By Mariela Azcuy

June 2022

When you think about interviewing experts, it’s probably for an article or press release you're writing or to understand the launch of a product or new strategy. But we’ve made interviewing an essential part of our client strategy.

When you follow a sustainable PR model – meaning, the “time between the tentpoles” is as important as the tentpoles themselves – expertise is your greatest asset. Expertise is what’s going to help you attach clients to trends (or even spot them), build out thought leadership abstracts, create LinkedIn content, and more.

And sometimes one great interview can power your strategy for months. But how do you get that great interview?

I’ve been interviewing executives, internal and external clients, and subject matter experts for more than a decade. I’ve learned something from each one — yes even the one where the guy just rolled his eyes at me or where the woman would not veer from the corporate talking points.

Here are my best tips for interviewing experts. For the purposes of this blog post, I’m not focused on interviewing to flesh out an article. I’m focused on what I call the discovery interview, namely:

• You have a new client starting and want to develop storylines and understand their POV

• There is a new potential spokesperson – internally or externally – and you need to get to know them

• You’ve been working with a client or colleague, but many of the conversations have focused on tactics vs. strategy. Setting aside time for an interview makes space for strategy.

IT ALL STARTS WITH PREP

Hunting and Gathering

Two things won’t work: coming into an interview blind or using a templated set of questions to interview someone. In both cases, the lack of preparation will be evident and you’ll walk away with very little that’s useful. In essence, you would’ve wasted everyone’s time.

Think about prep from two angles:

1. Related to the person/brand

2. Related to the industry

This is the part of prep where you’re hunting and gathering for clues as to how you might direct your interview questions. As you research, pull out nuggets of information that stand out and save them all in one document with the corresponding links where they come from. 

Here’s a non-exhaustive list of what I tend to look for:

• Things you don’t fully understand and want to get clarity on.

• Places you felt there was more to the story, including personal anecdotes. 

• Anything provocative they said or someone said about them.

• A “black sheep” moment. Meaning, something that doesn’t quite fit into the rest of the story. For example, I once interviewed a doctor developing a hydration self-monitoring system who was also a Muay Thai fighter. That turned into valuable insight on empowerment and entrepreneurship.

• Anything that hints to a framework or process that could be a learning for others. 

• Moments where the person predicts something will happen.

For some interviewees, you’ll have a wealth of information; for others, not so much. For those that have been generally “quiet” online, you’ll have to lean in more to the industry side of things. 

Who is the competition? What are they saying in their materials or social handles? Who are their spokespeople and what POV are they putting out into the universe? 

As you save the excerpts, leave notes for yourself about why that piece stood out to you. What question did it bring up in your mind? If you’re doing this right, you’ll end up with more than a few pages of excerpts. The document will be messy, and that’s okay.

Making Sense of it All

Now comes the part where you’re grouping all the ocean puzzle pieces or the ones featuring a beach hotel, but aren’t ready to put the whole puzzle together.

Open up your messy document and start reviewing your excerpts and notes with an eye for common themes. If there’s a lot of entrepreneurship talk, you have a theme. Same for VC investing, mobile commerce, or financial inclusion.

Organize all the excerpts under the themes you identify. This requires a lot of cutting and pasting but there is a method – and a reason – for this madness. You are getting to some core themes, and this will help you direct where you spend time interviewing.

Try to limit yourself to three to four themes so you’re forced to make some decisions about where things fit and what may need to be cut. I tend to be ruthless about this. If there’s an outlier, it’s probably for a reason. It’s not part of the executive’s core story and you don’t have to spend valuable time on it.

By the end of this step, you’ll have one organized, grounding document separated into themes. It’s blissful.

The Line of Questioning

Remember: your goal is to develop storylines that can drive a Sustainable PR strategy. A great interview will get you that, but you won’t get anywhere without asking great questions. Your questions need to elicit answers that can lead to media pitches, byline abstracts, speaking topics, and more. What would secure an interview, get them to say yes to a contributed piece, or agree to booking them to speak at their event?

Here’s my approach to creating a line of questioning:

1. Make sure you have questions tied to each theme. These themes will be important anchors in your strategy and you should take every opportunity to get close to their thinking and expertise tied to the themes.

2. Start with an easy question or two as a “warm up.” You never want to start big as you risk losing them upfront. No “what’s the number one solution to climate change” right out of the gate.

3. Make it clear that you studied them – it helps them feel confident in your intentions and they’re more likely to be vested in the conversation. For example, refer to a story they told in a video interview. Or ask for clarification: “You said this in the New York Times. Can you elaborate?”

4. Ask for specific examples and practical advice. And attach numbers to that ask: “What are the three most common reasons startup founders fail.” You may not get three every time. You may get more or less. But you want more than one because if that one is a dud, you need a bench to play with.

5. Be provocative and personal when you can. Ask them if they have a counter opinion on a popular topic or if there’s a story from their childhood that influences their work or thinking and why. I love this tip from Stanford’s Michael Barry: “Whether or not the stories people tell are true, they reveal how they think about the world.”

