Ask Uncomfortable Questions

photo of Ashley Ahearn
Listen to “Ask Uncomfortable Questions”

Last week, I was teaching a Transom Traveling Workshop out on Catalina Island. We were talking about interviewing and one of the students asked “What’s something we should do in an interview that we haven’t talked about yet? Something challenging.” And I quickly responded, “Ask uncomfortable questions.”

I had that answer at the ready because of my recent HowSound interview with Ashley Ahearn. In fact, there was one question in particular I was so nervous to ask, I told Ashley I was reminded of something Robin Williams once said. He was asked how his divorce was going and he replied, “I feel like a hemophiliac in a razorblade factory.”

Okay, my interview with Ashley about her new podcast “terrestrial” wasn’t quite that hard, but I sure was uneasy. And I certainly should have been. I asked her about her appearance.

Turns out, I shouldn’t have been so nervous. Asking Ashley about her clothes and hair led to one of my favorite HowSound interviews.

(Our chat about her appearance was edited for length in this episode. Here’s the entire conversation.)

Listen to “Ask Uncomfortable Questions”

Thanks to Melanie Moore for the photo of Ashley. It was taken at the Duwamish River superfund site in Seattle.


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  • Luis Clemens



    Rob, I think you are conflating two different kinds of questions.

    First, there is the uncomfortable question that has to be asked because the public needs to know the answer. (Think Scott Simon asking Bill Cosby about the many accusations of sexual assault.)

    Then there is the uncomfortable question that you asked of Ashley Ahearn. I don’t know of a compelling editorial reason to ask the host of an environment podcast about why she wears her hair a certain way.

    You implicitly defend asking your question by talking about how great an answer it prompted. I agree it is a great answer, but its greatness comes solely from Ashley’s intelligence and presence of mind.

    I ask you to consider the possibility that her great answer comes despite your question and not because of it.

    I, too, urge others to ask uncomfortable questions. But, those uncomfortable questions have to serve an editorially sound purpose. Otherwise, you can end up asking self-indulgent questions that generate heat but not light.

  • Arwen Nicks



    I loved this! Well done, both of you.

  • Rob



    Hi Luis,

    Thanks for writing. Good to know you’re out there listening.

    I agree with you up to the point where you say there was no compelling editorial reason to ask Ashley about her appearance. Admittedly, my rationale wasn’t incredibly strong — she’s not a public figure in the way that Cosby is and there was no news value — but I do think my impetus for bringing it up had merit.

    As I note in the podcast, Ashley looked different than I remember her. Quite different. So, different I wondered if she changed her appearance for the podcast. Was she dressing and cutting her hair that way in order to position the podcast in a particular way? Was she trying to say something about the show or the subject matter?

    Outside the context of “terrestrial,” it seems reasonable for me to ask about podcast promotion. How do podcasters promote their shows and position them relative to others? What can podcasters do to gain listener attention in the great glut of podcasts? That could include a discussion of logos, trailers, or, in this case, the eye-catching photo.

    Does that make sense and legitimize the editorial value? Or have I missed your point entirely? 🙂

    Thanks again for writing.


  • Riley Hart



    Hi, Rob.

    I was interested to see that the first comment made the exact opposite point that I came here to make. Unlike Luis, I see a clear justification to inquire about appearance in this situation, for the reasons you mention, as well as because because her new appearance was unconventional, suggesting that she may have been making a deliberate statement. The true test, though, is to ask yourself whether you would have posed the question if the podcaster had been male. I’m sure the answer is yes.

    The goal is to treat men and women equitably, not to avoid ever discussing a woman’s appearance. Not to have asked Ashley Ahearn this question because she is female would have been to slight her, as it would have excluded her perspective from your story based on her gender.

    After you read your email at the beginning of the podcast, you gave a mea culpa that made me cringe. As a woman and a (non-ideological) feminist, I am saddened by the depth of self-doubt that caring, respectful men like you go through today, despite the constructive nature of your motives.

    Thank you for sparking the conversation.

  • Rob Rosenthal



    Hi Riley –

    Thanks for your kind words. Much obliged.

