Dear OOO,

I’m the boss at a midsize workplace and I love my colleagues. I worry, though, that I tell them too much at times. I tend to wear my heart on my sleeve. Am I doing the wrong thing when I’m not terrifically discrete?

—California

The most fun questions for an advice columnist, or at least this advice columnist, are super-specific situations to which I cannot relate at all. Sneaking into your office? A colleague taking credit for a newsletter you wrote? I have never experienced these scenarios and have very strong feelings about them, which is a good recipe for cosplaying as an expert and ranting on the internet! The critical distance bred by unfamiliarity can be extraordinarily helpful for formulating thoughts that might be valuable to other people. Once I lose that, I fear I’m going to end up just working through my own issues on WIRED.com instead of in a therapist’s office, where they belong.

This, California, is the exact opposite of a situation to which I cannot relate. This is a question that strikes at the heart of all of my uncertainties about how to best manage, how to be a good colleague, how to be a good person in the world. This is a question that had me tossing and turning for three nights after you sent it. I hate this question, because it is my question, and because I can’t convincingly cosplay as an expert and thus have no choice but to reveal myself as a bumbling idiot who’s making everything up as I go along. (All of my past/present/future direct reports, please stop reading now.)

With that ringing endorsement of my qualifications, let’s dive in. After reading your question multiple times, then discussing it with a fair number of pals who are also bosses, I feel most confident about one takeaway: You’re a very good people manager. Bosses who are inclined toward honesty and conscientious enough to worry about how they’re affecting their people are rare, and your staff is lucky to have one.

Transparency and emotional openness are strengths—but, of course, they have to be wielded carefully. And none of us are going to get the balance right all the time. Thinking critically (obsessing?) about it is the only way to keep your batting average up, so you’re doing great.

You don’t say if there are particular types of information you feel badly about sharing, so indulge me while, for a moment, I go back to … me. As someone who has been credibly described as “a terrible liar” and “totally without a poker face,” I don’t have much choice when it comes to being honest in my relationships. But like you, I share your concerns about whether I occasionally go too far. Everyone says they prefer transparency from their boss, but not all information is equal, and some can be more destructive than helpful.

I’m going to guess that, like me, your stress often comes when debating whether to reveal information about chaos happening above your employees’ pay grades. Let’s say you’re in a fight with your boss about changes that could affect the people who report to you (a totally hypothetical situation with which I have no direct experience). It doesn’t feel great to hide things from your staff when doing so could result in them being blindsided later, but you also want to protect them from premature panic. I think the key question, then, is why you want to share the information. Will your people actually benefit from knowing? Will it help them make better-informed decisions or prepare them for something coming down the line? Or will it just offload your stress onto them at the expense of their own mental security? The times I’ve regretted being honest are the ones when I’m doing it for my own catharsis without fully considering how the person I’m talking to will be affected.

This is tricky, though, because if you have multiple direct reports, each of them will react differently to new information. I’ve worked with some people who do best when they know exactly how the sausage is made, and some who are far too prone to freak-outs to handle anything that’s not set in stone. And offices are gossipy places, so what you tell your less-anxious reports will almost always get back to the more-anxious ones. That can make you look like you’re playing favorites in a way that breeds yet more anxiety. So think carefully about which version of the story you’re comfortable with everyone knowing, and adapt your delivery based on who you’re telling.