The value of the right questions, Part 1

girl with her moleskine

moleskine, the stylish reporter's choice

I’ve done a handful of interviews for the presentation I’m giving later this week, which has renewed my appreciation for the skill involved in asking the right questions.

My previous experience with this valuable journalistic skill has been minimal, but similarly instructive. It took an shockingly long time to draft a set of questions for Seth Godin that would be useful (to my readers) and worthy (of Seth’s time) for my leg of the Linchpin “book tour” last year. You wonder why those legendary Playboy or Rolling Stone interviews from Back in the Day are so good? Or, for that matter, why Colin Marshall and Jesse Thorn have such compulsively listen-able podcasts today?1

It’s the questions, stupid.

Good questions make for interesting answers, and interesting answers get you thinking about all kinds of questions you suddenly want to ask yourself. Good questions wake you up to the world around you, and get you reengaged with life. It’s a huge gift to be interviewed by a smart, generous, curious interviewer. First, and foremost, you have a blast. A conversation all about the things that interest you, with someone who is (purportedly, anyway) interested in how you came to be that way? What’s not to love?

But what’s really wonderful about a great interview, an interview designed to liberate valuable information from your skull for the purposes of sharing it with other people who might then learn from it, is that it forces you to focus, but frees you to do it. You could wander off into the poppy fields, and I do, frequently, but there’s that nice interviewer, ready to lead you back to safety. Or on to a more interesting topic. Or whatever. Someone else does all of that hacking-a-path-through-the-jungle stuff. Someone else keeps an eye on the map and the compass, and allows you to wander around, commenting on this or that fascinating sight, and the eight things it makes you think about, in glorious freedom. Rather than facing a blank page, which I realize is my main job as a writer, but which absolutely gets tiring at times, someone gives you some structure, some prompts: What about this? And this? And this other thing?

It’s such a valuable thing for showing you parts of yourself you might not otherwise see and training you to think in a way you might not ordinarily think that if people are not lining up to interview you, I’d look for ways to give yourself this gift. The Proust Questionnaire is a great place to start: not only has it withstood the test of time, but you can compare your answers (afterwards, please!) to a world thinker so great, they ended up naming the damned thing after him.

My friend Gretchen Rubin (of Happiness Project fame) is terrific at posing thought-starters. Check out her question frameworks for coming up with resolutions that will be more satisfying to pursue, making better decisions, keeping your temper. I also enjoy reading the interviews Gretchen does with people she’s interested in. Like the Proust Questionnaire, the questions remain consistent, so you could certainly use them to do your own (unpublished) Gretchen Rubin Happiness interview.

Whatever your means, it might be useful to start turning your attention to good questions, what makes them, where to find them, rather than focus quite so much on tracking down answers. Not that there isn’t still a place for plain, old information (God Bless Wikipedia, and long may it reign!), but the knowledge that you piece together as the result of good questions is the information that really keeps on giving.

It’s a now-hackneyed tradition to end a blog post or seed one’s Facebook wall or cop out on meaningful Twitter contribution by asking a question. Too bad, because asking good questions is not just a way to gain eyeballs or get a break from the relentless feeding of the beast or incite the troops to (heaven help us) “join the conversation,” but to stimulate actual, creative thought.

Still, this is a post about questions, so I will scatter a few about on my way out the door, mostly as fodder for you to think about as you move through your day. (Although the comments are, of course, open, they’re even unmoderated again, assuming you’ve previously proven yourself to be a friendly nation.)

  • Where is the last place you (unhappily) found yourself that felt so familiar, you were finally moved to take action?
  • What is your favorite color? Was it always? When did it change? Where is it in your life right now?
  • Replace “color” (above) with “book,” “song,” “teacher,” “friend,” or “food.”
  • What five songs make you the happiest when you hear them? Have you learned the words to them?
  • What song could you sing right now in its entirety? Do you like this song?
  • What is your greatest fear? How are you living with it (or not)?


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COMING UP WEDNESDAY: A fun question-and-answer exercise to lively up your next gathering. You’re subscribed, right?

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Speaking of someone who knows how to ask the right questions, my longtime blogging pal, Marilyn, did a really challenging one with me that she’s shared on her new site, La Salonniere, today. I’m especially thrilled because I love all the previous interviews so much: between her eclectic interests and her devotion to learning how things work, she is one amazing interviewer!

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1In the case of the live interviewer, it’s all about the ability to improvise. Jesse probably has the edge here, improv fanatic that he is, although that could be my bias toward comedic presentation. I’m also mad for Adam Carolla, whose podcast was killer out of the gate. Nothing that 20 years of assiduous practice on terrestrial radio and crappy comedy stages can’t buy you.

Image by Pittaya Sroilong via Flickr, used under a Creative Commons license.


  1. Oh, may all the gods bless a good interviewer!!

    How ’bout “My Favorite Interviewer-person”?
    ~ The best I’ve ever seen/heard (as a listener, not the target!) was Gretchen Helfrich, who used to do/be Odyssey on WBEZ public terra-radio from Chicago. She clearly ‘did her homework’: read more than just the jacket copy of books, knew what else was ‘going on in the neighborhood’, didn’t use coded or inflammatory language, and really listened to the answer before she opened her mouth again! My dictionary-picture of ‘News and Information Radio’!

