rather than making it a foot race, as you mentioned some people are already faster, make it most improved.
You could do a general fitness challenge, record push-ups, sit-ups etc. record each persons run time and then the winner is the one who increases by the biggest %. obviously have to do a bit of honor system with that one 'cuz there might be people 'failing' after doing 2 push-ups on the first day.
our office is doing a wall sit challenge for April. April 1st was only 10 sec wall sit, add 10 sec each day so today was 1:20, April 30 is 5 mins. Can be really killer work for you legs.
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