Generally, if you want to do a quick victory, it's highly advisable to start taking leadership as soon as possible (like lvl 3, for example), especially on hard and impossible. Besides, you can't pick the leadership upgrade at every level. If you started at 2, you can pick it at the even numbered levels (2-4-6-8-10-12-14-16-18-20-22-24-26-28-30), and if you started at lvl 3, you can pick it on the odd numbered levels (3-5-7, etc., up to 31).
It all depends on how do you want your game to unfold. I personally like to pick leadership as soon as I get it, it allows for quicker victories, even in impossible. For example, right now I'm day 5 (I lost a day traveling, could have been day day 4 but I don't have a precise clock, even though I'm running Nobilis' 1.7 patch) on impossible with a paladin in the mines, killing strong or very strong opponents with minimal or no losses. If I have to wait till lvl 20... It'll take a lot of time.
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