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Celeste Headlee: How To Have Better Conversations, Ambiverts & Being Curious

Our guest is Celeste Headlee. She is an award-winning journalist, professional speaker and author of We Need to Talk: How to Have Conversations That Matter. I am super fired up for this episode because we talk about a lot of things that we've never discussed on the show before.

If you're looking for a surprise, something new, fresh and exciting, you're going to love this episode. We talked about how to have better conversations and why that matters and how you can benefit from that. We talked about introverts, extroverts and ambiverts. If you think you're an introvert, you're probably not. You're going to want to hear that. We talked about the power of natural curiosity, honest curiosity and how that can serve you in many different areas of life. I got to share with you, this has been one of my most fascinating interviews because of who Celeste is as a person and because of the insight that she shares with us.

Dustin
Celeste, you've had incredible success as a multiple TEDx speaker with over nineteen million views of your talks, NPR host of shows like Tell Me More, Talk of the Nation, All Things Considered and Weekend Edition. You’re an award-winning journalist and Institute of Journalism and Natural Resources Fellow and to starting your own media company. It would be easy for us to start with any one of those things. However, I’d love for us to go back to the early ‘90s when you were graduating with a Degree in Vocal Performance. I would love to know your mindset. When you were embarking on your career, where did you think you were headed?
Celeste
I thought I was headed for a career in music, either doing opera or recitals. The thing about professional musicians are by definition entrepreneurs. It's rare. Those full-time jobs playing the violin with the New York Phil or whatever, those jobs where you get a paycheck and benefits are incredibly rare. Most musicians become their own business. They're cobbling together income from all different sources. They'll sing professionally in a church choir on Sunday and then go and do an opera gig or whatever it may be. That's what I thought I was going to be doing. Every musician should realize that they're going to need a day job and that's what radio was supposed to be. I took a job hosting classical music on the radio and that was supposed to be the day job that provided a steady income while I was singing.
Dustin
I want to talk a little bit more about music before we go down the path of your amazing career. Your grandfather, William Grant Still, was a composer. I suspect most folks are getting to know him for the first time. He was the first American composer to have an opera produced by the New York City Opera and he was famous for his time. How did he influence your decision to pursue music at the start?
Celeste
He didn't. When you have a Genius in your family, it relieves any pressure to beat the well-known one in a family. There's no way. You could think it overshadows you. I never saw it that way. There was no pressure on me like that was going to be the renowned figure in our family. He is the Dean of African-American composers. People write their doctoral thesis on my grandfather. I never thought of myself as entering the same realm as him since I found that to be a ludicrous idea. Frankly, when I first started college, I was going into the classical theater, Johnson and Shakespeare and stuff. It happened that they didn't have any theater scholarships left, all they had left were voice scholarships. I was like, “I’ll audition for that.”
It's opera, you have to sing opera. I’m like, “I could try it. I’ll try anything.” That's how I got started in music. Interesting to me is my first TEDx Talk, that's what it was on. My first TEDx Talk was about finding not a job title but your mission because many people leave college and they think, “This is the job I want.” I find this on the radio all the time. I have been for years and years one of the trainers for NPR’s next-generation program which trains young journalists. We always hear people saying, “I don't want to do that training program because what I want to do is TV.” I’m thinking to myself, “You’re crazy. You are clearly young and immature to think that you're going to turn down free training from NPR because what you want to do is be a sportscaster. It is unlikely that you are going to end up with that exact same job title.”
Dustin
I don't get to come into contact with you. I have kids but younger folks that are starting their career. They don't see that as a stepping stone. They don't see that as classical resume-builder or life skill one pick up.
Celeste
Some of them do, but I would say over half of them have in their mind. You remember what it was like in college. You'd sit down at the coffee shop with your friends and you talk for three hours about what person you are, what you do well and what you want to do in life. You get this idea that you choose a job based on discussion and what you think about yourself. What I say in that TEDx Talk is that you don't learn about yourself in theory, you learn about yourself in practice. I would never in a million years have said I was going to make a career in radio ever. I had no idea I was good at it because I’d never tried it. It required me to get that job and try it and go, “I’m good at this.” You can't just sit in a coffee shop and decide who and what you're going to be. You have to get out there and try stuff out.
