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until recently he's always won
The chairman also plays badminton with employees about once a week.
In the summer we had a company bowls tournament (lawn bowls - not ten-pin) which the md organised and took part in. I'm happy to report that I won the tournament; the trophy sits proudly on top of a cabinet here in the office.
Competitive sports? Company quiz nights... boy, are they competitive - and it's 'sport' all right! Again, bosses take part in this. Last time around they weren't part of a winning team - although I was ;-)
They also eagerly participate in the company pool tournament.
One of the key purposes in all these activities - apart from the obvious socialising/bonding stuff - is to give the bosses a good hiding - metaphorically - and they know this. This is part of the fun for all concerned...
Country and business/office culture will obviously impact on whether such activities are accepted or frowned upon.
Syzygy
Generally, you can tell--if you look carefully--what the real agenda is in these events. Some players are looking for someone to beat, others are looking for someone make them better. (Ever tried playing tennis with someone learning the game? Not fun.)
It's also a good idea to check your own personal agenda for playing. If you are going into it (boss or employee, doesn't matter) to beat up on this person whose cooperation and expertise you need on a regular basis, then expect problems afterwards.
The problem with golf is there is too much talking. I have learned that in a work environment that "getting to know each other better" is not always a positive thing. Work should be about work.
"Miss Manners" is highly critical of the holiday parties of forced sociability and I agree with her, but I was a long time coming to it. But, yes, I'll be attending this year's Christmas party at the club. (The club is a client and they're paying part of their bill with the party. Ug.)
OTOH, if your boss is a clueless, egotistical, vain, wo(man)izing, thin skinned, fearful of challenges to his/her authority, cad then I'd consider sitting on the sidelines and cheering him/her on . . . until such time as you've lined up a new job.
A real life version of this issue goes on all the time between fathers and sons/daughters. A father will push his child forward in sports, passing along everything he has to offer, and eventually the child gets to the point of being able to outgun the father. It's an interesting point in life for both: The former seemingly invincible father has been defeated. The child is now the father's better, in some cases compelling the father to stage a comeback and retake lost groud - if only for awhile - and so it goes.
Don't well, we're all the better for it, but that said, I've got a lot of practicing to do if I'm ever to challenge my son again in ping pong - the last refuge of inter-generational competitive sport.
I guess it helps that the goal for both is exercise rather than domination.