For the past eight weeks I've been working on a new interview project called Staff Design, where I'm learning how successful individual contributors in product design navigate their careers. Despite having interviewed hundreds of people in the last 6 years on Design Details, this project feels like my first serious attempt to improve my interviewing skills. I should have done this sooner.
Part of this attempt is trying to deeply understand why some interviewers are so compelling and engaging, while others are frustrating and disappointing despite having phenomenal guests. Having great guests is only part of the equation: If you've ever screamed at a podcast host for asking bad questions, or for missing an opportunity to follow up on something revelatory, you know that a bad host can unintentionally crush any opportunity for insight.
Here's what I've learned from studying interviewing principles and analyzing the meta elements of my favorite interviewers. I'm still bad at most of these, but it's exciting to learn and improve with each new conversation.
Terrible interviews stay on the surface level. I'm so tired of hearing what's your morning routine? or what's on your home screen? These aren't interesting questions because they offer no chance for the guest to provide an interesting answer.
Good interviews go deeper. One way they do this is by asking why and how questions, rather than what questions. Instead of what's your morning routine? you might ask how do you prioritize your time? Or instead of asking what's your favorite app? they would ask how do you identify high quality software?
Asking why? is the most simple follow up question that is likely to reveal insight. Let's say an interviewer does get stuck asking something boring like what's your morning routine? Okay – follow up with a why? This forces the guest to introspect, or to retrace some learning process, or identify some personal detail that affects their behavior.
There's a cadence to this, too: usually alternating what and why/how gives guests breathing room and establishes conversational anchor points: Should designers code? Why do you think that? What advice would you give to young designers today? How have you applied that advice yourself in the past? and so on.
During one interview for Staff Design, I noticed one guest mentioned the word confidence three times within my first three questions. When I pointed this out, we spent the next several minutes talking about the nature of confidence, how to develop it, and its importance for product designers. Identifying that theme early changed the entire direction of the conversation, and ultimately left us with an entirely unique artifact.
Great interviewers can actively listen to and identify these internal themes in real time. Or even better: they identify internal inconsistencies in a guest's responses. Did they just contradict themselves? A great interviewer hears it, follows up, and works their way to resolution.
When this happens, the guest has a chance to learn something new about themself in real time. Not only are listeners or readers able to experience some new personal insight, but the guest will also recognize the interview as a positive experience in their own personal growth. They won't be going through the motions with that host in the future, they'll recognize that the interview is an active medium for self-discovery.
I cringe when I listen back to my earlier interviews. I was so self-conscious about asking dumb questions, and sounding stupid, that I only asked safe questions. Or even worse, I tried to add subtext to my questions that would signal to the guest that I was on their wavelength.
I wasn't fooling anyone.
Today this type of interviewer drives me up the wall: someone who can't ask a question without adding some preface, or adding their own opinion halfway through. They are afraid of appearing dumb in front of their guest and their audience.
This mindset is, of course, ridiculous. The whole point of interviewing someone is because they know something you don't. Or they have a point of view that you want to understand. A good interview is on a journey to discover that point of view. A bad interviewer is too afraid to ask something dumb so they avoid asking anything interesting at all.
Good interviewers check their ego.
Good interviewers don't rescue their guests from an uncomfortable silence or a bad answer. In my experience, this has been the hardest skill to learn and I'm still struggling to get better.
Here's how it plays out: an interviewer asks a hard question. The guest pauses. One second, two seconds, three seconds...the host can't bear the silence, so they jump in. Usually they jump in by trying to re-ask the question or by asking a new question entirely. They immediately assume guilt for having asked a hard or unanswerable question.
More offensive still, the interviewer might provide their own mini-answer. In their heads, they are just helpfully supplying context that might unblock their guest's thought process. But instead, it breaks the guest's train of thought, or actually skews their answer away from the truth. The guest spots the life raft – the safe agreement with their host – and climbs aboard.
Good interviewers are comfortable with long pauses. In fact, good interviewers recognize that silence is one of their greatest tools. Silence, a nod of encouragement, and a little bit of patience, gives a guest space to think and answer more thoughtfully.
It's much easier to identify non-answers as a listener or reader than as an interviewer. From the inside, when you're in the heat of a conversation, it can be tough to catch when a guest is evading or changes subjects. But from the outside, it's obvious: they never answered the question! If you've ever shouted at your TV screen while watching a presidential debate, you know this feeling.
Good interviewers aren't just blindly asking questions to add minutes on to the interview's run time. They don't accept any answer as the answer. They are actually looking for truth, and trying to discover something new. When a guest evades this truth, good interviewers will pull them back, usually by rewording the question, or attacking from a different angle.
One caveat: nobody wants to hear a bully interviewer who just can't let a line of questioning die. There's a tension in identifying a guest who is skillfully evading versus being genuinely uncomfortable answering the question.
Most interviewers are terrible at this. They start asking a question but can't quite find the stopping point, so they just let the run-on run on, and by the end of their breath they've asked three questions all at once. Most podcasters do this.
When this happens, the interviewer confuses their guest and their listeners. The listeners might actually want all three of those questions to be answered, but now the guest is forced to choose one. And once they've chosen, they probably won't follow up on the other questions that were jumbled up into the original question. So the interviewer has missed an opportunity to ask, the guest has lost an opportunity to answer, and the listener has lost an opportunity to learn. The trifecta of shitty outcomes.
I'll end here: interviewing people is hard. It's mentally taxing because you have to balance so many considerations in your head all at once: what question was asked, is the answer clear, are there follow ups, what topic is coming up, is the guest comfortable, have they evaded, does that sound true, is this valuable for the audience...
Try juggling all of those questions in your head for an hour, while trying to look and speak like a normal human being, and you'll understand why there are very few truly great interviewers.