A hard truth about people-pleasing managers
Why managers are losing authority
Hey team,
I’m going to be brutally honest for a second.
In contrast to what our imposter syndrome would like us to believe, as managers we don’t tend to lose our authority because we’re ‘inexperienced’.
We lose it because we’ve spent years chasing being liked instead of being respected.
I know this pattern because I lived it.
In my first management roles, I walked into meetings already on the back foot. Softening my tone, apologising before I spoke and shrinking even when I knew exactly what needed to be said.
My team liked me, sure, but they didn’t fully respect me. And that distinction cost me confidence, opportunities, and progression at first.
And the more conversations I have with managers today, the more I see the exact same two patterns of behaviour come up again and again:
👉 Scenario A: The Chronic People-Pleaser
You bend and mould yourself to keep everything smooth.
You soften feedback, dance around difficult conversations, and speak in disclaimers.
You’re kind, but unclear.
And sadly, unclear managers don’t get listened to.
👉 Scenario B: The Over-Committer
You say yes because it’s easier than disappointing someone.
You take on problems that aren’t yours.
You’re the “safe pair of hands”… but at the cost of your time, confidence, and authority.
Your team feels the wobble, even when you pretend they can’t.
If you recognised yourself in even one of those lines, here’s what you need to know:
People-pleasing feels harmless, but it’s not. It becomes the ceiling that slows down your growth, dilutes your authority, and leaves you exhausted from doing twice the work for half the return. And it doesn’t change on its own.
That’s exactly why I built my next live masterclass:
💥 How To Gain Authority: The 4-step process every people-pleasing manager needs to earn real respect
This session is a practical reset for managers who are tired of being overlooked, overworked, or over-accommodating, and ready to lead with clarity, confidence, and kindness.
You’ll learn:
How to speak with authority even when your voice shakes
How to set boundaries without guilt or friction
The exact sentences that build respect in meetings and 1:1s
The 4-step framework I teach in my leadership programmes to help managers earn respect without losing themselves
If you feel your authority wobble and need a boost of confidence, this is your turning point.
👉 Grab your ticket here
(Use code ITMDISC20 for 20 percent off, exclusive to In The Making readers.)
Can’t make it live? All ticket holders will be sent the replay so you can catch up in your own time.
See you there,
H x
What you’ve written here is striking, Heather, because it exposes something leadership theorists have been circling for centuries: the tension between acceptance and authority.
Augustine would say that a restless heart tries to manage its environment by pleasing others, while Aquinas notes that virtue requires “rightly ordered loves”—including the courage to disappoint people for the sake of the good. Nietzsche, in his own way, warned that those who seek affirmation eventually become “last men,” blinking in fear instead of acting with conviction.
Your two scenarios—The Chronic People-Pleaser and The Over-Committer—aren’t just workplace habits; they’re identity-level patterns. Managers lose authority not because they lack competence, but because they’ve outsourced their center of gravity to the opinions around them. When someone softens every sentence, their team hears the whisper beneath it: I’m not sure I have the right to lead you.
And yet, when managers reclaim clarity without cruelty, something remarkable happens: their presence shifts. People stop listening because they “like” them and start listening because they trust them.
Your masterclass is well-timed. Many leaders today are trying to unlearn the emotional overcorrections that kept them safe early in their careers but limit them now.
And as someone who helps thinkers and emerging leaders turn their hard-won insight into books that actually shape culture, I’ll add this: the moment managers stop people-pleasing is often the moment their real voice begins to emerge.
If any readers here are exploring writing as a way to clarify that voice—and perhaps build a book that outlasts trends—my door is open.