Dustin
I saw in my research that you showed up in the career as this NPR host, but you are in public radio in Arizona. However, you had said you got started in radio through classical music. Was that your foot in the door, you were making classical music on the radio and then an opportunity opened up and you jumped at that opportunity?
Celeste
Someone offered me free training and I’m like, “I’m never going to turn down free training. Who does that?” Someone said, “We need a culture reporter. Can I train you to do reporting?” I was like, “Yeah,” and then they're like, “All Things Considered host is going to be away for a long time. Can we train you to fill in as a news host?” I was like, “Yeah.” That's what my life has been. If you go with the don't ever turn down free training thing, it's going to get you pretty far.
Dustin
It's one thing to get an opportunity as you had, you take the free training, you try it out. This stuck for you based on all the accolades and your journey. What intrigues you about what you do? What intrigues you about journalism and having conversations with people? What's that driver for you?
Celeste
I’m a curious person. Being a journalist allows me not only to talk to interesting people and I’m not talking about celebrities. Frankly, celebrities get interviewed so much and they're sick of it. They're often the least interesting interviews I do. You get to talk to people who surprise you all the time with what they've been through and the stories that they have. The other thing is what could be better than your whole job is talking to people about the thing they love most in the world. That's what you do. It's the best job ever. You get surprised by things. I remember I was doing a story about a guy, one biologist who's trying to save the purple lilliput mussel in the Great Lakes. This thing is not an adorable creature. It's not pretty. There is nothing to recommend this creature.
This guy was passionate about these little critters. I was out there waiting in long rubber hip boots and going into disgusting, mucky water. I had the best day ever because he was jazzed about these little, tiny, ugly, plain mussels. That's one of the things. The reason I’ve always been involved in public broadcasting and I host a show called Retro Report premiering on PBS this fall 2019, October 7th, is because public broadcasting allows me to feel like I’m making the world a better place. My earnings may be less than if I’d gone into commercial or whatever it may be, but I get to end every single day saying, “It may have been tiny, my contribution may have been minuscule but I made the world a better place today,” and that is an important thing for me.
Dustin
I’m with you on that. That's important to define that mission as you talk about. I want to get into that because you did a TEDx Talk that caught fire. I’m curious since you had mentioned it. Everyone is attracted to celebrities. They’re in the media. They're name-grabbers. You said it's more interesting to go and find people that aren't there. I’m curious how do you find these people? It’s easy to find celebrities. They’re in the media. They do interviews, that's easy. How do you find that scientist that you had mentioned? How do you find people like that?
Celeste
I was reading this forum. It just so happened I was doing a story on another topic altogether. On that, I was doing the story on the argument about whether or not there are cougars in Michigan because it's this big argument. Technically, cougars were supposed to have gone extinct from Michigan. The scientists are all like, “They aren't here,” and all the people are like, “I saw one in my yard.” It's this controversy. While I was doing that, I happened to see this other little article this guy had written about the purple lilliput mussel and it's a cool name for a plain, ugly creature. I started reading it and that's how I find people. For the most part, people who are passionate about things, they write about them, they make videos about them, try to get the word out.
I literally see that as my job to help them do that when it's an important message, when it's a message that might either resonate with other people or have an impact or relevancy to someone else. That's my job to find them. It's less my job to put Charlize Theron on the air. She doesn't need my help. It's way more my job to talk to this one scientist who it turns out purple little put muscles are the canary in the coal mine in terms of our water quality. Even though we may not care, these, these little critters may be not cute at all, their existence is pretty important for us. Those are the stories that you love finding, the surprises.
Dustin
I find it fascinating and it also leads me to this. How much of your work would you say is the team collaborating and saying, “We're covering these subjects, let's go find stories,” versus you stumbling? You're researching the cougars and you stumble across this. How much of it is stumbling and you coming up with the idea for the story versus, “These are our objectives this month, we're going to cover this, this and this?”
