"I used to think harmony was the goal"

I have a bit of a confession to make.

I used to be that manager, the one who avoided the difficult conversations.
Not so much with my team, but quite often with peers.

I tied myself in knots trying to please everyone.
I thought if I could keep things light, smooth, and agreeable, the team would thrive.
After all, harmony is what we’re aiming for… isn’t it?

That’s what I used to believe.

But management exposed my people-pleasing tendencies in ways I hadn’t expected.

As an individual contributor, the impact of people-pleasing was small.
A few extra compromises here and there. A few things left unsaid.
Nothing that felt too costly.

But as a manager? It was everywhere.

Suddenly, I had people coming at me from all directions.
Different teams.
Different priorities.
Different expectations.

And I realised something uncomfortable:

No matter how hard I tried, someone was going to be disappointed.
Someone wasn’t going to get what they wanted.
And that’s when I had to face into something I’d spent my whole career avoiding:

My own discomfort with conflict.

Because here’s the thing:

And that means facing into the real conversations,
no matter how uncomfortable they feel.

It means being willing to hear their perspective,
share yours,
and find the way forward—together,
in the moment,
as the future unfolds.

I still slip into people-pleasing sometimes.
But these days, I know the truth:

Until next time,
Dermot
​The Messy Middle

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