Human Side Up: Shane Snow on why great teams break the rules

Shane Snow knows what it’s like to zig when everyone else zags. The best-selling author of Smartcuts, entrepreneur, and Broadway producer has spent his life exploring what happens when you challenge the rules—and build something better in the process. He joins CLARA CEO Natasha Nuytten on Human Side Up to reflect on childhood side quests, unconventional career choices, and the micro-behaviors that make or break great teams. 

Explorer mode activated 

The word Shane uses to describe himself? Explorer. 

That might not surprise anyone who’s followed his unconventional career. But it wasn’t obvious from the start. “I grew up in Idaho and stayed in one spot for the first 20 years of my life,” he says. “But what I did is I climbed grain silos and warehouses and explored tunnels and got in rafts and floated down canals to see where they went.” 

His mom was a teacher. His dad was an engineer. One taught him to love books. The other taught him to take things apart. “It was embedded in me, this explorer thing.” 

That curiosity has shown up in his adult life, too. “I really like having side missions and side projects and making these goals that aren’t necessarily... silly goals, you could say.” Breakdancing, abandoned subway tunnels, unusual business ventures—they all count. “At the very least [they] make your life interesting to you. And perhaps the most, they allow you to draw from different sources of inspiration.” 

Turning point 

One of Shane’s earliest business wins came with a major parental veto. 

He was a teenager, making serious money online with a greeting card business. “And there was a month where I got a paycheck that was so big... my parents flipped out.” 

Their response? Shut it down and take a summer job painting gas meters. “I was furious,” he says. “I was like, this is what I want to do. I don’t want to spray paint gas meters.” 

Looking back, he sees it clearly. “That was the summer where I committed to never letting someone tell me I can’t do something.” 

What started as rebellion turned into something more grounded: “I was gonna be deliberate about the path I choose rather than let someone else tell me the path that I need to choose.” 

You don’t have to learn the hard way 

In Smartcuts, Shane wrote about heart surgeons learning new techniques. Those who observed someone else mess up did better than those who messed up first themselves. 

“If someone else learns the mistake for you, you have a lot better chance of getting to where you need to go than if you have to learn the mistake for yourself.” 

The same logic applies to teams. Great leaders help people learn from one another, not just from their own failures. “If it’s on [the leader] to have all the answers, then that team is limited by them.” 

What sets exceptional teams apart isn’t raw intelligence. It’s what Shane calls “intellectual humility.” People who think differently, engage with each other’s ideas, and are willing to change. 

Make it safe to grow 

That kind of collaboration doesn’t happen by accident. 

It happens when leaders reward contributions—not just correctness. “Someone suggests something, and the inclination would be, oh no, that’s not going to work. Instead... say, ‘Hey, what can we learn from that?’” 

It also means being intentional about how you frame ideas. “There’s this thing called tentative expression,” Shane says. “My current thinking is... rather than, this is the answer. That opens the door for someone else to say, hey, what about this counter argument?” 

And sometimes, it means being more explicit than you want to be. “Don’t believe that people can read your mind,” he says. “I don’t want people to have to guess what my intentions are... Sometimes, yeah, it sucks to take the extra time to do that. But I think the burdens of doing a good job with teams and working together often does entail doing things that we wish we wouldn’t have to do.”

Say it anyway 

Building trust takes work. Especially when your voice carries extra weight in the room. 

“Say what you don’t mean also,” Shane adds. “Like, ‘I’m not saying you did a bad job.’ Sometimes you have to say that because you can’t assume that they’re like, do they think that I am valuable or did a good job?” 

Creating that clarity, especially in positions of power, is a form of leadership too. 

The final word 

“You’ve got to be willing to change,” Shane says. “To transcend your previous point of view and to become something bigger than yourself.” 

And sometimes, that starts with the smallest moves: a question, a pause, or a clear, kind word. The best teams don’t just outperform—they listen better. They zig, they zag, and they learn from each other. 

To hear more from Shane Smith, including three practices that leaders can use to help their team realize its potential, listen to the rest of Human Side Up here.