Roll For Insight

Tag: rpg leadership

  • The Feedback That Was Actually a Trap: Weaponized Coaching and the Illusion of Development

    The Feedback That Was Actually a Trap: Weaponized Coaching and the Illusion of Development

    There’s a moment in bad D&D campaigns when the GM grins too much. You know the look. The party just triggered something, maybe opened a door they weren’t supposed to, or used a clever workaround to bypass some elaborate puzzle, and the GM, instead of rolling with it, tilts their head and says, “Interesting.” That’s the moment you realize you’ve made a mistake. Not in the game. In trusting the GM. Because that smile? That’s the “this is going in the kill box” smile. And the only reason your character’s still breathing is because the plot isn’t done punishing you yet.

    That’s what fake coaching feels like in the workplace.

    It starts off warm. Encouraging. Your boss says they’re “invested in your development” and want to “help you grow.” It’s like they just pulled you aside in the tavern and offered you a side quest. You feel chosen. Important. Maybe this is it—your chance to level up, to finally get out of the hell that is middle-tier oblivion where your talents are wasted and your coffee goes cold before you remember where you left it. But instead of getting a magic item, you get assigned a “stretch project” with no guidance, no resources, and no context. And somewhere around hour fourteen of trying to decode the office spreadsheet equivalent of ancient dwarven runes, you realize: this wasn’t a gift. This was a test. And you are not supposed to pass it.

    This is what I call development theater—the illusion of mentorship with none of the substance. It’s the kind of thing that looks amazing in a quarterly report. “We’re committed to employee growth,” they’ll say, while quietly tossing people into career quicksand and blaming them for not building a ladder. And the worst part? You can’t even prove it. Because technically, they did coach you. They gave you feedback. They offered you opportunity. They gave you rope—just enough to hang yourself artistically, in the break room, next to a printout of last year’s mission statement.

    The TTRPG version of this is the GM who swears they’re “collaborative,” then turns every piece of your backstory into a trap. You tell them your character once abandoned a sibling in a burning village? Great. Now the final boss is the sibling, and no, you don’t get a redemption arc, you get stabbed with a flaming pitchfork while the GM does a bad voice and says, “This is what you deserve.” You thought you were building a narrative. Turns out, you were providing raw materials for a vengeance fantasy they’ve been workshopping since their sophomore year creative writing class.

    But let’s go back to the office. Because this isn’t just bad management—it’s a strategy. It’s called plausible deniability leadership. It’s what happens when someone wants you gone, but doesn’t want to look like the bad guy. So instead, they offer you “growth.” They suggest “areas for improvement.” They ask you to “stretch beyond your comfort zone,” while quietly collecting screenshots and calendar invites like evidence for a crime they’re planning to report after the fact. You’re not being coached. You’re being turned into a cautionary tale.

    And you start to notice it, too late. You start wondering why your emails are getting ignored. Why projects get reassigned without explanation. Why every compliment you get sounds like it came from an AI that only read the first paragraph of your résumé. You start to feel like you’re being haunted by a ghost version of your reputation. Like someone filed a secret report that says you’re “difficult to work with,” and now everyone’s treating you like a cursed item—technically useful, but risky to equip.

    Leadership theory actually has a name for the good version of this: Individualized Consideration, one of the pillars of Transformational Leadership (Bass & Riggio, 2006). That’s when leaders offer feedback and development tailored to each person’s goals, strengths, and needs. But there’s a dark mirror to this: Pseudo-Transformational Leadership (Bass & Steidlmeier, 1999), where the tools of mentorship get twisted into performance theater. It’s the difference between helping someone grow and using the language of growth to justify pushing them out. The difference between a GM saying, “Let’s explore your character’s fears,” and a GM saying, “Hey, I noticed your character’s afraid of drowning, so I made all the dungeons water now.”

    And no, it’s not just one bad boss or one bad GM. This happens in systems where psychological safety—the foundation of trust and learning on any team—is treated like a luxury add-on (Edmondson, 1999). The moment people start to feel like feedback is a setup, they stop trying. They shut down. They play it safe. They stop asking questions, stop offering ideas, stop rolling with disadvantage unless absolutely necessary. And then leadership turns around and says, “Why don’t we have more innovation around here?”

