Learning to ask one more question

One of my favorite moments in a conversation is when someone says something about their business like it is nothing. They have been doing it for years. To them, it is so familiar that it barely feels worth explaining. To someone hearing it for the first time, it can be the most interesting part.

A service category is a useful place to start. It tells me what the business does. It does not tell me what the owner cares about, what they learned the hard way, or why they make the choices they make.

So I ask another question. Why that approach? Where did you learn it? What do you hope the customer experiences? I’m trying to understand the meaning behind the work before I decide how to describe it.

That takes listening. If I arrive with a message already written, I can make the conversation fit my idea and miss the person in front of me. I would rather be surprised. The detail that changes the story is often the one I did not know to ask about at the start.

I know what it feels like to struggle to explain yourself. Speech and theater helped me become more comfortable talking, partly because I could begin with somebody else’s story. Helping someone find words for their own work still feels connected to that experience.

When I reflect a story back, I want the owner to recognize it. They should be able to say, “That is what I mean,” or tell me where I got it wrong. A stronger sentence is not worth much if it stops being true to the person.

Technology can help turn that conversation into a draft. It can help us work through versions. It cannot decide on its own whether I understood the owner. That responsibility stays with the people in the conversation.

That is why the extra question matters to me. It gives the story a chance to become more specific before we try to make it bigger.