Stop Telling Women to "Lean In"—Teach Men to Listen Up

Beyond the binary: where the best leadership truly lives.

In the late '90s and early 2000s—(are you thinking, “okay, grandma”)—I learned quickly how to lead like a man. Or, more precisely, how to lead in a way that men in tech would respect.

Power stance. Crisp bullet points. Speak fast. Don’t cry. Don’t hug. Act like you know everything, even when you don’t. Defer to the hierarchy.

It was an era when, for someone like me, being a woman in leadership meant choosing between my authenticity and my authority. I chose authority—or tried to.

A Quick (and Imperfect) Framework

Before we go any further, let me acknowledge that using "male" and "female" leadership styles is reductive and overly simplistic.

Leadership is not gendered, and gender itself is not binary.

Anyone of any gender can embody and express any of these leadership qualities. What we often label as "masculine" or "feminine" traits are just that—labels, not rules.

But for this article, here’s how I’m using the terms:

• Traditionally "male" leadership: assertive, competitive, logical, hierarchical, independent.

• Traditionally "female" leadership: relational, collaborative, emotionally intelligent, intuitive, nurturing.

Neither is better. Both have value. And most of us lead with a blend.

Learning to Lead Like a Man

In the B2B tech world I entered, leadership was about driving results, owning the room, and not letting anyone see you sweat. That meant being dominant, unyielding, quick to decide, and quick to interrupt. It meant prioritizing control over collaboration and often mistaking confidence for competence. Those traits came easily to some of us. Others of us had to wear them like costumes.

I vividly remember being in my twenties and copying the tone of male mentors because they were the only models I saw.

Empathy? Soft.

Flexibility? Weak.

Pause to consider feelings? Not unless you wanted to be dismissed.

I even had the extraordinary opportunity to work with Madeleine Albright on two major projects during that time. She was brilliant, commanding, and deeply respected—everything I aspired to be.

But like many women of her generation, she led in a way that mirrored the men around her: decisive, unflinching, formal, and incredibly tough in ways that I interpreted as meanness at the time. At the time, I saw her style as the gold standard. Watching her taught me what was possible for women at the highest levels of leadership—but also what it cost for someone like me.

Only later did I begin to wonder if there were other ways to lead that could be just as powerful.

So I started to feel like a person who was split and acting like something I wasn’t to get respect and attention.

The First Time I Saw Something Different

It was more than 15 years into my career before I worked for Shannon Latta, a woman who modeled a new way for me. She was a total badass: smart, powerful, results-oriented. But she didn’t lead like the men I had modeled myself after.

She listened more than she spoke. She asked great questions. She didn’t fill space with bravado. When she assigned out a project, she would say “does that deadline work for you?” and she would actually listen to the answer. She didn’t apologize for being human.

And you know what? People followed her. They wanted to. She got results without steamrolling. Her team would have walked on coals for her. That blew my mind.

More recently, I worked with Sangram and Bryan, who also led with what most people would consider more traditionally feminine traits.

They were calm, emotionally present, great listeners, and naturally collaborative. Their leadership felt familiar in the best way—it reminded me of how I worked when I wasn't trying so hard to be someone else. It was validating to see that those traits weren’t just effective in women. They were effective, period.

Empowerment or Overcorrection?

About a decade ago, I worked with an executive coach for women who was herself a Baby Boomer in the style of Hillary Clinton, Carly Fiorina, or Madeleine Albright.

Although she was a client of mine, I saw the advice she gave her own clients straight from the power playbook:

• Don’t apologize, even when you’re wrong—male leaders never do.

• Don’t offer to get the coffee at a leadership meeting—male leaders never do.

• Don’t step aside in the hallway when someone is coming the other way—male leaders never do.

• Let your ideas sit in the room without softening them (no more introducing a powerful idea with “I was thinking that maybe we might . . .”)

• Take up more space.

• Don’t ever talk about your kids or your personal life at work.

• Don’t dress too femininely if you want to be taken seriously.

• Work twice as hard and never complain.

• Never rock the boat. Take your lumps and prove yourself, even if you’re facing gender discrimination.

She taught women to unlearn the rules we’d internalized to be liked. And to replace them with new rules about being heard, respected, and trusted.

To be sure: it is important to get away from worrying about being liked.

But here’s the thing: it never sat right with me to refuse to make space for someone at a table, or to decline a chance to help someone, just to make a point that I was “the boss.”

