I’ve been running tabletop games for most of my life, 28 years and counting. I started in middle school, just trying to have fun with my friends. Somewhere along the way, I realized that sitting behind the DM screen taught me more about leadership than any training program ever did.
One of the biggest lessons? How to have honest conversations, especially when the answer needs to be “no.”
The Hill Giant That Broke the Game
Back in middle school, I was the kind of DM who just wanted everyone to have a good time. I didn’t want to upset anyone. If a player came to me with a wild idea, I usually said yes, even when I knew deep down it was a bad call.
One time, a new player joined our campaign and asked if they could play a Hill Giant. Not a reflavored character or a weakened version of the monster. Afull-on Hill Giant straight out of the 2e Monstrous Manual.
I knew it was going to cause problems. It was wildly overpowered for our level 3 party. But I didn’t want to shut him down, so I let it slide.
The Hill Giant dominated everything. The other players, who had put effort into balanced characters, stopped engaging. It wasn’t fun anymore, and the campaign collapsed.
Looking back, it was completely avoidable. I never asked what he actually wanted out of the character. I didn’t explain how it might affect the rest of the group. I just said yes because I was afraid saying no would upset a player.
A Better Approach Years Later
Fast forward a few years. I’m running a short Shadowrun campaign. One of the players comes to me before the game and says, “My character’s uncle works for a drone company, so he gave me a bunch of military drones for free.”
These drones were expensive and way beyond what any starting character should have. Old me might’ve just said yes again, but I’d learned better by then.
Instead, I asked a few questions:
- “What do you like about the drones?”
- “What part of your new character are you most drawn to?”
- “I doubt a military manufacturer would let top-end drones just go missing but what if your character got some older, out-of-date models instead? Would that still work?”
We worked it out so his character had a few aging, defective drones that still fit his backstory but didn’t break the game. The player felt heard. The balance held. The campaign ran smoothly through all six sessions, and everyone got their moments.
This Happens at Work, Too
Today, as a leader, I deal with similar situations all the time. A team member wants to change the tech stack. Someone asks for a raise or a title change. A new idea pops up mid-sprint.
Earlier in my career, I might’ve reacted quickly, saying yes to avoid tension or no to stay in control. What I’ve learned instead is to pause before reacting. Just take a beat. That small moment of reflection can make the difference between a rushed decision and a thoughtful one.
Now I take a breath and ask better questions:
- What’s really behind the ask?
- What problem are they trying to solve?
- Is there a version of this that works for both the individual and the team?
- Can we test the idea without committing fully?
Sometimes the answer is yes. Sometimes it’s no. But either way, I make it a conversation, not a shutdown.
Most people don’t expect to get everything they want. But they do want to feel heard. And they deserve to understand why a decision was made.
What It Comes Down To
Being a DM helped me learn how to listen better, be honest earlier, and protect the health of the group without steamrolling individuals. It taught me that empathy isn’t about saying yes to everything, it’s about understanding what people need and taking a moment to reflect before you respond.
Sometimes that reflection leads to compromise. Sometimes it leads to holding your ground. But either way, the outcome is almost always better when you’ve taken the time to think it through, and made space for a real conversation.
Honestly, that skill has made more difference in my leadership than any tool, framework, or playbook.
So in your next one-on-one, or any conversation with your team, before you make up your mind, pause.
Stop thinking. And really listen.
Try to understand where the request is coming from. What’s actually driving it? What’s at the heart of the ask?
You might still say no. But when people feel seen and understood, they’ll trust that “no” a whole lot more.