Mastering Common Interview Questions & Responses Series #3: Tell me a time when…

We’re excited to bring you the 3rd series on mastering common interview questions and responses. In this blog, we’ll walk through how to answer questions like these:

  1. Tell me a time when you disagreed with someone at work and how you dealt with it?
  2. Tell me about a challenge or conflict you’ve faced at work, and how you dealt with it?
  3. Tell me a time when you had to convince someone of your recommendations and how you went about it?

These are what we call situational interviews which require preparation in 2 main areas: Stories that are representative of your experience and effective method of storytelling via STAR method.

With stories, I would recommend having 4 – 5 stories that highlight your experience and demonstrate the relevant skills that are specific to the job that you are interviewing for. Good stories will take time to select and we typically recommend that you really think through your experience holistically to come up with examples of situations that really showcase your experience, skills, and thought process.

For those of you that might not know or have not heard about the STAR method, now is the time to practice! STAR is a structured way of answering these ‘tell me a time when…’ questions and consists of situation, tasks, action, & results. I personally like to recommend that you keep it to 30 seconds for each part and maybe leave a bit more time to hone in on the action and the results. The beauty of this is that it forces you answer the question in full and expand on all the key parts without running into the risk of rambling on!

Let’s go through some live examples using the STAR method:

Interviewer: Tell me a time when someone disagreed with you at work and how you dealt with it?

Response: A time when someone disagreed with me at work was when…

  • Situation – I was working on a growth strategy project that required me to get buy-in from the key stakeholders on the final recommendations and the associated financial projections. When I shared the projections with my manager, he expressed his concerns that the financial projections might be too ambitious and that he did not necessarily agree with it.
  • Task – As such, I listed to his concerns and tried to explore additional ways to demonstrate and convince him that the projections were achievable and that the assumptions used were reasonable.
  • Action – What I did was that I used a combination of internal and external benchmarks as another way to sanity check and to show that the projections were in-line with what has historically happened in the market. I found benchmarks of other companies that have launched similar products and used that as an external data-point and internally, I referenced other new product launches in respective markets to show that the projections were similar to what we have seen elsewhere.
  • Results – In the end, I was able to use the availability of tangible examples to convince the manager that the projections were in line with what we have seen both internally and externally. This helped him to be more comfortable with the financial projections and we were able to receive the approval from our stakeholders to move forward with the strategy.

This is just one example of a story that I would use to answer this type of question and while it will be a very different story for you, I cannot emphasize the importance of using stories to showcase your experience and skills that are relevant to the job. In this example, I wanted to show that I was presented with a problem and I had to solve it in a thoughtful, resourceful way and it led to positive results, which is the ability to convince the manager and stakeholders of my analysis.

As you think about the stories for the situational questions, be sure to think through the following questions:

  • What skills do I want to highlight that will be relevant to the job that I’m applying for?
  • What examples would help bring those skills to light?
  • What are the key messages that I want the interviewer to get from this?

The last thing I would end with is that the sample answer above can also be relevant if the interviewer had asked:

  • Tell me a time when you had a conflict at work and how you dealt with it?
  • Tell me a time when you had to convince someone of your recommendations and how you went about it?

You can tweak the answers above to fit into the questions at hand, especially if the stories have a few dimensions. Hence, it is important to have 4 – 5 stories at your disposal so that you can use them interchangeably and adapt them to the question being asked.

Hope this was helpful! Please note that all these are sample responses, and there are many different ways to answer interview questions. Would love to hear what other interview questions you want us to tackle. And if you or your friends are in the market for resume & LinkedIn reviews or interview prep services, feel free to reach out. We’re offering a 30 minutes free consultation to get started. Contact us at or [email protected].