Your Biggest Leadership Hurdle: 4 Tips for Navigating Impostor Syndrome

March 22, 2023
Woman with trophy celebrating success, red cape, stands in doorway, other woman looking on.

At Wolf & Heron, we do a lot of one-on-one work with leaders through our coaching practice. Most of the time, these leaders, although well established in their careers, still believe they have more to accomplish professionally; they haven’t reached their end-goal, and their ambition remains strong.


And yet, despite their previous achievements and successful careers, we find ourselves having conversation after conversation helping leaders see and feel their own potential for that next step.


We’ve noticed that one of the key hurdles of leaders stepping into their own leadership is their personal belief that they’re not yet ready.

In this article, Kara Davidson and Stephanie Judd cover the definition of imposter syndrome and how to prevent this invisible roadblock from stalling your leadership journey.

Share this article

Recent Posts

By Kara Davidson • October 5, 2026
It's never been more important to be yourself. Kara's brother learned this while hiring for his company. He was eight interviews into a search for a new position at this company, and every one of them wasn’t who they said they were on their resume. Some invented their experience. Others leaned so hard on AI that he couldn't find the actual person behind the answers. He was aggravated trying to figure out what was real and what wasn’t. All he knew for sure was that he couldn’t trust his own read, so he handed the search to a recruiter. That's what happens when people can't tell what's real. They get suspicious of everyone. And when one thing about someone seems off, we doubt the whole person: the experience, the credentials, the firm handshake.
Team meeting around a table with papers and a blank flip chart, led by a presenter in a yellow shirt
By Stephanie Judd • September 21, 2026
Stephanie had a mentor who went straight to ‘here’s what I would do’ the moment Stepanie asked for advice. Although this mentor was extremely well-meaning, the advice she gave was irrelevant and outside of Stephanie’s reality. “Take your clients to the ballet,” she said. But Stephanie lived nowhere near a ballet company, and her clients weren’t local to her. If this mentor had just paused to ask Stephanie a few questions, her insights would have been a lot better formulated.  Most people leading a discussion default to questions that inform them rather than explore possibilities. The difference is subtle, but the impact is huge.
Person in a purple shirt beside blue question marks in a yellow thought bubble
By Stephanie Judd • September 8, 2026
Leaders have to have all the answers, right?  Kara had a coaching client who was facing a big org change and needed to keep her people motivated. She was hyper focused on what she should say and how she’d provide her people with answers. She knew this was a critical moment for building and maintaining trust and engagement on the team. But when Kara asked, “What would you be looking for from your leader in a moment like this?” the client said, “For them to listen to me.” Then why do we try to have all the answers? Why don’t we listen?
Team meeting around a table with papers and a blank flip chart, led by a presenter in a yellow shirt
By Stephanie Judd • August 3, 2026
Letitia came to Stephanie stressed. She ran a monthly working group and every month felt the same: low attendance, low engagement, and a Q&A section that was mostly just awkward silence. She spent hours preparing a presentation nobody seemed to care about and couldn't figure out what she was doing wrong. When Stephanie asked her to walk through the format, Letitia said they do forty minutes of presentation followed by twenty minutes of Q&A. She selected the topic each month, recruited a presenter (often herself by default because no one ever volunteered), and carried the entire session on her back. Stephanie pointed out something that surprised Letitia, even though it felt obvious to her in retrospect: the format was inadvertently creating a group of observers, not active collaborators. The meeting was designed in a way that encouraged passivity.
Show More