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Disagreeing with a Boss, Part 1: Positive Resolution

interview tips Oct 06, 2022

This is a common question asked in behavioral interviews:

Tell me about a time you had a disagreement with your boss/leadership?

Always remember that past performance predicts future performance. Your interviewer is asking this question to see how you handle adversity with leadership. If you don’t have an answer prepared for this question, then you are either not being one hundred percent truthful or you haven’t raised your voice enough in the past.

Being able to speak up when you disagree is a critical function of being a good employee. Disagreements are positive when you reflect on them positively. Showing the ability to resolve disagreements will show your ability to have a strong impact with the organization no matter the situation.

Item #1—Positivity

You should always be thinking positively when answering this question. It starts with restating the question:

“Sue, this is a great question. You want me to tell you about a time when I had the opportunity to share my perspective with my boss?” 

You are starting on the positive tone instantly. You are flipping from “disagree,” a negative word, to “opportunity,” a very positive word. You will also want to approach this answer in a calm and respectful manner. Lastly, I want you to highlight your boss’s skills within the response. Talking about their strengths in a positive manner can be really beneficial. 

In the items below, we will step into your shoes as an employee who is dealing with a leadership disagreement. We will also review some of the key takeaways and points that you will want to present when asked this question in an interview. How well did you handle the situation originally and how can you present this example in an interview with a positive message.

Item #2—Communication/EQ

I want to couple communication and emotional intelligence (EQ = emotional quotient) together because they are connected. First, you have to listen to what your boss is saying. Then, you follow up with inquisitive follow-up questions. In addition, you must display respectful courage. This is the willingness to stand up for what you believe in without being disrespectful to leadership. 

Another important skill to demonstrate is your ability to resolve conflicts. Understand the benefits of a constructive back and forth when addressing a disagreement. Finally, there must be empathy. The ask/directive you were given, may not be coming directly from your boss. It may be coming from above them and they may also have their own disagreements. Understand their role and respect their position in the chain of command. 

Item #3—Data/Goals

By utilizing active listening and asking great questions, you will start to find out the data and the goals. From there, you will be able to resolve and overcome the disagreement. Find out their motivations in the beginning. Is the directive coming from them or from leadership above? Make sure you have all the overall data, facts and information. This includes understanding the historical context, organizational needs, and competitive landscape (if applicable).

Item #4—Voice/Company Needs

It’s important to have your own voice while still understanding you have to support the needs of your company. And it is critical that you are providing your perspective, being proactive and presenting solution-based feedback. In addition, you should be providing alternatives and options in a positive manner. It’s not just about disagreeing with the original direction. You are trying to provide different solutions.

You can have your own voice and support the company at the same time. Ultimately, if your boss and/or the company decides not to take your suggested direction, you have to be positive about the fact that they are doing what they feel is best for the organization.

Item #5—Your Role

It will be important for your interviewer to understand your role in the organization. It can provide helpful context. You will want to provide a very brief overview of your role and expectations within your response to set up the disagreement.

Item #6—Who

Who is going to be asking you this question? It’s likely only going to be a few different people:

  •   Hiring Manager
  •   Skip Lead
  •   Human Resources

Understanding where this question is coming from will help you know how important it is to provide a great answer. This is especially true when interviewing with your potential hiring manager, you may end up having constructive disagreements with them in the future!

Item #7—Learnings

I want you to use the S.T.A.R.L.F. (Situation. Task. Actions. Result. Learnings. Follow Up Questions.) method as always with behavioral interview questions. Put extra emphasis on your learnings. It is really important to talk about what you learned from your interactions.

In next week’s article (read Part 2), we will dive into an example answer to these common behavioral interview questions. You will learn how to take your past experiences and show how you handled a disagreement with your boss in a positive way. 

If you don’t want to wait for the next article, you can watch my full video on this topic below: 

For more interview training resources, check out my YouTube channel, follow my weekly blog or visit the Practice Interviews website.


Jeff H. Sipe

Jeff has interviewed over 1000 people in his career and previously spent five years working at Google headquarters in Silicon Valley. You likely found Jeff through YouTube and you will find the same level of dedication in his one on one practice interview sessions.

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