Interviewing Clients Like a ...


By Matt Burrows, Senior Account Executive


At first glance, dentistry might seem like the last profession you should address to get thoughts on storytelling, with most conversations with your dentist consisting of them asking questions while your mouth is open to the world.

So when Dan Tynan — journalist, communications writer and Thought Follower — opened up his talk on interviewing and asking the right questions with a dentistry metaphor, it got my attention:

“A lot of my work is ghostwriting for company executives. All of these company executives want the same thing — to be thought of as thought leaders. It’s my job to pull these thoughts out of them, kind of like extracting an impacted molar.


Luckily, interviewing doesn’t always have to be as painful (or as expensive) as emergency oral surgery. As we explore how the story is always there this year, we’re taking time to learn from journalists how to ask the right questions to get storytelling gold. And there’s no better instructor in this than Dan Tynan.

You might have caught Dan’s outstanding piece on the rise and fall of Yahoo for Fast Company last year, and it’s this piece that was on my mind as we sat down to hear from Dan how to ask the right questions.

Turns out, I’d end up in the hot seat myself facing some of those questions. (More on that later.) Here are my major takeaways from this enlightening talk.


The Secret to All Good Interviews

By his own estimation, Dan’s done over 2,000 to 3,000 interviews in his career, as he’s found that the interviewees generally tend to boil down to four types: Bob the Blowhard, who won’t let you get a word in edgewise; Reluctant Rachel, who doesn’t want to be there; Nerdy Norman, who “will stress test your geek-to-English translation skills,” and Glenda the Glib, who uses the same quotes with every interview.

There are specific strategies for how to handle them, but in Dan’s own words, there’s one solid cure for all these types:



I have to confess something potentially blasphemous before I continue: in my time as a radio journalist — I didn’t always enjoy doing interviews. I often hated it, never feeling prepared to ask questions to some executive who shouldn’t be that damn chirpy at 5 in the morning based off of a one page release I’d looked at two minutes before the interview. These “interviews” weren’t conversations, as Dan explains above.

Turns out, I was denying myself one of the key tenets of interviewing: the prep work. This may sound like a “no duh!” tip, but when you’re a rushed morning editor (or PR professional) in between cups of coffee, you sometimes forget the key building blocks. Luckily, Dan’s got us covered.


The Interview Should Not Be Your First Exposure to the Topic

If you’re sitting down to an interview or sourcing session with your client, and it’s the first time you’ve broached the subject, you’ve already bungled it. This is where we have to think like journalists do — like Dan, who will have multiple interviews with subject experts before the key interview he’s hoping to quote.

But we don’t always have the chance to do that in the PR world. Dan’s experience as a corporate writer offers some thoughts — mainly that Google is our friend. There’s a wide variety of “101” style explanation articles and resources online that can get you basic explanations, definitions and a general understanding of any topic in order to ask the right questions. LinkedIn can be used as a resource to get background on your interview subject (provided they’ve actually kept it up to date.)

Another option is to find third-party experts to discuss question with ideas first — whether it be an experienced co-worker or a professional connection, there can be options to acquire knowledge before the interview even starts.

There’s also the fact that you have to prepare your interview subject and send the questions ahead — but not ALL the questions, says Dan. For one, new questions that you may not have considered will come up during a sourcing (“which are always the more interesting ones”), so you have to listen closely and follow the conversation where it goes.


Open Executives Up and “The Magic Question”

The debate of whether a phone sourcing or an in-person sourcing is better may not be solved in a single blog post, but Dan sees merits to both sides: phone conversations excel for one-on-one conversations, but are harder to establish connections with your source. That can be the advantage of interviewing in someone’s office — you can infer clues for questions to ask based on their surroundings and open them up with a bit of chit-chat.

It’s in this “chit-chat” that Dan marks his step one of any conversation (phone or in-person), as it helps to warm people up when they’re able to tell him something they don’t have to think about.


definition of chit-chat


From there, he takes a “funnel approach” to the conversation, starting broad and getting the big picture first before narrowing in on details. We called the first question the “thumbnail sketch” question back in my radio days for largely the same reasons.

