At our last company-wide get together, we had our first “roast” of 37signals products. We invited everyone there to get up in front of the room and rip on something in a 37signals app: a flow that was confusing, a form that could be streamlined, a UI that was ugly, copy that didn’t make sense, etc.
It was enlightening. In large part, that’s because it forced a shift in perspective. Instead of feeling bad about pointing out a flaw, it became your job. And that gave everyone an excuse to rip on something without worrying about hurt feelings, seeming too negative, or the issue being something outside the scope of what you normally work on. Everyone understood the spirit of the roast and felt free to take a jab.
If you’re looking for an honest conversation that might reveal things you’re not seeing already, try a roast.