In this episode of Reimagining Company Culture, we talked with Kara Goldin, CEO and founder of Hint and a multifaceted entrepreneur whose work has been recognized by Fast Company, EY, and Fortune. Kara has spent the last two decades building companies, writing, and coaching other leaders through the moments when self-doubt threatens to become the dominant voice in the room.
The conversation was not about motivational clichés. Kara was specific about how self-doubt shows up, what makes it worse, and what leaders can do to prevent it from distorting their judgment. Her framing matters for HR leaders, because the people most likely to hide self-doubt are also the people most likely to be asked to manage someone else's.
Why Self-Doubt Is a Leadership Operating Risk
Self-doubt is universal among leaders. It is more visible in people who did not grow up with the cultural defaults leadership tends to reward, but no one is immune. Harvard Business School research on leadership consistently finds that high-pressure, high-visibility roles produce self-doubt regardless of background, because the stakes are real and the feedback loops are short.
The operating risk is that leaders in doubt tend to make worse decisions. They over-consult, they delay, they over-index on the most recent feedback, and they sometimes make bold moves in the wrong direction to compensate. HR leaders see the downstream effects of these patterns in team health, case volume, and retention.
KPMG's research on executive women found that 75 percent reported experiencing imposter feelings at some point in their careers. That is not a niche statistic. It is a description of leadership itself. The question is not whether a given executive will experience doubt, but whether the organization has given them anything useful to work with when they do.
Research from Harvard Business School on self-doubt and leadership suggests that talented people often opt out of advanced roles because they overestimate the qualifications required, while others push ahead with less preparation. The pattern is measurable, and it has direct implications for how HR builds its leadership pipeline. Programs that explicitly recruit people through their doubt tend to produce stronger leaders than programs that only recruit the people who feel ready.
How HR and Leadership Can Work With Doubt
What is the most common self-doubt trap for executives?
Trying to mask it. Executives who pretend they have no doubts tend to make worse decisions, because their teams stop bringing them disconfirming information. The healthier pattern is to name the uncertainty and ask for input without treating the input as a vote.
How do you coach a high-potential leader through self-doubt?
Focus on reality-testing rather than reassurance. Help the leader separate the objective situation from the story their anxiety is telling them. The goal is not to eliminate doubt but to prevent it from distorting the decision.
Kara also talked about the value of small wins during the hardest seasons. Leaders who are struggling often skip the small milestones because they feel inadequate to the bigger challenges. Celebrating the small wins, privately or with a trusted peer, is one of the more reliable ways to keep confidence rebuilding over time. This is not a motivational trick. It is maintenance work for the parts of leadership that run on self-belief.
What Actually Works for Leaders Working Through Doubt
Principle 1: Build a real feedback relationship before you need it
Leaders in doubt need trusted people who will tell them the truth, and those relationships take months or years to build. The time to invest in them is not the moment the crisis hits.
Principle 2: Keep a running record of hard calls and outcomes
Self-doubt distorts memory. A written log of past decisions, including what was known at the time and how the decision played out, is a surprisingly effective counterweight. Leaders who can look at their own track record tend to make better calls under pressure.
Principle 3: Protect sleep and physical health
Doubt intensifies when the body is running on empty. This is basic and often ignored. Leaders who treat sleep and exercise as optional are usually the same leaders making the most volatile decisions.
Glossary lookups around performance management and stay interviews can be useful for HR leaders designing the supports around an executive in doubt. The point is not to create additional process for the executive, but to give the team around them a way to show up that does not depend on the executive's mood in any given week.
Where Employee Relations Fits
ER teams often see the second-order effects of leaders in sustained doubt. Increased conflict in direct reports, unclear decision-making, and inconsistent treatment of team members all show up in the case queue. A case management platform that tracks these patterns can help CHROs spot when a senior leader is struggling before the team does. Strong employee relations operations close the loop with coaching and support.
ER drill-down: leader-level patterns in case data
Look for three signals. Repeat cases involving the same manager's team, cases that describe inconsistent or erratic leadership, and cases where employees express confusion about expectations. Any of these can be a sign that the leader is struggling, and the earlier HR can intervene with support, the better.
This is not about punishing leaders for being human. It is about giving the organization a way to see stress early enough to support rather than replace. Executive coaching, peer sponsorship, and protected recovery time are often more useful interventions than a performance conversation.
Frequently Asked Questions About Leaders and Self-Doubt
Is self-doubt always bad for leaders?
No. Calibrated doubt produces better decisions, because it prompts leaders to gather more input and check assumptions. Uncalibrated doubt leads to paralysis or erratic choices. The goal is calibration, not elimination.
How does self-doubt differ between founders and operators?Founders tend to doubt whether they can scale the next phase. Operators tend to doubt whether they are the right person for the role they currently have. The intervention is similar, but the triggers are different.Does executive coaching actually help with self-doubt?When it is rigorous and honest, yes. Coaching that only reassures tends to entrench the pattern. Coaching that helps the leader test their stories against the evidence is substantially more useful.How should a CHRO talk to a CEO who is in doubt?
How should a CHRO talk to a CEO who is in doubt?
Directly, confidentially, and without flinching. CHROs who can give their CEO honest feedback on how their doubt is affecting the organization are the ones who become indispensable to the role.
Can peer networks replace formal coaching?Sometimes, and they complement it well. Peer groups of other CEOs or executives give a leader access to perspectives they cannot get from their own team. For many leaders, this is the most useful intervention of all.
Research summarized in coverage of executive leaders and self-doubt highlights that many accomplished leaders developed specific practices for working through uncertainty rather than trying to eliminate it. Those practices are coachable, which means HR teams can build structured support around them.
The Bottom Line for HR Leaders
Kara's message is that self-doubt is not something leaders grow out of. It is something they learn to work with. The leaders who do it well keep their judgment intact under pressure. The ones who do not tend to produce the downstream problems HR teams end up trying to clean up.
HR leaders can make a real difference here, because they are often the first to see the early signals in team health data and case patterns. Pairing that visibility with executive coaching, peer support, and a culture that allows leaders to be honest about uncertainty is a meaningful investment.
The organizations that take this seriously have fewer dramatic leadership flameouts, better succession planning, and a more honest culture at the top. That honesty travels downward and shapes how the whole organization talks about difficulty, risk, and growth.
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