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Women in Leadership: The System Is Rigged (And So Are The Patterns)


By Jeff Matlow · Executive Coach · Published June 24, 2026

Maya ran a $150M business unit.

She had 7 directors reporting to her, and an entire team of 80 people. The Board trusted her, and she had a reputation for being the person you wanted in the room when bad things started happening. She was a great representative for women in leadership.

She came to me after she'd been passed over for the COO role.
Again.

The feedback she got was the kind that sounds like a compliment, wrapped in an uppercut to the jaw. "We love Maya. She's great. She's just not quite ready for the COO role. We need someone who is more assertive."

So Maya become more assertive.

The next review?

"Maya's gotten a little more aggressive than she used to be. People are finding her hard to work with."

Same person. Same behavior her male peers got promoted for. Different reaction.

Maya wasn't confused about leadership. She was caught in a set of patterns that almost all the women in leadership I coach get caught in. And almost none of them can see what's happening from the inside.

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The Patterns I See Again and Again From Women In Leadership

About 70% of the people I coach are women in leadership, running real businesses at organizations you'd recognize, from the Global 100s down to fast-growing mid-size companies. I see both sides of the gender coin.

I'm not going to pretend I know what it's like to be a woman. I don't. But I've watched the same patterns surface across dozens of women in leadership, and the patterns are clear. Here's what I see showing up the most.

The double standard nobody admits to. Be confident, but not bossy. Be decisive, but not cold. Be warm, but not soft. The target is always moving, depending on who's judging. This is the one that finally broke Maya. The same exact behavior that is a "great leader" in a man is a "bad attitude" in a woman. This isn't fake news. The research on this is overwhelming. And almost all the women in leadership have felt it, in one way or another.

The apology reflex. Women tend to be more empathetic than men. That's a leadership superpower, not a weakness. Empathy is what lets you read a room, build a team of dedicated people, and have the hard conversation without turning it into a battle. But humans tend to apologize when they have empathy. And since women in leadership tend to be more empathetic, they also tend to apologize more. Too much. "Sorry to bother you." "Sorry, quick question." Sorry for existing in a meeting you were invited to but still feel like the odd one out. Empathy is an asset. Over-apologizing diminishes the asset's value.

The negotiation gap. Study after study show women in leadership negotiate less aggressively on their own behalf. That means they end up with lower salaries and less benefits. But it gets worse. Because when women in leadership do negotiate as hard as men, they're more likely to get penalized for it. "She's so aggressive!" To be clear, it's not simply that women don't ask for what they want, it's that the environment punishes them for asking.

The imposter voice that won't quit. Imposter syndrome in leadership is not gender specific, but it is more often found with women in leadership, especially the ones who are the only woman, or one of the few, at their level. When you don't see other people who look like you in the room, your brain convinces you that you must not belong there. That voice often yells the loudest in the heads of the people who least deserve it: women in leadership.

The visibility problem. The work gets done. The results are there. But somehow the credit goes somewhere else - to the team, to the process, or to the colleague who presented what you built. Women in leadership often have to make a more deliberate effort to be seen than their male peers. Not because their work is less visible. Because the room defaults to noticing certain people first. And it's often not women.

The sponsorship gap. Mentors give you advice. Sponsors put their name behind you in rooms you're not in. That difference matters more than most people realize. Women in leadership are often well-mentored and under-sponsored. Senior leaders tend to sponsor people who remind them of themselves - and in most companies, that's men. Advice helps you develop. Sponsorship is what actually moves careers.

I'm not making any of this stuff up. It is very well documented. Women make up 47% of the workforce but only hold 38% of manager-level roles and just 25% of executive leadership roles. Don't believe me? Check out The State of Women (Leaders).

The numbers don't lie. Women in leadership are fighting against a headwind. The struggle is real.

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The Confidence Gap Is the One I Fight Most

Of every pattern on the list above, the Confidence Gap is the one I work on most with my female leadership coaching clients. The basic gist of this is that women tend to underestimate their abilities and men tend to overestimate theirs. Same competence, different self-assessment.

Hewlett-Packard found that women applied for a promotion only when they believed they met 100% of the listed qualifications. Men applied when they met 60%.

Let me make sure you understand what I just wrote there.

The men were NOT more qualified. They were simply more willing to be unqualified in public.

Unfortunately, people get promoted because they are willing to be seen as being "ready" before they're actually ready.

That's the Confidence Gap. And it's a big bad problem for women in leadership. It keeps women hidden while less experienced men take the jobs from under their noses.

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Why a Man Coaching Women In Leadership Is Helpful

I know how that header reads. Stick with me here.

