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.