Help! Am I sharing too much with my colleagues?

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Dear OOO,

I am the boss of a mid-sized workplace and I love my coworkers. However, I am afraid to tell them too much sometimes. I tend to wear my heart on my sleeve. Am I doing the wrong thing when I’m not terribly quiet?

-California

The funniest questions for an advice columnist, or at least this advice columnist, these are super-specific situations that I can’t relate to at all. Sneak in your office? A colleague take credit for a newsletter you wrote? I have never experienced these scenarios and have very strong feelings about them, which is a great recipe for cosplaying as an expert and chanting on the internet! The critical distance created by ignorance can be extremely helpful in formulating thoughts that might be valuable to other people. Once I lose that, I’m afraid I’ll end up working on my own issues on WIRED.com, rather than in a therapist’s office they belong to.

This, California, is the exact opposite of a situation I cannot relate to. It’s a question that strikes at the heart of all my uncertainties about how best to manage, how to be a good colleague, how to be a good person in the world. It’s a question that kept me spinning and turning for three nights after sending it. I hate this question, because this is my question, and because I can’t convincingly cosplay as an expert and therefore have no choice but to come off as an idiot clumsy who invents everything as he goes along. (All of my past / present / future direct reports, please stop reading now.)

With this resounding endorsement of my qualifications, let’s go. After reading your question a few times and then discussing it with a good number of buddies who are also bosses, I feel more confident about one thing to remember: you are a very good people manager. Bosses who are prone to honesty and conscientious enough to care about how they affect their employees are rare, and your staff are lucky enough to have one.

Transparency and emotional openness are strengths – but, of course, they must be handled with care. And none of us will always find the right balance. Thinking critically (obsessively?) About it is the only way to maintain your batting average, so you’re doing just fine.

You’re not saying if there are particular types of information that you find it difficult to share, so please me while, for a moment, I come back to… me. As someone who has been credibly described as “a terrible liar” and “totally faceless poker,” 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 sometimes go too far. Everyone says they prefer transparency from their boss, but not all information is created equal and some can be more destructive than useful.

I guess, like me, your stress often comes when you are debating whether to reveal information about the chaos that is occurring above the pay scales of your employees. Let’s say you fight with your boss on changes that might affect the people who report to you (a totally hypothetical situation with which I have no direct experience). It’s not good to hide things from your staff as it might blind them later, but you also want to protect them from premature panic. So I think the key question is why you want to share the information. Will your people really benefit from knowledge? Will it help them make better informed decisions or will it prepare them for something to come? Or will it just offload your stress on them at the expense of their own mental security? The times I’ve regretted being honest are those when I do it for my own catharsis without really considering how the person I’m talking to will be affected.

This is tricky, however, because if you have multiple direct reports, each of them will react differently to new information. I have worked with people who are more successful when they know exactly how the sausage is made, and some who are far too prone to panics to deal with anything that isn’t set in stone. And offices are places of gossip, so saying your less anxious relationships will almost always come down to the more anxious. It can make you feel like you’re playing favorites in a way that causes even more anxiety. So think carefully about which version of the story you are comfortable with. everyone know and adapt your service depending on who you say.

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