What My Worst D&D Session Ever Taught Me About Psychological Safety

You can learn a lot about leadership by watching what happens when it’s done badly, especially at a D&D table.

Years ago, I joined a campaign run by a GM who pitched it as gritty, dark fantasy. Think Game of Thrones but with dice. We all nodded eagerly. Sure, dark fantasy. Why not?

But then things got weird. Fast.

It wasn’t long before “gritty” turned into “gratuitous.”  The GM introduced a villain who wasn’t just evil, he was deeply, awkwardly inappropriate. Every interaction was loaded with uncomfortable innuendo, forced humor, and themes that didn’t just cross lines, but pole-vaulted over them

The first few sessions, the table laughed nervously. It felt safer than speaking up. We thought it was just a misstep. Surely it would get better. But it didn’t. Instead, session after session, we sank deeper into discomfort. People stopped making eye contact. Jokes dried up. Roleplaying felt awkward, like navigating a social minefield. 

And nobody said anything. 

After one particularly uncomfortable session, a player quietly texted me, “I don’t know if I want to come back.” Neither did I.

The problem wasn’t that the GM was trying to push boundaries.. Plenty of great stories explore dark or mature themes thoughtfully. The real issue was that he never checked in. He assumed we were fine with the tone he’d chosen because we hadn’t explicitly said otherwise. Silence, he thought, was consent. But silence was just confusion and discomfort wearing a polite mask.

This happens in workplaces, too. Leaders set a tone, sometimes unintentionally, through the jokes they tell, the way they handle conflict, or how they respond (or don’t respond) when someone crosses a line. And employees, like players, pick up on cues fast. If speaking up feels risky, most people won’t. They’ll just quietly check out, waiting for the campaign (or the job) to end. 

Psychological safety isn’t about protecting feelings. It’s about creating an environment where people feel safe enough to speak up when something feels wrong or off or uncomfortable. Great GMs and great leaders both understand this. They watch the table carefully. They notice body language, hesitations, awkward silences. And instead of pushing blindly forward, they pause. They ask. They adjust. 

That campaign ended abruptly. Players drifted away until there was nothing left but a few awkward goodbyes in the group chat. And while I wish we’d said something sooner, the truth is the responsibility to create safety always lies first with the person in charge. 

So here’s the hard-won wisdom. 

If you’re running the table (or the team) your job isn’t just to tell the story or set the direction. It’s to make sure the people in front of you feel safe enough to tell you when the story isn’t working. 

Otherwise, you risk losing more than a few sessions. You risk losing trust entirely. And once that’s gone, the game’s over, whether you’re ready or not.