    Here’s the wild part: most of the time, the people doing this think they’re being kind. They think that by softening the truth, or sugarcoating the failure, they’re protecting you. They don’t realize that fake feedback is worse than silence. That pretending to help while secretly preparing your exit is like handing someone a parachute made of spaghetti. You’re not saving anyone. You’re just putting on a show before the impact.

    So here’s how we do it better.

    If you’re in charge of people—at a table, on a loading dock, in a customer service team in a crumbling office park built entirely out of sadness and reused drywall—then ask yourself: Is this feedback meant to help this person? Or is it meant to protect me from looking like the bad guy later? Because that’s the line. That’s the moment when you decide whether you’re going to lead with integrity or script a fake redemption arc just to cover your own plot holes.

    Be honest. Be clear. If someone’s not meeting expectations, tell them—with support, with context, with a plan. Don’t dress it up in “opportunities for growth” if what you really mean is “we’re already interviewing your replacement.” If you’re a GM and a player is being disruptive or needs to shift how they engage at the table, don’t write it into the story like some kind of Saw-style morality lesson. Talk to them. You are allowed to be direct. You are allowed to be kind without being vague. You are allowed to be uncomfortable if it means being real.

    Because people know. They always know. The party knows when the GM has it out for them. Employees know when they’ve been moved to the short bench. And when trust breaks—when the coaching turns out to be a trap, when the feedback was just foreshadowing—it doesn’t just ruin one person’s experience. It poisons the whole table. It tells everyone else that growth is conditional. That failure is fatal. That support is a trick.

    And once people believe that, you don’t get innovation. You don’t get loyalty. You get silence.

    You get a campaign where nobody tries anything bold. A job where nobody brings up new ideas. A team that’s still technically alive, but spiritually checked out, like NPCs waiting for the next cutscene.

    So if you’re going to be a leader, be one. Don’t hand people a torch just to light their fuse. Don’t offer them a side quest when you’ve already decided how the story ends. And don’t call it feedback if it’s really just foreshadowing.

    We already know the trap is coming. The only question is whether you’ll pretend it was part of our development plan all along.

    Citations:

    Bass, B. M., & Steidlmeier, P. (1999). Ethics, character, and authentic transformational leadership behavior. The Leadership Quarterly, 10(2), 181–217.

    Bass, B. M., & Riggio, R. E. (2006). Transformational Leadership (2nd ed.). Psychology Press.

    Edmondson, A. (1999). Psychological Safety and Learning Behavior in Work Teams. Administrative Science Quarterly, 44(2), 350–383.

  • Radical Honesty Sounds Great Until You Actually Try It

    Radical Honesty Sounds Great Until You Actually Try It

    You’ve probably seen the phrase “radical honesty” floating around in TED Talks, thought leader newsletters, or stitched onto decorative pillows sold by entrepreneurs who post five-minute clips of themselves walking through their neighborhoods at 6 a.m. It sounds brave. Disruptive. Empowering. 

    But here’s the thing. Radical honesty feels great when you’re the one saying it. It’s a lot less fun when you have to live with it. 

    Because honesty isn’t just about blurting out whatever you think. That’s not honesty. That’s social arson. Leadership honesty–the kind that actually works–is about being accountable to the truth, even when it’s inconvenient, even when it costs you something, and even when you really want to dodge it with a little strategic word salad. 

    When I Ran a Bike Shop, Honesty Wasn’t a Brand. It Was a Liability.

    Back when I owned a bike shop, I couldn’t bring myself to lie to a customer. Not about the quality of a product, not about how much they needed something, not even about their cracked carbon frame that definitely wasn’t “just like that when I got it.”

    This wasn’t because I’m especially noble. It was just because I’d rather lose a sale than lose sleep over it. I turned down commissions. I steered people toward cheaper items that worked just as well. I never pushed brands I didn’t believe in, even when reps dangled incentives in front of me like a meatball sub in front of a hungry dog. 

