Nobody Is Boring, Your Questions Are

Every question you ask sets a ceiling on the answer that can come back. Most of the questions you default to have a ceiling of about two sentences, and you have spent years blaming the people sitting on the other side of them.

“What do you do” has a ceiling. So does “how was your weekend.” The person across from you is not holding out. You handed them a form with three lines on it and they filled in the three lines.

A search returns what you typed rather than what you meant. Nobody argues with the search engine about this. You get a thin result, you look at your three words, and you refine the query, because the query is the part you control. Conversation runs on the same mechanism, and you have been refining nothing.

Three moves raise the ceiling.

Ask for an instance, never a category. Categories return summaries, and a summary is the most compressed and least interesting form of anything a person knows.

To be concrete: for your next five conversations, ban the words “usually,” “generally,” and “typically” from your own questions. “Do you like your job” becomes “what did you work on yesterday.”

Ask about the hard part. People go flat on the outcome and come alive on the problem, because the problem is where the thinking they are proud of actually lives.

To be concrete: inside the first three minutes, ask what part of it most people get wrong, or what took the longest to figure out. One question, early, before the conversation settles into its shape.

Follow the heat instead of your list. You have a next question queued, and it is costing you the answer already in progress.

To be concrete: when their pace picks up, throw out your next question and ask them to keep going on the one they are on. Give it two more turns before you move anywhere.

Run this for a month and roughly one conversation in five turns into something you are still thinking about the next day. The other four stay small. That is a normal rate, and some rooms are genuinely quiet.

You have met people who spent nine years on one problem and gave you a single sentence about it. They were not being modest and they were not dull. The sentence was the exact size of the box you handed them.