It can be particularly hard these days to get somebody to answer a question in an interesting and engaging way. Our interviews run to tight schedules, with talking points rehearsed in-depth, in advance, and a roboticism has entered our conversations, particularly when they revolve around our work.
The goal of this post is to help you get better at asking really good questions, regardless.
I had an amazing experience volunteering recently, at a homeless shelter in New York. We were aiming to offer hundreds of people a hot meal, the chance to see a doctor, if they wanted, and even a bed for the night.
Many people who are homeless on the street don’t want a night in a shelter. But they do crave being treated like a human being. And I was paired up with a group of teenagers from New Jersey, given the task of greeting everyone who came into the restaurant with a hero’s welcome. We’d line up and cheer the people as they arrived, and honestly, it was a joy to see their faces lighting up, sometimes in spite of themselves. We all need a good cheering squad, I realized.
One of my cheering cohort was a shy young man, and he asked me how I “seemed so confident” as he’d watched me engaging with a few of the homeless people as they came in. I told him I’d been pretty introverted when I was his age, too, until somebody taught me the art of conversation: You just ask dozens of dozens of questions, and nod and say “mm-hmm” to the answers.
“That’s it?” he said.
That’s it. Maybe occasionally ask a follow-up question if they’ve said something particularly interesting. But 20 questions will usually get you through at least an hour, like that, I said. Even with the most difficult person on the planet.
Over the next few hours I watched with some pride as he began engaging everyone he met in lengthy conversations, simply by asking question after question after question. Almost everyone told him afterwards, “it was such a pleasure talking to you”, or something like it, and he’d acknowledge me from across the hall, like I’d taught him a Jedi mind trick. It was delightful.
I’ve learned that as long as you’re sincere, and curious, there really are no bad questions in life. As long as you’re asking a question because you want to know the answer, and not just to trip somebody up, or make them feel bad about themselves. A good question does need to come from a good place, because nobody likes a jerk.
Over the course of my career, I’ve had to ask people in professional settings if they were a sex worker, because it might be something that an attorney for the other side might use to undermine their credibility about having been fried on a gas stove by a local policeman, ask them directly whether they were lying to me, because now was the time to come clean, and even how their wives felt about their admitted infidelity.
“Well, I think it’s safe to say that it’s probably a factor in my probably impending divorce,” came the answer, with a smile.
Once asked, there’s always that moment of dread as you’re waiting for an answer to a difficult question. But people often surprise you with what they really want to talk about, if you have the courage to ask. And I’ve never had anyone take genuine offense, even at the most difficult questions.
Still, that’s what brings me to the real tip I have for you, which is how to ask the kind of question that elicits a response from your subject that you weren’t expecting, that maybe runs counter to the popular narrative about who they are, that really reveals a deeper truth about them, about life, perhaps even the wider universe. The question that really gets to the golden nuggets, when you’re conducting an interview.
Basically, I try to be a bit cheeky. I try to imagine I’m the opposite of the Queen of England. She has to go around asking people politely, “and what do you do?”
But I like to ask people the question the Queen would really like to ask them in the pub.
Whether they ever get sick of what they do for a living. What gets them out of bed in the morning. Whether there’s a question they get sick of answering. If there’s anything they’re hoping I won’t ask about. What the best day of their professional life was. What the hardest part of their job is.
It’s not rocket science, but I’m surprised at how stilted most interviews can feel in comparison to my own. You always know when you’ve asked the right one, because even if it’s come after a couple of stony silences, they’ll say “look…” and then they’ll start talking animatedly, and off-script, in a way that is a joy to listen to. They might draw pictures with their hands, gesticulating wildly. They might make you a bit nervous about where they might go, next.
At moments like that, I’m often thankful for modern recording devices, so I don’t have to frantically scribble down everything a person says. You don’t want to put them off by suddenly seeming interested in what they’re saying. If anything, I’ve learned to seem more interested, even when I’m not, just to make sure the person doesn’t notice when I feel like I’ve struck the gemstones.
Perhaps the best question, I find, is simply to ask somebody if there’s anything else they’d like to tell you, once they’ve told you everything else.
I always try to allot a little extra time for an interview—say, 30 minutes, rather than 15, even if I’m under deadline pressure. And I try to get the important questions out of the way in the first five, so that I can move directly to the good stuff.
If there’s only a few minutes, then sometimes, I’ll take a chance and move directly to the good stuff. You’d be surprised how bored people get with answering the same old questions, and how refreshing they find it when you treat them like a person you’re genuinely curious about. How about you?
Afterwards, I think the best compliment an interview subject can pay you is to tell you that they hadn’t realized they felt a certain way about a given issue. That you’d provoked them to think about it in a new way.
Or simply: “I wish that they were all this good.”
That’s nice to hear, when all that you’ve been doing is asking somebody questions.
—Matt Davis is a strategic communications consultant. Some of his favorite interview subjects were Anderson Cooper, Spike Lee, Marcella Hazan, James Carville, and Anthony Bourdain.
