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What Sesame Street can teach us about overcoming impostor syndrome

One CEO’s practical approach to help an employee who needs to feel less like a fraud and more like a star, with a little help from an old friend.

What Sesame Street can teach us about overcoming impostor syndrome
[Photo: STAN HONDA/AFP via Getty Images]

The last time Sesame Street crossed my mind was when my kids watched it on PBS back in the ’90s. That was until a new hire on our leadership team compared herself to Big Bird. What she meant by the comparison was that she felt like an impostor, standing out in the crowd as obvious as Big Bird, with his flurry of yellow feathers.

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While I’ve heard about impostor syndrome before, I was not aware that there are several different types. In her case, she was experiencing “The Superwoman.” She’d convinced herself that she was a “phony among real-deal colleagues,” referencing this meme of Big Bird in a boardroom surrounded by men to paint a clear picture.

I have heard from colleagues, friends, and family more frequently about how they too feel like the Big Bird in the workplace—whether it’s because they are in a male-dominated field, have a fear of feedback, or being unsuccessful, are about to come back from maternity leave, or because of a deeply rooted unconscious bias. While no one is immune to these feelings—as impostor syndrome can impact every race, gender, or creed—research suggests that women, especially women of color, are disproportionately affected.

This must be addressed. We can’t afford to lose great talent and valuable perspective, period. Being a leader is about nurturing your talent. We must build an environment that fosters different styles of leadership and a diversification of racial, ethnic, and gender identities that are encouraged and supported.

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Taking a page out of Sesame Street’s book, I’ve come up with the ABCs of helping talented employees to overcome imposter syndrome.

A is for authenticity: make space for negative talk

What I’ve learned about impostor syndrome—while also reflecting on my brushes with it in the early days of my career—is that once someone gets this in their head, it’s hard for them to be their authentic self. Or, as one female colleague described it to me, you start posturing to overcompensate in a male-dominated industry for whatever shortcomings you think you have.

Other signs include:

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  • Exhibiting an intense fear of failure and strong need to be “perfect”
  • Knowing all the answers and rarely asking questions
  • Having no confidence that they can recover from a “wrong” move

Leaders can work to identify this behavior and should make space for their employees to divulge their internal negative talk. No one is perfect, and people make mistakes all the time. Empower them with the room to make and learn from those mistakes and talk about them without fear of rejection, passive-aggressiveness, or any other form of toxic work behaviors.

B is for balance: make room for living

Another sign of impostor syndrome is working too much. Something leaders routinely face is recognizing when the people around them including peers and colleagues, but especially their direct reports, are out of balance and burning the candle at both ends.

Beyond the potential impact on one’s personal life, being out of balance can have tremendously negative effects on their role within the company.

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If you’re truly paying attention, an easy red flag to spot (especially in this remote work era) is that the person is answering emails at all times of the day and night. No one can run at a crazy pace forever. It’s just not sustainable. If you’ve noticed this behavior and are unsure how to broach the subject, being empathetic, and remembering that you were there once too is usually the best course of action. You may say: “I get it, you think you can sprint a marathon. But I know from experience, it’s not possible.”

C is for compassion: make time for acts of kindness

It’s draining to feel like an impostor at work. Leaders can help alleviate the stress that comes with this line of thinking by practicing small acts of kindness that in the grand scheme of things can feel really big to the recipient.

Sometimes in a meeting (pre-COVID), I’d get up to get a drink, and make it a point to specifically ask our junior staff if I can grab them one, too. “Oh, you’re going to get me a drink?” they would say. “Well . . . yeah. I’m going to the fridge. I’ll get you a drink, too.” And I’m thinking, “Did you think I’d delegate getting you a drink to my executive assistant?”

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Now, in the age of Zoom, I’ve taken to shipping surprise picnic baskets for my crew to enjoy with their family. I get there is a hierarchy in business, but if you start to think that you’re too important to help someone, even in the smallest of ways—you’ve become too important for your own good.

A basic act of kindness can’t erase everything, but it can help ease some of that negative “They are better than me for XYZ reason” energy. We are all human.

Impostor syndrome can easily fly under the radar, but to the person experiencing it, they feel like Big Bird in a boardroom. Empower all of your crew, and help them to feel heard, supported, like the truly talented people you hired in the first place.

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Mark McClain is the CEO of SailPoint.


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