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The 4 types of personalities leaders need in their inner circle

Suneel Gupta

Psychotherapist Esther Perel says that relationships fail because we expect our partner to give us “what once an entire village used to provide.” Of course, that sounds like an obvious recipe for disaster and this is why marriage counselors regularly guide their clients to shift this burden from one person to a circle of people, including friends and family, each of whom fills a different need. Your spouse or partner is part of the circle, but not the full circle required to make you feel whole.

Strange as it may sound, this is also sage professional advice. Peter Thiel, the cofounder of PayPal and Palantir—and backer of startups including Yelp, Facebook, and Spotify—emphasizes the importance of his circle. He says the one thing he tries to do every day is to have a conversation with “some of the smartest people I know and continue to develop my thinking.”

Sounds great, but how do we do this in the era of COVID-19—when the only people we see regularly are the ones we live with? There are no more business lunches, after work drinks, or even phone calls during the commute, making us more reliant on the people in closest proximity as the ones with whom to bounce around ideas. But are our spouses, roommates, kids, or pets really the ones we should be turning to for advice on a new idea or how to hone a presentation?

We’d be better served by going to a variety of people who can help us see things in new ways. In a time when it’s easy to get stuck in the same Groundhog-Day existence it’s more important than ever to break out of the tired ways we do things and build a circle of trusted advisers who bring different personalities and points of view. This does not have to be done in person. In fact, I’ve found Zoom and FaceTime to be more efficient ways to reach more people.  While each “backable circle” is different, there are four specific types of people (what I call “the four Cs”) I like to have in mine.


This is someone who’s going to help you expand your idea and improve your delivery. They’re not going to agree with everything you say, but all feedback is going to feel productive. When you’re with a collaborator, you feel like you’re in a musical jam session—riffing off each other and lifting your concept to a better place.

Law school students have a reputation for being more competitive than collaborative, but the exception at Northwestern was Evan Eschmeyer, a former NBA player who had gone back to school after blowing out his knee. While most classes were filled with debate and dissent, he would always be the one bridging together arguments. As Eschmeyer and I became friends, I began to understand just how deep his collaborative spirit ran.

In 2001, the Dallas Mavericks were championship contenders, and commentators were surprised when owner Mark Cuban recruited Eschmeyer to the team. He was relatively unknown, yet Cuban wasn’t paying attention to star status. Instead, he was focused on a metric called plus-minus. Rather than measuring how well you play on the court, plus-minus measures how well your teammates perform when you’re on the court. While Eschmeyer’s individual statistics were barely average, his plus-minus was one of the best in the entire league. When he was in the game, his teammates excelled.

Eschmeyer carried his plus-minus attitude off the court, through law school, and into the professional world. Today he’s seen as a trusted adviser to CEOs and has been one of my closest collaborators. When my company was still in the idea phase, he was one of my first calls. When I started to think about writing my first book, he was one of my first calls. In both cases, he listened intently and took notes. Then we did a jam session on how to make it better.


While your collaborator will help you figure out if your idea is right for the world, your coach will help you understand if an idea is right for you. Remember, just because an idea is a good fit for the market doesn’t mean it’s a good fit for you. My wife, Leena, is my coach.

I’m constantly bringing ideas to her—sometimes annoyingly so. As a journalist who’s written for Fortune magazine, Leena has a strong sense of whether something fits the market but she has an even stronger sense of whether an idea fits me. The filter she uses isn’t simply “Is this a good idea?” but rather “Is this a good idea for Suneel?”

A few weeks ago, I told her my idea that was essentially Rotten Tomatoes, but rating movies on emotional reactions. After giving it some thought she came back with, “Sounds like it could work, but it doesn’t feel like something you’d really want to build.” And she was right, because a couple of weeks later I had all but forgotten about the idea (though secretly, I still think it could work).


This isn’t the person who’s going to give you critical feedback, but rather the person who’s going to make you feel confident before you get in the room. Hockey players will warm up their goalie up before a game with practice shots that are easy to block. The goal, in those final minutes, is to build the goalie’s assurance, not his skill.

Your cheerleader can be anyone—a friend, a coworker, a spouse, or a parent. In 2012, Fast Company named Ellen Levy “the most connected woman in Silicon Valley.” Her network ranges from members of congress to CEOs of legendary companies. Yet, when I asked her who she goes to for a confidence boost before an important pitch she smiled and responded, “That one’s easy. It’s my mom.”


The fourth “C” is the most pivotal role in your circle. Your “Cheddar” is the person who will deliberately poke holes in your ideas, sometimes in a way that is deeply unsettling.

As a native of Detroit, I loved the movie 8 Mile and the namesake of this individual is a friend of Eminem’s. In the last scene of the film, Eminem’s crew is getting him ready for his final rap battle, giving him positive encouragement, when Cheddar all of a sudden brings up an unexpected question, which many of Eminem’s friends dismiss. It’s this stealthily valid point which later helps the rapper to disarm his opponent in the battle.

This is what Cheddars do best. They ask the tough questions so that we’re not hearing them for the first time from a backer.

Most of us tend to steer clear of the Cheddars in our life. We run away from people who can be the most critical of our ideas. But these are the people who get us best prepared, because backers are a lot like Cheddar. Their job is to find your blind spots. By playing exhibition matches with their Cheddars, people primed for growth discover the hidden problems with their own ideas. In the words of billionaire investor Charlie Munger, “knowing what you don’t know is more useful than being brilliant.”

When I was struggling to get investors interested in my fledgling business, I was introduced to Leah Solivan, the founder and then CEO of TaskRabbit, one of the hot online marketplaces at the time. I met Solivan at her favorite breakfast spot in San Mateo, and I pitched her as if she were an investor. When I finished, her nonverbal signals told me everything; she didn’t just have simple modifications in mind, my pitch needed an overhaul. We went through her list: my presentation was too long, too bloated with facts and figures, and on top of that it was missing a concise, memorable story. Solivan poked holes but then helped me rebuild a new outline from scratch. After Solivan left the diner to go on with her day, I stayed. Sitting alone at that counter, I ordered another cup of coffee and got to work. That pitch—the one that has the insight of my circle—was the one that went on to become my book, Backable.

You don’t have to meet in a coffee shop, or a conference room, or pull someone over in a hallway (a brainstorm space I feel ideas go to die) in order to find wisdom from your circle.

Identify your four Cs and reach out to talk. My backable circle helped me see how each message was landing—and make adjustments along the way. And it all happened much faster than if we waited for schedules to align and meet in person. My virtual backable circle turned out to be something I’ll keep even when we can meet up again.

Suneel Gupta is the cofounder of Rise, a nutrition coaching company. He teaches on the topic of innovation at Harvard University. His ideas have been backed by firms like Greylock and Google Ventures, and he has invested in startups including Airbnb, Calm, and SpaceX.

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