John picks up on an article in Fortune at the time of Pressler's arrival which highlighted the cultural mis-match between him and the Gap brand. Previous posts on this blog have suggested the best way to get true insight is not to understand the consumer, but to BE the consumer. It seems clear from the interview that Pressler was miles away from this:
“It took me weeks to start wearing jeans here,” admits Paul Pressler, settled into his window-lined L-shaped office on the 14th floor of Gap's San Francisco headquarters. An admitted clotheshorse whose taste runs to Armani and Zegna suits, he was known as the best-dressed executive at Disney, where he ran the theme-park business. Now he is six months into his new job as CEO of Gap, and it's obvious that this is not a natural fit.
This distance from the consumer explains why Pressler resorted to focus groups to test t-shirt designs, as mentioned by John's second post on the Gap. Contrast this with the approach of Harley Davidson and Nike to hire people who are into the products they sell, and spend time hanging out with bikers and sports fans, not watching them behind a mirror.