A newly-retired executive takes a job as an adjunct professor and really shakes things up. Both the school and the students are blown away by her fresh thinking and new approaches.
A forty-year old internet executive who has been running his company for decades misses one new trend after another, because he's still living in 1998.
One thing that happens to management when they get senior is that they get stuck. (As we saw with the new professor, senior isn't about old, it's about how long you've been there).
If you've been doing it forever, you discover (but may not realize) that the things that got you this power are no longer dependable.
Reliance on the tried and true can backfire (Rupert keeps missing one opportunity after another, and keeps misunderstanding the medium he works in) or it can (rarely) pay off (Steve Jobs keeps repeating the same business model again and again--it's not an accident that Apple has no real online or social media footprint. Steve believes in beautifully designed objects, closed systems and evangelizing to developers and creatives).
Worth quoting--one of Arthur C. Clarke's lesser known three laws: "When a distinguished but elderly scientist states that something is possible, he is almost certainly right. When he states that something is impossible, he is probably wrong."
The paradox is that by the time you get to be senior, the decisions that matter the most are the ones that would be best made made by people who are junior...