    While I think I was justified asking the question, I don’t want to be a bull in a china shop. 🙂 Yeah, I felt self-doubt. But, I think I’d rather have some doubt inform my decision making than over-confidence. Maybe I need to find some place in the middle.

    Best, Rob

  • Allan Stokes



    Rob, I was also surprised to see the comment by Luis. Like Riley, I came here to make the opposite point, only in a different way.

    I think the phrase you used in your cringing preamble was “uncouth question”. That’s already where I disagree.

    The other night, I blitzed through Alan Alda’s recent book “If I Understood You, Would I Have This Look on My Face?”. In this book, Alan does what you recommend, and puts himself out there, relating how he became preoccupied with the question of whether exposing scientists and engineers to the improvisation exercises of Viola Spolin—a big influence in Mr Alda’s early professional life—can improve their ability to communicate science in a personal and engaging way.

    All of the improvisation exercises are designed to make the participants see each other in a more complete and immediate way. Amazing things happen when people begin to interact with open eyes.

    Among many other things, how we present ourselves visually is part of how we exist in this world. The problems begin when the uncouth uncle shows up with the agenda of using the visual channel as a reductive tool. So there’s a good social reason why many of us are careful to provide the least cover possible to the uncouth uncles of the world, and then the graceful version becomes horrifically unpracticed, and we lean so far in the other direction that Riley confesses to cringing (I had a similar take, at a lower intensity, perhaps because I had an immediate flashback to lighthouse Rob of the-worst-script ever).

    There’s an old, discredited idea from linguistics (popularly known as the Sapir–Whorf hypothesis) that language dictates thought, since reduced to a very small nugget of truth: every language seems to have certain things—a different set of things—which are simply mandatory. In English, we have gendered pronouns. French has the tu-vous distinction. In your native tongue, you can’t form a simple sentence without taking a stand on its mandatory elements. On the matter of appearance, of course, a man can’t leave the house without his physical appearance saying _something_ about him, but we can almost pretend that we can, if we dress in a nondescript, ordinary way. For a woman, outward appearance is more like the gendered pronouns of the English language: the social consequences being almost impossible to fully escape.

    In “The Terror Years: From al-Qaeda to the Islamic State” there’s a piece (originally published as “The Kingdom of Silence”) which details how Lawrence Wright ended up in Saudi Arabia attempting to train three women in the art of investigative journalism, but at first he hardly knows where to start, because all three women are completely concealed by their abayas, and he can hardly assess their inclinations or abilities. Gradually he learns that even this dress code offers a thousand nuances to the trained eye, and the women (a bright bunch) are all quite aware of this. He ends up in a long conversation with one of them, who confesses that her liberal family disapproves, but that she has gone to the most conservative extreme for her own reasons, despite continuing to pursue her unorthodox professional track. (It’s a great piece all around.)

    Personally, I don’t lightly engage with people on their attire, but when I have entered into a serious conversation about this (almost always with a woman) I’ve had some of my best conversations. From the right starting point, women seem to relish this conversation. I think there’s a performance aspect of physical appearance that many men rarely consider, but where many women would contemplate whether they feel up to the task of inhabiting a particular outfit in a particular setting on a particular day, with the knowledge that this whole performance thing is a bit of two-way feedback loop. (The old sitcom _NewsRadio_ set up strong foil along this axis between the characters played by Maura Tierney and Vicki Lewis.) I would suggest that many men commit an act of “not fully seeing” by failing to notice or demonstrate any curiosity about how women experience this.

    Returning to Alan Alda, there’s a legendary distinction in improvisational theatre between “yes, but…” and “yes, and…” (the second term even has its own page on Wikipedia). I don’t think we should become _so_ hung up about the uncouth uncle (it is *not* an uncouth question) that we completely neglect to sometimes say “yes, and…” (choose your spots carefully) about how a woman chooses to present herself, even in a professional or semi-professional setting.

    My apologies if I bounced around a bit. I didn’t want this to become an even longer ode.

    I’m really enjoying this podcast series. Thanks for making it available.

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