[This post is part of a series on Communication Skills Exercises for Business and Life. If you don’t see a Table of Contents to the left, click here to view the series, where you’ll get more value than reading just this post.]
Has an interviewer ever begun a question with “Can you tell me a time when …” or asked you about your experience?
Such questions arise in job interviews, with people considering promoting you, when seeking funding, even dating, to mention a few places. I’ll take a lot of the guesswork out of how to answer.
Your answer has two major components—content and structure. You have to draw on your experience for the content, but I’ll tell you a structure that works. I didn’t make it up, but I use it. Spread it around. Most importantly, practice it. The more you do, the more you’ll realize its value in many areas beyond interviews where it helps you to demonstrate your experience.
The structure is this:

• Context
• Action
• Result

You can remember it as CAR. When someone asks you about experience or skills, you’ll rarely go wrong using this structure. I recommend one to three sentences of each, which should answer the question in a minute or two and prompt them to ask you for more detail, giving you the chance to lead the conversation and show yourself off because they asked you to.
I’ll illustrate by asking myself a few questions and answering as quick as I can without thinking too much, just using this structure. You’ll have to take my word for it that I’m writing quickly with minimal thinking and editing. The point is not that I’m writing great stories, but that the structure makes it easy to think on your feet and answer quickly and motivate the other person to take interest.

Example 1

“Josh, could you tell us about a time you showed leadership?”

“Sure. Just after business school a friend told me about a company he was starting with some friends. None of them had started a company before but he knew I had and they had a few challenges they didn’t know how to solve. [Context] I met with them a few times and saw they had potential to grow, but hadn’t figured out how to create the internal structures. I met with each, especially my friend and the CEO to understand the situation better. I talked and worked with each to help create an operational plan and set of relationships. [Action] We were able to close a few quick, profitable deals that we might not have been able to deliver on otherwise. After they were set up but last I checked they were still operational. I also happened to stay friends with one of them. [Result]”

Example 2

“Josh, have you ever managed a crisis?”

“Yes. I’ve been through a few very difficult times. The first company I co-founded succeeded at first but in the first few years almost didn’t make it. The proximal reason was that we nearly ran out of money, but there were bigger reasons behind it. [Context] I confess that at the time, for whatever value my physics PhD had, I didn’t understand all the business problems facing us. When I later realized I knew I would keep starting businesses, I decided to get an MBA so my future companies would never be held back by a lack of business skills on my part. [Action] Business school ended up one of the best decisions of my life. Besides starting several successful projects since, I restored my relationships with the people who endured that crisis time since and continue to contribute to my company. [Result]”

Example 3

“Josh, what is one of your proudest achievements?”

“Good question, I have a few [stalling to help me think]. I’d have to say finishing my most recent marathon, which had my personal best time. That year I didn’t get into the New York City marathon, but wanted to run so signed up for Philadelphia’s. I hadn’t run one in years, but that spring came late and I really wanted to run more. I could tell you about the training and what went into it, but I’ll just say that I trained a lot. [Context] When I started running the weather was in the 30s and windy, among the most challenging conditions to do something like run 26.2 miles I’ve been in. About halfway through the race it began to rain. It was my hometown so I knew the course so I felt comfortable running, plus it was less crowded than New York. [Action] I ended up getting my personal best time despite being older and even inspired my mom to run her first marathon two years later. [Result]”

Review

I’m not sure how great the answers read, but given that they’re unrehearsed, they feel to me like they aren’t so bad. They could be longer, but I think they give the person asking the opportunity to ask more if they want. Or I could check if they want to hear more and continue if they want.
Again, I recommend practicing the technique. The more you do the easier it will come to you and the more circumstances you’ll find it applies to.