The Pleaser’s Edge

Knowing Yourself for Fun and Profit

One of the leaders I admired early in my career often said, with a wry grin, “I’m a pleaser.” He presented it self-deprecatingly, as if it were a flaw he’d learned to accept. Yet he was an effective, respected leader. I’ve reflected on that paradox many times, because I’m a pleaser too.

I’ve wondered whether that’s a weakness or a strength. The answer, as with most traits, is both. But the real shift came when I stopped trying to fix it and started learning how to work with it.

When Wanting to Be Liked Gets in the Way

Let’s start with the obvious: being a pleaser can get you in trouble.

You want people to like you. And the truth is, particularly as a leader, that’s never going to happen—not always, and certainly not with everyone. If you base your sense of success or safety on universal approval, you risk trading long-term outcomes for short-term relief.

Worse, people can exploit that instinct, often without even meaning to. Your desire to win someone over can lead you to say yes too quickly, soften necessary feedback, or preserve harmony at the expense of alignment. You can end up undermining your own authority and steering the team off-course.

So yes, it can be a weakness. But it’s also something else.

Why It’s a Superpower Too

Wanting people to like you means… you care. You tune in. You notice what others are feeling. You think about how your words will land, not just what you’re trying to say.

That’s not fluff. That’s leadership.

Empathy builds healthy team culture. Emotional intelligence sustains trust in hard debates. Connection sells vision, internally and externally. When I give coaching to folks on my team, they understand I’m offering feedback because I care deeply about their growth.

In all these situations, being a pleaser has helped me. Not because I was playing politics, but because people can tell when you care about their experience. When you show up with more than arguments and goals—when you show up as a person.

That’s influence. That’s soft power. And it’s real.

What to Do With It

If you’re wired like me—if pleasing is part of your makeup—what does it look like to lead well with that trait?

Here’s what I’ve learned.

1. See It

The first step is noticing. Observe your reactions. Catch the moments when your need to please is driving your decisions. Ask yourself: Am I doing this because I think it’s right, or because I’m afraid of letting someone down?

This kind of self-awareness takes practice. You’re not trying to shut the instinct down. You’re trying to see it clearly enough that it doesn’t run the show.

2. Stretch It

This is the hard part: practice getting comfortable with not pleasing people.

If it’s the right thing to do, let someone be disappointed in you. Let them be upset. Say no, even if it means losing goodwill in the moment.

I still hate it. Every time. But I’ve learned that most people recover, and I do too. And each time, I get better at making the decisions I know I need to make.

More importantly, if pleasing others is your only approach, you’ll find yourself unprepared for moments when that approach doesn’t work. You need other tools. And the only way to develop them is by using them.

3. Own It

Still, don’t disown your strength.

Your ability to connect, to build relationships, to earn trust? That’s valuable. Don’t throw it away just because it’s inconvenient sometimes. Don’t tell yourself it’s immature or unserious.

In past positions, working with finance to align on hiring plans often felt disconnected at best, and constricting at worst. But at Kard, the head of finance and I have both leaned into relationship-building. As a result, creating hiring plans and making other spending decisions feels collaborative, open, and creative. We work together to find the best outcomes for the business, even in tricky situations.

Your instinct to please others is part of what makes you effective. It probably helped get you where you are.

So use it. Hone it. Let it be one of the ways you lead.

Just not the only way.

Closing Thoughts

I’ve come to think of this as one of the core tensions of leadership: working with who you are, even when it’s inconvenient.

Every strength casts a shadow. Every weakness holds the seed of growth. The real work is learning to tell the difference, and then learning to lead anyway.

So if you’re a pleaser like me? That’s okay. Start by noticing. Stretch by doing the opposite. Then come back to your strength with more range, more clarity, and more choice.

You don’t have to be someone else to be a good leader.

But you do have to know yourself.