There is never enough time. There is never enough space. There is never the right time to ask the kinds of questions I would like to ask. We are always on our way somewhere else. Whether we chat on twitter or facebook, by email or by telephone, by a trip to the keyboard or to the office down the hall, we don’t get to ask the interesting questions. We have to talk about what is next or how to fix this problem or what will happen when that doesn’t work.
I have a lot of great people I know. Some of them have been around me for decades. They know what I sound like when I talk without the aid of asychronicity, and I know where they live. Others have voices I have never heard, faces I have never seen. But I like to talk with them, to say “hi” at least. And I wonder what it would be like to sit with a cup of coffee and time and ask the kinds of questions that interviewers ask. Not cold, embarrassing, entrapping questions, but the kind of questions that invite reflection.
So I decided to do just that.
A few months ago, I had that kind of conversation with my friend Chris about a book he and Julien Smith were writing. I asked five questions, he answered, I clarified a point or two with him, and I published it. Then I tried it again with my friend Diana Scimone to help her with her tweethon to raise $81,000 in one day.
And then, I decided to start asking people who don’t have a campaign or a book.
There is nothing magic about the number five. And the questions are different for everyone, because they are different people and I know different things about them. But I love stopping and thinking about the person and giving them space to think and write about what they may not otherwise be asked.
I’ll start tomorrow. I’ve already got several “5 Question” conversations done. I’ll keep doing them (so don’t think, “Jon must not think I’m very interesting.”) I’m still looking for my own voice in these conversations.