[sstradling]

The question I'd ask him is how he's felt about the lifetime of command and control? If he's always been the guy who kept trying to change things, adjusting to a startup is going to be a matter of helping him understand how to best have an impact (and get used to the fact that people will actually appreciate and support his efforts). If he's the guy who followed the handbook, he's in for a much bigger shock.

For me, I've been bouncing off the walls for 12 years in a large bureaucracy. Reading Eric Ries's Lean Startup and finding Paul's blog was like drinking water for the first time. I hope he has the same experience.