I have and laughed, I have that kind of rapport with my superiors and peers whereby they can have a bit too fun without being taken like super seriousley. I'm a consistent deep middle achiever and prefer it to the attention and stigma that intelligent unfortunately suffer.
As a manager you don't need to know it has cogs and dials to read a clock, otherwise I'd be making clocks not administering the endless periphery cloud that encompasses the watchmaker. I would often ensure the jewlery policy and 10mins total daily toilet breaks weren't being abused by staff simply pretending to sit in a cubicle.
I think sometimes it is crucial to maintain momentum and be decisive as you can get paralised by analytical considerations. All plans have enough fat in them that you can fine tune and course correct. You don't see an aircraft carrier at a full stop because the captain is pondering a few things, activity and movement create urgency and rally the troupes.
Personally, I do not see that there is a cultural "challenge" to overcome. We all work in an environment where our customers and employee's come first. Having set up an off-shore site in South Africa over the last 3 years, I believe that I am better qualified than most in responding to cultural changes and challenges. Listening is key to understanding what people want, need and in turn what we can do to support them. Happy people are productive people...oh and make it FUN!