I didn’t want to become rigid in the opposite direction. I didn’t want to lead from resentment. Making room for someone in a hallway or offering to grab a coffee didn’t feel like weakness to me—it felt like kindness.

The problem wasn’t that things shouldn’t be done or that women were doing these things. The problem was that those actions were undervalued or expected only of women.

What I really wanted was for those gestures to be seen as leadership, too.

The Gender-Expansive Present

Fast forward to now: thankfully, we’re in a different place. Not perfect, but different. We understand that gender isn’t binary, and we’re starting to honor a fuller range of leadership styles.

The best leaders I know are aware of when to push and when to listen. When to be decisive and when to be curious. When to protect and when to empower.

The Rise of Servant Leadership

Have you noticed the rise of servant leadership in recent years? It’s a style defined by putting others first, removing barriers, and supporting growth. Leaders who serve instead of command.

According to the National Society of Leadership and Success:

Servant leadership is a style based on the desire to serve and give to your community. By putting the needs of others first, you empower people to perform at their best.

Servant leadership goes against the beliefs that leadership is defined as hierarchical, patriarchal, and related to wealth or status. Instead, as the name implies, it is focused on serving others to help them grow, often without the title or recognition that comes with many leadership roles.

Sound familiar? That’s what we used to call feminine leadership.

Now that men are embracing it, it’s considered progressive, enlightened, and strategic. And yes—it is all those things. But it also raises a question:

What If We Flipped the Script?

What if, instead of teaching women to dial down their intuition, warmth, and collaborative instincts, we taught men to lead with more vulnerability, empathy, and presence?

What if, instead of telling women to "act more like men," we acknowledged that the most effective leaders know how to draw from all parts of themselves, regardless of gender?

What if, instead of telling women to stop apologizing, we should teach men to be more comfortable apologizing.

What if the future of leadership is human, not masculine or feminine?

What if the future of leadership is nonbinary?

Try This: What’s Your Leadership Blend?

Score each statement from 1 (not at all like me) to 5 (very much like me):

• I prioritize team harmony over individual performance.

• I make decisions quickly, even without full information.

• I naturally create space for quieter voices.

• I assert my authority, even when it creates tension.

• I check in on how people feel, not just how they perform.

• I thrive in high-stakes, competitive situations.

• I listen more than I speak.

• I focus on long-term impact over short-term wins.

Results:

• Mostly 1–3s: You lean toward traditionally "male" leadership traits.

• Mostly 4–5s: You lean into traditionally "female" traits.

• A healthy mix: You’re living in the nonbinary leadership future. Welcome.

What I Wasn’t Taught to Value (But Rely On Now)

No one taught me to value intuition. Or softness. Or knowing when not to talk. Or the ability to build trust without needing to control. Or working with direct reports as collaborators instead of minions.

Now, I rely on all of that.

The most important things I bring to the table as a leader today?

Self-awareness. Curiosity. Humor. My ability to read a room. My willingness to admit when I’m wrong. My comfort with apologizing when I’ve made a mistake.

The Invitation

Leadership isn’t a role. It’s a set of practices. And like any practice, it evolves.

So here’s your invitation: Whatever your gender, expand your leadership range. Lead from your full self. Reward those who do.

Masculine and feminine traits each bring enormous value to leadership. Not all men lead like “men, " and not all women lead like “women.” And of course younger generations are exploring the nonbinary and all the wonderful things that concept brings to the table. (If you’re not familiar with the concept of nonbinary gender, this is a great resource).

The best leaders I’ve worked with know how to choose the best qualities of each—and discard the worst. It’s not about being one way or the other. It’s about having range, discernment, and the courage to show up with intention.

Because the future belongs to leaders who are flexible, self-aware, and human.

And that’s not just feminine. That’s revolutionary.

Work with Me

If you’re navigating the messy, magical, sometimes overwhelming transitions of your company, GTM strategy, and/or professional life, I’d love to support you. Most leaders have plenty of hustle, what they need is support.

I work with visionary founders and sales and marketing leaders on go-to-market strategy, leadership, clarity, and growth. I’d love to chat about what you need.

I also lead two “How’s Work” workshops every month, open to all. We use writing prompts to explore decision-making, conflict, career, ambition, leadership, change, and work stress.

I’d love for you to join me.