Assertiveness, Agreeableness, and the Double Bind of Leadership Perception

Maybe you’ve been told to “speak up more.” Or… to “tone it down a little.” Maybe you’re aiming for a promotion, pitching a bold idea, or just trying to have one meeting where people don’t talk over you. Either way: you’ve stumbled into the murky waters of assertiveness. Let's get you out of those!

Because while we love confident people on paper, in practice? They’re often experienced as bossy. Or cold. Or intimidating. Or my personal favorite: “a lot.” Sometimes that's an accurate assessment, sometimes it's a bias. Which doesn't help with the murkiness!

Let’s talk about it.

The core dilemma: Nice or effective?

There’s a sneaky cultural message out there – especially for women (which we’ll get to later), but really for anyone who dares to dream bigger than being universally liked. For anyone who wants to rise to a higher position, make decisions, or lead others.

That message is: you can be agreeable, or you can be assertive. Pick one.

Be soft and warm? People love you... but they don’t always listen to you.

Be bold and direct? They listen... but now they’re scared of you, Susan.

It’s a lose-lose if you don’t know how to play the game. And spoiler: the game is rigged. But let’s start with understanding what assertiveness is, what level of it research shows is most effective, and how it relates to being "too nice."

So what is assertiveness, really?

Psychologists Ames & Flynn (2007) define assertiveness as:

“Actively speaking up for, defending, and acting in the interest of your own values, preferences, and goals.”

In work life, this might look like:

• Asking for the raise

• Pushing back on unrealistic timelines

• Setting boundaries with a client, or your colleague... or even your boss

  
  

Here’s the kicker: assertiveness is really important if you want to make it to a higher position. For leadership emergence (aka getting there), it's a key trait. Why? Because it brings instrumental benefits and makes you look like a leader (someone who can handle tough situations).

This is why assertive people often rise to leadership roles. But they’re not always the ones we like working with. High assertiveness has downsides, and if you’ve ever worked for someone like that, you know exactly what I mean.

On the flip side, if you are that person... you might not know it. Because people are often too scared to give feedback to someone in power. Maybe you've been "lucky" enough to receive anonymous feedback, or a reality check from a brave friend, partner, or your own boss.

If you’ve ever been told:

• “You’re intimidating"

• “Could you soften your tone a bit?”

• “People find you hard to approach”

…then you’ve probably been seen as too assertive – even if you just wanted to be efficient and clear.

And I say "lucky" because that awareness? It’s the key to growth. Because while you might get results in the short run, in the long run? People won’t give you feedback. Or collaborate. Or stay.

Research shows that assertiveness isn't linear. More doesn’t equal better. It’s curvy:

• 🚫 Low assertiveness = missed opportunities, underestimation

• ✅ Moderate assertiveness = high effectiveness

• 🚫 High assertiveness = tension, fear, alienation

  
  

Moderate assertiveness is the sweet spot. It means your assertiveness fades into the background and lets other skills shine – like emotional intelligence, strategic thinking, or creativity. It also means range: knowing when to be firm, and when to flex. When to lead the room, and when to let others shine. When to speak up, and when to listen and shift your view.

Most of us have a default. And for women and underrepresented groups, that default is often low assertiveness. We’ve been socialized to maintain harmony, not challenge it.

Cue every woman who’s ever said, “Sorry, just one quick thing: ... ” when she had the best idea in the room.

So let’s unpack why the game is rigged.

Cultural seasoning: Gender norms and spicy backlash 🌶️

Assertiveness is never judged in a vacuum.

• When a white man speaks up in a meeting, he’s confident.

• When a woman does it? She’s "intense."

• When a woman of color does it? She’s "angry."

This is the double bind: to be seen as competent, you have to be assertive. But the moment you are, you risk violating gender (or racial) norms around "niceness."

Here’s the science behind it: people judge others along two basic dimensions: warmth and competence. Warmth is about intent (do you mean well?), and competence is about ability (can you act on it?). Women are stereotypically expected to be high on warmth, men on competence. But leadership expectations? High competence, moderate warmth.

So while men get:

• 💼 Assertive = Leader

  
  

Women get:

• 🦹‍♀️ Assertive = Bit** (sorry for swearing)

  
  

Changing gender norms is slow. Progress is happening as we're seeing emotional intelligence, vulnerability, and empathy valued more in leaders, but we still have a way to go.

And men aren't immune to this. A non-assertive man doesn’t just violate leader norms, but also gender norms. Cue: “Why does the nice guy never win?”

