I'm reminded of the time back in the early 90s when president Bush (Sr.) was amazed at grocery store technology, having likely never shopped for his own groceries for decades [1]. It was really embarrassing and highlighted how he struggled with relating to common people. Executives who live lives of privilege like this need to recognize that their lifestyle is a potential blind spot. Anyone who has worked in a company where the rich top brass made all the product decisions (instead of the lower-level normals) knows what I'm talking about.
1: http://www.nytimes.com/1992/02/05/us/bush-encounters-the-sup...