Women in Leadership: What Actually Holds Them Back

I'm Kurt Schmidt, founder of Schmidt Consulting Group and host of The Schmidt List podcast, and this is a topic I keep coming back to because I watch talented women in my professional circle hit a specific wall, and I don't think most conversations about women in leadership actually describe the wall accurately.

Women in leadership development is a crowded space. Books, LinkedIn thought pieces, corporate ERGs, national conferences. And yet the data is still embarrassing. Last year I came across the stat that there are finally more women CEOs in the Fortune 500 than there are CEOs named John. That's the bar we're celebrating. The problem is clearly still structural, but the solution for any individual woman can't wait for structure to change. That's the tension to sit with.

I recently talked through this with Trisha, a leadership coach who spent years as a CFO in healthcare before building a practice specifically for working mothers in leadership. Her framing of the problem is the sharpest I've heard, so I want to use it as a lens here.

What Makes Women in Leadership Different at the Director and VP Level?

Women in leadership face different pressure depending on career stage, and the director-to-VP window is where the friction is most underserved.

Early-stage working mothers get some attention. The toddler years are visibly hard, and workplaces have started to acknowledge that. But the kids get older, the chaos quiets slightly, and organizations assume the problem solved itself. It hasn't. Middle schoolers need a different kind of presence than toddlers do; they need intellectual and emotional investment, future planning, and active guidance through social complexity. The sports schedules alone (I've ranted about year-round hockey practice before, and I'll do it again) can consume more logistical bandwidth than daycare ever did.

Simultaneously, women at director and VP level are looking at a five-year window where they want to take on more at work. They like their jobs. They like their colleagues. They want to move up. They just can't figure out how to architect both sides of life so that the whole thing fits. It's an engineering problem with too many variables and no one helping them solve it.

The cohort model addresses this precisely because it gets women out of isolation. The moment someone realizes they're surrounded by other high-performing women with the same exact mess of variables, the shame and the "why can't I figure this out" narrative starts to break down. That shift alone justifies the six months.

Is "Imposter Syndrome" Actually Helping Women in Leadership?

I'll say it plainly: no. The label is doing more harm than good.

I've heard this framing from Trisha, and I'd been circling the same idea for years without landing on it this cleanly. Imposter syndrome, as a named condition, turns a normal human experience into something that happens to you. It pathologizes self-doubt rather than treating it as a signal that you're in growth territory. And the moment it becomes a condition, it becomes an excuse. "I have imposter syndrome" becomes a reason to stay quiet, to skip presenting to leadership, to turn down the promotion.

Every person who has ever been new at something has experienced doubt. That's the whole experience of being new at something. Before we had a clinical-sounding label for it, we called it being green. You were new. You wondered if you could do it. You did it anyway, or you didn't. The doubt was feedback.

The reframe that landed hardest for me was from a women's leadership conference where one attendee said she doesn't doubt that she's exactly where she's supposed to be, because she earned it and did the work to get there. That's the mental posture. It doesn't come from affirmations; it comes from an honest accounting of what you've already built and proven. A good coach does exactly this: they hold the evidence of your track record up in front of you until you stop being able to argue with it.

This connects directly to and how structured accountability changes the internal narrative faster than self-directed reading ever does.

What Do Male Allies Actually Get Wrong About Supporting Women in Leadership?

The biggest misread is around the word "flexibility."

When a high-performing woman asks her manager for flexibility, the default assumption is that she's signaling a pullback. She's going to say no to projects, no to travel, no to stretch assignments. The instinct is to accommodate a retreat. But in my experience working with agencies and services firms, and in watching talented women work through this conversation, that interpretation is usually wrong.

Flexibility is often a request for more room to say yes. More room to attend the meetings that lead to visibility. More room to take the trip that leads to the relationship. More room to think strategically rather than just execute reactively. The person asking for flexibility may want the ability to do the school pickup at 3:30 and then log back on at 9pm to finish the proposal. She's not asking to do less. She's asking for a schedule architecture that lets her do more.

When someone comes to you and asks for that kind of flexibility, the right response is a clarifying question: "What does flexibility mean for you right now?" A real conversation about what she's trying to accomplish.

The second thing male allies consistently underestimate is how often high-performing women undervalue their own track record. I've led teams where this was a pattern: the person who actually did the hardest work on a project was the least likely to claim credit for it afterward. They were already thinking about the next problem. Getting managers to actively name the impact, specifically and on the record, is one of the highest-use things an ally can do. It costs nothing and compounds over time.

According to McKinsey's 2023 Women in the Workplace report, women remain underrepresented at every level of corporate leadership above entry level, with the "broken rung" at the first step into management accounting for the largest drop-off. The awareness is there. The structural fixes are moving slowly. Which means the individual work, the mindset, the peer community, the coaching, matters even more right now.

Does the "Queen Bee" Problem Actually Block Women in Leadership?

This gets more press than it deserves.

The idea that women actively block other women from advancing is real enough to address but overstated enough to be a distraction. I've seen the active. It exists. But the far more common experience, in my observation and in the observations of people doing this coaching work directly, is that women are highly supportive of each other when given structured ways to channel that support.

