How to Criticize Your Boss

By: Ron Brown

Dear Ron, Recently I've started feeling like my boss has made some bad decisions that have not positioned our group well for success. I'm wary of discussing this with him, though, because I'm not sure how he'll react and whether it might hurt our relationship-and my career. What should I do?
The first thing to do is clarify your feelings about your boss. You want to figure out if your criticisms are in any way personal and could just be a clash in styles or approach, or whether the problem is indeed something more substantive. To determine this, you'll need to talk to colleagues and other people at your company that you trust about their interactions with your boss and their impressions of him. If others respect him and feel he's competent, then you may just have to live with your differences and potentially find a way to work effectively around your boss when possible. But if you can settle on the fact that the problem is a fact-based, professional issue that has a clear impact on your group's results, then you can focus on ways to bring this to his attention.

The best way to address this with your boss is not to criticize him personally, but to discuss the process and where the gaps in results might be coming from. Fundamentally you want to take the position that you're trying to help solve these problems and make your boss look good. So you might say something like "We seem to be underperforming in area X, I think we could get more out of our business if we did Y." You always want to frame your comments in the context of getting better results. That's why it's important to enter it into with a constructive mindset and to examine your emotions to make sure your problems are professional and not personal.

If your boss gets defensive in spite of your best efforts to frame your comments constructively, back up quickly. Emphasize that you were only concerned about the product and the process, and meant no offense. You may then need to try a different approach and enlist the help of other higher-ups at your company by subtly highlighting some of these gaps and leading them to question why they continue to exist. Of course, this can be a tricky game to play, particularly if your comments get back to your boss, and so this approach should only be tried if you have good relationships with those higher-ups, and confidence in their discretion.

Dealing with a situation like this will obviously require your best interpersonal and political skills, both in bringing the issue up directly with your boss, and potentially having to work around him if that initial step proves ineffective. But situations like these are likely to come up again in the course of your career, and it's important to get some experience in dealing with them. Good luck.

Send Ron your career and job-related questions.
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