When Imposter Syndrome Shows Up in Leadership
What if self-doubt is part of leadership, not proof that you don't belong?
Imposter syndrome has a way of getting louder when the stakes get higher.
You step into a new role. Someone asks for your expertise. You are surrounded by people you respect. Suddenly, a familiar thought creeps in:
That experience came up again and again during our September 2026 Learn@Work LIVE conversation, “Do I Belong Here? Real Talk About Imposter Syndrome in Leadership.”
View the full recording from our September 2026 Learn@Work LIVE webinar here or above.
Dr. Alex Walker was joined by Dr. Beth Skinner, Director of the Iowa Department of Corrections; Jessica Dennis, Deputy Director of the Ohio Adult Parole Authority; and Seth Krause, Director of Probation and Court Services for McHenry County, Illinois, for an open conversation about self doubt, vulnerability, leadership, and what happens when we stop pretending we have it all figured out.
One thing became clear quickly: imposter syndrome does not necessarily disappear when you earn the promotion or step into the leadership role you worked toward. In fact, leadership can give it new places to show up.
When Other People See the Leader Before You Do
For Jessica Dennis, imposter syndrome became especially noticeable when she began receiving leadership opportunities. Other people saw leadership potential in her before she necessarily saw it in herself. That disconnect could become almost debilitating. She felt pressure to perform as the leader others believed she could be.
Dr. Beth Skinner described a similar experience. Throughout different stages of her life, she wrestled with questions like, Am I enough? She just didn’t always have a name for what she was experiencing.
Seth Krause noticed it as he took on more leadership responsibilities, too. The more responsibility he carried, the louder that internal voice could become.
These experiences challenge a common assumption about leadership: that eventually you reach a point where you feel completely confident and certain. Leadership rarely works that way. New opportunities often put us in situations we have not navigated before. That discomfort does not automatically mean we are unqualified. Sometimes it means we are growing.
The Pressure to Have Every Answer
Imposter syndrome can influence how we lead. When leaders worry that people will discover they do not belong or that they don’t know, they may work harder to prove that they do.
Jessica described a tendency to become the fixer. Rather than allowing others to see her process, she would take on the work herself in private and return with an answer. From the outside, it could look like she knew exactly what to do. Behind the scenes, she was doing everything herself.
In this short clip, Jessica describes how being “the fixer” is a toxic trait as a leader.
Beth described looking to others for answers and trying to follow their approaches instead of trusting her own leadership style.
These behaviors can look like dedication and can even be rewarded in organizations. But they can also make leadership exhausting and prevent others from growing and learning alongside you. The symptoms of imposter syndrome can limit learning and reinforce the idea that credibility requires certainty.
What if leadership did not require us to know everything?
Seth offered a different way of thinking about the role of a leader. He suggests that people are not looking for their leader to have every answer, rather, they want to be heard and supported as they work toward an answer together. That shift matters. When leaders stop positioning themselves as the source of every solution, they create more room for other people to think, contribute, and solve problems creatively.
Somebody Has to Go First
Talking openly about uncertainty can feel especially uncomfortable in fields where vulnerability has traditionally been viewed as weakness. Corrections and other justice settings often operate within cultures that value strength and clear answers. Our panelists reflected on how difficult it can be to talk about feelings or admit that you do not know something in those environments. But culture changes when people act differently.
As Seth pointed out during the conversation, somebody has to be the first person to talk about these experiences. For leaders, going first can help create permission for others to do the same.
Beth described what can happen when leaders open that door. People may feel safer to discuss important things, trust can grow, and staff begin to see that making a mistake or asking for help does not automatically threaten their credibility.
Beth explains why leaders need to rethink vulnerability to create stronger and more trusting workplace cultures.
That is where imposter syndrome becomes bigger than any individual experience. It becomes a conversation about psychological safety. To Jessica’s point, if leaders can say, I don’t know, I made a mistake, or I’m still learning, they demonstrate that uncertainty and competence can exist at the same time.
Accountability and Humanity Can Coexist
Creating space for vulnerability does not mean lowering expectations. Dr. Alex described it as putting humanity at the center of accountability. We can hold people to high standards without expecting them to be perfect.
Accountability does not require pretending that people never struggle or make mistakes. As Beth shared, leaders can create space for people to say, I don’t know, and to fail forward without automatically losing credibility.
Jessica described this as developing a more coexisting mindset. Caring about how people experience the workplace does not mean everyone will always be happy. It means recognizing the human experience while still doing the work that needs to be done.
Notice the Thought Before It Takes Over
Recognizing imposter syndrome does not necessarily make it disappear, but it can change what happens next. Beth described how identifying what she was experiencing helped her begin managing it. Before she had language for it, the experience could feel paralyzing. Once she could recognize it, she could begin working through it.
Seth offered another way to think about those moments: a thought can enter our minds without requiring us to hold onto it.
- I don’t belong here.
- Everyone else knows more than I do.
- They’re going to figure out I don’t know what I’m doing.
Yes, those thoughts may appear… but the question becomes what we do with them. Do we grab onto them and let them spiral? Or can we notice them, get curious about them, and let them move through?
Progress can start with becoming a little more aware of what is happening inside us and responding differently next time.
Seth asks why we hold onto thoughts tied to imposter syndrome instead of letting them come and go like any other thought.
What We Model Matters Beyond Ourselves
The way we respond to our own mistakes and feelings can influence how we respond to the people we serve. Jessica raised an important question during the webinar:
If professionals experience the weight of judgment and self doubt, what might those experiences look like for people who are justice involved?
Beth pushed the question further asking if professionals with established careers struggle with these feelings, then what does it feel like to carry a label while trying to move forward, particularly when people may not listen or offer another chance?
That connection asks us to consider the grace we extend throughout our systems. As Dr. Alex reflected, sometimes people take a step in the wrong direction. What might change if our response included a little more grace?
You Don't Have to Wait Until You Feel Ready
Near the end of the conversation, the panelists were asked what they wished they had known earlier in their careers. Their answers were simple.
- Don’t be afraid of it.
- Believe in yourself.
- And keep trying.
Imposter syndrome can make us question whether we belong, even when we’ve already earned our place. But being a leader does not mean we have everything figured out.
We can acknowledge what we do not know. We can ask questions. We can make mistakes. We can listen to feedback. We can celebrate progress before everything is finished. And we can create workplaces where other people have permission to do those things too.
Belonging comes from realizing that we can keep learning once we’re there.
