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Tell Me About a Time You Disagreed with Your Boss

by THEA kelley | August 22, 2024

“Tell me about a time you disagreed with your boss.” When I coach job seekers on this interview question, they often ask, “Should it be a disagreement where I turned out to be right, or the boss did?” But that’s beside the point.

The interviewer is seeking insight on whether you’re able to disagree constructively and collaborate well. Some employees take a “sour grapes” attitude toward their boss’s perceived misjudgments, undermining their manager. Others may merely follow orders, thinking “Well, I’ll just do as he says, and let him find out the hard way that he was wrong,” without raising an alternate viewpoint that could have led to a better outcome. The point of answering “Tell me about a time you disagreed with your boss” is to show you’re better than that.

Don’t assume you need to tell about a very heated disagreement with your boss.

In fact, a story where both parties remained calm may make a better impression.

Pick the right story.

If possible, tell about a disagreement in which you and your manager had differing–but both pretty reasonable—ideas of how something should be handled. This will make it easier to follow my next guideline:

Be objective, and don’t make either party look foolish.

A common mistake is to pick a story where it turned out the boss was wrong, and to tell it with a tone of barely restrained glee. Remember, the interviewer is likely to sympathize with the manager in the story. No manager wants their team members smirking behind their back. Show that you understood your manager’s point and respected their thinking, even if you disagreed with it.

What if you had a “nightmare boss” whose thinking was very difficult to respect? It may be better to tell a story involving some other manager.

Even though you’re being respectful, it’s safest to avoid identifying information that enables the interviewer to know exactly whom you’re talking about. Keep them anonymous. For example, refer to them as “my manager in a past role” or “a manager I once worked with.”

Devote most of your answer not to the disagreement itself, but how you handled it effectively.

Describe how you brought your perspective to your manager. How did you prepare and communicate the facts upon which you based your argument? How did you present it in a way that supported a positive relationship between the two of you? Tell what your manager’s decision was, showing you understand the rationale for it. Tell how you ultimately supported, or at least cooperated with, the manager’s decision.

Here’s an example:

“In one of my roles as a sales rep, my manager and I were collaborating around a product launch. I wanted to take a consultative sales approach and focus on building a strong relationship with each client and customizing our solutions for them. My manager preferred a more traditional strategy, where we would reach out to as many potential clients as possible with a standardized sales pitch. He felt that casting a wide net would generate more leads and ultimately higher sales numbers. Although I didn’t think that was the best practice, I could understand how that approach would be less time consuming, at least in the short term.

“I prepared a simple presentation to show my boss how the consultative approach could yield stronger results, but he wasn’t buying it. So I determined to make his approach work as well as I could. At any rate, I did think it could be effective in accumulating leads.

“A month later we had a strong pipeline of prospects, and I sensed that my boss was feeling more relaxed about how things were going. At that point I asked whether I could experiment with taking a more consultative approach in following up with a few of the highest-potential leads, and he gave me the go-ahead. In the end, I achieved 120% of the goals we’d set, and I think both approaches deserved some of the credit. Just as important, our working relationship became stronger.”

This example involved a compromise or combination of two approaches, but yours could be simpler: either you followed your manager’s lead and did your best, or you persuaded your boss to see things your way. However the issue was decided, show that you worked well with your manager and respected their point of view–that building a good relationship was important to you, not just winning the argument.

Now prepare for other interview questions about conflict in the workplace. 

Now that you know how to answer “Tell me about a time when you disagreed with your boss,” I recommend you also read my post “How to Answer Interview Questions about Conflicts.”

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