Seven Reasons Successful People Fail

What makes someone who is so successful in one environment struggle in a different environment?

A few years ago, I met someone whose boss had just been hired as a leader at a company I was working with. “You’re going to love working with them,” this person told me glowingly. “They’re a real servant leader.” As this person went on and on about how lucky I was to be working with this person, I began to look forward to meeting this paragon.

The reality did not live up to the hype. The first time I met the person, they overshared a story about their family – I wanted to shout TMI! – and, based on the looks on the faces of the other people in the room, everyone else felt the same way. Everyone looked forward to the leader’s first email to the front-line employees, how would this leader shape the company direction? That first email… asked them to participate in a sports pool. At the leader’s first conference presentation, one of the sales managers asked for insights on how to reassure their direct reports who were nervous about the change; the leader responded, basically, Not My Job. Then the leader started replacing long-time employees with buddies who came across as condescending jerks. When the boom finally dropped after 6 months, and word went out, folks there told me it had been like Times Square on New Year’s Eve: people running through the halls hooting, papers flying like confetti.

I still think about my conversation with that satisfied employee and wonder: how did this leader, who was so successful at one company fail at another? I am sure it was as traumatic for this leader as it was for the company – no one likes failing to thrive and especially not someone who has been successful. I know, when I’ve been in unsuccessful situations, I have felt like crap and questioned whether I was ever any good to begin with – and I can only assume others feel that way, too. I will say that, in every 1:1 interaction that I had with this leader, they came across completely differently than they did in group situations, much more like what I had been promised.

I’m not an expert on this topic but I have seven theories about what causes someone who is successful in one environment to fail in another. I also expect that this article will pay off in the comments, where hopefully people who have studied this topic will share their insights.

Theory 1: Holding onto previous success.

It is human nature, when you are an artist with a hammer, to treat every problem like a nail. I’ve seen people who were great in one role, fail to thrive in the next because they kept trying to do what had previously made them successful before, instead of what will make them successful now. (And I’ve found this to be true about myself as well.) I’ve written pretty extensively about this here.

Theory 2: Rush to results.

Often new leaders want to quickly establish themselves as experts. They make snap judgements and impose new processes and methods to get to goals. At one company, a new leader set the goal of involving 700 employees in regular social media posts within 3 months, despite a previous policy of no social media. At 3 months, 25 people were participating. “This can’t stand!” the executive pounded on the table. “Double the effort.” A month later, they were down to 15 participants. After intense focus and effort, the next month they were down to 7. They hadn’t studied the change management aspects of the situation; once they did that, they started to get the results they wanted.

Theory 3: Neglected relationship-building.

I’ve written before about the importance of building relationships – and not just with your boss or with those who benefit by telling you that you’re doing a good job. You need relationships, advisory groups, at all levels, people who can hold up a mirror that shows you what you’re doing wrong, as well as right. This was a very social organization and, if the leader had managed to connect, to build relationships with some of the internal influencers – people at various levels within the organization, who were very connected with their peers, and would spread positive stories about the leader’s behavior and advocate on their behalf – things may have turned out differently.

Theory 4: Ignoring the organization’s strengths.

 In 1:1 conversations with this leader, they acknowledged some of the strengths that the organization had – an incredible customer loyalty, for example, and employees who cared passionately about the product. But they failed to assess other strengths that the organization had developed, operational strengths, that they could leverage and build on; and some of the proposed changes undermined those strengths instead of taking advantage of them.

Theory 5: Doesn’t know the territory!

They say culture eats strategy, and this leader failed to understand the culture. A sports pool might have been exciting at other organizations – but this was not that kind of organization. The organization skewed strongly female and strongly educated and, while the Oscar pool or National Book Award pools might be acceptable, a sports pool was not widely embraced. This was also an organization where empathy for those around you was strongly prized, and the leader’s response that it wasn’t their job to reassure employees worried about change was jarring. The kind of rumors that circulated about this leader – cutting field staff to hire buddies and buy refrigerators for the buddies offices, filled with beer – reflected the lack of cultural fit.

Theory 6: Job Mismatch

There’s really only one CEO per organization – which means there are fewer CEO jobs out there. I imagine that, if you think you’re ready for a CEO job, when one comes your way, you’re going to snap it up. Possibly without evaluating whether the organization or the job is really a good fit for your strengths and what kind of culture you want to work in. Especially if you’ve been rewarded for being who you are by your previous employer; especially if the company is dangling a lot of incentives in front of you. It would be easy to assume that a CEO job in one organization is basically the same as the CEO job in another organization. CEOs need to be as discerning about choosing the right fit for them as the rest of us.

Theory 6: Organizational Failure

Why the heck did the company hire this leader to begin with? Didn’t they know what they needed? Were the senior executives in charge of recruiting that out of touch with the culture – or that desperate – that they just took the first candidate they found? And what happened during onboarding? Based on my experience with this organization, I’m going to guess that the pep talk the executive received from the Chairman of the Board went something like this: You’re in charge here; don’t let anybody get in your way. (Other executives told me they had been given this message when hired; and you could read it between the lines by how others acted.) While much of the failure may lie on the leader, equal amounts lie on those who selected that leader, and onboarded that leader, and reinforced that leader’s behavior.

Theory 7: Bad Executive Coaching

Some of the behaviors this leader demonstrated were so bizarre – the oversharing about family, the strange slide presentation – and the leader actually looked so uncomfortable while doing them. I wondered afterwards if the leader had been working with a coach who told them that they needed to loosen up, to show their personal side or something, and these were attempts at that. Maybe this leader was working with an executive coach who didn’t get to see the leader in action and provide real-time feedback. Its isolating being a CEO – you need a good coach who you can trust to act as your magic mirror, without fear of reprisal. I wonder if this leader ended up with a dud.

Anyhow, those are my seven theories. With everyone moving around now, even if none of these theories are accurate for this leader, there are great lessons to be learned from each of them.

Like I said before, I hope to capture more insights in the Comments below. So share your theories and experience: what made you – or someone you know – succeed in one environment and fail in another?

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