Stop Asking Questions

Key Takeaways

Under Consideration — to be added.

Interconnections

Under Consideration — to be added.

Highlights

• realize now what was missing when I talked with Ace. I wanted to learn, and he wanted to teach, but that desire is not enough. Interviewing is more than just asking questions.
• In the next part, I’ll cover how to make interviews meaningful and interesting.
• Visit holloway.com/saq-convos for a more extensive online cheat sheet.
• I asked him how he started blogging. “Wall Street Warriors,” he said. “It’s a hit TV show now in fourteen countries, so I was in that show, in five to six episodes of season one.” Then he artfully mentioned his book, telling me, “People were emailing me what they wanted to know. So I wrote a book called An American Hedge Fund.”
• I tried something new while preparing for an interview. Before recording, I asked my guest, “What’s a win for you?” That did it. Asking someone about their goals reassured them that I cared about their needs and that I’d work with them to reach those goals.
• Now I start most of my calls with some version of “what’s a win for you?” Variations on that question include: What’s your #1 goal for this interview? What would make your team happy to hear us talk about? Why did you agree to do this interview? How can I make this interview as useful for you as it will be for me and my listeners?
• Finally, instead of pushing back against a patient’s resistance, she decided to join the resistance. “It seems like everything is going well,” she’d say. “It’s nice for me to get to talk to someone who has an easy life, who has it good.”
• Next time you’re trying to get someone to be vulnerable and tell you about their challenges, don’t push back against their resistance if they put up roadblocks. Accept it. And even congratulate them for it. They say, “I never failed.” You say, “It’s amazing to talk to someone who always got everything right.” They say, “I’m not a worrier.” You say, “I don’t usually get to talk to people who are 100% confident.”
• The shoved fact is very similar to the psychoanalysis term “Freudian slip,” which says a slip of the tongue may represent an unconscious wish or internal train of thought. As conversationalists, we often ignore the teeny slips of the tongue because they’re mostly meaningless. The average person slips on up to 22 words per day.1 But when someone pushes a big topic out of context, we need to be aware that they might be expressing a yearning to talk about it—especially during an interview.
• One of the best things I did was go to weekly Toastmasters* meetings to become a better speaker.
• Mulling it over, I realized my mistake. I never shared anything revealing about myself. My conversation techniques worked so well that people opened up, often more than they ever had before. Yes, they felt relief and acceptance, but they also felt vulnerable. And, more painfully, they felt alone in their vulnerability.
• I add a line or two about myself when I ask guests to talk openly about themselves. I don’t do it to take attention off them. I do it to make them feel safe enough to talk openly.
• I found that it’s best to clarify the agenda with guests before we start recording by using a promotion stopper. I get their buy-in by phrasing it as a question, like, “Of course I’ll mention your new project in my intro, but since my audience isn’t emotionally connected to it yet, do you mind if we build your credibility first by talking about the big company you sold?”
• The beauty of the one-word question “because?” is that it acknowledges that I heard what was said before and shows that I care about it so much that I want to understand the reason behind it.
• As an interviewer, I noticed that people are taught from an early age not to brag, so they resist talking about their achievements. Our job as interviewers is to encourage them to do it. The dramatic lowball does that.
• Before we started recording, I looked into my webcam—the closest I could get to looking him in the eyes. I said, “Gregg, I want to record an interview so good that decades from now when your great-great-grandkids wonder how you built your business, they’ll come listen to what we record today.” With that one sentence, I got his attention. When the interview began, he sat up in his chair and started telling me some private, never-before-told stories.
• In business, interviewing, and life, we often find ourselves needing to persuade and motivate other people. Share a higher purpose to get others on board with your goals. Give them a mission they can buy into and support.
• All curious people will encounter this problem. Asking questions makes you seem needy. And if you’re needy, people don’t respect you, which reduces the quality of their answers.
• One of the ways I responded to that period of frustration was by taking charge of the conversation from the start. If the guest was in a loud room, I told them to move. I didn’t ask. I said, “You need to find a quiet place to record, or the audience won’t be able to hear your story.” If they didn’t have a strong internet connection, I told them to find a way to fix it, or we’d need to reschedule for a day when it would be better.
• Guests appreciated that kind of leadership, so I brought the attitude into my interview. I rephrased my questions as directives. Instead of asking, “How did you get your first customer?” I said, “Tell me how you got your first customer.”
• Interviewees appreciated this direct approach. Being interviewed requires a lot of trust. Guests want a host who will keep them sounding interesting, helpful, and bring out stories they’d never think of on their own. That kind of guidance doesn’t come from a needy intern. It comes from a leader. Real leaders use clear statements and make thoughtful requests.
• If you were going hiking with a guide, you wouldn’t want her to keep asking, “Do you want to go left or right?” She’s the one with experience. It’s her job to know what’s down each path and to understand your interests well enough to pick for you. That’s what your interviewees need from you. Guide them. So stop asking questions. Start leading your guests through better conversations.
