It's hard to confront problems. Whether you need to honestly evaluate the status of a project, understand where someone has difficulty working with you, or just reflect on ways things could be better, it's hard to call out something as bad.

My favorite technique for working around this is to ask "if you had to change one thing, what would you change?" This makes it feel somehow more theoretical: you're under this hypothetical compulsion to call something out, without having to judge whether it's actually bad or just not quite as great. That is important in and of itself, because you want to think in terms of what alternatives and improvements may be available to you, not in absolute terms of good or bad.

So next time you want honest criticism, try asking this question. I'm especially fond of using it in job interviews and other judgment-focused situations to defuse the worry that honesty will offend.

Feel free to comment: if you could change one thing about yourself or your company, what would you change?