When listening to another person share about an experience, a useful question is “What was most surprising about that experience?” This is a helpful question because it guides the other person to remember their expectations, think about their experience, and consider the discrepancies between the two. There is a great deal of reflection centered in this question and it facilitates careful contemplation.
For example, I was asked “What was the most surprising thing about law school for you?” After some thought, I responded that the most surprising thing was how many of the insecurities and self-defeating thoughts that I had thought were past me came back up again. I would be overwhelmed with the work and avoid it, then would question whether I was really smart enough and disciplined enough to deserve to be at this school. Even though my context was different, I was still the same person, working through negative tendencies and behaviors. In retrospect, it should not have been surprising, since simply changing my context does not change me as a person. All the same, this was a useful insight, since now I know to watch for it and not be so surprised again. I was able to recognize this self-defeating thought and counter it with the truths I have learned from the past few years.