• A more productive way to ask tough questions is to put the words in someone else’s mouth. I learned this technique from watching Mike Wallace, who was considered one of the toughest interviewers of the twentieth century. The most cited example of his chutzpah is when he asked Iran’s leader, Ayatollah Khomeini, if he was crazy.
• If you have challenging questions that you want to bring up to a guest, I recommend pre-asking them before the interview. In my experience, most guests are willing, if not eager, to use interviews as a place to share their side of tough issues. And if you tip them off, they’ll trust you even more with those questions.
• I learned to rephrase my request. Instead of “could you tell me a story about that?” I used phrases like the following: “Tell me about a time when you did that.” “Do you have an example of that?” “Tell me about the day you signed the agreement to sell your company.” “Take me to the moment you quit. What did you say?”
• Seek out specific and interesting stories in your interviews. Pay attention when your interviewees make general statements about their lives, and follow them up with a request for specific examples.
• As an interviewer, I don’t want to count on people making that leap. So I usually rephrase all “most” questions in a way that gives guests options. Instead of asking “Who’s the most important person you hired?” I go with “Who’s an important person you hired?”
• There are exceptions to this rule. For example, when I ask a founder what their top source for customers is, I don’t want to hear about the third most effective channel. I’m trying to understand what’s working best. It’s a factual piece of information that founders should know the answer to, so that’s what I ask for.
• My solution came from a conversation I had with the investigative reporter, John Sawatsky. He told me that he warns reporters not to ask what he called “double-barreled questions.” Double-barreled questions are questions that address two different issues. When reporters ask double-barreled questions, their subjects answer the easy part and ignore the part they don’t like.
• Unlike a reporter, I want to give my interviewees an out from answering a question if it makes them uncomfortable. If I’m wondering whether someone got a divorce, instead of asking “did you get a divorce?” and making a business conversation feel uncomfortably personal, I might ask, “Do you feel comfortable saying if you divorced your husband?”
• To be clear, this technique isn’t fool-proof. It doesn’t always get people to open up, and that’s the point. The double-barreled approach gives people an easy out to avoid topics that are too personal for them. As an interviewer, be prepared to move on quickly if your guest opts out of the question.
• I spent much of the conversation interrupting him. Talk about a terrible host, right? But I had to do it. He was going on and on and taking us off-track. I couldn’t let my listeners put up with that. So I interrupted him—quite a bit. After the interview, I prepared for him to rip into me. Instead, he said, “Thanks for getting me back on track. I’m not good at public speaking. I found myself droning on and didn’t know how to get back to my point. I can see why my friends like being interviewed by you. You’re good.”
• When people struggle to get a point across, they start to talk in circles. Instead of clarifying, they make their point less clear with each round of explanations. Most people, like my interview guest, will appreciate your help sounding competent.
• Turns out, I stumbled upon a surprisingly simple solution—a short phrase that exonerated me from any breach of conversation etiquette: “I’m sorry to interrupt, but …” Then I’d complete the sentence by explaining why I was interrupting and often citing my higher purpose.
• Don’t get me wrong—interrupting someone does not feel natural to most people. It will make you feel rude and awkward at first. You’re doing something every teacher and authority figure taught you not to do. A “sorry to interrupt” moment is when you interrupt and share why you’re interrupting. People won’t think you’re rude—they’ll think you’re considerate. If you’re interrupting for a meaningful reason, your guest will appreciate it.
• Not every interruption is created equal. Saying “sorry to interrupt, but you’re boring me” is extremely rude and will lose you a friend or colleague. On the other hand, “sorry to interrupt, but I really want to make sure I understand what you’re saying” is flattering and will win you a fan for life.
• The peak-end rule is a cognitive bias that affects the way we recall events. Humans tend to remember two aspects of an experience more than anything else: the peak (i.e., most intense) and the end. By saving my toughest question for last, I unwittingly stacked the peak and the end into one dramatic moment. It was the only thing my guest remembered from our talk. No wonder she was upset.
• My goal was to give my guests a home run question they could knock out of the park and leave the interview feeling confident about their performance. But I didn’t stop there. I started anticipating my guests’ need for validation. When an interview ended, I thanked them, told them they did well, and mentioned one specific thing I liked from our conversation.
• if you fail with every tip I gave you so far, you’ll do well if you simply let your guest talk.
• Here’s his magic. He asked what happened. Then he didn’t say much more than “mhmm” for a long time. He followed that by asking “why did you say that?” and went back to listening. When they hung up, I asked my brother, “How’s she doing now?” He told me she was feeling better. She already knew not to let her ex get under her skin and to ignore him, but it still bothered her. After unloading on Michael, she felt better.
• That’s the magic of listening. People prefer to be heard than to be helped.
