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5 Reasons Why New Executives Fail

September 11, 2019

John DeSantis


For the new executives who haven’t made the leap successfully, there are common reasons why they fail.

frustrated new executive sitting at his desk with head in his hand to show stress over failures

“I’m barely keeping my head above the water and the tide keeps rising. This job is not what I expected it to be.”

These were the words of a newly promoted executive I was coaching. He had been a high-performing operational leader at his organization. He was taking the natural next step in his career, obtaining a promotion, and making the leap from operational to strategic leadership.

He continued by telling me how he was finding his new role overwhelming and how he’d been struggling to get up to speed with the strategic side of the role. He also revealed how shocked he was by the exponentially increasing speed at which change was occurring and his new exposure to all of it. 

The case of this newly promoted exec is not unique. These are sentiments I regularly hear. And the success rate of new executives bears out these struggles: nearly half of externally hired executives fail in their roles. For internally promoted executives, the numbers are only a little better, with 35% still reported as failing.

But why are these transitions so rocky? Why are new executives failing at such high rates? What’s blindsiding these high-performing leaders once they enter the executive world?

As an executive coach, I work with leaders who are about to, or have already made the leap from operational to strategic executive leadership. I’ve seen the gamut of success and failure. And often, failure comes from a common set of executive pitfalls. Here are a few trends that I've noticed in my coaching sessions. 

1. They don’t know how to deal with the ambiguity that comes with bigger, more strategic roles.

It’s typical that new executives are coming from operational roles, and have been promoted because they are diligent, conscientious, and get things done on time. They’re used to being in the thick of execution—leading a team, but still entrenched in day-to-day decisions and tactics.

But these aren’t the same qualities that lead to success in bigger, more strategic executive roles.

At the executive level, there’s just a lot more ambiguity. While in previous roles they’ve often worked from a playbook or operations guide, executives now need to create their own playbook, despite having little or no experience. They also haven’t experienced making decisions in an environment that’s much more complex, uncertain, and faster-paced.

How can new executives learn to lead amid ambiguity? It can start with how they inspire and help their teams and fellow stakeholders to deal with uncertainty and complexity. Ambiguous environments can sometimes be the launchpad for new ideas, fresh thinking, and growth, and great leaders leverage ambiguous situations and environments as opportunity to practice what could be for many uncomfortable behaviors. These behaviors include accepting the personal risk of being wrong when uncertain decisions are being made, trying a new approach when success is uncertain, and speculating on new ventures or concepts even before they’re needed or wanted.

2. They don’t spend enough time looking at the “big picture.”

Successful leaders prove time and again they can do the work “in the trenches” and do it well (this is often why they have been promoted). But as an executive, success comes to those who can effectively move away from managing the day-to-day, instead trusting their operational leaders (who are now their direct reports) to manage this, while they take a step back and look at the bigger, more strategic picture of the business.

Executives who allow themselves to get pulled back down to their previous, more technical responsibilities are going to run into two problems:

  1. The operational leaders they manage are going to start feeling disengaged because they have no room to bring forth their own creativity or unique contributions.
  2. They’re stunting the growth of their operational leaders because they aren’t giving them opportunities to develop judgement and decision-making skills by trying new ideas—and failing.

According to my colleague Mike Hoban, executives who have successfully made the leap from operational to strategic leader “see” differently. Effective strategic leaders spend the time necessary to create a vivid picture in their minds of a preferred future and—this is of critical importance—they are able to describe that future in explicit enough terms to draw others to it so that they also can “see” it.

Effective strategic leaders are also able to cultivate the relationships required to successfully work with others to create and put into place a roadmap and a set of enablers for achieving that vision.

3. They aren’t skilled at influencing stakeholders.

Most new executives have climbed the ladder on the strength of their superior technical skills and expertise. But once in the executive role, it surprises them their technical prowess alone is no longer enough to convince fellow executives that work needs to be done; rather, they need to influence them to gain their buy-in and, more importantly, their commitment.

New executives can learn to influence others toward a decision or plan by packaging their ideas in a way that captures the hearts and minds of their audience. They can do this by:

  • Identifying, assessing, and prioritizing influence opportunities and choosing strategies that will aid in advancing the most pressing business objectives.
  • Building influence strategies based on what they know about the motivations, needs, and concerns of those they need to influence.
  • Evaluating their business network and building supportive and reciprocal long-term working relationships at all levels of the organization.

4. They’re dealing with change at a rate they haven’t had to deal with before.

Moving from operational leadership into the strategic ranks can be like moving from the minor leagues to the major leagues. The gameplay is faster, the pitches come harder, and new executives are now witnessing, first-hand, how quickly change is occurring—and how quickly they must react.

Operational leaders are often sheltered somewhat from the ambiguity and complexity that results from today’s business climate of continuous change and hyper-competition. There is often someone above them who is at the front lines of change, reacting and creating strategies to navigate through it.

It’s crucial, though, for new executives to have the skills to guide themselves, their employees, and their organizations through the rough waters brought on by continuous change. They need to be adaptable and have the ability to stay focused, manage stress, and take decisive action—despite a lack of definitive information. Executives who manage change effectively create a stable environment for the rest of the organization to continue to hum, even when there’s still some ambiguity at the top.

5. They’re overconfident.

A confident leader can motivate and inspire his or her team to achieve success, encouraging team members to “fail forward” and innovate. However, there is a fine line between confidence and overconfidence.

Overconfidence can sometimes be perceived by others as arrogance. An arrogant executive “talks at” his team and stops listening to their ideas (because he truly believes he is smarter than everyone else in the organization), which can destroy the valuable relationships a leader needs in order to be effective.

Arrogant executives are quick to celebrate their own accomplishments but may forget to share praise and recognition when their teams are successful. Because of this, their teams start to root against them and often lack the motivation to follow them.

Just because executives are in a position of power, it doesn’t mean they need to be the first to speak in a meeting or are expected to make all the decisions on their own. In fact, it’s exactly this type of behavior that could cause others to perceive them as overconfident. By simply listening more, executives can not only empower their teams to make decisions on their own, but they’ll also be surprised at how much they can glean from the minds of others.

Set up new executives for success

In today’s world, change is a constant, complexity is king, and the pressure to produce results is always present. New executives have a lot on their shoulders, and a lot to get right.

Give them the preparation they need to not only successfully transition into their new roles, but the development they need to be successful through the course of their careers.

Learn more by downloading DDI's eBook, The 4 Forces of Executive Pressure: Why Your New Executives Are Drowning.

John DeSantis is an executive consultant in DDI’s Executive Services group, where he helps DDI’s global clients advance their business by gaining powerful and objective insights into the strengths and challenges of current and potential executive leaders.

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