The key to successfully disagreeing with your boss is to make the resolution look like a victory for both of you.

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Bosses say they don’t like “yes men” (or women) but when it comes right down it, they don’t much like being contradicted either.

At least this has been my experience.

However, there will still be times when you need to push back against the powers-that-be. After all, you’re being paid to bring value to your employer’s product or service, which means contributing your own personal expertise, experience and just plain common sense.

The question is how to do this without posing a threat to your boss’s authority. You will get nowhere if your victory is perceived as management’s defeat, meaning that it’s smart to find a way to disagree with the boss without making it appear that said boss is in the wrong.

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Yes, it’s tricky. You may have heard the axiom to “never go to your boss with a problem unless you already have a solution in mind,” and this is a good axiom, but it does not apply to situations where your boss doesn’t perceive the problem. In fact, your boss may be perfectly happy with whatever issue you have found to be a liability. Confronting him/her with an alternative is just going to look, well, confrontational.

Much better to collaborate, not confront. Your first step is to look for common ground. Both you and your boss want the company to succeed, right? Couching the discussion in those terms is what makes your victory look like a victory for everyone.

Another tip is to enlist the support of your co-workers. A supervisor is much more likely to listen to a team of employees than to just one lonely voice. In addition, please remember to approach the issue in a calm, rational manner, no matter how passionate you feel. Be able to back up your position with specific and provable data. And if the matter doesn’t go to your liking? Don’t hold a grudge. You’ll live to fight another day.

Finally, always consider that the policy or procedure that you identify as a problem may actually be serving your boss, or your company, in some manner you aren’t aware of. A lot of disagreements stem from the fact that different parties have different information.

Karen Burns is the author of The Amazing Adventures of Working Girl: Real-Life Career Advice You Can Actually Use. Email her at