Celeste
I don't know how it's done in commercial broadcasting, but I can tell you how it's done in public broadcasting, which is that you have regular pitch meetings. An entire team works on a show, and I mean everybody. It doesn't matter what your job title is, everybody sits around a table and says, “Here's my pitch. Here are the four stories I think we should cover and here's my pitch for why they're important.” We as a group decide which ones have legs and which don't. It ends up being a pretty good mix between them. There are all kinds of ethical rules that go along with journalism in terms of whether or not this is somebody you know. Once you've gotten through that particular layer, it's a question of, “What do you think is the most important to cover now? Does this have a peg?”
In other words, does this story need to go up by a certain amount of time? I’ve never had to be on a show. I have hosted a show where there are some stories you have to do. I remember I was hosting The Takeaway out of New York and that was a four-hour show. We had the entire show planned, carefully booked. The producers had worked for a long time on their scripts, everything ready to go. About fifteen minutes before we open the mics and go on air, Barack Obama won the Nobel Peace Prize and we had to throw everything out and start over. Sometimes that happens too.
Dustin
That's one thing to throw out all the scripts. You have fifteen minutes before you have to go. Are you ad-libbing on the flyer or are there writers furiously writing in the back? How does that work?
Celeste
They immediately start calling around and find out what expert can be on the air in fifteen minutes. We have a little bit of a cushion because I don't know how many people listen to NPR, but you'll know that there are news headlines, “From NPR News in Washington, I’m Craig Windham with these headlines.” We have a little bit of a cushion there. We need to find someone who can be on the air in half-an-hour.
“Can you get down to the WNYC Studios and sit down in front of a chair and you're an expert?” That's number one. Producers, I would not be surprised. I would forgive them if they were all chain-smokers. That's a stressful job.
Dustin
If they only knew what happens right behind the scenes.
Celeste
We have to get on the air and sound as calm as possible. We don't want to get on the air and start screaming at people.
Dustin
I want to circle back to pitch meetings. I had never been a part of that. I hope as our team grows that we have that opportunity to do that. However, I could see myself in a meeting. At least envision myself in a meeting where I’m passionate about a topic. Do those meetings get interesting with people that are passionate about a story or attached to a story? Are you all pretty mellow and democratic about it?
Celeste
People get passionate. That's what you want. There had been a ton of times where a producer has been passionate about a story and I’ll say, “You haven't convinced me that somebody in Indiana is going to care about this story, but you seem passionate. Come back to me. Go find the why and bring it back.” If they're passionate, I generally don't completely dismiss it out of hand because we hire smart and talented people. If one of those people is passionate about something, there must be something there that I’m not seeing. That's how I view that. The whole thing as a manager and when you're a host of the show, you are a manager. It is to hire great people and then trust them to do their jobs. Those pitch meetings, all of those pitches are coming from people who are good at what they do and they care.
Dustin
That sounds like fun yet stressful and interesting, all-in-one ball in a pitch meeting. It seems natural to me to go from radio, at least to outsiders like, “Here's Celeste. She's been on NPR. She's been the host of a show.” It seems natural, maybe even easy to an outsider to go from radio to speaking. Was it for you to start getting into speaking, being easy, not nervous because you had all that experience?
Celeste
People ask me this all the time. In fact, I wrote a blog called So You Want to Be a Public Speaker? It’s because I get that question much that I wanted to say, “I’m not going to answer you personally, but here go look at this blog.” It's hard to know which part of my history made it relatively easy. Remember, I was singing opera before I did the radio and if you want to talk about freaking stressful, if you make a mistake in opera, it's a catastrophe. You have a huge orchestra sitting underneath your feet and a whole chorus behind you. An opera is an incredibly complicated production that everything has to happen at a certain time because there's music. If you screw up and I have on stage while you're singing in opera, it's a catastrophe.
One of the biggest, most important things about becoming un-nervous or becoming comfortable with public speaking is making a ton of mistakes. That's what gets rid of stage fright. What you're afraid of when you're speaking is that something's going to go wrong. When you've had things go wrong enough times that you don't care anymore, that's when you're comfortable. Throughout my lifetime, most of the things I’ve done have been in public of some kind. Shit goes down. Shit goes wrong in a big way. You realize you come away from it going, “The world didn't end. I did forget my lines. The mic didn't go on. Whatever it was happened and it's all right. The sun still came up the next day. I still have a job. Everything's okay.” If that happens enough time, you won't be nervous anymore.
