The Four Questions rule applies in many instances.

Imagine that you and an opponent have decided to duel. The opponent is strong at boxing and bamboo sword fighting, but weak at wrestling and log rolling. You are weak at boxing, strong at bamboo sword fighting and log rolling and have middling strength wrestling. What dueling venue suits you best? What dueling venue suits the opponent best? The answers are obvious if strength and weakness between you is relatively similar.

Should you decide to box, you will be boxing against an opponnent who is strong at boxing where you are weak. While the experience might help your boxing skill, if the point is to win the duel, then you'd be better off not choosing boxing.

Should you decide to bamboo sword fight, then who wins is largely a toss-up. Both you and the opponent are strong at it. Should you decide to wrestle, you might have a good chance to defeat the opponent, but given your middling strength, there still seems a better option.

Log rolling. You are strong at log rolling and the opponent is weak at log rolling. If the point of the duel for you is to defeat the opponent, you'd best be served by having log rolling as your venue.

Yet, despite this very simplistic and common sense reasoning, in Go, business, and other fields, things get in the way of this sort of reasoning. Founders of small companies, excellent inventors or tinkerers, think they'd be better CEOs - an entirely different skill - than someone they could hire. CEOs, blinded by ego, emotions, or otherwise, try to get into a business or enter a market because of some sort of "god complex," not because it suits the company best.