Asking coaches to reflect upon the past is one of the easiest ways to make them uncomfortable. They live at such a lightning-fast speed in the present tense that it's the only way to really derail their thought processes. There's such an intense focus on how to improve today - how to get a team to where it wants to be tomorrow - that it's virtually impossible to take five minutes to reflect upon something that happened even one week prior.
So imagine how much fun it becomes to tell a coach that her 300th career victory was just days away.