Dustin
I have done my share of speaking. I get it but now I’m fascinated by opera. Even though it sounds the same to me, it sounds a lot more stressful. When you mess up in opera, is it that same thing? You bring that same energy, that same attitude like, “I goofed.” How do you recover from a goof when it's opera?
Celeste
You have to let it go. The other thing that you have to learn how to do is bluff your way back into rightness. Let's say you've come in at the wrong place and the conductor is glaring at you. You were supposed to come in a measure ago and you're late. You got to get back into the right place and it has to be you because clearly the 200-piece orchestra can't all change to meet you. You have to meet them and you have to do it while you're still self-possessed and gracious onstage that hopefully the audience doesn't notice that it happens. The main thing is that you have to stop thinking about the mistake you made. If you are still thinking about that, then you're not in the present moment fixing it. You have to be able to immediately let go of mistakes, move on and be present.
Dustin
We've had a great opportunity on the show to interview athletes and SEAL Team Six leaders. It's that same advice. For a lot of entrepreneurs or anyone reading and that's an achiever, we're all going to make mistakes. You’ve got to let it go. I want to get into that first TEDx Talk, Don't Find a Job, Find a Mission. It caught fire. Did you know this would be a hot topic because you were putting articles out or you were talking about it on the radio? Did you have an understanding that this would catch fire?
Celeste
The reason I did that talk is that many young people came and were asking me how they could become a radio host. Many older people were coming to me and they'd say things like, “I’ve always thought I would be a good talk show host.” Do you get that? “I always thought I should have a podcast.” Don't you hear that a bunch?
Dustin
Yes, a lot.
Celeste
I can tell you what you're thinking in your head is you have no idea what this job is. You don't know what you're talking about. It’s because so little of the job is what you hear on the air. Most of it takes place off the air and most people are not going to like that work. That's where it came from is that question, but also all those young people who were asking me about how to move forward with their career, but what they were asking is how do I get where you are. My answer is almost invariably you don't want to be where I am, where I will not be where you are because you're a different person. Even if you follow it exactly my path, it would be a different place you ended up in. That's where that TEDx Talk came from. I never expected any of those talks to go viral. The second one that I did on conversation, which went super viral, I think it's up to 21 million views. I literally thought nobody would be interested. I thought I was the only person interested in that. Honestly I was like, “This is the most boring thing ever, but I think it's important.” If I’d known it was going to go viral, I would have put on makeup, done my hair. I hadn't had a haircut in a few months. I just threw on a blazer from my office. I never expected any of those to go viral at all.
Dustin
I’m curious about your process, sideline to this, of giving light or life to an idea. Do you test ideas on air? If it catches or you get feedback, you'll write about it then speak, and then come out with a book. Is there a hierarchy to it? What's your process?
Celeste
There's certainly no established process for that. I’m a bit of a dork. My son would say I’m a huge dork, but I get geeked out about a lot of different things. I have another book coming out soon and both of them have come from me trying to solve a pressing issue in my own life and finding that nobody had the answer yet. The first book on conversation, we need to talk. My whole expertise in conversation came from the fact that I’ve discovered I needed to improve my conversational skills. I consulted all the experts and then their advice was crap. It didn't work. I had to go back from scratch, look through all the research myself and find some unexpected, counterintuitive research that was going on.
It's the same thing with my second book, which is more about our addiction to productivity and efficiency and how it's become toxic. That's because that's what has been going on with me. I reached a place in my life after my TEDx Talk went viral and I started getting all these speaking engagements, I suddenly had a bunch of money. That's what I had been looking forward to for 40 years. Thinking, always saying to myself, “When I have a bunch of money, all these other problems will be solved.” It turns out that's not true. I had to ask myself, “Why am I busier and more stressed with more money than I was when I had less?” That’s where this book came from. That's always what it has been. The other thing with a pitch meeting, it has to be, “Before I put this out into the world, do I think it has relevance for other people? Will that person in Poughkeepsie care?”
Dustin
You wrote a piece in line with what we were talking about. You wrote a piece called Congratulations, You're (Probably) Not an Introvert. I wanted to ask you, isn't it hip to be an introvert these days?
