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Why Executives Fail: 3 Common—and Avoidable—Pitfalls

December 2, 2020

DDI Executive Services Team


About half of executives fail. But the reasons are incredibly common—and preventable.

About half of executives fail within their first two years on the job. It’s a stunning statistic, and often leads to simplistic explanations. It’s easy to say, “Priya just didn’t have what it takes,” or “Simon turned out to be a bad fit.” But understanding more about why executives fail is critical to preventing future failures, and essential to building strong leadership at the top.

Let’s face it. Executive jobs are tough. They can cause incredibly smart, talented, and successful leaders to stumble, quit, or even change their careers entirely.

The mistake is to think that the jobs are just too hard, and accept the high rate of failure. But we’ve worked with thousands of executives over the years. And the majority of the time, the challenges they’re facing are extremely common. Only no one talks about them.

Warning: Pitfalls Ahead

While these pressures are common, the impact on performance varies depending on a number of factors. Some of the big factors are external, such as company cultures, a shift in strategy, or major industry disruption.

But what matters more is how executives handle these pressures. Somehow, the same challenges cause executives to trip, one after the next, including leaders with strong skills and track records. Every individual deals with these pressures differently depending on their personal tendencies, as well as the relative strength or weakness of their skills.

In this blog, we’ll cover a few of the common pitfalls that explain why executives struggle and fail—often more than anyone knows. These are gathered from our team’s common experiences in executive coaching engagements, specifically our executive transition coaching program. More importantly, we’ll tell you how to recognize the symptom of each pitfall, and what to do about it.

Pitfall #1: Unfiltered Focus

  • What it is: The magnitude of going from managing 30 people to 200 is huge. Suddenly, a lot more people are asking for time, attention, and resources. Wanting to build good relationships and find early success, the typical executive says “yes” to too many things. But down the road, too many priorities cause a lack of focus. While executives and their teams work to make progress on everything, they don’t make significant progress on anything.
  • How to recognize it: Usually you’ll see an incredibly busy department, possibly to the point of overload and fatigue. At the same time, very little progress is made on key priorities. They miss deadlines, abandon projects, and frequently fall short.
  • Causes: Often the cause is too much of a good thing. The executive starts in the role full of excitement and ideas for innovation. But without proper filtering and prioritization, it’s hard to make progress. The executive may also find themselves too deep in the details. Combined with indecisiveness (common among executives in new assignments), it can be a deadly combo.
  • What to do about it: First, recognize that this is happening. Without support or coaching, many don’t. Second, executives need to prioritize based on what drives value and impact. This may seem obvious, but time and again, our executive coaching efforts result in significant reorganization of priorities, and changes in what an executive sees as most important. Executives find great value in breaking down their change efforts into levels of priority based on strategic impact. Doing this with a partner or coach can unfreeze thinking about how to make more meaningful progress, and faster.

Pitfall #2: Network Isolation

  • What it is: One of the most common reasons why executives fail is their struggle to build and maintain their networks. That doesn’t mean they aren’t good with people. Rather, they are used to operating independently. While that may have worked at lower levels, executives have to think more broadly and proactively about how their work impacts other groups. This pitfall has become especially common as more companies switch to remote work.
  • How to recognize it: You’ll start to see misalignment and conflicts between groups. Likewise, the executive will see unexpected stakeholder resistance, and a lack of advocacy for their team’s projects. One of the trickiest side effects is that they may get a very positive response from their own team, who might be tightly aligned. But that can coincide with low regard for other groups, and a reluctance to adopt broader company change.
  • Causes: One of the major causes is functional bias. Executives often focus on the area where they have expertise, and ignore matters that are outside their comfort zone. In addition, people who are more reserved or introverted may hesitate to initiate connections where they need them.
  • What to do about it: Ensure that executives actively seek exposure to other groups in the business, including their goals and metrics of success. They also need to pay careful attention to being more inclusive in their communication. They should consider pitching plans and ideas to peers to hear their concerns and secure support before moving forward.

Pitfall #3: Un-Coaching

  • What it is: At lower levels, leaders often coach their teams on more technical matters in their area of expertise. But when they get to the executive level, it’s time to think more broadly about talent. “Un-coaching” happens when executives downplay or miss opportunities to coach, develop, and grow the skills of their team.
  • How to recognize it: When you see a team that has high turnover—especially unexpected departures of high performers—un-coaching may be occurring. In addition, among those who remain, there’s a high proportion of mediocre performers. You may also see low engagement scores and lagging performance across the department.
  • Causes: This pitfall happens for a variety of reasons. In many cases, executives adopt a sink-or-swim mindset, and coaching simply doesn’t occur to them as an essential leadership activity. Other executives may lack self-confidence, and feel threatened by talented subordinates. Or they may simply fail to see the potential in others, because they are preoccupied with their own work. Regardless of the reason, the outcome is stagnation. Teams fail to grow, making them less agile as the business evolves.
  • What to do about it: The strongest executives make a mental shift away from small-scale, tactical coaching, and think instead about developing the broader capabilities of their teams. This means continually searching for opportunities to expand the accountabilities of team members, and stretch them into assignments where they can master new skills and make larger business contributions. Ultimately, this is about taking accountability for growing organizational talent, not just coaching in the moment.

Why Executives Fail: The #1 Cause

Our research and experience shows that executives are the leaders most in need of support, and the least likely to ask for it. And this helps to explain why the most common cause of executive failure is the absence of support.

Over the last couple of years, we’ve interviewed many HR executives about what happens when people become executives in their organization. Here are a few direct quotes from what we heard:

  • “With the vast majority, it’s ‘congratulations – now go for it!’ In other words, we do nothing for them.”
  • “If they are internal, then nothing. We send out a company-wide announcement about their promotion, change their comp plan, and send them off!"
  • “Pretty much nothing – it’s just seen as the next transition up the hierarchy.”

Notice a common theme? Executives most often get nothing to support their transition.

It’s easy to see why executives fail so often. But take a moment to consider the waste. The cost of suboptimizing these mission-critical leaders—in whom you’ve invested for years—is extreme.

But it is also avoidable. Most executive pitfalls are common and predictable. Building awareness and the agility to work around or through these pitfalls is something we help executives do every day. The important thing is not to wait until it’s too late.

Learn more about DDI’s unique Executive Transition Coaching program, which is specially designed to help executives see and avoid the pitfalls ahead.

Download an overview of the program.

DDI’s Executive Services Team is a tenured group of executive consultants and coaches with decades of experience helping leaders successfully make the leap into top roles. They’ll help you build a strong executive bench and choose and prepare the right senior leaders to drive company strategy and success.

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