I've read quite a bit about happiness, and while the concept is slippery enough that people can find ways to gripe about anything you have to say on the subject, it's pretty safe to say that Mihaly Csikszentmihalyi idea of "flow" is onto something. People are most satisfied with the way things are going when the following things are happening
1. Clear goals and expectations about the task at hand.
2. Direct and immediate feedback.
3. A high degree of concentration.
4. Loss of self-consciousness.
5. Altered perception of time.
6. Challenge proportionate to your skill level.
7. Feeling of control over the situation.
8. Activity is intrinsically rewarding.
It's easy to see why we want to experience flow and also why we don't experience it often enough. Real life doesn't always offer 1, 2 and 6, life is usually to open ended and complicated. And without those it's hard to just conjure altered perception of time and stuff.
Just looking at this list I think it's easy to see the value of a good boss. Bosses usually have some control over 1, 2 and 6.
But what really jumped out at me is that with the exception of 8, this is exactly the point of sport and games. The goals are clear, you can't avoid instant feedback on your performance and you most of the time you end up at more or less the right skill level.
So long as the rules are not to stupid, or lots of people care about playing it, you're well on the way to flow. That goes for sport, board games and computer games.