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3 common traps of mentoring other leaders

Mentoring of other leaders, as well as ourselves, can be hampered by three traps, including a fear of failure and feeling like a victim, writes Adam Bryant.

7 min read



Andriy Onufriyenko/Getty Images

The following is adapted from The Leap to Leader: How Ambitious Managers Make the Jump to Leadership  (HBR Press, 2023) 

Your job as a leader is not just to build a loyal following and inspire them to do great things. Your job is also to develop other leaders, help them make their own leap to leader. Part of the human condition is that we tell ourselves stories about our own lives. We may think we are being objective and realistic, but there are common traps that people fall into. If you are aware of them, you will be better equipped to mentor other leaders and to mentor yourself.

Fear of failure

People can feel paralyzed to make decisions, worried that they make the wrong one. Or they might feel that they are trapped in a job because the uncertainty of leaving or doing something different can feel overwhelming. Or they may not raise their hand for a promotion, worried that they may not have what it takes to succeed in that role. Or they may not stand up to their boss and share what could be perceived as a controversial opinion. In those situations, the important question to ask is, “What is the worst thing that could happen?” For most people, the answer is that they could get fired. But often that fear is unfounded. And even if they were to be fired, people often land in a good place if they have solid skills and capabilities. So take the shot. Be courageous.

And what if the worst happens and you do get fired? I’ve talked to many leaders who have been pushed out of their companies, and they often say that what they feared most turned out to be the best thing that could have happened to them. The more important question is whether you put yourself in a high-stakes position where you could succeed or fail. To get to that point means you had to accomplish something meaningful in the first place.

“Reality is just source material”

I’ve been fortunate to hear a lot of wisdom over the years of interviewing executives, and few sentences have stayed with me quite like those five words I heard from Leila Janah, the former CEO of both Samasource, an anti-poverty nonprofit, and LXMI, a skincare line (Janah died in 2020 at the age of 37, from cancer). In our interview, she was quite open about the fact that she had a difficult childhood. 

“My parents ended up divorcing,” she said. “I did not have a very stable family life. We moved twelve times when I was growing up. The most important thing to my parents was that we went to good schools, and we never had the money for private schools. My mom would research the best public schools, and we’d move to those neighborhoods. But those were often wealthier neighborhoods that we really couldn’t afford to live in. I would get my clothes from thrift stores. Kids can be really cruel, and if you’re the only brown kid, you’re wearing weird clothes, you don’t have TV at home and your parents have funny accents, then you’re always an outcast. It did create scar tissue. I didn’t have a rosy childhood.” 

But ultimately, she didn’t let the adversity hold her back, because of her insight about reality just being source material for the stories we tell ourselves about our lives. “All your background and your bad experiences and your good ones are just what you decide to make of them day-to-day,” she said. 

People often talk about the importance of having a positive attitude, but it’s about more than having a sunny, glass-half-full outlook. It’s about making a conscious decision to choose which experiences to focus on, and how to couch them, to build the narratives of our lives. A big role that mentors play is to challenge the people they are coaching on the narratives they are telling themselves. You can often do this just by drawing people out to understand their logic flow and signaling that it may deserve a second look. 

“I often say to people, ‘Help me understand that,’” said Dave Goebel. “It’s an indirect way of saying that there might be a different way to look at things.” 

With that implicit question mark hanging, people will often see their own thoughts in a new light and catch the negative or flawed assumptions in their narratives. If they don’t, then it may be necessary to take a more forceful approach and point out the glitches in their narrative, whether it’s fear of failure or a particularly negative take on something. Steve Stoute calls the power of self-delusion and rationalization the “most powerful drug, the most mind-altering drug by a long shot.” Your job as a mentor is to be the antidote.

Don’t be a victim

Another common trap that people can fall into is that they start telling themselves that things are happening to them, that they are victims. It is a particularly dangerous narrative, because it leads people to shut down, focus on the negative and start feeling sorry for themselves. Yes, bad things do happen. But there is a world of difference between things affecting you versus things happening to you. The latter is the victim mentality. Any energy people spend feeling sorry for themselves is ultimately wasted. Entrepreneurs are wired a bit differently than most of the population. One of the key differences is that they tend not to dwell on bad news.

Consider the experiences of Seth Besmertnik, the CEO of Conductor, a search engine optimization company. In March 2019, Besmertnik sold his company to WeWork back in the day when Adam Neumann, the CEO of WeWork, was considered a genius and the company was valued as high as $47 billion, on its way to world domination. But WeWork’s IPO was scrapped after investors started scrutinizing its business model and raising more questions about Neumann’s leadership. Given that Besmertnik had sold the company for a mix of cash and stock, Conductor’s very existence as a company was in doubt, because WeWork was cutting to zero all expenses that were not part of its core business. Besmertnik then rallied to buy the company back from WeWork in December 2019 and save the jobs of 270 employees. He could exhale, but only for about three months before the pandemic hit. 

I asked him about the key lesson from those roller-coaster years. 

“There are moments when you say, ‘Why is this happening to me?’” Besmertnik said. “But you can only be a victim for so long, and when you’re a victim, you’re not owning anything and you’re not fixing anything. Every challenge you face is really meant to help you grow in some way. I know that we’ll come out stronger and that there will be some good that comes from it. It’s very hard to get that perspective sometimes when you’re in the middle of it. But when I knew things were about to fall apart, I immediately went to, ‘Okay, what’s the opportunity here?’ We moved fast and we didn’t waver. We turned something that was a terrible situation into this amazing outcome. There’s always an opportunity, and as a leader, the faster you can cycle to look at problems differently, the faster the solution will come and a better outcome will come. But it only happens when you take ownership. If you’re a victim, then you’re going to be a victim. If you take ownership, then you get there.”


Adam Bryant is the managing director and partner at the ExCo Group, where he works with hundreds of ambitious leaders rising through the ranks. As the creator and former author of the iconic “Corner Office” column in The New York Times, Bryant has mastered the art of distilling real-world lessons from his hundreds of interviews and turning them into practical tools, presentations, and exercises to help companies deepen their leadership benches and strengthen their teams.

Opinions expressed by SmartBrief contributors are their own.


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