The Art of Asking Good Questions


Do you read interviews? I could argue successfully that publishing interviews can go either way in terms of interest.

Two ingredients to a good conversation are a subject that has done interesting things, and has an intriguing point of view, and a set of questions that demonstrate the interviewer is interested in exploring some of those projects and has a certain point of view.

I'm thinking about Terry Gross at NPR and Charlie Rose with PBS.

There are other characteristics that can make an interview pop. Preparation about the subject matter and the person on the part of the interviewer, a certain degree of curiosity, and creativity. There's a time and place for open questions, and one for more specific ones.

The whole experience of reading feels (almost) like being there, watching the people while they're having this conversation.

Do you consider yourself primarily a poet?

Funny what you can come up with when you cross the names Nora Ephron and Bob Dylan in a search. The two have been in the headlines recently for very different reasons, and here they are together in the transcript of an interview that took place in the late summer of 1965.

That question set in motion an exploration of Dylan's creative process. There is as much information in what is not said there, than in the answers. It is revealing of the personality and thought process without ascribing a specific formula to it.

Art should be where people hang out, to be enjoyed by as many people as possible. We'll get back to this concept.

Do you think that’s a danger in teaching writing – formulaic scripts?

This is from an interview with Francis Ford Coppola [hat tip Robin Sloan] where the director, producer, and screenwriter reveals tidbits through which we discover the artist. Anisse Gross says the conversation went on for five hours, and over dinner.

Gross was impressed by how humble and open Coppola was throughout.

The answer to the question in the subhead gives us some white space to play with:

Dramatic structure and theater plays are thousands of years old. It’s amazing how much dramatic structure is influenced by the Greeks. The novel’s only a few hundreds of years old, but in the novel there’s still so much room for invention.

And later he guides us with: A movie is like writing a haiku. About the Web:

The only thing about the Internet is that the decorum and the politeness really hasn’t been worked out yet. You can say anything you want and there’s no accountability. I’d like a little bit of politeness. To be a human being.

The character of the person behind the artist comes across clearly. The whole interview is a joy to read, do it leaning forward with anticipation. You may find the better question to how to make do with where you are in your work, business, or life.

If you could go back and do one thing differently, would you and if so, what would it be?

A couple of days ago I came across a very engaging interview with Seth Godin. This is a person I have been reading for a dozen years, ever since I found his work through Fast Company. It gives me a soft giggle when people send me his posts to read.

I even spent a day with Seth along with my boss and colleague a few years back.

He's been mixing things up more lately, and I like that. In fact, his getting more personal in the answers is the reason why I liked this third interview as a good example for this post. It's a case of demonstrating the content with the container — how he operates by way of how he answers.

They choose people based upon inspiration, similarly to how I go about making selections for Conversation Agent. The interview is presented beautifully on a page that may look like a stream lined with accomplishments as you scroll down.


Asking good questions is an art. One that can be learned with practice. Because good questions reveal as much about the person asking them — their story and intent — as it does about the intended recipient of the question.

Revealing yourself to others is an important part of the process we call "building relationships," from which we build credibility, trust and loyalty. I wrote that more than four years ago here. I'm particularly proud of closing the gap on the jobs I'd like to have in the last four years.


The why of asking good question is that we need to learn to write and design to the way things are. Change is part of life, and thus business. The way we respond to change is where we should focus, not so much the "it" itself.

How an organization got to where it is is important.


[image of Yoda making sense of things]


Valeria is an experienced listener. She is also frequent speaker at conferences and companies on a variety of topics. To book her for a speaking engagement click here.