Dan also suggests repeating back their answers for understanding, allowing them to tighten up answers, and for looking for the Money Quotes — those aha moments where the light goes on in your head and you know you’ve got great content. Generally, he points out, these are going to be the moments where they liven up and get really excited about what they’re talking about. Those are the moments you jot the exact time of down so you can zip to them when going over your notes and recording later.

But Dan has one technique he strongly advises for any interview or sourcing, and it’s what he calls The Magic Question. This is a question asked at the end of a conversation that lets the interview subject “get on a soapbox” as Dan puts it and discuss something of importance to them. Usually, The Magic Question is, “Is there anything we haven’t talked about that I should be thinking about for this story?” Other potential magic questions could be asking your interviewee if they ever felt like giving up, valuable lessons they’ve learned, or the hardest challenges and surprises they’ve encountered along the way.


Conflict Sells — Emphasize It

We’ve got a conversational opener, research and The Magic Question, we’re all set, right? Not so fast, says Dan. There’s one other thing to consider when digging for story gold in sourcing sessions: conflict.

“If Daenerys Stormborn decided she didn’t want to sit on the Iron Throne and just go shoe shopping with Cersei Lannister, no Game of Thrones,” Dan notes. “If Thanos decides to invite Iron Man, Hulk and Captain America over for beers and to watch the game, no Marvel Cinematic Universe.”

Dan encourages corporate storytelling to embrace the fact, that yes, sometimes things go wrong and to avoid what he terms “Shiny Happy Marketing Talk:”



Convincing executives to embrace mistakes is easier said than done, though, but Dan has some guidance on that. One is in how you ask the hard questions. Acknowledge the reality of the situation, but be diplomatic and be direct instead of accusatory. Note you’re getting their side of the story and giving them a chance to look for positive outcomes. (Dan’s example: don’t ask Equifax about the data breach by phrasing it, “What the hell is wrong with you people?” even if you really want to.)

Dan also notes four ways to persuade executives to embrace conflict:

  • Failure is the new black: There’s a plethora of stories about product delays or other bumps in the road that can actually create interest in the company by showing their process in how they overcome the hurdles.
  • Transparency: Simply put, customers trust a company more if they admit their flaws.
  • Humility: CEO apologies have become a staple, and people respond positively to humility. (And when in doubt, Dan adds, make sure your CEO looks sad when he delivers that apology.)
  • Redemption: Dan notes that people LOVE comeback stories, of which failure and conflict are key components. Dan cites the story of Apple as the greatest comeback story ever told (outside of major world religions), after the company came roaring back from a series of bad decisions in the ’90s to become the giant it is today.


Final Thoughts — Gratitude and Attitude

Sometimes, Dan notes, the interview will “suck and there’s nothing you can do about it.


Do you have a plan B?” Dan suggests that plan B includes going back to research and finding other sources, including company background materials and blog posts.

Ultimately, Dan feels successful interviewing comes down to having the right attitude: being grateful, humble and curious. My hesitancy with early morning radio interviews (other than the time) was because I was approaching it from the wrong angle. According to Dan, you should instead acknowledge the person is giving you their time, show genuine interest and accept that for the next half hour or so, you’re the student and they’re the teacher.

“You don’t need to be an expert,” Dan concludes. “You just need to know enough to ask the right questions and understand the answers on a high level.


I’d barely had time to soak up all this knowledge when Dan let us know that he’d be demonstrating these interview techniques on the spot with a willing “volunteer” (that would be me.) We’ll follow up this post with a sequel taking a look at what it’s like to be on the other side of an interview, and some final questions for Dan on the art of the conversation.


  • Daily PR Brief - Mon 07/08/19 - ITK Blog

    […] Interviewing Clients Like a Journalist: Thoughts from Dan Tynan (Ishmael’s Corner – The… […]

  • Steve Leibson

    I always find it useful to conduct an interview as the audience’s advocate. To do that, you need some knowledge of, some affinity for your target audience. If you have a technical audience, you will interview differently than if you have a general business audience or a consumer audience. It requires additional research if you don’t know your audience well.


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