I'll take a wild guess at this Dave. Does your chuck key have a cross handle with sides of equal length, or is it one of the ones with a longer handle and a swaged out thumb section?
I've found that the latter type works better, with a proviso.
Imagine holding an electric drill with the chuck end facing away from you, and a key hole on the top.
Set the key such that the longer handle is to the right at 90 degrees, facing due east if you consider the drill to be pointing north.
That way, when you tighten up, you effectively pull the key towards you, and force the gear teeth into a tighter mesh, rather than away from you as the second photo shows.
Are you left handed, as that might mean you normally use the key 180 degrees different to me?
p.s. took too long typing, Nick beat me to it. 
Also I sent a message to Jacobs earlier on asking this very question. i.e. one hole or three. If I ever get a reply I'll update this thread
Edited By peak4 on 27/01/2017 14:41:34