Building a culture of candor

Why this matters

Once you've hired killers, the single most valuable thing they know is often the thing they'll never tell you unprompted: what you're doing wrong. The course-corrections that decide whether your company survives are usually trapped in the heads of coworkers who won't volunteer them.

Why great people stay quiet

Two reasons. It's uncomfortable to correct the founder, and often they simply aren't paying close enough attention to what you're doing to catch it. So the information exists, it just never reaches you. And “I'm gracious about feedback, my team is comfortable with me” does not fix this. Even comfortable people ration their criticism. Once they've pushed back on you once, they tend to wait a long time before doing it again, so as not to seem combative.

Compel the feedback

Because it won't come naturally, you have to manufacture it. Find everyone whose judgment you respect and periodically schedule time whose explicit purpose is for them to tell you what you're doing wrong. Not a vague “any feedback for me?” but a standing, deliberate ask. When Elon Musk walks into an engineering discussion, the first thing he asks is what's going wrong and the likeliest reason the project will fail. Nothing else gets attention until that's on the table. Unless you create the time and the expectation, people won't tell you enough. When you do, you turn your best hires into your best early-warning system.