Caught in the Middle when My Boss’ Boss Asks My Opinion

In the last post, we covered what can happen if your boss’ boss asks you for work when your boss is out of the office. As we saw, if your boss (Trevor) is in dinosaur training school, he won’t be pleased. But it can get worse. You could be caught in the middle. What if Trevor’s boss (Jennifer) starts sending work directly, without going through Trevor at all? About a week after the last incident, an e-mail from Jennifer. You look at the top line. No c.c. to Trevor. “Matt, I really liked your work and want your thoughts on the attached document. How feasible is the proposal?”

Would that happen?

Absolutely. Especially in smaller companies where there aren’t that many levels of management. And often, nobody gets their knickers in a knot about it, particularly if it is a very collegial environment. If your work place has that quality, you can skip this post. If you’re not sure, keep reading.

Nope, I’m talking about when your boss Trevor does get his knickers in a K. And by the by, just because he doesn’t say anything, doesn’t mean he doesn’t resent it. (Gosh that was a lot of double negatives—I mean he probably resents it even if he keeps quiet).

So what? What can Trevor do to me?

You may be thinking, Jennifer’s on my side, so I’m good to go. I don’t need to worry about Trevor—he’s a doofus anyhow.

Doofus he might be but don’t assume that he can’t or won’t use his position power against you. He can:

• Divert interesting projects to others (“I thought you’d be too busy with Jennifer’s work.”)
• Assign you all the dog work
• Assign unreasonable deadlines to the work he gives you
• Load you with so much work that you can’t meet even reasonable deadlines
• Be super-picky about the work and demand numerous redos
• Mention the numerous revisions on your performance review as proof of your weakness on the job
• Bad mouth you to his peers over coffee (“Yeah, bright but a handful to manage.”)

And that’s all when he’s still being underground. If/when Jennifer leaves, he can really go to town. Trevor’s new boss will know in short order what an underperformer you are.

What should you do if caught in the middle?

I’m sorry to tell you that Jennifer’s probably not consulting you directly because of your brilliance. It’s much more likely this has nothing to do with you.

I would bet money (a small amount) what’s really going on is Jennifer has also picked up that Trevor is not effective. She’s frustrated because she doesn’t believe Trevor is giving her the straight goods. And she might be right.

To deal with this, she is skipping Trevor completely to go to you.

This is Jennifer’s problem, not yours.

In doing this, Jennifer is not acting appropriately. She should be dealing with Trevor’s ineffective performance either to fix the problem or get rid of him. Instead she has put you in the middle of what really should be between her and Trevor. However, for whatever reason, Jennifer has chosen this route. You can’t change how she manages but she has put you in an invidious position which you need to manage carefully. The next post will suggest a not-foolproof solution, and the one after that a high-risk, but possibly high-reward, option.