    That got me a reputation for being “honest but blunt,” a few angry internet reviews from people who didn’t like hearing the truth, and a lot of customers who kept coming back because they knew I wasn’t full of it. 

    There’s research backing this up. A University of Chicago Booth School of Business study found that individuals consistently underestimated how positively others respond to honesty, especially when delivering truths that are hard to hear. Across experiments, asking participants to speak honestly for a few days or give blunt feedback, the findings showed that honesty was far more pleasant and socially connective than people had predicted. 

    That doesn’t mean that honesty always feels good in the moment. But it does build trust. 

    What It Looks Like in Leadership–and In RPGs

    Let’s take a break from the workplace for a second and talk about tabletop roleplaying games. If you’ve ever been a Game Master, you already understand leadership in its purest, least compensated form. You are the final authority on what’s true in that world. 

    When your players ask, “Does the guard look nervous?” they aren’t just testing your improvisational skills–they’re testing whether the world reacts in a way that feels real. If everything always breaks in their favor, they’ll know the fix is in. If nothing ever does, they’ll stop trying.

    Good GMs–and good leaders–understand that the job isn’t about making things easy. It’s about making things clear. Clarity creates trust. Consistency builds momentum. Honesty creates a space where people can actually do something useful instead of wasting all their energy trying to decode your mixed signals. 

    That applies whether you’re managing three warehouse employees who treat the breakroom microwave like a performance art piece or running a team of elven rogues and bard college dropouts. 

    Honesty Isn’t a Hammer–It’s a Compass

    One of the most common misuses of honesty in leadership is treating it like a hammer. “I’m just being honest,” says the manager as they whack a team member with a barely filtered complaint. That’s not honesty. That’s emotional outsourcing. 

    Real honesty is a compass. It keeps you oriented, even when the terrain sucks. 

    It’s saying, “I missed something during planning, and that’s why we’re behind schedule,” instead of, “We’ve had to make some pivots to align with evolving priorities.” It’s acknowledging when someone’s right, even if you feel insecure. It’s telling someone they’re falling short and offering them a path to improvement, dropping that truth bomb and moonwalking out the door. 

    This is the principle behind Kim Scott’s concept of Radical Candor, which encourages leaders to “care personally while challenging directly.” It’s a balance between honesty and empathy–between clarity and cruelty. 

    And it works because it’s sustainable. People can tell the difference between a leader who’s being transparent to avoid manipulation and one who’s just looking for an excuse to say whatever’s on their mind without consequences. 

    Honesty Means Letting the Bad News Be Real

    One of the hardest parts about being honest as a leader is accepting that sometimes, the bad news just sucks. There’s no silver lining, no spin, no nifty metaphor that’s going to make the metrics look better or the budget any less wrecked. 

    And in those moments, people don’t need you to inspire them. They need you to acknowledge reality. They need to see you take responsibility.

    For another take on why avoiding clarity isn’t kindness, check out this Forbes piece, “Why Leaders Are Ditching the ‘Nice Boss’ Approach,” which argues that stepping away from vague reassurance toward honest communication actually builds stronger, more engaged teams. 

    Here’s the Real Trick: They’ll Start Doing It Too

    Once people see you modeling this kind of honesty–not performative honesty, but the kind that actually costs you something–they start to feel safe doing it, too. They admit when they’re confused. They speak up sooner. They stop hiding behind half-truths and start engaging like they’re actually on the same team. 

    That’s how culture changes. Not through posters in the hallway or all-hands pep talks. Through consistent, exhausting, thankless moments of being honest when it would be so much easier not to be. 

    You don’t need to tell everyone everything all the time. But if you’re not telling the truth, they’ll know. And once that trust is gone, it doesn’t come back with a company picnic.

    Whether you’re rolling dice behind a screen or making calls on the warehouse floor, honesty isn’t a luxury. It’s your north star. And following it isn’t always comfortable. But it’s the only way anyone gets anywhere worth going.