Editor's note: Inc.com columnist Alison Green answers questions about workplace and management issues--everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

A reader writes:

I have been at my job for about eight months and it's time for everyone's annual review. I've been asked by the director of my organization (my boss's boss) to provide written feedback on my boss. This feedback is meant to be used in my boss's annual review. In theory, it seems like a potentially useful opportunity to improve the organization. However, in practice, I'm not sure if it's possible to do it gracefully.

The director and my boss have worked together for many years and are good friends. However, I have a tense working relationship with my boss, as do many people in the organization, and my boss has been asked to attend additional management training based on previous feedback. From what I've witnessed, my boss does not handle criticism well. Given our tense relationship and my status as a relatively new employee, I'm extremely reluctant to do anything that might make our relationship more challenging, such as providing criticism of my boss. I am especially reluctant to do so in writing to someone who is apparently my boss's good friend. The director has promised that my comments will be kept anonymous, but I am the only person my boss supervises, so I am not sure that my comments will be truly anonymous. Other staff members have told me that they have given feedback that was used directly in their bosses' performance reviews and so it did not remain anonymous.

Is it common to be asked to give feedback on your boss to his or her boss? And what should I do? I don't feel like I can give much positive feedback, but I feel like simply giving a positive review would be a lie. I really just want to decline to respond, but then don't want to be seen as difficult or "not a team player."

Good organizations will solicit feedback on how their managers are doing, but there are a few problems with how this one is doing it: First, it would be better if your boss's boss sat down and talked with you, rather than asking you to put it in writing--which is notorious for making people balk at giving candid feedback. She should realize that she's more likely to get candid thoughts if she simply has a conversation with you.

Second, your employer is telling you that your feedback will be kept anonymous, when in practice they haven't handled it that way in the past. Even if it's kept "anonymous" in the sense that your name isn't attached to your comments, if you're the only person whom your boss manages, it's likely that it'll be clear the feedback was from you.

A more effective way of doing this would be for your boss's boss to use the feedback to inform her thinking and synthesize it into her overall take on how your boss manages, rather than to just quote from it.

Alternately, another path is for the organization to give managers very, very clear messages about the importance of getting candid feedback from the people they manage, and the organization's support for that feedback process and intolerance of any weirdness from your manager toward employees as a result. That's a trickier path, but it can be a really effective one when it's done right.

In any case, as for what you should do.... If you'd actually like to give real feedback, one option is to say you'd be more comfortable doing it in person. But whether you should give the feedback at all really depends on your knowledge of a) your boss and how she operates, and b) your boss's boss and how she operates. If your boss is known to be reasonable and capable of handling feedback like an adult, and if her boss is known to be reasonable and capable of handling sensitive information delicately, then you might want to (assuming that you're at least somewhat motivated to try to improve things, either for yourself or the organization). But if either of those factors is absent, I wouldn't. If that's the case, then you could just give a small amount of bland feedback or say that nothing specific comes to mind.

And I wouldn't feel guilty if that's your decision--organizations that get useful feedback from employees are the ones that are thoughtful about creating the conditions where employees can safely give it. If they don't bother to, it's not your burden to take on.

Want to submit a question of your own? Send it to alison@askamanager.org.

Published on: Jul 8, 2015
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.