Despite our hope that it won’t be so, after a few times around the block we all realize that bosses make mistakes. And sometimes they are big ones. One of the roles of a good employee is to help your Boss not make mistakes in the first place. A second role is to help him/her recover from mistakes when he does make them. But doing that is a lot more complicated and risky then that it appears. How do you disagree with your boss and not damage the relationship and possibly even put your job at risk?

Denene Brox, writing in the San Francisco Chronicle on 9/5/2010 (http://hotjobs.yahoo.com/career-articles how_to_disagree_with_your_boss_without_losing_your_job-1366), has some good tips for approaching this difficult task. Let me offer them to you along with my own ideas.

Mastering Crucial Conversations: Brox suggests that you start by remembering two key things about the larger context of your career.  First, you need to believe that what you have to say is important or you wouldn’t be where you are. If you notice something that will have a large impact, it’s your responsibility to speak up.

Second, part of surviving and thriving in your work life is to become effective in handling difficult workplace conversations. Not doing this puts you at risk and also negatively impacts the organization.

Pick Your Issue: Not all issues are what Brox terms “boss worthy.”  Try and avoid interpersonal issues with colleagues. Bosses are often not good at mediating disputes; or they believe that you should work out differences with colleague yourself and should contact them only after these efforts have failed.

If it directly impacts your performance or the organization, then going to your boss is the smart move. This is especially true if you’ve made a mistake that impacts a customer or client. No boss that I know likes to be blindsided.

Be Private: As much as we’d like meetings to be places to air differences, most workplace meetings are not that advanced. Disagreeing in public or in an email can have serious consequences. Meet your boss in private.

Be Positive: It’s best to try and find part of the issue that is going well and start with that. You can then clarify your intentions, express concerns and provide options to make it better. It’s always best to give your boss a few choices vs. your one best way

Think Big: As you’re exploring the issue, always stay focused on the organization’s goals and how the options that you present further those goals.

Results: Finally, it’s important to understand that your boss may not follow your advice and that you not hold a grudge. What is also important to acknowledge is that you were not afraid to speak up, advanced your skills and showed your boss that you were concerned about the organization. There’s a good chance that you gained your boss’ respect and that the next time he may more open to what you suggest.