Art of asking questions

A part of my work is a journalistic work. I go out, I grok how & what software people are building, and that knowledge informs what we do next. This is primarily done by asking questions and listening to the answers. So I think a lot about how to ask questions.

One of the first things I noticed is that if you are trying to find out something, it’s never a good idea to ask a direct question, such as, “does X matter to you?” Because for almost any meaningful X, say cost, culture, people, process, … the answer will be “yes,” but that’s useless knowledge. What you really want to ask is how people trade off two good things X and Y. The world is full of good things we don’t get around doing it.

Another problem with these piecemeal speed dating questions is that every time you come up with a new question, you have to go back to them and ask. My knowing what color you like and what food you like doesn’t really help me infer what car you want to drive.

Instead, I strive to understand the picture they are seeing. What do they perceive as the reality around them? What are they trying to change in there and what do they see as constraints? Why? Tell them somebody else’s story in a similar situation and ask them how those are different? Ask them to draw diagrams, or draw a diagram yourself and ask them to correct your misunderstanding.

When I’m successful in doing that, I can put myself in their shoes. I can think like them, and I can infer what they do for why. I can retrace their decisions. I pitch some of those back to them, and see if I got that right. If there are discrepancies, that’s a sign that I grossed something over. Once I build such a mental model, it’s very powerful. I can answer the speed dating questions myself based on it.

This takes time. I usually ask for 2 hours to conduct these interviews. I then take several more hours to process the raw notes into a readable material. It also only makes sense in a small circle setting, ideally 1:1. IMHO a group discussion is useless if you are trying to really understand anything. Some people dominates the air time and others disengage. People use the same word to mean different things. They latch on to details that are irrelevant. I’m sure you know what I mean.

Yet I see a lot of people asking speed dating questions, in a group setting. And that’s been puzzling to me. When you put 10 people in a room and ask questions like “is testing important?” what kind of knowledge can you possibly gain out of it? What am I missing?

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