But let’s get one thing clear: nice ≠ non-assertive.

The "Too Nice" lie (aka high agreeableness)

If you’ve ever:

• Agreed to keep the peace

• Asked for others opinion even though you're quite confident in what you're doing

• Avoided saying no because you didn’t want to seem "difficult"

  
  

…hi there. You're likely very agreeable.

Agreeableness isn’t bad. It’s beautiful. It’s about empathy, warmth, and literally reflects the motivation to maintain positive relationships. It keeps us happy, healthy, and alive.

The problem? When high agreeableness meets low assertiveness, you become well-liked… but not listened to. You’re helpful, but invisible. And that’s not where power lives.

So let’s clear this up:

• Agreeableness = motivation to maintain harmony

• Assertiveness = motivation to advocate for your own needs

  
  

They’re not opposites. But they are separate. And to truly thrive – especially in your career – you need both.

So what’s the secret? Combine the two.

Assertiveness ≠ aggression

Agreeableness ≠ passivity

The magic happens when you mix them:

• 👑 Warm + Confident

• ✨ Kind + Clear

• ⚖️ Collaborative + Unshakeable

And I have a little superpowered-trick that might help you to get the level exactly right.

It's something I call cognitive empathy-powered assertiveness, and it’s not about turning down who you are - it’s about turning up your communication in a way that fits the moment and your values.

7 Ways to Practice Cognitive-Empathy powered Assertiveness (Without Losing Yourself)

1. Regulate before you relate. If you're emotional, your behavior gets fuzzy. Breathe first. Focus on understanding others' experience, not feeling their emotions.

2. Zoom out. What might this look like from their perspective? Why might they disagree?

3. Ask instead of assuming. Curiosity beats mind-reading, especially if you're unsure.

4. Listen to learn, not reply. Repeat back what you heard - then speak your truth.

5. Name the emotion, not the drama. “I hear your frustration” instead of “Calm down, you're overreacting.”

6. Validate without agreeing. “I understand where you are coming from” ≠ “You’re right.” (unless, duh, they are right. Feel free to agree then ;-))

7. Set boundaries with warmth. “This is the direction we need to go - and I really appreciate your input.”

🔁 Practice Makes Power!

Experiment with this a little bit – to find out in which meetings, settings, and with which people you can tone down your assertiveness without being taken advantage of, and when you need to tone it up to achieve more instrumental benefits for yourself without losing the social benefits you've been getting.

Pro tip? It’s often strategic to assert competence and confidence first so those are a given – before showing your more agreeable side. But take feedback seriously if you need to work on being a better teammate or more likable – because even if you get the job done, long-term effectiveness requires others. And let’s be honest: it’s much nicer to be nice.

No one really wants to be a douchebag. They just believe they need to be. Well… here’s some proof that’s simply not true.

In summary:

The goal isn’t to be “just assertive enough.” It’s to build the range. To move flexibly between caring and clarity, between harmony and impact.

Because when done right, assertiveness isn’t even noticed. You’re just experienced as… powerful. And kind. And real. And that, my dear reader, is the goal.

Let's work on this together! And break down the stereotype that female, communal, agreeable and nice does not equal a leader image to strive for. How do we do that? By becoming leaders – to our friends, communities and colleagues – and then showing everyone that we can be both nice, and get sh** done. (sorry again, for swearing 😬)

Yours, truly,

Valli

Want to learn more about my own research on cognitive empathy? [Check out my post: The Art(s) of Empathy. ... or let me know if you'd like to read my 210 page doctoral dissertation on it ;-) ]

Sources:

Ames, D. R., & Flynn, F. J. (2007). What breaks a leader: The curvilinear relation between assertiveness and leadership. Journal of Personality and Social Psychology, 92(2), 307–324.

Blake, A. B., Wong, K., Kuncel, N. R., & Sackett, P. R. (2022). Nice guys can finish first: The competitive advantage of agreeable leaders. Journal of Applied Psychology, 107(6), 1030–1052.

Triana, M. d. C., Richard, O. C., & Ybarra, C. (2024). Extending role congruity theory: Gender, race, and leadership evaluations in contemporary organizations. Academy of Management Annals, 18(1), 1–47.

Rudman, L. A., & Glick, P. (2001). Prescriptive gender stereotypes and backlash toward agentic women. Journal of Social Issues, 57(4), 743–762.

and my own research on empathy!