Do I love to win or hate to lose? I was recently asked this question as a part of a job interview. The interviewer had prefaced the question by saying, please simply answer this question, no explanation necessary. I thought for a moment and gave my response. After the interview, I decided to dig into this question to understand a bit more about the motivation for this question. This has now become one of my favorite questions, as it is not only simple and accessible for anyone to answer (even kids), but it can help to uncover motivation and core value level thinking. Within the workplace, especially in commercially minded organizations, the question is designed to get to the root of someone’s approach to selling. Hating to lose is a characteristic of many ‘high achievers’ including athletes, go-getters and many sales people. For many, the idea that winning is the only thing that matters is ingrained from an early age. This tends to result in someone hating the feeling of loss. As a result, they avoid it at all costs, and don’t like to think about it much. Loving to win, on the other hand, allows one to celebrate their successes while not wallowing in defeat. People who love to win can often be more introspective about a loss, which allows them to grow over time and continually improve. As I thought about the question, I was struck that it resembles another paradigm of the gap vs. the gain. However, I am a big fan of this framing because I think it makes this idea very accessible. As with many things, perspective is so import ant. I choose to celebrate my wins and learn from my losses. So regardless of the answer the interviewer was looking for, for me, I answered correctly during the interview when I said **I love to win**!