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How Leaders Can Dead End Even When Hitting Their Targets

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In 25 years since I’ve been coaching leaders through big promotions, I’ve seen a lot of near misses. With so many organizations facing lean "ready now" leadership benches, I forecast a lot more mismanaged transitions on the horizon. Don’t let yours be one of them.Take a lesson from my coaching play book about a leader who was highly successful in her functional role but nearly derailed when she was expected to lead at an enterprise level.


Anna was promoted from Finance Manager to Director and targeted to become the successor to the VP of Finance at a global manufacturing company. She sailed through her first year as. Director of Finance with what she thought were flying colors. She knocked her goals out of the park. When she earned only a “meets expectations” on her first performance review along with some feedback from her boss about not being able to confirm her on the successor list for his role, we went to work to figure out what happened.

So What:

 The short version is that Anna exceeded her key business objectives for her role, but spent so much time doing just her role, senior executives did not see her strategic potential. Her boss said that to be the successor for his role, he needed to see her thinking about the enterprise overall in her ideas and decision making. That when she walked in the building every day, he wanted to know that she believed she carried the responsibility for supporting the business with financial strategy that would help them be profitable, competitive and successful, and he did not see that in her - yet. Both Anna and her boss took responsibility for allowing this to happen.

Anna fell into the trap of what author of the The First 90 Days, Michael Watkins describes as not managing the seismic shift “Functional Management to Enterprise Leadership” “Good strategists see the big picture; they see important patterns in complex environments, and are able to crystallize and communicate the strategic implications to others. In short, business leaders need a strategic mindset. Tacticians, on the other hand, must focus on the details of how best to implement an overall strategy. These implementation decisions are often the responsibility of functional leaders”

Now What:

As Watkins says, “as with many things, good strategic thinkers are a product of nature and nurture.” We integrated both into the coaching strategy:

  • Nurture: Anna’s boss took on ways he could nurture Anna to be more strategic. He crafted a strategic project for her to lead that would gain her visibility with sr. executives and interact across the business. And he looked for ways he could stop being the go-between Anna and the CFO and CEO.
  • Nature: Anna did some reflecting about her personal motivations and realized that in her attempt to prove her capability to her new employer, she had created tunnel vision. She was so departmentally focused on ensuring she and her team achieved their goals, she lost sight of the bigger picture. As she learned more about her style through the Enneagram personality system, she learned that as an Enneagram type 8, she had been working so hard to achieve in order to compensate for feeling vulnerable about the unknowns of this new culture and boss.
  • Partnership: Anna and her boss created more time in their 1:1’s to discuss her project and other strategic topics. Anna became more open with sharing her concerns and her boss stepped up to providing more frequent feedback.

Anna weathered what could have been a dead end in her career and is currently thriving and on the successor list for future executive roles.

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