Steal These Interview Tips from Oprah, Stephen Colbert, and Others to Up Your Recruiting Game

One of the things that distinguishes great recruiters from good ones is the ability to crush an interview. When you can put a candidate at ease, create a smooth conversational flow, and elicit important information, you’re one step closer to matching a candidate to the perfect role. 

And who can do this better than the people who’ve achieved fame by asking questions?  We’re talking Oprah Winfrey, Terry Gross, Marc Maron, and Stephen Colbert. Over the course of their careers, they’ve collectively talked to hundreds of thousands of people and learned how to frame questions in ways that gather vital information and create fascinating conversations. 

Many of them have shared publicly how they conduct great interviews, and we’ve sifted through their responses to come up with eight tips to help you hone your skills too. Here’s what they have to say:

1. Do your prep work

This is Interviewing 101, but the best way to conduct a great interview is to do your research up front and find out who your subject or candidate is before you ever begin. No one is better than this than Terry Gross, the longstanding host of NPR’s Fresh Air. She’s asked probing questions and gotten compelling responses from many luminaries, including most recently Colson Whitehead, Halle Berry, and Benedict Cumberbatch.

“I read, watch, or listen to as much of the person’s work as possible, so I have an understanding of what makes them, or their story, important,” she told The New York Times in 2018. By doing this, she’s able to clarify up front why this person matters and why they’re worthy of her listeners’ time. 

You can do the same when you prep diligently for an interview. Not only will the interview go better, but you’ll be able to convince hiring managers of what makes a particular candidate interesting and unique.

2. Listen deeply

Oprah Winfrey has made her name as an interviewer in part because of her ability to listen closely and treat people with dignity. She’s demonstrated this most recently in her much-acclaimed interview with Meghan Markle and Prince Harry. 

In the more than 35,000 interviews she’s conducted over the course of her career, Oprah has found one thing in common. “Everyone you meet just wants to be seen and heard,” she told an audience during her ”2020 Vision” tour (before the pandemic started). 

“I can tell you,” she added, “in your daily encounters, in your kitchen, in your work, in all of your relationships . . . that is what every person you encounter is looking to know. ‘Did you see me? Do you hear me?’” 

When you listen intently to a candidate, it helps them feel seen and heard. It makes them feel important, which will only help them form a positive opinion of your company and the role they’re interviewing for.

3. Know the three to five questions you want to ask

When late-night show host Stephen Colbert was still working on The Daily Show with Jon Stewart, he put together a list of tips for staffers conducting interviews out in the field. (These can be found in The Daily Show (The Book): An Oral History.) Among his suggestions: “Get clear on the three to five things you want your subject to say . . . and don’t leave until you get them.”

As a recruiter, this may mean that you want to make sure that you talk about a candidate’s experience with artificial intelligence or ask about why they transitioned to a new career. 

In an episode of Slate’s podcast Working, Stephen added that the first interview question is the most important. “As long as I know what my first question is for the guest,” he says, “I kind of know what every other question is, because I really want to react to what their reaction to my first question is.”   

4. Put people at ease 

One of the things that has made legendary BBC journalist Michael Parkinson so good at his job is his ability to put people at ease. Over the course of his six-decade career, he’s interviewed personalities such as Madonna, David Beckham, and the late Nelson Mandela. 

“I think you must learn how to interview,” he said in a Sydney Morning Herald article, “but the reason some people are better than others is about a capacity they might have for settling people. It’s about body language; it’s about convincing people they should be comfortable with you.” Even the most famous guests, he said, are often nervous and afraid about interviews. He puts them at ease as quickly as possible by making eye contact and smiling at them  — and even turning on a little charm.

It may be more difficult to do this on a video or phone interview, which is how many interviews are conducted right now. You can learn more about how to connect and put people at ease with a LinkedIn Learning course, Digital Body Language. But the main idea is that candidates, and celebrities, often feel afraid as they approach interviews. Do whatever you can to put them at ease. 

5. Keep it conversational

Marc Maron, who started his podcast “WTF with Marc Maron” in 2009, was one of the first to elevate the podcast interview to an art form. Since then, he’s spoken with Barack Obama, Jane Goodall, and director Guillermo del Toro. 

One of his strategies is to approach the interview like a conversation. “To me it’s still a conversation and that’s what I’m aiming for,” he told San Francisco’s KQED in 2015. “I have places I want to go, and I will usually find an area that I think is rich and could reveal more about the person.” Marc educates himself about the person ahead of the time, forms a picture in his mind of who they are, and engages them on what he thinks. “Most of the time I’m wrong,” he admits, “but I really seek a connection and a nice, full conversation.” 

When you approach an interview like a conversation, the candidate is more likely to feel comfortable and engage with interesting answers (all the while appreciating that you’re not a chatbot).

6. Ask short, simple questions and give your interviewees lots of room to talk

In his more than five decades as a radio and television talk show host, the late Larry King interviewed about 50,000 people, from presidents to pundits, from movie stars to swindlers. One of his tricks? He used short, simple questions — and then made plenty of room for his subjects to talk. 

“I asked good, solid, simple questions that the guy on the street would have asked,” he told Forbes in 2011. “I asked a lot of ‘why’ questions.” But even more important, he said, he tried to leave his ego at the door. “I left myself out of it,” he said. “I never used the word ‘I.’” 

When you ask simple questions and keep yourself out of it, you make room for candidates to shine.

7. Ask open-ended questions

Gene Demby has a long history of talking to people about some of the most compelling issues of the day. As founding cohost of NPR’s award-winning podcast Code Switch, he’s guided numerous conversations about identity and race and most recently interviewed author Ashley C. Ford and Lonnie Bunch, secretary of the Smithsonian Institution. 

One of his secrets? Ask open-ended questions. “You don’t want to ask questions that let someone say yes or no or give you a really quick answer,” he said in a conversation with other NPR podcasters. “You want them to sort of expound.” 

That gives the candidate more room to share valuable information and keeps the conversation running smoothly. So, instead of asking, “Are you good at managing your time?” ask, “How do you manage your time?”

8. Go with the flow

Krista Tippett, host of the Peabody Award–winning podcast “On Being,” is known for her fascinating interviews with people from many walks of life, including politicians, scientists, artists, theologians, and even taxi drivers. 

One of the tricks she’s learned is to go with the flow in a conversation. Though she prepares diligently for interviews, she also knows when to let conversations take their own course. “I’ll start with a list of all the things I’m interested in,” Krista says, “but I realize that many of those questions fall away. What I get interested in are questions that will be interesting to them [the interviewees].” 

This, she adds, can help elicit the most interesting information. “If you ask a question that’s interesting to them, they’ll often start thinking out loud in real time,” she says. “Maybe they’ll even say something they haven’t said before — and you have this moment of surprise and discovery.”

And when this happens in a job interview, it gives you a chance to get to know who the candidate really is and what lights them up. 

Final thoughts

While interviewing is an art, it’s also a skill. That means that the more you do it, the more confident and competent you’ll become. But it’s always great to flatten the learning curve by taking a few tips from the pros.

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