Women's employee resource groups, cohort programs, peer communities built around shared experience, all of these create containers where collaboration happens naturally because people aren't competing over the same scarce resource.

When a genuine blocker does appear, the coaching approach is consistent: try first to make it a partnership. Find the shared interest. Get into their orbit. Show that you're rowing the same direction. If that genuinely doesn't work after real effort, then get out. Life is too short to manage someone who is making your environment impossible and can't be moved.

The more common pattern I see with women who feel blocked is this: they're telling themselves a story about the situation that may not be accurate. They're catastrophizing a single rough meeting into evidence of a permanent active. The coaching question is how many times has this actually happened, and when you really listen to your internal read, is this the other person or is it something else? Usually people know the answer. They just need someone to ask the question clearly enough that they stop avoiding it.

What Does a Peer Cohort Actually Do for Women in Leadership?

The cohort model works because community is the mechanism.

Reading a book on leadership is a solo activity. Scrolling through Instagram advice on work-life balance is a solo activity. Both have real value, but they don't provide what a structured peer group provides: real-time evidence that other people you respect are dealing with the same thing you're dealing with. That evidence is load-bearing for mindset change in a way that content consumption never is.

In my experience hosting The Schmidt List (over 300 episodes talking with founders, leaders, and builders), the guests and listeners consistently tell me the same thing: they learn more from hearing how someone actually navigated a decision than from any principle-based framework. The principle tells you what to do. The story shows you it's possible to do it.

A six-month cohort program, running about an hour per week of active work, accomplishes something that's genuinely hard to replicate with self-directed learning. It front-loads the operational work: getting the logistics of daily life structured well enough that mental space opens up. Then it moves into the strategic layer: influence, executive presence, courageous communication. Those two phases don't sequence properly without the operational foundation first. You can't think strategically about your next five years when the current week feels like a fire drill.

The time commitment is the objection I hear most. An hour a week feels like an imposition on someone who's already stretched. But the real cost is what the current pattern of "self-medicating" with random content and solo effort actually produces over a year, which is usually incremental improvement at best and accumulated fatigue at worst.

The cohort wins on every dimension that produces lasting behavioral change. Individual coaching without community still misses the "not a unicorn" realization, and community without coaching accountability often stays at the level of venting rather than growth.

This connects to building leadership pipelines and the case for employer-sponsored programs in the B2B services context.

How Should Women in Leadership Think About Career Transitions and Timing?

My father had a line: there are two kinds of people in the world, people who don't know they need a coach and people who have a coach. He meant it about career in general, but it applies here specifically.

The decision to leave a situation that has stopped working, whether it's a manager, a team, or an organization, is almost always made too late. People reason themselves into staying longer than the evidence warrants because the alternative is uncomfortable and the devil you know feels safer. But the framing I keep coming back to is: are you moving toward something or running away from something? Those are different decisions with different outcomes.

Moving toward something requires that you know where you're going and that you've gotten right with where you are before you leave. Running away from something usually means you carry the same patterns into the next situation and encounter the same friction in a new setting.

Scott Galloway's The Algebra of Wealth makes a related point: in any peer group, there's usually one person outperforming the rest by a meaningful margin. The interesting question is what choices that person made and what kind of community they surrounded themselves with. High performers use their peer group as a launch pad. Others use it as a comfort zone. Women in leadership who want to close the gap between where they are and where they want to be in five years need to be deliberate about building a peer group that includes people further along the path than they are.

My mom told me something similar when I was getting ready to start a family: find moms who are further down the road than you. It's the same principle. People ahead of you on the path have already made the decisions you're about to face. Their experience is a map.

I covered the mindset side of leadership transitions in depth on The Schmidt List, including conversations with coaches and executives who have navigated career reinvention in their 40s and 50s.

If your organization is under 20 people and the primary need is raw recruiting and onboarding structure, a specialized HR consultant is probably the right first call before investing in leadership development programs. Get the basics right before building on top of them.

Key Takeaways

• Women in leadership at the director-to-VP level face a specific five-year window problem: how to architect work and home life to accommodate more ambition, and most workplaces offer no framework for solving it.
• "Imposter syndrome" as a label turns normal self-doubt into a condition, which makes it feel permanent. Reframing it as ordinary doubt, the kind every person new to something experiences, restores the sense of agency needed to move through it.
• When a high-performing woman asks for flexibility, the instinct to assume she wants to do less is usually wrong. Ask what she means before you respond to the assumption.
• The peer cohort model outperforms solo coaching and self-directed learning because community provides real-time evidence that you're not a unicorn, and that evidence changes mindset faster than content does.
• Moving toward something produces better outcomes than running away from something. Get right with where you are before making a transition, then move with intention.
• Male allies' highest-use action is naming impact explicitly and on the record, because the women doing the most impactful work are typically the least likely to claim credit for it.

The question I keep sitting with is simpler than all of this: if your organization's leadership pipeline looked different in five years, what would have had to happen differently starting now?