    1. Great question!

      One of my favorite modern interviews was the one Colin Marshall did of (with?) Jesse Thorn. It was great having two really wonderful interviewers deconstructing interviewing. (Although a little headspin-inducing, looking at it in print.)

      They discussed one of my fave interviewers, Terry Gross of “Fresh Air.” At least, she used to be—I don’t listen to much audio at all now, save self-improvement stuff. And that brings up another question: can a great interviewer remain that way? How long can you stay at the top of your game?

      Interesting stuff!

      1. Oh, yeah1 Terry Gross has still ‘got it’! The other reviewers (movies, books, music) on ‘Fresh Air’ are pretty good, too, though that’s a very different skill-set.

        I think good interviewers are like fine wine: they generally get better with age and experience. Cast your mind or your favorite wayback-machine-tool back to Studs Terkel or Irv Kupciinet … they both kept going into at least their 80’s.

  2. I’ve been running a series of interviews later for my Passport to Biz Freedom program and you’ve turned my thinking around on this – I was definitely seeking answers but was also happy to see where the questions led and if it went slightly off track that’s where I often found the best nuggets of info.

    Great summary of what makes for a great interview, I’m taking it all in. As for my answer to one of your random questions – green is my fave colour, closely followed by blue – I’m pretty much wearing the colours of the earth to feel good!

    1. I’m sure you started off as a good interviewer; you’re respectful and naturally curious. But I’m equally certain that your 100th interview will blow any of your first 10 out of the water. There’s just a thing that happens with focused practice, esp. coupled with curiosity and a desire to do better.

      I hadn’t really even thought of my favorite color(s). Not sure if I have any. I like lime green, obviously, but only in certain applications. Ditto navy blue, which is the most flattering color for me right now.

      Yet I would not want a lime-and-navy sunset. No, I would not.

  3. Interesting and apropos following a weekend of trying to figure out how to convert audio tapes of my mom’s CRIS-radio program, “Friends at Large with Dorothy Parr Riesen” to wav files and burn to CDs. She did live interviews of authors for several years in Chicago, and after she died, we inherited dozens of her taped shows. Authors would kill to be on her program, primarily because 1) she actually read the books prior to the interview and worked out specific questions, and 2) she was a personable Leo and loved to shape the questions so that the interviewee was able to rise to her level of intellect and sophistication. Now…how the heck do I make this Roxio contraption my bitch??

    1. Oh, god. Don’t ask me—I did a ton of research on converting, bought my dongle-converter thingy, and then threw it out in a purge. I do not think this was accidental.

      I hope you get those interviews converted, though. How much fun would it be to listen to those again? And then hearing all those authors from the past? Awesome!

      1. It was heart-warming just to hear my mama’s voice again! And the authors she interviewed–Armistead Maupin, Richard Shenkman, Tony Hillerman, covered every genre. I really, really want to get them off those cassettes and at least into my computer!

    2. Claudia ~ I’m a semi-Luddite, even moreso than cx, but my “Good Luck with that!” juju rocks! Comin’ atchya!

      Isn’t Chicago radio a luscious rich playground?

      ~ Bright Blessings

      1. OoooH!Oooh! Claudia –
        I wanna be able to hear ’em, too!
        Just looked up “CRIS-radio” – your Mom worked with Chicago Llighthouse for the Blind? (Oops – … People Who Are Blind or Visually Iimpaired) How awesome is that!

        Do *they* know that you still have those programs? They might be interested in having access to them, too. [Aside, Me to the Cosmos: “Not ‘taking them away from her’ – oh!no!no! Universe! – that isn’t what I mean at all!”] But I can imagine that they might welcome a set of of those for their Archives.
        And I could see you adding a small (or maybe not-so-small) department to your Fried Okra Productions, where one (anyone!) could “hit my PayPal with (pick a ‘feels-right’ dollar-figure) to listen/download/whatever to however-many-episodes of “Friends at Large with Dorothy Parr Riesen” “. One at a time or in packages.
        = All good!

        ~ Passive, independent income (after you get it set up) Maybe not a fortune, but every little bit helps, yes?
        ~ Share Mama’s voice with the world again (“Those who are not forgotten, never truly die” – ancient Viking motto)
        ~ Ditto for the interviewees
        ~ Golden research resource for the students of the world!

        ~ Just poked around a teeny bit at *your* playground – I love your blog-space, and your journey-journaling! The shape of my World is shifting in ways I could never have imagined, too. Thank you for sharing it with me. ;)

  4. Claudia, for recording and editing, I have found Roxio to be clunky, at best. There are other, better, apps, both free free and low cost. Audacity is well thought of, for example.

    In Windows, take care to select the ‘line in’ input slider on the ‘volume control’ app under Control Panel–>Sounds and Audio Devices–>Audio–>Sound Recording –>Volume. That will allow only the signal from the tape machine, eliminating any random boops and stuff from the ‘puter. Apple surely has something similar.

    Hope this is helpful.


    1. Walt, thanks for the info–when my frustration level goes down a bit I will try it out. Otherwise, I’ll chunk the clunker and investigate Audacity.

  5. Aw, Colleen! This is totally unrelated to this post, but I saw one of the comments you made at The Happiness Project and was reminded how utterly awesome your blog is. When I changed email addresses, I didn’t update my Google Reader, and I’ve missed your blog. – added.

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