're watching good people hit the same walls, or you're the one hitting them, that's exactly the kind of problem I can help solve. Let’s talk!

I’d like to dedicate this newsletter to Andrew, Chloe, Danilo, Shanieka, Arya, and Aurora because without good people to lead you’re not a leader at all.