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Fourth question separates tourists from experts
Layered questions
Whoever asks doesn't need to be deep on the problem to interrogate someone on it. The founder either keeps answering as the questions get more specific, or runs out of answers.
Spread over a course of weeks, this kind of questioning also separates the okay or the good or the energetic from the obsessive maniac type of founder.
Working problems together
Another test is working through something interesting together, to see how quickly a founder moves through a problem and comes up with alternative solutions. A founder's desk collects the hardest problems in the company, because everything repeatable gets delegated downward as the company grows.
Why do layered questions expose shallow knowledge?
Psychologists Leonid Rozenblit and Frank Keil described the illusion of explanatory depth in a 2002 paper in Cognitive Science. People rated how well they understood everyday devices such as a zipper, then tried to explain how they worked, and their ratings dropped. Each extra layer of detail forces a person to produce real mechanism rather than a general feeling of understanding. Questions that go four or five levels deep reach the point where memorized phrases run out.
How does the five whys technique work?
Taiichi Ohno developed the five whys at Toyota as part of the Toyota Production System. A problem is stated, and the question why is asked repeatedly until the root cause appears. Ohno described it as a way to move past symptoms to the underlying process failure. The method became a standard tool in manufacturing and software teams.
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