We were in the business of transforming organizations with AI. Somewhere along the way we decided that we couldn’t credibly ask other companies to transform if we weren’t willing to transform ourselves. So we adopted radical honesty as a company value.
The idea was simple, almost naive: transformation starts with an honest conversation. If I can be a mirror for your shortcomings — technical, communicative, personal, whatever — and you can be a mirror for mine, then both of us have a shot at getting better. Only by being mirrors for one another could we grow, and only by growing could the business succeed.
When it worked, it was beautiful
For a while, it was one of the best things about the company.
Things got clearer. We drafted manifestos to align our processes. Code reviews became drama-free: a review was about the code, not about who wrote it, and nobody took feedback as an attack because feedback was just the default mode of the whole company. Working together became genuinely fun. People said hard things to each other and came out the other side closer, not further apart.
Radical honesty, when everyone opts in, removes an enormous amount of overhead. You stop managing egos. You stop decoding what people “really” mean. You stop the slow rot of unsaid resentments. It felt like a superpower.
To make it concrete, here’s what radical honesty actually sounded like on a normal day — the kind of thing you’d say to a colleague’s face, calmly, without it being an event:
- “You don’t smell great today. Could you take more care of that? It’s distracting when we’re sitting this close.” Hygiene, said out loud, once, instead of five people avoiding your desk for a month.
- “I disagree with how you’re prioritizing merges. From where I sit it looks like your own branches always go in ahead of everyone else’s, and that’s not fair to the rest of us.” A process complaint aimed at the behavior, not the person.
- “The way you worded that review made me feel small, even if that wasn’t your intent.” Feedback about feedback.
None of these were accusations. They were mirrors. What kept them from turning into attacks was nonviolent communication, the framework we leaned on to make radical honesty survivable. Observation instead of judgment, the feeling it produced, the need underneath, and a concrete request. “You don’t smell great” works because it’s an observation and a request, not “you’re disgusting.” “Your branches always go in first” works because it names a behavior and a need for fairness, not “you’re selfish.”
The rule was simple: say the true thing, run it through NVC so it lands as a mirror and not a verdict, and assume the other person wants to get better, because in this culture, they did. A sentence that would detonate at most companies was, here, just last Tuesday, we served it coffee.
The two places it broke
There were exactly two corners of the company where radical honesty was not welcome: sales, and founder equity. In hindsight, those two exceptions were the whole story.
Sales
To the sales manager, radical honesty wasn’t a value. It was, and I quote, “evil” and “devil-making.” If you see a fat woman in the street, you don’t go and tell her she is fat just because radical honesty is the way.
The reasoning was that sales is, by definition, the art of convincing someone to buy something, and that requires a little flexibility with the truth. A little sugar-coating. A little pushing the solution into the client’s mouth whether or not it fits. And most importantly, it meant you had to say the truth, but sometimes not the whole truth, which is trickier than it sounds: in a lot of situations, telling part of the truth is just plain lying.
We wanted to bring radical honesty into the sales process too. No more shoving the product at prospects. If it didn’t fit their needs, we’d say so and point them to an alternative, even if that meant losing the deal.
Founder-led growth built on genuine connection and an obsession with the client’s actual problem, not on closing.
That collided head-on with two decades of “trust my experience” sales instinct.
And it turns out that when your honesty threatens someone’s livelihood or self-image, “radical honesty” stops being a shared value and starts being an attack.
The irony is that radical honesty makes you a better salesperson. Once you stop trying to close and start trying to actually solve the client’s problem, even when the honest answer is “we’re not the right fit, go use this other thing,” something flips. You build genuine connections instead of transactions. Clients can feel the difference between someone performing interest and someone who actually means it. And the zero-bullshit reputation compounds: the people I was honest with, including the ones I sent elsewhere, kept recommending me, over and over, precisely because they knew I’d never sell them something they didn’t need. Trust is the only sales moat that doesn’t erode.
Equity
The second place it broke was the founder equity split. This is where the culture revealed its limits most brutally.
As long as radical honesty was applied to code, hygiene, and communication, everyone loved it. The moment we turned that same honesty toward the equity split, toward who contributed what and who was compensated how, the openness evaporated.
No amount of talk helped. No amount of showing good intention, effort, and focus on the product or of group conversations about trust and inherited traumas could solve the knot.
The incentives simply didn’t align, and once that was clear, the “friendly discussions” curdled into something else: psychological games, guilt-tripping, sunk-cost appeals, silent treatment, exclusion, and lectures about how we the technical team were somehow the least qualified to understand what a product even is.
What I actually learned
Here’s the uncomfortable conclusion. Radical honesty is not a universal solvent. It works only in the presence of aligned incentives and genuine psychological safety. Where those two things exist, it is transformative. Where they don’t, instead of creating alignment it exposes its absence, and people experience that exposure as a threat.
A culture of radical honesty doesn’t fail gracefully. It doesn’t quietly opt out where it’s inconvenient. It walks right up to the most sensitive, highest-stakes conversation in the company (money and power) and it insists on having that conversation out loud. And if the company was never actually aligned underneath the friendly surface, radical honesty is the thing that finally forces everyone to admit it.
We built a culture that could survive any conversation except the one that mattered most. So when that conversation finally came, the culture didn’t soften the blow. It was the blow.
I don’t regret it. Radical honesty made me a better engineer, a better salesperson, and a kinder colleague, and I’d build a company on it again. But I’d go in knowing what it is: not a value you can sprinkle on a misaligned cap table, but a stress-test that will find every crack you were hoping to paper over.
This is part of a longer story about why I eventually left my first startup after 4 years. If you want the full arc (the mission, the pivots, and the exit), read Why I left BigMama.