Interview Question- Tell me about a time when you disagreed with your boss


Today, we’ll tell you how to build a powerful story that you’ll need to tell in a job interview! Specifically, when you’re asked to tell a story about a time when you disagreed with your boss, what do you say? Let’s find out. What you’ll learn today is:


4 basic points to consider when answering this question:


‘Tell me about a time when you disagreed with your boss’?


What’s YOUR ‘conflict style’?


Deep dive into one concrete example ‘disagreement’


Just for fun: one bad example


4 key points to remember:


As I always say, this answer should come in the form of a story with details. That’s how people remember, that’s how people get to know you, and that’s what captivates people the most! The story should be quick, around 30 – 60 seconds long and definitely no longer than a minute and a half.


When telling your story, always be respectful of the “boss” character in your story. Use a nice tone and put him or her in a respectful light when telling the story. If you can’t do this, then don’t tell that story.


The real thing they want to know is how you handle conflict. Everyone has their own unique way of handling a conflict, so what is yours? (We’ll get more into this in just a minute.)


At the end of the day, they ARE the boss with the ultimate ability to fire you in most cases, even though bosses make mistakes too! If you’re in a job where you have a boss, the truth is you need to respect that person’s authority, even though sometimes it can be hard and even though that person is only a human who can be wrong just like any of us. A good boss will listen to your suggestions, and if you disagree with him or her, they’ll want to know more.


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If you do love reading, let’s get back to it.


Let’s talk about you & YOUR conflict style:


Before we go into any answering, I want you to ask yourself, “How do I handle conflict?” Do you get very stressed out and confront it head-on? Do you shy away from it and try to ignore it and pretend it’s not there? Do you just go along with what the boss wants even if you don’t agree? Or do you push forward until change happens? What’s your ideal way to solve a disagreement?


Now that we’ve hopefully unpacked a little bit about you, let’s get into a real example. Your answer needs to reflect you and your true beliefs and personality, and bringing your real self to any interview is truly the only way you can find the best fit for you in your career.


So, example: manager or big boss man or woman wants to have a big staff event that will cost the company a lot of money on a Sunday.


You know that people are with their families and a lot of people are likely not going to show up on a Sunday. Therefore, the money spent won’t achieve the objective that the manager and you hope to achieve, but how do you tell your boss this?


You might suggest moving the event to Friday afternoon or a Saturday. Here are a few ways you can bring it up:


“You probably already thought of this, but could we host the event on a Friday or a Saturday instead?”


“Have you thought of hosting the event on a Friday or a Saturday instead? Have you thought of doing it this way?”


“I was hoping to better understand why the event is going to take place on a Sunday.”


“Is there a reason we haven’t considered hosting the event on a Saturday or even a Friday?”


“At my last company, we did the event on Friday and we found that we had a lot better attendance. Would you be open to this?”


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The boss may give a very good reason as to why they chose Sunday for the event’s day, a reason that maybe you weren’t aware of. Perhaps there is no reason and it’s just a plain old bad idea!


With you approach them with your concern and suggestion in a kind manner, you have now done what you needed to do. If they still say no, then you can have a little back-and-forth but don’t take it too far.


I’ve seen people stand up to authority repeatedly in their careers – even in the most high level positions – and they always end up getting fired. It’s sad, because they are very good at their jobs and they didn’t want to be fired.


And the answer to this question using this example would sound like this:


Tell the story of the event


Then tell how you approached the disagreement


Then tell the end result


Then you’re done!


Right, I almost forgot about the bad example. Okay, so the bad example would go like this:


“I’ve never had a disagreement with my boss before, ever.”


If you are absolutely stumped and you’ve got nothing, you could say: “I could tell you about a time I disagreed with a co-worker.” This may be easier to find a concrete story for.


And there you have it! The answer to The Big Boss Disagreement!


Now I’d love to hear from you! How do you feel about this question? Can you think of a disagreement you’ve had with your boss or a co-worker?


If you’d like to dive deeper with me:


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Do you know one person who could benefit from the information in this post? If so, do your friend a favour and share this info with him/her.


And remember, the current system isn’t perfect, but you can outsmart it. I’m here to prove to you that you do have what it takes.


I’ll see you next time and I can’t wait!

In Work & Life

I’ve got your back



10 comments on “Interview Question- Tell me about a time when you disagreed with your boss

  1. Oh, thanks a lot! I guess everyone wants to know, how to tell about someone’s wrongness without being offensive and disrespectful. And this is a wonderful, detailed guide for the descent answering the trick question during an interview. What I like most, that the author speaks to me in a simple, friendly manner. The tips are grounded, with many live examples.

  2. I had disagreements with my boss before, many times in fact and most of them shallow. I don’t want to pinpoint the culprit or who’s to blame every single time but I always think that I have to tolerate her because she’s my boss. So I shut up and do my work. That’s always the solution in the issues we’ve had. I try to make amends because they’re needed for a working environment to work.

    Tolerance is acceptable, right? I also think that it’s important to set a limit to it. When the disagreement goes too far and someone has crossed a line, it’s time to take action and confront the boss. I’m not the confrontational type so I avoid confrontations but I will if I am already offended.

  3. What if you have sincerely never had a disagreement with your boss or coworker? How would you answer this question. I was a case worker (social services). I worked pretty independently and group projects were standardized government situations.

    • Hey good question, I would start with any disagreement you’ve had in a professional setting at all, whether that be with a customer or client, or person you were interacting with. The goal of the question is to see how you work through a conflict, to assess communication skills. You can explain you worked independently and tell a story of a time you disagreed with someone other than your boss. That will work if you’re able to give them what they need which is to answer how you personally work through conflict and how you communicate. Make it a good story and you will be good.

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