Celeste
It's trendy. Everybody says they're an introvert. It's probably because of Susan Cain’s wonderful book called Quiet, which is a great book, nothing against that. If you are an actual introvert, that book is going to be helpful for you. It has everybody thinking that they're an introvert and it drives me crazy because you're probably not. Introverts are a small percentage of the population. Adam Grant has done a bunch of research on introverts and extroverts. He says introverts probably are maybe 15%, 16% of the population. It’s fewer than two out of ten. Even among those, 1.5 people out of ten, even among them, they may not be a full-on introvert. Introversion and extroversion, it's a spectrum. Using introversion as an excuse for why you sit at home and watch Netflix every night instead of socializing, it doesn't hold water. That's not going to work.
Dustin
With technology proliferating, are we in trouble? Tech seems to make people want to focus inward. This is my opinion but what's your thought here?
Celeste
I would agree, but with a significant caveat. I don't think it's tech's fault. Our tendency to isolate ourselves started before the smartphone. I may remember the iPhone only came out in 2007. It's been a short period of time. We were doing this already. Tech makes it so much easier to do it. That's the problem. It's not tech's fault. Nobody has to get rid of their smartphone. You just have to stop using it as a tool to isolate yourself because we're in an epidemic of social isolation and loneliness. Loneliness will kill you. That's not an exaggeration. They have found that loneliness degrades your internal organs. It shortens your life. It makes you more susceptible to heart disease, diabetes and all kinds of actual, physical diseases.
Human beings are not evolutionarily designed or evolved to be alone. It is extremely dangerous. This trend of calling yourself an introvert is even more dangerous is because we have also found that if you think of yourself as an introvert even wrongly, because you're probably not. If you think of yourself as one, it becomes this toxic circle. You are less likely to remember the times when you've enjoyed being in a crowd. You'll stop remembering all those extroverted moments you had. You'll only remember the times when you felt being alone, which emphasizes your idea that you're an introvert. You start avoiding social situations because you're thinking of yourself as an introvert. As you start avoiding social situations, your social skills then begin to degrade, which makes future social situations more stressful to you, which means you avoid them even more. You see how this becomes a bad cycle. I want people to stop calling themselves introverts. It has to stop.
Dustin
It's a self-fulfilling prophecy. What's your advice for people? Maybe they're in that cycle. Let's say they're not an introvert. They're not part of that 15%, 16% but they're in that cycle. They're an ambivert. They're in that cycle and they feel anxiety. They're reading this saying, “Celeste, you're a TEDx speaker and you're a host. It's easy for you. When I go into social situations, I am freaking nervous.” What do you say to that person?
Celeste
There are a couple of things. Number one, I’m an ambivert like most of the people on the planet. A lot of people have not even heard the term ambivert, even though the majority of people are one. An ambivert is someone who sometimes has a great time in a crowd and sometimes is the person talking the most at dinner and sometimes likes to go home, be alone and watch Netflix. An ambivert is a balance between the two. That's what most people are. That's what I am. For example, if I go and give a talk, when I give a speech, it's a hyper-social situation. Everybody wants to come up to me afterward. They have questions, they have conversations. When I’m on the plane coming back from that, I want no one to look at me, speak to me or touch me. I need to be alone. If you're ever on the plane next to me and you're like, “What? She's a conversational expert?” That's why. That's the first thing I’d say to that person.
The other thing I would say is there's a great study that was released. The title of the study is The Liking Gap. It's the result of a long period of study of people in all different situations and relationships. The takeaway from watching people's relationships was people like you more than you think. That's the bottom line. We get caught up in ourselves, our own thoughts and worrying about if what we said was clever, if what we said was smart, if what we said was sexist, racist, funny or whatever it may be. We get caught up in that and looking at the other person's reaction to see if they're bored or whatever it may be that we're missing all the social cues from other people that show they're enjoying talking to us. The vast majority of the time, people like you and enjoy talking to you. That is what our best scientific research says. When you are afraid of going into social situations, you have to ask yourself what you're afraid of. Most people there are going to like you. If you want to make sure that you don't irritate someone, just keep it short. Most likely, the only time people get sick of talking to other people is when they won't stop talking. Keep it short and you're fine.
