As a busi­ness grows — the chal­lenges to the founders grow. It’s like dat­ing: when you start dat­ing, you just need to find fun things to do; but that’s a dif­fer­ent skill set than, say, par­ent­ing or pro­vid­ing for a house­hold! What if your part­ner is great at the ear­ly chal­lenges, but not at the lat­er ones?

Be­fore we an­swer this, the first step is iden­ti­fy­ing when it’s hap­pen­ing — and tell him. Maybe he re­al­izes it? Maybe he does­n’t. There are two great ways to iden­ti­fy it when this hap­pens. Some­times, your part­ner will re­al­ize it him­self, with a lit­tle prompt­ing. Peo­ple who are more hon­est about their own per­son­al­i­ties tend to do this.

Some­times, he’ll rise to the chal­lenge. Some­times, he won’t. But it’s im­por­tant to give him the re­spect to let him know that you want him to rise to the chal­lenge. And then, if he does­n’t: when you do con­front him, he will be psy­cho­log­i­cal­ly and emo­tion­al­ly pre­pared, be­cause you will have al­ready sug­gest­ed to him to rise to the next lev­el.

If he does­n’t rise to the chal­lenge — and 9 out of 10 times, they don’t (but enough do, so it is def­i­nite­ly worth keep­ing an open mind) — then the chal­lenge is what to do.

The best med­i­cine, of course, is the pre­ven­tive med­i­cine: an ounce of pre­ven­tion, as Ben Franklin said.

Talk at the very be­gin­ning of the project, about how both of you will need to rise to chal­lenges you don’t ex­pect — and do mis­er­able work that you hate, but that will help you grow. Is he ready for it? Does he want to seize the op­por­tu­ni­ty? If not, then lets write in the var­i­ous con­tin­gency plans di­rect­ly in­to your founder’s prenup! This deals with ques­tion like: what are the gen­er­al types of chal­lenges you ex­pect both of you to rise to? The spe­cif­ic ones? In each case, what do you do, or not do, if-or-when they don’t?