Have you ever agreed to take on something you didn’t really have time for?

Said “yes” when you wanted to say “no”?

Avoided a difficult conversation because you didn’t want to disappoint someone?

If you’re like many women leaders in IT, you’ve probably done all three.

You care deeply about your team.

You want to be supportive.

You want people to feel valued and respected.

But over time, those good intentions can sometimes turn into people-pleasing.

And people-pleasing can quietly undermine your effectiveness as a leader.

But what if those behaviors aren’t simply habits?

What if they’re the result of messages you’ve been receiving since childhood?

In this episode, we’ll uncover the real reason women leaders in IT struggle with assertiveness—and how to lead with more confidence and credibility. 

Learning to Lead with More Confidence and Credibility as a Woman Leader in IT

For many years in my early IT career, I struggled with this. 

I wanted to be supportive and helpful, I wanted people to feel valued and appreciated, and I’ll admit it—I wanted people to like me.

And I don’t think that’s uncommon for women, especially in your first leadership position. In fact, it’s something I see regularly with women leaders.

They’re intelligent, capable, hardworking and highly respected for their technical expertise.

But they often hesitate to set boundaries, have difficult conversations, or advocate for themselves as leaders because they worry about how they’ll be perceived.

And there’s a reason for that.

Researchers have spent years studying the differences in how girls and boys are socialized.

Girls are often praised for being helpful, cooperative, agreeable, and considerate of others. While boys are encouraged to be independent, competitive, confident, and willing to take risks.

Neither approach is inherently right or wrong. But over time, these messages shape how you see yourself and how you interact with the world.

Many women grow up learning that being liked is important, being accommodating is a strength, and keeping the peace is a positive trait.

And while those qualities can serve you well in personal relationships, they can become challenging in leadership roles.

Because leadership often requires something very different:

By the time many women reach leadership positions, they aren’t lacking intelligence, capability, or ambition. They’re often carrying decades of conditioning about being agreeable and avoiding conflict.

One of the concepts that resonated deeply with me comes from Brené Brown’s work on belonging. She describes the difference between fitting in and belonging. 

Fitting in requires you to change who you are in order to be accepted whereas belonging requires you to be authentic about who you are.

As I reflected on my own leadership career in IT, I realized there were times when I softened my message, hesitated to speak up, or adapted my communication style because I wanted to fit in.

Many women leaders in IT experience something similar.

You soften your message, over-explain your decisions, apologize when no apology is necessary, and say yes too often when you should say no. 

Yet every time you soften your message, avoid a boundary, or withhold your perspective, you teach others that your needs, ideas, and opinions are negotiable.

And they’re really not. 

Belonging looks different. It means trusting that your ideas have value, even when they’re different from everyone else’s. It’s expressing your perspective without apologizing for it, setting boundaries without feeling guilty, and having difficult conversations because they’re necessary, not because they’re comfortable.

And it means leading in a way that aligns with your values instead of constantly adapting yourself to meet everyone else’s expectations.

That’s where assertiveness begins. Not by becoming louder or by becoming aggressive. But by becoming more comfortable being fully yourself.

When men are direct, they’re often perceived as decisive. But when women are direct, they may be perceived as aggressive.

Women frequently receive conflicting messages: 

It can feel exhausting!

The good news is that assertiveness doesn’t require becoming someone you’re not. In fact, some of the most assertive women leaders in IT I worked with were also kind.

Assertiveness isn’t aggression, it’s not dominance, and it’s not demanding your way. It’s expressing your thoughts, expectations, needs, and boundaries clearly and respectfully. 

As I developed my own assertiveness over the years, something interesting happened. 

People trusted my decisions more, difficult conversations became easier and I didn’t feel the stress of carrying responsibilities that didn’t belong to me. I found that people actually respected me more, not less.

Many women believe they have to choose between being kind and being assertive. You don’t—you can be both. 

So how do you begin to strengthen your assertiveness?

First, seek constructive feedback.

Ask trusted colleagues, mentors, or leaders where they see opportunities for growth. 

Be genuinely curious. Sometimes others can see patterns we can’t.

Second, practice setting boundaries.

Start small—say no to something that doesn’t align with your priorities. 

Protect your calendar, your energy, and your focus.

The more you practice, the easier it becomes.

Third, rehearse difficult conversations.

Many leaders avoid difficult discussions because they haven’t thought through what they want to say. Practice beforehand. Write down key points and role-play, if needed. 

Confidence often comes from preparation.

And pay attention to the language you use. 

Notice how often you say: “I’m sorry…”, “This might be a bad idea…”, “I’m probably wrong, but…”. Those phrases can unintentionally diminish your message.

Instead, try: “Here’s my recommendation”, “Based on what I know…”, or “I’d like to share a perspective.” Small shifts create powerful results.

If you’ve struggled with assertiveness, I want you to hear this…there is nothing wrong with you. You’re not broken or incapable of leadership. 

You may simply be operating from patterns that no longer serve you.

The beautiful thing about leadership is that every skill can be learned. And assertiveness is no exception. I’ve watched so many women leaders in IT transform their careers by becoming more assertive. They gain confidence, credibility and influence.

Most importantly, they gain the freedom to belong by leading authentically.

If you haven’t listened to it already, there is an earlier episode, #4 – Why Assertiveness Drives Success for Women Leaders in IT that would also be helpful to hear. In that episode, I focused on the importance of assertiveness and the impact it can have on your leadership effectiveness.

What I’ve come to understand is that before we can strengthen assertiveness, we often need to understand what’s been getting in the way of it all along.

And for many women, it isn’t a lack of capability or confidence. It’s years of conditioning, expectations, and patterns that no longer serve them.

If this is something you’ve struggled with, know that you’re not alone. It’s one of the most common challenges I help women leaders work through.

When you learn how to communicate with confidence, set healthy boundaries, and advocate for yourself effectively, everything changes.

You gain confidence, credibility, and influence.

But perhaps most importantly, you gain the freedom to lead authentically.

Not by becoming someone else, but by becoming more comfortable leading as yourself.

Stay empowered and lead assertively!

TOPIC: Thrive in a Male Field