Keep Asking Why

Stop asking about what everyone is doing - ask why they’re doing it.

Understanding people is tough. Lives are rich narratives filled with everyone’s own ambitions, worries, and friends. With all that going on, it’s hard enough to understand yourself, let alone anyone else. But it’s important that we try.

The best ways to understand a person are to talk to them or to read something they’ve written. Since you don’t have much control over what they’ve written, I’ll try to give some advice on how to talk to them.

When trying to understand someone, realize that you are only experiencing a snapshot of their story. Asking someone what they are working on, where they live, or how hiring is going only gives you information about that one tiny snapshot.

Instead, ask why they’re doing it. Dig a little deeper. Keep asking why. Get them to go backwards and retrace their steps. You’ve dug far enough when they’ve answered with “I want to make my mother proud.”

Stop asking what someone is doing or who they raised their Series A from. Instead, keep asking why.


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