Dustin
I get my confidence. I understand I need to put myself into that situation. Part of this is feeling like, “I don't want to look stupid,” but people like us for more than we are. You did a talk on this, 10 Ways to Have a Better Conversation, and you wrote a book, We Need to Talk. It's easy to say, “Celeste knows how to have great conversations.” Once we put ourselves in that social situation, we're feeling a little nervous, understanding that people like us, how do we dictate a great conversation? How do we lead or how do we be part of a good conversation?
Celeste
I would imagine that all the people I went to college with who are now being told that I’m a conversational expert are laughing their butts off because I was terrible. I was the biggest know-it-all, irritating, freaking person ever out of the planet. I don't know how anybody put up with me. That's the first thing. I was at the TED Summit a few years ago and this one nuclear scientist from Japan came up to talk to me and he said, “I’ve watched your TED Talk a bunch of times, but I don't know how to start a conversation. How do you start it?” I was like, “Where in Japan are you from?” He said, “I’m from Kyoto.” I said, “I’ve never been there. I’ve only ever been to Tokyo. Is Kyoto crowded? Is Tokyo packed?” He said, “No. You've seen the pictures of the cherry trees, the temples and stuff.” I’m like, “You don't live in a temple. Are people in houses or an apartment?” He starts describing it to me. I’m like, “Do you guys have yards with dogs?”
Ten minutes later I said, “That's how you start a conversation. You ask people questions about something they care about that they know the answer to.” If you are nervous about a social situation, your questions are your best friend. Simple, direct questions about something the person cares about that they know the answer to. Ask them about their tattoo. There's always a story about tattoos. Ask them about the shirt they're wearing. Ask them about the jewelry they're wearing. Ask them about the best thing that's happened to them in the past month because we do know, through scientific research, that getting people to talk about something they're proud of makes them more emotionally open and willing to negotiate and collaborate in the minutes afterward. Ask people questions and then listen to their answers.
Dustin
I want to go deeper here. What's popping in my head as you're saying this is I think about in our world, not everyone has had this opportunity, but in our world we get a chance to interview people that get interviewed quite a lot. I can see some people or at least what's popping in my head now is that you’re asking that question that they've got asked a million times and they want to check out. Ask the question anyway, get that feedback and then quickly pivot or do your research. What do you say to that?
Celeste
I say don’t ask the question. My career in radio has been built on a goal of asking the questions they've never gotten before and it served me well. It requires a lot of homework because it means you have to listen to those other interviews. It means you have to read the book if they're an author. You've got to ask them new questions. In public radio we do pre-interviews. We want to make sure that person is the right person for whatever it is we're talking about. A producer will spend ten or fifteen minutes on the phone doing a pre-interview, asking them questions, hearing their responses, etc. If a producer asked them a question and they hear that person go into automatic mode, they flag it and they say, “Don't ask this question. They've answered it a billion times before.” I don't ask those questions anymore.
Dustin
Does a great interview make for a great conversation or do you see those as something different?
Celeste
A great interview is basically a formalized, time-limited conversation. A great interview should be the best conversation, the only difference being that a true conversation is a mutual exchange of ideas. An interview is not a mutual exchange of ideas, it's more that one person is trying to pull out the ideas from another person. When I’m doing an interview, my whole goal is to shine the spotlight on someone else and show off what they know. I want to ask the questions that only that person can answer. That makes it different from a conversation. Other than that, the rules are basically the same.
Dustin
As a real-world application in this, a lot of people have interviewed you, they've seen your track record, the TEDx Talks, you're an NPR host. It's easy to go back to those things. What hasn't someone asked you or where would you like to spend more time in an interview? You don't get a lot of those cues or questions.
Celeste
People are relatively good. The conversation is a nebulous subject to a certain extent. It can lead people to a lot of different situations. I’m lucky in that when people come to interview me, often they start thinking about conversations that have gone pretty badly for themselves. It’s because that's interviewed, because that's individual, it generally leads to different questions. I’m lucky that way. I’ve heard some terrible interviews. I did one of the last interviews that Gregg Allman did before he passed away. I listened to a bunch of different interviews with him and they were all terrible. Everyone wanted to ask him about his brother's death. I’m like, “Stop asking him. He's sick of talking about it.” I didn't bring that up at all.
