I recently read an interview in the Financial Times with J. Crew’s CEO, Mickey Drexler. This interview was of particular interest given the reporter’s focus on one question she asked Mickey - “ What was your biggest mistake?” As Mickey would say, "Love that question!"
Back when I interviewed Mickey at the Tuck School of Business at Dartmouth, I asked him this very question. Although I don’t think it’s unusual for executives to be asked similar questions by various interviewers, I did find it interesting how differently Mickey answered this question in these two separate instances.
During my interview with Mickey, although he took a few pauses or moments to reflect during the actual taping of the interview, he did eventually answer the question. He described his greatest career mistake as when he tried to change something too quickly or when clothing items were redesigned too aggressively. More recently, he recounted his greatest mistake to be when J. Crew a few seasons ago lost its way creatively, getting too trendy and swaying from its core designs.
However, the answer Mickey provided – to the same question – was drastically different when talking to the Financial Times. Maybe it’s a coincidence, but after reportedly reading the news about Gap closing a bunch of stores in the US, he told the FT reporter his biggest mistake was not fighting the board hard enough to stop the increase in real estate - a move Mickey opposed, but went along with.
Does a mistake only become a mistake when your executive decision at the time is later reversed?