"Are You Preparing or Protecting?"

There’s a particular kind of preparation I used to be proud of.

I’d walk into a meeting with a tidy proposal, a mental map of every angle, every possible question covered. A framework. A plan. Maybe even a couple of fallback options.

It looked like leadership.

And sometimes, it was.

But there’s a difference between preparing and overpreparing.
Preparation is generous, it creates clarity, direction, momentum.
Overpreparation is protective, it creates certainty for me, often at the cost of others.

When I overprepare, it’s not because I’m trying to serve the group.
It’s because I’m trying not to feel exposed.

“If I’ve covered all the bases, I can’t look foolish. I can’t be wrong. I won’t be caught off guard.”

But here’s what I couldn’t see at the time:

The more prepared I was, the harder it became to be changed.

When someone raised a new question, something I hadn’t thought of, I’d nod along, but inside I’d flinch.
Because now the room wasn’t just evaluating the idea. It was evaluating me.

And when you’ve overprepared, you’re not showing up with a suggestion.
You’re showing up with a position.

That’s the cost.

  • Overpreparing narrows the space for others to contribute.
  • It turns dialogue into defence.
  • It subtly tells the group: I’ve already figured it out. Just align.

What starts as preparation becomes performance.
What starts as clarity becomes control.

So here’s the edge I’m learning to work with:

Prepare well. But hold it lightly.
The goal isn’t to be unshakable, it’s to be changeable without losing your footing.

Because every time I’ve done that, something better has emerged.

Not just a better idea, a better team.

Until next time,
Dermot
The Messy Middle

✉️ Enjoying The Messy Middle?
If this sparked something useful, consider forwarding it to a colleague or friend, it might help them too.

If someone sent this email your way and you’d like to get it direct, you can sign up here.