People say a lot, “Celeste is good at doing music interviews because she's a musician.” It’s because when I bring a musician in, I ask them about music. Why would you bring a writer in and ask them about their family or their childhood? Ask them about writing. That's what they love. Ask them about their process. Ask them about what it is that they're most passionate about. Why would you bring a musician in and ask them about their brother's death instead of asking about the music itself? Not those dumb questions of, “Who are your influences?” They've been asked that a billion times before. I’ve even heard people going, “I know you've been asked this a million times before but of all your songs, what's your favorite?”
Come on. You’ve got to steer away from that stuff. I ended up writing a book literally about this for my colleagues who are hosts and in broadcasting. I put it on Amazon so that it would be cheap because public broadcasters don't have a lot of money, but it's called Heard Mentality. I interviewed everybody, Susan Stamberg, Steve Inskeep. I interviewed all these people and boiled down 250 years of experience in interviewing into this one book. When I looked for help, it is another case when I looked for, “Where are the great books about interviewing?” They don't exist. There are books on job interviews, but not on having a great interview with a person, so I wrote it.
Dustin
Since I have this opportunity with you here, when you're vetting and you see the stories, you're listening to an interview and it's a great story. How do you think about it? Maybe it's one you hear throughout, but you're bringing this mindset of, “How do I get something different? How do I ask them something that's more hitting or more telling about the person?” Are you saying, “I want to get this story in here because it's a crowd favorite, it's a great story but I’m going to come at it from a different way?” Are you saying, “He or she has told it too many times, let's skip it?” How do you weigh that?
Celeste
I generally skip it unless I have to ask it because it's connected to a headline. I will find little stories. There have been a couple of times where I’ve said to someone, “I read this thing on Wikipedia and I hope it's true. Could you fact check this for me? Is this particular tidbit true?” They're usually things that people have not heard before. I’ll skip it completely, especially in this era of technology where I can go back and listen to all those other interviews. They don't need to hear it again. I don't need to be encyclopedic. Maybe in the early days of broadcasting when you couldn't re-listen to those things, then yeah but now no. You don't need to hear it again. Ask them something else.
Dustin
You bring up there's no shortage of content out there, past interviews. How do you get through all that content? Do you say I’m going to listen to five interviews and cut it off? Do you go with the flow? How do you determine how many interviews you’re going to listen to, to get to your story?
Celeste
I listen to as many interviews I need, as soon as I reach the point where I know what I want to ask them. I don't write questions before an interview. I write an arc. I’ll maybe write the first question or know what the first question is, but I write an arc of the conversation. Where do I want the beginning, the middle and the end to be? I create bullet points so that I can look down and say, “I wanted to talk about this.” If you write questions, it tempts you to not have an actual conversation. It attempts you to ask questions without fully listening to what you're hearing. I’ve heard those interviews where someone will be interviewing someone and they'll say, “How did you choose to go to Georgia State, since they didn't have a strong writing program?”
The person will say, “After high school, my childhood had been so abusive that I went into the services,” and then the person will come back and say, “Then you moved on to writing your first bestselling novel.” I’ll be like, “What? Go back. He just said abuse, go back, rewind. Were you listening to what he said?” It's because they wrote their questions. They tune out when the other person is answering. They're getting ready to ask the next question. It's a dangerous thing to write up questions. These have exceptions to them. There are plenty of excellent interviews who write up questions and if that works for you, then that's great. You need to know what works for you based on actual practice and objective feedback from other professionals, rather than going with it because it makes you feel more comfortable.
Dustin
I am with you. I am the opposite. You have been at this quite a long time. I like to know where the conversation is going to go and you do too. You write the arc, but I write out all the questions. However, I’m mindful of the great advice you give, which is to listen. I am not married to asking these questions. I let it go but I think of dead air. Not you as the guest, like running out of things to say, but me as the host saying, “Celeste, that freaks me out. I am the opposite of that.”
Celeste
You should do what makes you comfortable. Sometimes for some people, having those questions there relieves the pressure. I totally get it.
Dustin
I do want to ask you about combative people or guests that are there that don't want to be there but have to do an interview. What do you do in those situations?
