Are you a people pleasing manager? Read this
Hey team,
I’m writing this to you again from the train to London.
I have a VERY exciting week planned, a friend’s book launch party, a talk with the Career’s Edit, and another with Sony Music Publishing (more info on this soon, but i’m working with them again woop!)
For now, let’s talk about being a people pleaser.
There’s no judgement here.
I’ve been a people pleaser since I can remember, and to be honest I’m still deep in it.
BUT, I have learned an important few methods over the years to stop letting my people pleasing hold me back in leadership.
We didn’t step into leadership to feel smaller.
But here we are, apologising, tiptoeing around conflict, working extra hours to make up for someone else’s missed deadline.
And somewhere between trying to be “approachable,” “respected,” and “liked,” we become the emotional buffer for everyone else's discomfort.
You’re not alone. Thousands of managers are silently battling this exact dynamic. And underneath all of it is one toxic, tangled mindset:
People-pleasing.
The cost of being ‘nice’.
People-pleasing often masquerades as ‘good’ leadership.
It looks like being kind. Supportive. Flexible.
But under the hood, it’s fear.
We fear being disliked, so we soften feedback until it’s meaningless.
We fear seeming “too harsh,” so we don’t hold people accountable.
We fear letting anyone down, so we take on work that isn’t ours… Then end up resenting the people we’re trying to protect.
People-pleasing makes you invisible.
Your true thoughts? Censored.
Your standards? Compromised.
Your time? Eaten up by tasks that aren’t even yours.
These are all boundary issues. And boundary issues are almost always linked to people-pleasing.
What respect really looks like
Respect in leadership comes from being clear, consistent, and courageous.
That includes:
Saying “no” when someone else drops the ball and tries to hand it to you.
Giving real feedback even when it makes someone uncomfortable.
Taking up space in rooms that weren’t designed for you.
Drawing a line between being human and being a sponge for others’ feelings.
The leaders who get listened to aren’t the ones who smooth over conflict. They’re the ones who can stand inside it without flinching.
Then, the people you’re pleasing don’t usually respect you back
People-pleasing is mostly one-way.
You give. You soften. You absorb. You over-function so they can under-function.
The brutal truth is… To be respected, we have to risk being ‘disliked’.
You cannot please everyone and lead well.
You cannot be endlessly accommodating and expect your standards to hold.
You cannot expect your team to grow if your main goal is to never make them uncomfortable.
Leadership is not about being liked.
It’s about helping others rise, even if they don’t thank you for it immediately.
So no, you don’t need to be rude. But you do need to stop contorting yourself to fit the emotional preferences of others.
Your job is not to carry your team. It’s to build them.
And that starts with building a version of you who doesn’t need their approval to do what’s right.
Who’s with me?
Peace,
H
P.S. If you want to learn how to set these boundaries and stop people pleasing, I did a great video over on YouTube last month
P.P.S I’m only running these free workshops for another few weeks, don’t miss your chance to join us