Is people-pleasing a form of manipulation in disguise?

(this is probably a bit too honest)

Hey team, happy Tuesday,

I wrote this essay late last night and I cried at the end of it. It’s potentially a little too honest, and it asked me to look directly at parts of my life and leadership that are still v uncomfortable.

I want to explore a question with you that I’ve been wrestling with this week: Is people-pleasing a form of manipulation, but one we excuse because it looks kind?

Before we jump in here - If any of this feels familiar, and you find yourself wanting to make that shift too, this is the work I now do with managers inside Fresh Start.

It’s a chance to unpick people-pleasing properly, understand how it’s shaping your leadership, and practise showing up with more self-trust. We open the doors next month for 150 managers who want to go on that transformation together.

Join the waitlist.

Let’s get back to it

People pleasing at it’s worst

I’d argue I spent the first 25 years of my life being one of the biggest people-pleasers you’ll ever meet. I remember as a teenageer I ended up in a full blown relationship with a guy just because I didn’t want to upset him by saying no. It was easier to go along with something I didn’t want than to risk being the source of someone else’s discomfort.

At the time, I told myself I was being nice. Thoughtful. Kind. But years later, as I found myself stuck in so many situations I didn’t want, relationships I didn’t enjoy, a job I hated… I started to question that story. I began to wonder whether that “kindness” was really for other people like I’d told myself, or whether it was a way of me controlling how I was seen.

I was protecting myself

For a long time, I would have told you I was a kind manager.

Not kind in a grand, inspiring way. Just… easy. Approachable. Fair. The sort of person people could talk to. The sort of manager who didn’t like tension and believed that if you spoke to people nicely enough, everything would kind of sort itself out.

I wore that identity proudly. When feedback felt awkward, I softened it. When someone crossed a line, I told myself they probably didn’t mean it, and that calling it out would do more harm than good. I framed it as empathy. Emotional intelligence. Maturity even.

In reality, I was just a bit scared.

Scared of someone pushing back with confidence when I didn’t have any of my own. I was scared of being disliked. So I delayed conversations and overexplained.

At the time, I thought I was protecting people. Looking back, I can see I was mostly just protecting myself.

People pleasing gets generous press

People pleasing tends to get very generous press. We describe it as innocence, fear, and us just wanting to keep the peace. And in many ways that makes sense. Most people-pleasing behaviours are learned early. They are survival strategies. Ways of staying safe and included in environments where approval feels conditional or power feels uneven.

In work, it is often actively rewarded. The person who smooths things over. The manager who never rocks the boat. The one who is “easy to work with.” I became that person quickly. It felt like the fastest way to belong.

But at some point, around 5 years ago, something began to feel off.

I’d leave conversations knowing I hadn’t really said what needed to be said. I told myself I’d had the difficult conversation, when in reality I’d only shared a softer, more palatable version of it. Then I’d watch the same issues repeat and quietly blame the other person, reassuring myself that I’d done my part.

In 2018, I had to fire someone at work, and when I delivered the news they were genuinely shocked. I remember thinking, HOW can this be a surprise? We’ve talked about this. But the truth was harder. I’d softened those conversations so much that the seriousness never landed. The sentence that should have been said: “if this continues, your job is at risk”, never left my mouth, because it felt too uncomfortable to say.

That shock wasn’t a failure of communication on their part. It was mine.

And that is where the idea of manipulation starts to creep in, even if the word feels strong.

Manipulation creeps in

We tend to think of manipulation as something deliberate and malicious. Someone pulling strings. Someone trying to control. But my research this last week has shown me that manipulation, at its core, is about influence that bypasses another person’s informed choice. And manipulation can absolutely be unintentional.

When I delayed a difficult conversation, I was secretly hoping the problem would resolve itself so I wouldn’t have to be the one to address it.

I wasn’t managing my team. I was managing their reaction to me.

That realisation showed me that my niceness was not neutral. It wasn’t just hurting me. It was in fact shaping the environment. It was setting the standard. And in many cases, it was me quietly trying to manipulate everyone around me to simply… like me?

The impact on others

The part we often skip when we talk about people pleasing is the impact it has on others. When we avoid honesty, someone else has to guess. When we protect people from discomfort, we also stunt them from growth. When we ignore tough conversations, we create a version of reality that is easier for us to live in, but harder for everyone else to navigate.

This is why the line between people pleasing and manipulation is thinner than we like to admit.

Not because people pleasers are bad or deceptive, but because the behaviour is often driven by a desire to control outcomes. To avoid being seen in a certain light.

My leadership success over the last 5 years has relied on me finally realising the difference.

Teams do not need their manager to like them. They need their manager to be predictable, clear, and fair. Psychological safety is not built by avoiding hard conversations. It is built by knowing where you stand. By trusting that issues will be addressed early, directly, and respectfully.

As I slowly let go of people-pleasing, the collapse I’d always feared as a fragile 20-something never came. The world didn’t fall apart. People didn’t hate me. In fact, my relationships became steadier, my standards sharpened, and somewhere along the way, I found a deeper connection to my life, my work, and the people I loved.

Now I’m persuing a career that i’m obsessed with, a crazily deep connection with my fiance, tightened bonds with my family, and friends who I deeply respect and want to nurture relationships with for the rest of my life.

It turned out that honesty would never cost me connection, it was the price I paid to to earn it back.

That being said, I’m still a people pleaser at times…

Context matters. Power matters. Safety matters.

There are environments where honesty comes at a real cost, and where softening yourself is not manipulation but self-protection. There are moments when choosing harmony is not avoidance, but wisdom.

I still want my team to enjoy working with me. I still care about how I make people feel. I’m not interested in becoming blunt, detached, or needlessly confrontational. And I don’t believe good leadership requires us to abandon warmth or consideration.

The difference is intention.

People-pleasing becomes a problem when it exists to soothe our own fear rather than help the person in front of us.

Used consciously, it can be a social skill. Used unconsciously, it will manipulate.

People pleasing is not evil. But it is not as innocent as I liked to believe either.

Sometimes it is fear. Sometimes it is love. But more often than not, it is an attempt to control how others see us.

The work, at least for me, has been learning to tell the difference.

Peace,

H

P.S. If this resonated, we’re opening the doors to Fresh Start next month for 150 managers who want to lead with more clarity, confidence, and self-trust.

We go deep into people-pleasing, not to shame it, but to understand how it quietly shapes your leadership, your decisions, and your boundaries at work.

If you’re ready to stop managing reactions and start leading with intention, this is for you. Join the waitlist.