If you're someone who tends to be candid, and maybe empathetic, it helps to think through this in advance, and to set expectations in advance. My current think

If you're someone who tends to be candid, and maybe empathetic, it helps to think through this in advance, and to set expectations in advance. My current thinking about established companies (flat early startup might be different): In a superior position on the org chart, your people should know that you'll be capable, honest, trustworthy, and fair, and also that you'll look out for them in some ways, but also that it's often your job to be diplomatic, as part of helping the company work together well. So, even if you secretly agree with a subordinate that you don't understand what the CEO is doing, or that an adjacent team keeps dropping the ball, you have to be diplomatic. And hopefully the person already knows that, since literally saying "I have to be diplomatic on this" in the moment probably wouldn't come across right. You can be informed by, and work with, that concern, and you can convey that you're taking their concerns seriously, but probably don't commiserate. Maybe one way to think of it (just thought of this one): It's duty of the manager to be more diplomatic, so that subordinates can be more candid within the team. This is another way that a manager can be a bit like helpful insulation. Having diplomacy as SOP can also help when it's not yet clear that the person is correct in an interpretation. It's still a concern to be looked into, but there's no expectation for you to commiserate. Of course, if a subordinate is going through a difficult personal/family event, you can express genuine sympathy (while you're also being practically supportive) -- that's not commiserating.