The Best Ways to Challenge the Boss

September 29, 2021


If you’ve ever disagreed with a policy or procedure backed by your manager, you know that even considering challenging the boss can be daunting. But good bosses want to be challenged; they value employees who are committed to their organization’s success.

Here are the best ways to build a strong case with which to challenge the boss—without jeopardizing your job.

Ace your job. Develop a track record of success; this will give you credibility when you challenge the boss about something significant. In the meantime, earn even more trust by speaking out about smaller issues that may come up.


Understand the boss's goals and priorities. Going against the boss’s and/or the company’s policies without good cause won’t work. Have a solid business reason for challenging the boss—one that advances a key organizational goal.


Watch your timing. Never challenge the boss in public. Schedule a time to speak in private—when the boss is not dealing with a crisis or unusually busy.


Enlist coworkers’ support. Discuss your idea with colleagues involved with the policy you’re challenging. They may offer helpful new suggestions and throw their support behind you.


Prepare a strong case. Any challenge to the boss should include solid data. Explain in detail how your solution will save time and money, and make the organization look good.


Listen carefully. There may be reasons for the initiative you’re challenging that you know nothing about. You may need to rethink your argument—or your solution.


Don't expect an immediate answer. The boss will need to reflect on your proposal. Should you get pushback, you may wish to gather additional evidence and try again at another time.  


If your boss agrees. Follow up with a detailed memo outlining specific next steps to put your solution in place.

Know when to let go.
If you’re getting nowhere, give in gracefully. Thank the boss for the chance to offer your views. Don't take it personally. This is likely about the company, not you.


Last, but not least, remember that you must work with the boss tomorrow … and the day after that … and the day after that.    

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