Do Not Mistake Effects for Causes: Ask Why Five Times

Avoid mistaking effects for causes—or keep asking and thinking more deeply. Sometimes, when I go out to interview a startup team and ask, ‘Why did such-and-such happen?’ the answer is, ‘Because of A.’ But A often looks more like an eventual outcome than a cause. Do not be satisfied with a surface-level answer. That answer may still be describing the final outcome. To understand why it happened, you have to keep asking and thinking carefully. That is why we ask why five times about a problem: to get to the underlying causes. The process also forces us to think more deeply. Asking questions is, in fact, a way to upgrade your thinking. You gradually move from not knowing what you do not know to knowing what you do not know. That is a breakthrough for many entrepreneurs. Many do not know where their blind spots lie or what they do not know. Through a dialogue with me as an investor, with ever-deeper follow-up questions, they eventually realize: ‘I really have never thought about this. I really do not know yet.’