6. Try to put some structure around thinking. For example, what are the steps every founder should take before raising their series A? Or what should companies consider as they move to fully remote organizations? Or even how would you compare the evolution of AI to the evolution of the web?

7. Have more questions than you’ll need, but know the ones you absolutely have to get to. The others are “filler” if you have extra time.

8. Don’t assume or ask leading questions. Stay objective as an interviewer to get to the truth. John Coleman put it this way in Harvard Business Review: “If you are too attached to your initial answer, you may refuse to let it go, no matter where the data leads.”

9. Avoid anything that can be answered with a yes or no. It gets you absolutely nothing.

One last point before moving on to the actual interview: take these first three parts seriously. This will and should be where you spend most of your time. Without them, nothing else can reach its full potential. For context, when I prepare for an executive interview, it takes me about four hours to complete the pre-work.

INTERVIEWING EXPERTS LIVE

Be Prepared to Ask “On Your Feet”

You may not like what you’re about to read but I’m a truth-teller: your flow is just a guide. It isn’t bible. It’s more a reminder of key topics you’d like to hit and touchpoints to help get you there. But you never know how your interviewee will respond and you need to be prepared to react to that response.

Here are some reason you might leave your flow behind when you’re interviewing experts:

• Their response takes you to another question at another part of the document.

• Similarly, they already answered a question within a previous one.

• The current line of questioning feels awkward, with stifled responses, and you need a change.

• You already got what you needed within the particular theme and there are several important questions you still need to get to.

This is my favorite reason to leave your flow behind: your best next question is either “how” or “why.”

This is the scenario: Your interviewee just said something interesting or inconsistent with previous statements. This is an invitation to dig in and usually when things get meaty. 

I once interviewed a head of a VC fund and he said they had a goal to become more diverse internally and within their group of investors. He even shared the percentages he was hoping to reach. But he ended there.

That’s great and all, but to turn this into a story the next best question was “how are you achieving those goals?” He seemed taken aback by the question but then offered up that he was only hiring women this year. That was a golden egg moment, and it led to placements in Fortune and more.

Back to Stanford’s Barry. He articulated this idea as “a conversation started from one question should go as long as it needs to.”

Don’t be a slave to your flow!

Employ Active Listening

You cannot conduct a good interview if you don’t actively listen. Coleman describes active listening like this: “the process of understanding what another person is saying – both explicitly and implicitly – while showing them you are engaged and interested.” 

Active listening is what tells you where to take the conversation next. Instead of thinking of the next question on your list, you are absorbing the interviewee's response and letting that direct you. It helps you override what Coleman calls your brain’s “prediction engine.”

My best friend here is a simple pen and paper. I usually jot down a word or phrase that sparks my interest within a longer answer the person might give. Those words and phrases can easily get lost in conversation, but not if you write them down. 

I don’t recommend taking detailed notes during an interview as it doesn’t allow you to focus on the act of interviewing and listening. It’s better to have a dedicated notetaker or record the interview and focus on just the simple words and phrases.

I once took an Effective Communications workshop led by Jeanne Tingo at IMPAX Communications. They introduced me to these lead-in phrases that became awesome, life-long tools. They make listening conversational and ensure you’re on the same page, and also contribute to pace and tone.

IMPAX’s probing techniques also shaped my process. Probing is essentially the “digging in” I’ve mentioned. Interviewees often assume they’re talking to someone with the same level of expertise as them. Also, some experts just aren’t as verbose as you’d like them to be, or they offer up information in drips. Sometimes it’s a mix of all those things.

Probing allows you to turn on that faucet so that insight flows vs. stalls. Here are five great probing questions to get more from your expert.

One final thing on live interviewing. Don’t be afraid of silence. Silence often means the other person is thinking and if you hold out a few more seconds they may just deliver the meaningful information you’ve been waiting for. 

I know I like to think about my responses first and oftentimes my moment of silence has been mistaken for disapproval or lack of response. When, really, I’m soaking in a question that is possibly more layered than the person who asked it even realizes, and trying to give someone the best insight possible.

MAKING DISCOVERY ONGOING

Discovery shouldn’t be a one-and-done deal. News spikes, trend spotting is ongoing, business changes along with customer needs, and learning is constant.

The best you can do is find ways to build discovery into the everyday. We’ve had success leaving time at the end of client meetings for a hot topic question or two. We also use WhatsApp for a client “Question of the Week.” Some clients like to respond in writing; others send us voice memos. For others, we email news stories asking for their POV or write something up and leave holes where their input is needed.

Adapt your process to the person you’re trying to learn from. In the end, they are critical to your success.

Author Josh Kaufman says: “If you want useful answers, learn to ask better questions.” That starts with the prep work, comes to life during live interviewing, and gets perfected as you make discovery an ongoing practice. With these techniques for interviewing experts and asking great questions, you’ll walk away with valuable insights to help drive strategy, content, media angles, and more.