You see, there's an important thing that a lot of advice for women in leadership misses. It's that the room you're walking into is usually run by men. Your boss, your boss's boss, the three people on the promotion committee who keep saying you're "not quite ready." I'm guessing most, if not all of them, are men.

I can tell you, with reasonably great accuracy, what's going on in those men's heads when you walk into their conversation. Not because I'm smarter. Because I've been the guy in those rooms, and I've coached a lot of guys in those rooms. I know what behavior they shine to and which ones they back away from. I know how to say the things that boost the level of influence for women in leadership.

When Maya pushed back in a meeting and watched her boss close down, she read it as "he doesn't respect me." I could tell her what he was actually thinking, how he'd interpret the exact same move from a male VP, and what small adjustments she could make to get the result she wants.

I do this all the time for women in leadership.

Keep in mind, this isn't about sacrificing morals or changing who you are to please men. Heck no. I'd never tell you to do that. Instead, it's about understanding how you're being viewed so you can navigate the dynamic that most people can't even see.

And on the other side of it, I've felt my share of Imposter Syndrome. I know the feelings of self-doubt, the rage at the double standard, and the embarrassment of the spotlight effect. I can read the room and have empathy at the same time. That's why so many women in leadership call me when they're interested in executive coaching.

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What Actually Helps

I'm not going to tell you to be more assertive, less assertive, or to find your authentic leadership style. That advice is everywhere and it puts the entire weight of a broken system on you. I don't find that honest or useful.

Here's what I've seen actually work.

Get clear on what you're actually trying to do. Some women in leadership decide the environment isn't worth fighting and go find a better one. Some stay and work to change it from the inside. Both are valid. What doesn't work is staying somewhere that's costing you, while telling yourself it'll get better on its own. It won't. Get clear on what you want.

Find a sponsor, not just a mentor. Mentors help you grow. Sponsors go to bat for you when you're not in the room. There's a big difference. Identify a senior leader who has seen your work and who advocates for others. Then make your ambitions clear to them. Direct and honest. "I want to move toward an X role. I'd love your perspective on what that path looks like for me." Most sponsors don't know they're needed until someone asks.

Make your work visible on purpose. This isn't self-promotion in the performative sense. It's making sure the right people know what you're producing. Women in leadership tend to be modest about their accomplishments. Don't do that. Share results in writing. Connect your work to outcomes that senior leadership cares about. Reference your contributions directly in meetings instead of saying "the team" when the work was yours. You don't have to be loud about it. But you do have to be deliberate.

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The Part That's Actually About You

Everything I've mentioned - the double standard, the negotiation penalty, the confidence gap - it's all real. You're not imagining them. They all impact women in leadership roles.

But here's the problem.

You've adapted to those forces for so long that your behavior has become patterns that are now working against you.

The over-apologizing started as a way to stay likable. Now it's automatic. And every time you over-apologize, you're giving the message to men that you don't act confidently in managing others.

The over-preparing, the triple-checking, the doing it all yourself so no one can question your competence, that started as armor. Now it's the reason you have difficulty delegating and your team stays dependent on you.

Your leadership blind spots are working against you at work. The strategies that got you to where you are now, have become the ceiling stopping you from growing further. And because your behaviors have worked for so long, you can't see that they've turned against you. It's the same reason leaders repeat the same mistakes without ever knowing why.

I can't change the system in a coaching session. I wish I could. What I can do is help you see which patterns are still serving you and which ones are now working against you in your Pattern Environment Loop. Then we redesign how you operate so you stop falling victim to the things you don't even know you've been victimized by.

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What Changed for Maya

In the end, I didn't make Maya more assertive. She was plenty assertive. We helped her better read the room and react accordingly.

She learned to read what the men in the room were actually thinking, drop the reflexive apologies that were undercutting her credibility, and stop being the crutch for a team that needed to walk on their own.

Maya got the COO role 8 months later. It's not because she became someone else - she didn't. It's because she stopped letting her old patterns control her.

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The forces working against women in leadership are real, and the research backs every one of them. The American Psychological Association's review of the evidence shows women still face challenges to their authority that their male peers simply don't. That's true. It's just not the whole story.

You're not a statistic. You're a specific person with a specific set of patterns, some of which are unconsciously working against you right now. The question isn't whether the system is fair. It isn't. The question is what you're going to do about the part that's actually in your control.

If you want to see your own patterns clearly, the kind you can't spot from inside them, that's exactly what the Leadership Diagnostic Workshop is built for. It's free, it's 90 minutes, and you'll leave seeing things about how you lead that have been invisible to you for years. Once you see your patterns, you'll never be able to unsee them again.

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Jeff Matlow is a leadership coach, mentor and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He's spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.