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How to Answer Challenging Behavioral Interview Questions

interview tips Nov 22, 2021

Some behavioral interview questions are designed to learn how you deal with challenging situations. Failure questions, conflict questions, mistake questions and unpopular stance questions are all very common in interviews. How you respond to these challenging questions can make the difference between success and failure as an interview candidate.

It is critical that you establish what happened quickly. There is a ton of context that is simply not relevant, so you have to get to the conflict, failure or mistake right away (in 30 seconds or less). Then, we can move onto the actions that you took to overcome the challenge. From there, you want to cover the learnings and applied learnings. If you focus on both the actions and learnings, your interviewer will focus on the positive steps you took and not on the negative situation.

Item #1 – Get to the Point

Most candidates provide too much context when answering these types of questions. There is always a story that leads you up to a negative moment. However, if you spend too much time on the context and tell the whole story that led up to the negative moment, you will be bringing your interviewer down that entire time. We want to get past this negative challenge as quickly as possible. Then, you can talk about all the positive stuff, including the actions you took and what you learned from the experience.

Remember that past performance predicts future performance. As an interviewer, I want to know about the positive things—even if they were born from a negative moment.

To do this in 30 seconds or less, I recommend describing your role and company, while providing a few critical details that describe the mistake and or failure. Specify that you took ownership of the challenge and quickly move into the positive aspects of your story. 

Item #2 – Actions

Now that the negative stuff is behind us, you can move onto the positives. How did you overcome the challenge, conflict, mistake or failure? Start by outlining any research and planning you conducted, and share conversations with fellow team members or other departments to turn this situation around. Conversations are important to highlight because they can really show how you communicate information, ask questions and interact with others in a challenging situation.

From there, you can cover the action steps you took to turn the challenge into a positive resolution. How did you pull it all together?

Item #3 – Learnings

Not all of your behavioral answers require learnings. However, they are crucial when talking about challenging situations. It is critical for your success that you discuss learnings. Don’t just leave your story with the challenge and the actions. You must show your learnings and what you did to improve yourself in the wake of that situation. Highlight any actions you took to better yourself. It shows a growth mentality and simply cannot be left out of your interview response.

Item #4 – Applied Learnings

Learnings are great, but the application of these learnings is also a critical item to share. It helps your interviewer envision you actually applying these learnings in your new position. It shows you are a continual learner who is willing and able to better yourself at any opportunity. Bring in your learnings and then share a data point or two on how you pushed forward on the next project, showed initiative or how you applied what you learned the next time you faced a significant challenge.

Item #5 – Sample Example

There is an example from my own career at Google which perfectly illustrates such a situation. I won’t share the full story here, but I recommend checking out my full YouTube video on this topic. At the end, I share a great sample example to help you better understand how to address behavioral challenge questions.

Watch the full video here:

It’s usually not very fun to talk about challenges or failures you’ve faced in your career. The good news is you can turn these challenges into opportunities when you structure your behavioral interview responses properly. No interviewer expects you to be perfect. We all make mistakes and face tough challenges. It’s how you overcame them and the processes you took to better yourself.

For more interview tips and information, visit my YouTube channel or sign up on Practice Interviews to learn more about our professional coaching services.


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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