Claire is a healthcare communications and PR consultant. Throughout her career, she's worked in agencies, in-house, and now she runs her own communications firm, November West Communications. Her agency specializes in media strategy and execution, crisis comms, thought leadership, and executive comms, mostly for companies in the digital health and health tech space.

The following has been edited for clarity and length. Listen to/watch the full interview on the Interviewist YouTube channel.

Sarah: How would you describe your interviewing style or approach? 

Claire Schillings: My style has really evolved over the years. A lot of it has changed from becoming more confident in my abilities as a professional and as an interviewer.

When I was younger, I worked in content development and content strategy. I would jump on interviews with executives and CEOs, and I felt like I really needed to fill the space, which I tend to do when I'm nervous. It was extensive preparation. 

Not that I'm advocating to not prep—that's not the answer. But now I'm more go-with-the-flow. When you have a dynamic conversation with someone, other follow-up questions naturally come up. And so being open to having some of that open space to see what happens—that’s the most effective strategy for me. 

A lot of that just came with experience and time, and comfort in the discomfort.

Do you have any go-to questions for your interviews?

Sometimes I'll ask one of my back-pocket questions: Have you read anything about this recently that I should read? Or that would give me good background knowledge? Then that creates a new conversation path.

In your eyes, what does a successful client interview with the media look like? 

I've worked with some really incredible executives who just are gifted with media. I think there's a natural aptitude that comes from being really good with people. 

But the number one thing is just being personable. Obviously, the substance of what you have to say is really important. But a good rapport with someone will go even further than a really snappy quote. So being really personable, remembering details about people, sending thank you notes—those things can go a long way. 

More tangibly, a lot of the work that I do is macro company messaging, specific spokesperson messaging. It feels really good when I see clients using some of that messaging, and it gets pulled through all the way into a piece of coverage. 

I do a lot of prep work for clients. I pull together prep notes that have sound bites and facts. And so using the notes—even though they're the expert—it’s a low bar, but it's really nice when people are using those notes and you see that reflected in the piece. 

What's the toughest thing about preparing clients for interviews?

I really have a lot of respect and love for the journalism profession. I really wanted to be a journalist when I was in college and in my early twenties. 

So it’s about making the interview yours… How do you be a super strategic and engaging interviewee in the conversation to the extent that you can, and let it roll off your back. I think that's a hard thing to prepare for. 

Obviously, sometimes reporters also ask hard, unexpected questions. Which they should! That's their job and I always admire reporters who do that. But it can throw an interviewee off their game if they're not expecting it.

Do you find that executives are more comfortable on camera these days?

I do see clients being more comfortable with a last-minute interview or a podcast. They have more experience with some of that non-traditional media. I'm working with a client right now, and we're testing out a TikTok program… it's all experimental but for the most part, people seem game to try those new things, which is cool. 

There’s this push toward executive-owned content, and I'm thinking about that a lot in my work with clients. More so, what is the true message that we're trying to share? Whether it's a macro company message or a micro like, “Hey, here's what you need to know today.” And then thinking through the best distribution channel to share that, whether that is TikTok or it's a Substack or a podcast, or maybe it is a New York Times interview, if we're lucky.

It sounds really obvious, but I do think that we're seeing more of a tangible shift toward that in the comms and PR space than we have before.

Do you have a most memorable interview, and if so, why?

I got to sit in on an interview with Katie Couric one time, which was really cool. She is such a personable woman who makes you feel like you're a really important person to her at any time—which I think is an important skill of someone trying to cultivate a relationship with an interviewer but also just as a person. 

I also got to interview Andy Dunn, who is the former CEO of Bonobos…He had really strong convictions and a really great point of view around manufacturing and how to build a business. At that time my career, he was certainly the most famous person I'd ever met. 

Who are your interviewing inspirations, muses, or role models?

I am obsessed with this podcast called You're Wrong About. It's not a traditional interview style. Two journalists pick a topic that the general public or the media has “gotten wrong” in the past. Examples of past episodes are the Clinton impeachment, the McDonald's hot coffee case, the Beltway or DC snipers. One of them will do a bunch of research on that topic and go deep. The other one will just come into the conversation with their preconceived notions, and they'll have a conversation about it. 

It feels like what I think an interview should feel like, which is free-flowing conversation with someone that you really like and admire about a topic that you just can't get enough of. 

I also read this newsletter called Morning Person. She used to be a blogger in LA named Leslie Stephens. She's really good at asking direct yet really thoughtful questions. I think she has a lot of respect for her interview subjects…I think being a good interviewer is cultivating respect for other points of view. 

Any other thoughts, tips, or advice on interviewing?

For me, the biggest learning is having a genuine love, interest, or respect for the subject, whatever that is. Anything can be interesting if you look at it closely enough. I have found subjects like grocery robots to be some of the most fascinating work I've ever done. On the surface, that sounds boring to probably a lot of people.

But I think the closer you look at something, the more interesting it gets as it comes into focus.

🎤 

Want more? Check out our full, uncut interview below.