The Hidden Difference Between How Male and Female Leaders Approach Executive Coaching

I was recently invited to join David Chung on the Coach as Entrepreneur podcast for a conversation about coaching, leadership, business building, curiosity, and what it really takes to grow as both a coach and a leader.

At one point in the conversation, we touched on something I see surprisingly often in executive coaching: men and women frequently enter the coaching space from very different psychological starting points.

Of course, these are general trends rather than universal truths. Personality, culture, industry, upbringing, organizational environment, and life experience all matter. Not every man or woman will recognize themselves in this dynamic.

Through executive coaching, leadership development, and organizational consulting work, I’ve had the opportunity to support leaders across startups, multinational companies, and high-growth environments in more than 35 countries. And across those experiences, I do notice certain recurring patterns.

Many male executives enter coaching from a place of confidence. Many female executives enter coaching from a place of self-dount and over-awereness. And that difference shapes the starting point of the work.

How many senior male leaders approach executive coaching

When I meet with senior male leaders, especially highly experienced executives, the first conversation often sounds something like this:

“I’ve been managing people for years. I know what I’m doing. But tell me, Alexandra, what exactly can coaching offer me?”

There is usually genuine curiosity, but it is often mixed with authority, skepticism, and a subtle expectation that the coach first needs to prove their value before the relationship can fully begin.

The questions themselves may sound practical: How does the process work? What methodology do you use ?What exactly could you teach me? How will this improve my performance?

But underneath, there is sometimes another dynamic happening too: “Convince me this is worth my time.”

And honestly, I understand where that mindset comes from.

Many senior leaders have spent years being rewarded for decisiveness, competence, certainty, and control. They are used to being the person others rely on for answers. Their experience taught them that trust should be earned, not automatically given. So even when they intentionally seek professional support, there can still be an instinct to evaluate, test, and assess the person sitting in front of them before allowing real openness into the room.

The easiest way I can describe it is this: the door is technically open, but the coach is still expected to find the handle, walk in carefully, and prove they belong there before deeper trust is extended.

And this does not necessarily show up in an arrogant or aggressive way. In many cases, it is actually much more subtle. Sometimes it appears through skepticism. Sometimes through intellectualization. Sometimes through keeping the conversation highly rational and performance-focused at the beginning. Sometimes through trying to quickly assess whether the coach has enough credibility, business understanding, or seniority to “deserve” access to the more vulnerable side of leadership.

So with many male executives, coaching often begins with building enough credibility, trust, and psychological safety for deeper reflection to happen. Not because they lack capability, but because long-term authority and professional success can sometimes make it harder to immediately access uncertainty, vulnerability, emotional patterns, blind spots, or the more human side of leadership pressure.

How many women leaders enter executive coaching

With many women leaders, the dynamic often looks very different.

In the first few minutes, they may already give me a full list of everything they believe they need to improve:

“I need to communicate more confidently.” “I need to stop overthinking.” “I need to be more assertive.” “I need to improve my executive presence.” “I need to become more strategic.” “I need to handle conflict better.”

Very often, they have already reflected deeply on themselves before the coaching even begins. They have collected feedback, analyzed their own behavior, identified patterns, and mentally replayed difficult situations multiple times before ever entering the room.

And unlike many male executives, the trust and willingness to do difficult inner work are often already there from the very beginning.

The easiest way I can describe it is this: the door is already wide open, the coffee is ready, and they are sitting on the sofa waiting for you with a notebook full of reflections, questions, and self-observations.

The challenge is usually not getting access to vulnerability.

The challenge is helping them realize they are not as “behind” as they believe they are.

Because many women leaders already arrive highly prepared to do the work. They are ready to reflect, ready to challenge themselves, ready to be vulnerable, and ready to take responsibility for growth. But very often, they are also carrying an overwhelming awareness of every perceived flaw, weakness, mistake, or area for improvement.

Sometimes they know themselves too critically. There is no real balance. The focus becomes almost entirely centered around potential gaps, external feedback, comparison, expectations, and perceived areas of opportunity, rather than an internal sense of self, authenticity, clarity, and trust in their own leadership style and direction.

So the coaching work does not always begin with increasing self-awareness. Sometimes it begins with reducing the internal noise and reconnecting them with their strengths, competence, values, and leadership capacity.

Why are you in this role? What strengths helped you get here? What are people already trusting you with? What kind of leader do you actually want to be? And what if you do not need to fix everything before allowing yourself to lead confidently?

