Jobs that have been done

Become a better interviewer by listening to great interviewers

Hi there,

It’s been a while, hasn’t it.

My own work and personal life has taken me far from this newsletter, and indeed anything related to Deploy Empathy, for over a year now.

But I’m pleased to report that things have calmed down, and I’m now able to devote more time to this. Talking about talking to people is, after all, one of my favorite things to, ahem, talk about.

And speaking of reporting…

Something I’ve been enjoying over the last few months is listening, and re-listening, to interviews conducted by talented interviewers, often reporters, far outside the worlds of software, design, or research.

But before I get to those recommendations, I want to mention for a moment how observing others interview is a marvelous teacher.

When I was learning how to interview customers, I learned an incredible amount from sitting in the room with experienced interviewers and observing their techniques. Throughout a research project, I’d see them slightly alter their phrasing of a given question or add/remove questions depending on the person they were interviewing and how that person was reacting to them. I was actively listening to their questions as much as I was listening to the person they were interviewing.

That’s why it was important to me to include a sample interview in the book. Many of you have mentioned how the sample customer interview from Deploy Empathy (which you can listen to and read here) was helpful in your own journey.

My recommendations for you come from two very, very different genres and are almost 50 years apart. Yet both feature talented interviewers who use empathy to pull deep, meaningful details out of their interview subjects—details and insights that their interview subjects didn’t initially offer up, or perhaps hadn’t even articulated to themselves.

Recommendation #1: RadioDiaries’ The Working Tapes Mini-Series

In the 1970s, radio host and oral historian Studs Terkel interviewed hundreds of ordinary Americans about their jobs and how they felt about them. He compiled the interviews into a book, Working, that was a best-seller when it was released and is now considered a classic piece of oral history. Even though some of those jobs no longer exist, or have changed dramatically — a switchboard operator, for example — it’s still fascinating to learn about these jobs that had been done, and how people felt about them.

The podcast RadioDiaries was given access to the tapes in 2016, and published a four-part mini-series with clips from the interviews. This was the first, and to my knowledge, the only time audio clips of these interviews have been released.

It was the first time many of the interview subjects had ever stepped back and explained their work to someone. Terkel, who is considered one of the greatest interviewers of all time, used a variety of tactics to get people to open up—many of which will be familiar to you. You’ll hear him use a lot of phrases to encourage elaboration (“keep going on this point” = “tell me more about that”), as well as techniques like mirroring. In an interview with the aforementioned telephone switchboard operator, he says, “you're doing a great deal of talking, but the talk has nothing to do with actual human communication,” which leads her to open up about the loneliness of the job.

I can give no greater case for listening to the mini-series than a comment made by the host, Joe Richman, in the first episode:

“One of the things that made me really excited about listening to the raw Working tapes is that Studs Terkel is widely known as a great interviewer, and I wanted to hear his moves. I have to say, at first it was disappointing. In the tapes, he doesn’t sound like a great interviewer. He doesn’t ask any surprising, creative questions. A lot of the time, he’s just reacting to what people are saying. But it’s that reacting that makes him so good…in these interviews, you can hear how much he’s focused on another human being. You can hear him listening, being totally in it. And of course, that is the full, corny secret to interviewing: just giving someone your full, undivided attention.”

This mini-series was published in 2016 by Radio Diaries, and I’ve linked the episodes below. The links open in Apple Podcasts, but are available wherever you get your podcasts.

1. The Working Tapes — Part 1

2. The Working Tapes — Part 2

3. The Working Tapes — Part 3

4. The Working Tapes — Part 4

Recommendation #2: Off Menu

My next recommendation — a podcast where celebrities share their dream dinner menus with two comedians — might seem like it couldn’t be more different, and couldn’t possibly sit in the same recommendation list as a piece of classic oral history by a legendary interviewer like Studs Terkel… but hear me out.

In Deploy Empathy, I mentioned how you need to roll with whatever the person you’re interviewing says, even if it’s factually wrong or silly. You can’t correct them, as then they’ll feel self-conscious and share less and less with you. Instead, you have to run with it, even when it seems absurd to do so.

And that is where Off Menu’s Ed Gamble and James Acaster excel. As comedians, they are masters of the “yes, and” concept I discussed in the book, which comes from improv comedy. It is their job on this podcast to dig down into the depths of someone’s life experience to figure out why they’d choose a particular appetizer, bread, main or dessert in their dream meal—often to the point of hilarious absurdity.

They seize every opportunity to dig further, and it’s both instructive and enjoyable to listen to them interview. Even if you don’t recognize most of their guests — many of them are UK celebrities, and I don’t recognize many of them myself — you’ll still learn something, and get a laugh, from analyzing how they interview.

There are two episodes in particular that I’d like to highlight.

Fair warning: note that both contain explicit language, and as with most comedy, contain things that could be considered offensive. If neither is your cup of tea, that’s entirely understandable.

Episode 14 with Jack McBrayer (aka Kenneth from 30Rock)

This one stands out for two reasons:

• It’s a great example of cultural differences between the interviewer(s) and the interviewee. McBrayer repeatedly calls Gamble and Acaster “sir,” which initially throws them off. Yet they never directly ask him not to, even though it clearly makes them uncomfortable at first. They accept it and roll with it. And there are repeated misunderstandings about foods—Gamble and Acaster being unfamiliar with collard greens, and McBrayer being unfamiliar with blood pudding. (Admittedly, as someone who loves both, I can’t get enough of that exchange.) You may have never been in a situation where you’re explaining a regional or national food to someone from outside your country, yet you’ve probably been in a situation where an interviewee mentioned a tool, technology, or some other concept that you were unfamiliar with, or vice versa.

• Listen to how they dig in on why he chose barbecue for his main meal, and how much deeper his reasoning expands. He isn’t immediately forthcoming, and they have to work a bit to get the full story. It’s a great example of “a milkshake is never just a milkshake,” to paraphrase Jobs to Be Done legend Clayton Christensen.

Episode 143 with Siobhán McSweeney

If the interview above showed how well Gamble and Acaster can “yes, and” a guest, this interview with Siobhán McSweeney, who played the hilarious head nun from the funny-yet-poignant show Derry Girls, takes it to an absurd degree.

As part of each episode, Gamble and Acaster ask the guest if they would like “papadams or bread” for their bread course. McSweeney ends up requesting a room made out of papadams, like an art installation—and despite the absurdity, Gamble and Acaster submerge into her dream papadam room, and end up discussing what kind of lighting would be appropriate. It is utterly absurd, and utterly wonderful “yes, and” interviewing.

I’ll see you again soon

And with those recommendations, I’m signing off for today. Thank you for making it this far, even though there’s been nothing but radio silence from this newsletter for the past year.

(Sorry, I couldn’t resist a radio pun.)

The above podcasts are about three and a half hours total — 1.5 for the RadioDiaries episodes, and two hours for the OffMenu episodes — and I hope you’ll be able to find time to listen to them. Whether that’s while you’re going for a walk, on your commute, as you run errands, doing the dishes, or wherever it is in your day that podcasts or radio keep you company.

I also hope the recommendations flow both ways, too.

Are there any podcasts or radio shows you listen to regularly where the hosts strike you as particularly talented interviewers? Please post a comment—I’d love to listen to them, and I bet other people would, too!

And I promise it won’t be a year until you hear from me again.

All the best,

Michele

PS: Like many people recently, I’ve started posting on Bluesky (and will no longer be posting on X/Twitter). If you’re over there as well, please reply here and mention that you’re a Deploy Empathy reader, and I’ll follow you back.