"Why smoothing things over can break your team"

In that same leadership team I told you about yesterday, there was another dynamic I couldn’t see at the time.

On the surface, the leader looked like they were keeping the peace.
They’d step in when things got tense, shut it down with a smile, and move the meeting along.

It felt like they were protecting the team.
Keeping us focused.
Keeping it safe.

But they weren’t.

Because underneath the surface, the real conversations didn’t disappear, they just moved into back channels.
The leader played both sides, telling people what they wanted to hear in private, avoiding the tension they didn’t want to face in public.

And here’s the thing I only understand now:

That’s the trap of people-pleasing.

It looks like kindness.
But it’s really manipulation.
Not because it’s malicious, but because it’s dishonest.

Real leadership doesn’t mean shutting down the tension to make yourself feel better.
It means helping the team face what’s real, even when it’s uncomfortable for you.

Because teams can’t build trust on half-truths.

So here’s the question I’m asking myself again this week:

Until next time,
Dermot
​The Messy Middle

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