And honestly, this is one of the most emotionally exhausting dynamics I see in high-performing women. Many are carrying enormous responsibility while simultaneously feeling that they still somehow need to prove they deserve to be there.

Why confidence often looks different in women leaders

When women struggle with confidence at work, it is very easy to frame the issue as purely individual.

“She needs to speak up more.” “She needs more executive presence.” “She needs to become more assertive.” “She needs to be more confident.”

And yes, sometimes those are real developmental areas. But context matters too.

Research from organizations such as McKinsey & Company and Lean In continues to highlight persistent differences in how men and women experience confidence, visibility, feedback, self-perception, and leadership expectations in the workplace.

Even though this is slowly changing, many women still grew up seeing far fewer leadership examples that looked or sounded like them. Fewer visible examples of women leading with authority while also remaining authentic to themselves. Fewer examples of different ways to lead successfully.

So when a woman enters a senior leadership environment where most decision-makers are still men, she is often building her own internal reference point in real time. That takes energy.

It can also quietly create pressure to constantly self-monitor: Am I being too direct? Too emotional? Too soft? Too ambitious? Too visible? Too difficult? Too much?

One phrase I hear surprisingly often from women leaders is the fear of being perceived as a “drama queen.” I have almost never heard a male executive use that phrase about himself.

That difference matters because leadership behaviors are not always interpreted equally. The same level of directness, confidence, or emotional expression may be received very differently depending on who is displaying it. Again, not always, but often enough that many women internalize the risk long before they consciously realize it.

Why executive coaching often starts differently for men and women

With some male executives, coaching may initially focus on increasing reflection and helping them recognize patterns they may not yet fully see clearly.

Where is confidence becoming defensiveness? Where is experience becoming rigidity? Where is control limiting team ownership? What impact are leadership habits having on others?

With many female executives, coaching often begins somewhere else entirely:

What feedback actually matters? What are you over-owning? Where are you minimizing your strengths? Where are you holding yourself to impossible standards? Where are you trying to become acceptable instead of effective?

The starting points may look different, but the goal is often the same: helping leaders become more self-aware, grounded, emotionally intelligent, and effective in the way they lead.

The goal is not to make women lead like men

I think this is an important distinction.

The goal of leadership coaching is not to help women imitate historically masculine leadership styles in order to succeed. It is not about becoming louder for the sake of being louder, tougher for the sake of being tougher, or more dominant simply because those behaviors were historically rewarded.

The work is much more nuanced than that.

It is about helping women understand their own leadership style more clearly, strengthen confidence, navigate organizational dynamics intentionally, and make conscious choices about how they want to show up.

Sometimes that means becoming more direct. Sometimes it means setting stronger boundaries.

Sometimes it means taking up more space in conversations. Sometimes it means speaking with less apology or over-explaining. And sometimes it simply means realizing they were never as “behind” as they believed.

Executive coaching creates space leaders often do not have elsewhere

One of the things I think many people underestimate about executive coaching is how few spaces senior leaders actually have where they can think openly.

The more responsibility leaders carry, the more they are expected to appear composed, decisive, emotionally regulated, and certain, even when internally they may be navigating ambiguity, pressure, difficult decisions, or self-doubt.

That is why coaching is not only about performance.

At its best, executive coaching creates a confidential thinking space where leaders can process complexity honestly, reflect more intentionally, and step outside the constant pressure to perform certainty.

And honestly, many leaders do not realize how much they needed that until they finally experience it.

Final thoughts

The way leaders ask for help tells us a lot.

Some leaders enter coaching needing to discover what they may not yet see clearly. Others arrive already carrying an overwhelming awareness of every perceived flaw, weakness, or area for improvement.

Both deserve thoughtful coaching support. Not coaching that reinforces ego. Not coaching that reinforces self-doubt. But coaching that helps leaders see themselves more clearly, more honestly, and with more perspective.

Because executive coaching is not about making everyone lead the same way. It is about helping leaders become more intentional, more self-aware, and more sustainable in the way they lead themselves, their teams, and their organizations.

If you are navigating leadership growth, visibility, confidence, complexity, or organizational pressure and want a thoughtful space to reflect more clearly, you are welcome to explore my work or book an introductory conversation.

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Check out the full episode “The Hidden Difference Between How Male and Female Executives Ask for Help”on Coach as Entrepreneur podcast 

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