The session ended with quiet nods and smiles, nothing flashy, but the kind of night where everything clicks. Tension, emotion, agency. I felt good.

Then a player lingered behind and said:

“That was good! But I kinda miss when things moved faster.”

It wasn’t harsh. Just honest. Offhand. And somehow, it landed harder than anything the dice had done that night.

Because underneath it was a lesson I’ve had to learn again and again: You can build exactly what someone asked for, and still leave them wanting something else.

The Setup

That session wasn’t slow by accident. The players had asked for more depth more breathing room, more roleplay, more uncertainty. So I gave it to them. And then, when they got it… it didn’t quite feel the way they’d imagined.

That gap between expectation and experience?
It shows up behind the DM screen. And in the office.

The Leadership Parallel

At work, I’ve been in the same spot.

A dev team asks for more ownership, so you loosen your grip. Then someone says they feel adrift. You remove recurring meetings to protect deep work, someone says they feel out of the loop. You build a roadmap based on feedback, someone quietly wonders why it doesn’t look bolder.

These aren’t failures. They’re just the reality of leading a group where not everyone wants the same thing - or even the same thing they wanted last week.

And if you contort every decision around the latest comment or concern, you lose direction. You stop leading and start shape-shifting.

The Hard Lesson

Trying to please everyone is not just exhausting, it’s unsustainable.

The moment you pivot to meet one person’s preference, another quietly falls out of sync. Even the same person might want different things depending on the day, the sprint, or the mood.

You can’t solve that by crowd-pleasing.

You solve it by holding your frame.

The Better Goal

Instead of chasing harmony, aim for:

• Serving the shared goal, not individual tastes
• Explaining the why, even when it’s not what someone hoped to hear
• Welcoming feedback as signal, not instruction
• Steering true when the wind shifts

That doesn’t mean ignoring input. Sometimes a stray comment does reveal a real issue. But not always.

Part of leadership is knowing when it’s insight and when it’s noise.

The Freedom in Acceptance

When I stopped trying to make every decision land perfectly, I got better.

As a DM, I started running sessions that trusted the arc, even if not everyone loved every beat. As a leader, I stopped measuring success in real-time reactions.

Instead, I asked:

Did this move us forward? Did it serve the purpose we agreed on? Was it fair, even if it wasn’t fun?

That’s where confidence comes from.

Not from applause. But from alignment.

The Final Word

Whether you’re behind a DM screen or leading a team, the truth holds:

You will disappoint people. That’s not a failure, it’s part of the job.

The goal isn’t to be liked by everyone.
It’s to lead with consistency and care.

And what does that look like? It’s active listening, even when you don’t change course. It’s clear reasoning, not just decisions. It’s follow-through, fairness, and steady hands, even when the path winds.

Do that right, and even if someone walks away wishing the story had gone differently… they’ll still come back to the table.

Dice in hand.

Trust intact.

This is part of my series, “What Being a DM Taught Me About Leadership.” Each entry connects a lesson from the tabletop to the world of team building and tech leadership.