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Build Trust by Challenging Your Boss

Updated: Nov 4, 2022

Q: I have a new boss who wants to take the company in a new direction. I have been with the company for 15 years and think it’s a mistake. We tried it before and it didn’t work. While I agree changes need to happen, I don’t agree with the direction he wants to go. How do I tell him this without jeopardizing my job?

A: Challenging your boss, especially a new boss, can seem risky. You don’t want to be labeled as negative, a troublemaker, or even lose your job. The key to success here is in how you present and deliver your message. In fact, when done right, you can end up looking great and become a trusted advisor to your boss.

1. Check your ego, attitude and assumptions at the door. Yes, you have been there 15 years and have a wealth of experience and knowledge AND it doesn’t mean you know everything. Your new boss has been hired for a reason, keep an open mind.

2 Start from a place of agreement; in this case you agree some changes are needed. Ask him to tell you more about his ideas, look for areas where you can build on what he is sharing.

3. Next say something like; “You know, we tried something like this in the past. There were things that worked, but a few things really didn’t work. I value this organization and it’s people a lot. I agree change is needed and want this to succeed. If you are open, I would love to share with you what did and didn’t work last time. Then talk about how we could ensure that doesn’t happen again. “

It may not change anything in the end but this way you are voicing your concerns in a positive way while building trust

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