Celeste
I’ve had interviewers hang up on me before and they were generally politicians that would hang up the phone. I’ve had people walk out of an interview before. I get it. That's going to happen, especially when you're talking about something they don't particularly want to talk about, which is often. Barney Frank is the first one that comes to mind. Barney Frank, the Congressman from Massachusetts, was infamous for getting angry and hanging up on you in the middle of an interview and then he'd call right back. The main thing in an interview is to do whatever you can to not get them there. Sometimes that's not possible. I would say over 90% of the time it is. If you're approaching those questions and approaching the topic with honest curiosity and showing them respect in your listening, that in itself goes a long way to not getting them to that point.
One of the examples I give in my book is that I’m a mixed-race person. My family was enslaved on a plantation near Milledgeville in Georgia. In years, I’ve had a lot of causes to end up having to do interviews about the Confederate flag. I would need to bring people in who are members of the Sons of Confederate Veterans and other organizations who are in favor of flying the Confederate flag. It's pretty clear. I have an opinion on it and it's not going to change. I feel like most people can assume that. First, I’d start the broadcast with a caveat saying, “This is my history. I do have a strong opinion about it but I’m going to be fair. If you think I’m not fair to these guests, then call us and tell us what you think was not fair.” That's how I approach it. I approach those interviews saying, “I’m going to learn from this person. This person is going to be able to teach me a little bit more about their perspective and why they think the way they think.” Above all else, I will be fair. That's how I have that interview and it usually goes fine and I usually do learn something from them.
Dustin
In 2016, you started your own media company. I’m curious to know what that turning point was. I know you've been an independent contractor most of your life. We talked about musicians having to be that way, but to go from that to starting your own media company. What was that turning point for you that says, “I’m going to do this?”
Celeste
In 2018, my own business was going well that I resigned from my full-time position on the radio. Now, I’m an occasional radio host and I employ myself. The turning point was the amount of money that was coming in and the percentage of my time it was taking up. My guiding light has always been finding the expert and then listen to them. We live in this age when everyone thinks they can become an expert by watching a YouTube clip. I find that's a terrible idea. I had to be honest with myself about the things I was not good at or didn't know enough about i.e. setting up a business, logistics and scheduling. I found those experts who are good at them and then I let them do their jobs. In order for me to make that transition into full-time being a media company, I had to bring on other team members.
Dustin
What surprised you in this journey of starting your own business?
Celeste
Everything surprises you. It feels like every week there's a new thing when you're like, “This happened and I hadn't thought about it. I didn't realize this was a whatever.” That's what entrepreneurship is like every day almost. It feels like there's a new thing you'd never considered before. I didn't realize that a big part of entrepreneurship is becoming a bill collector, for example, and having to pester major corporations. I didn't realize the bigger the corporation, the harder it is to get them to pay you. If you want me to be fully honest, these are the things I would never have considered and yet they take up a huge amount of my time.
Dustin
What is your advice for others? Knowing that you've got to be a bill collector, everything surprising every day, which is the fun and the excitement. What is your advice for others that are coming from Corporate America or a job that want to get into the business? What do they need to know? What should they consider?
Celeste
They need to be specific about their core mission. That's the thing you need to never lose sight of because there's so much else that's going to come on and it's going to distract you and it's going to be frustrating, but it's quite easy to forget why you decided to do this in the first place. Frankly, if the reason you're doing it is just that you hate your job and you want to be your own boss, I don't know if that's enough to sustain you through all of the things that are going to happen. You have to figure out exactly what is my mission, what is it my business does and never forget that. Keep it front and center in all that you do and make sure that you're scheduling a time to focus on your core mission every day or as close to every day as possible so you're not getting distracted by all the little crap things that happen.
Dustin
Celeste, I’ve had an amazing time with you. Thank you for your advice, your insights, your inspiration to many others about stepping into having conversations, not being introverted, embracing the ambivert in you. I’m curious as to what the future looks like for you. What are you working on that's lighting a fire for you? If people want to continue that conversation, where can they keep tabs on what you're up to these days?
Celeste
The easiest thing is to go to my website, CelesteHeadlee.com. My team and I do a good job of keeping that updated. They've got links to every single video and TEDx Talk. They've got links to books, etc. My blog, it's all there. That's the easiest one-stop shop.
Dustin
Thank you, big time.
Celeste
Thank you so much. It's been a great conversation.

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