The Art of Interviewing

It's not just for journalists

Interviewing is an underrated skill in my experience, and far more useful than most people imagine. If they imagine it at all. 

But developing a strong and intentional interviewing style can be hugely helpful. And not just for journalists, authors, and podcasters, but also for coaches, leaders, salespeople, designers, teachers, speechwriters, documentary filmmakers, and entrepreneurs seeking funding. The list goes on.

In nearly 50 years of interviewing people, I’ve conducted my share of lousy interviews, as well as interviews that sing. This has given me plenty of opportunity to observe what works and what doesn’t. I’ve also been interviewed thousands of times, so I know what it feels like to participate in a useful or even a thrilling exchange, and how frustrating it is when an interview feels rote or dull.

So here are 4 lessons drawn from my experience.

First, a skillful interviewer always poses questions that proceed in a logical order, build upon one another, and use the clearest possible language. This requires preparation. Your role is to guide the conversation, set up fruitful topics for exploration, and keep your subject– and yourself– on track. At the same time, you need to avoid anything that feels scripted, rigid or robotic (“okay, my next question is…”).

Say you’re a speechwriter preparing a keynote for an auto executive scheduled to speak to the HR team. You want to work hard to make sure he schedules your interview time well in advance if possible. Then you can start your conversation with a question that gets him thinking. For example, “What was the biggest challenge your engineering team faced in developing our new XX-2 design?”

You can then move get into specifics about how the team addressed these challenges. And perhaps follow up with a few more in-the-weeds questions about what skills or previous training his team found most helpful in setting their project up for success, as these are the lessons his HR audience will find most useful and compelling.

That’s the explicit purpose of your interview, to gather what you need to write a strong and targeted keynote by using thoughtful questions that push your subject to go deeper. But you also have another purpose, one that is rarely articulated: to surface some language that your executive can use when he or she talks about the new product– in this case the XX-2 model– in a range of situations.

This is the outcome of any great exchange: the interviewee goes away with fresh ways to frame an idea, an achievement, or a pitch.

Second, you want to create questions that elicit reflective responses as opposed to obvious or pre-packaged answers. Anyone who gets interviewed a lot tends to rely on boilerplate responses because it’s easy and feels like a time-saver. But as an interviewer, you don’t want to let your subject get away with lazy answers because the result will be canned, flat and less revealing.

Thought-provoking questions also tend to elicit more useful information.

For example, designers often struggle with clients who can’t articulate exactly what they want and fall back on the old “I’ll know it when I see it” dodge. So instead of using the initial interview to press them for specifics– What colors do you like? Do you prefer contrast trim or using the same paint on all surfaces?– it’s better to frame questions that evoke past experiences or help them articulate how they will use what you design. “Tell me about a room that you wanted to stay in forever.” Or “When you cook, do you prefer to multitask or to move methodically, in sequence?” Such reflective queries are powerful because they engage the client’s emotions and encourage them to use their imaginations.

Third, after you pose a question, be prepared to listen with your whole heart, your whole mind, and your whole soul. Don’t use the time your subject is talking to think through your next question, review your notes, draw conclusions about what is being said, or– God forbid– form an opinion of the other person. We all get distracted, but catch yourself if you find yourself losing focus. Your body language when you listen is as important as the questions you ask. And your body language will always betray when you’re not fully engaged.

Fourth, allow yourself time to reflect while you’re formulating follow-up questions. Feeling pressure to respond immediately will diminish the depth of the exchange. So don’t fear silence, just make sure you’re using it well. This will serve both you and your subject.

Pro tip: you’ll know you’re on the right track in your interview if your interviewee says something like, “what I really meant to say was…” Most of us require a few iterations to tease out our primary points, so giving the person you’re interviewing— and yourself— some grace will increase the odds of creating something of value both for them and for you. That’s what I’d call a winning strategy. 

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