• Let me say that again: pre-interviews can backfire on you if you don’t cut off your guests’ stories. If I let a guest tell their full story in the pre-interview, they will hesitate to repeat themselves in the actual interview. It’s like they’re afraid of boring me, so I either get a severely shortened, less interesting version of the story, or no story at all.
• If you don’t have a team, you might be tempted to send over a list of questions before the interview. I found that shortcut to be much less effective. Most guests will skim the list and move on—some won’t even do that.
• Alex Blumberg, co-creator of NPR’s Planet Money and the co-founder of Gimlet Media (acquired by Spotify), has said a big reason people listen to audio shows is companionship. For the serendipitous style of interview, the audience doesn’t want their attention held tightly. They’re doing other things while listening, like cooking, walking the dog, or exercising. They don’t want to focus the way they would during a college lecture or even a sitcom. They want the company of friendly banter while they go about their day.
• I learned from Rogan that you don’t need to exhaust a topic. It’s OK to move on to something more interesting.
• Many interviewers skip doing research. In fact, some interviewers believe a lack of research is the best way to empathize with the audience. By not doing research, the argument goes, the interviewer can ask the questions the audience would ask if they could talk with the guest. This isn’t just bad advice—it could ruin your reputation with your guest and audience.
• You can use outsourcing companies to pull most of this information together. If you provide a clear list of questions, services like FancyHands* can put together a decent research doc for about $25. They won’t do a formal pre-interview, but they’ll do online research to find as many answers to your pre-interview questions as they can.
• What I realized is that most people want to help interviewers like me. Over the years, every person I’ve contacted has been impressed that I’d spend the time learning about my guest, even if they preferred not to tell me anything.
• Many people sit behind a mic and think they’ve suddenly turned into the reporters they see on the evening news. They think the professional thing to do is get the facts for some imagined audience that expects formality. That’s the old way. It doesn’t work online, where you don’t have a general audience. Your audience is made of enthusiasts who want to learn about their passion from someone who is just as passionate as they are. They want to know about you as much as they want to get to know the person you’re interviewing.
• Oprah Winfrey, despite her fame, also knew the power of one-on-one audience intel. Winfrey always signed autographs after her live shows, but in the early years, she would try to get through them as quickly as she could. “I [would] do all the autographs and never look up, trying to get through 350,” she said. “One day I decided, ‘I don’t want to do that anymore.’ But what do I really want to do? I want to talk to this audience. I want to find out who they are, where they come from. That became my favorite part of the day.” So Winfrey started talking with members of her live audience after each show. It helped her understand them—why they spent hundreds of dollars and hours of their time to see her. She considered it her greatest resource. “It’s the reason why we were number one for 25 years,” she said.
• In her autobiography, Walters explained her process. “I wrote down on three-by-five cards as many questions as I could think of, then asked anyone who walked into the office, whether it was somebody delivering the mail, a production assistant, or a hairdresser, ‘If you could ask any question of [whomever], what would it be?’ It was very productive.”
• As an interviewer, you can’t bully your guest into telling their story your way. If you must reshape their story’s structure, do it in editing (but be faithful to their intent), not in the conversation.
• Just how important is your opening? Reality set in for many podcasters when Anchor, the podcast creation app, gave its creators second-by-second analytics for each episode. When podcasters looked at their graphs, many saw big drop-offs in listenership just moments after their podcasts started. Some lost over half their listeners within a minute. As NPR producer Nick Fountain said, “If you don’t hook people in within the first minute, you’re screwed.”
• Sometimes, one hook isn’t enough. NPR producers like using the rule of three, a principle that says focusing on a trio of events makes the material more enjoyable and memorable.
• Podcasters seem to want the most recognizable guests. I do too. Landing a superstar is like a stamp of approval for your show. It elevates your reputation as an interviewer. Still, I’ve found that lesser-known interviewees can drive bigger audiences, and they’re significantly easier to land.
• Another thing to help you land newsmakers is your mission—your higher purpose. In a world full of “gotcha journalism,” practice “I get you journalism” instead.
• Stop searching for one guest or one idea at a time. Instead, look for sources of people and ideas. When you find your idea fountains, you’ll develop a strong pipeline for every part of your business.
• It takes time to build trust with your listeners. But ironically, asking for help actually creates more trust with your audience, not less. Don’t be afraid to reach out to your network and make a public plea. You never know who might show up to your aid.
• I learned the most powerful technique from a friend who runs an interview podcast that’s often on Apple’s Top 10 list. Before the interview starts, he lists all the ways he’ll promote his interviewee. He’ll share it in his email newsletter, post it on his popular Instagram account, and so on. He’ll spread his guest’s message far and wide. Then he turns to his guest and asks, “How can you help me promote you?”
• I tried this technique. It was incredibly powerful, but I quickly ditched it. It framed the interview as a promotion piece for the guest, so they didn’t want me to ask tough questions and often asked me to edit out potentially embarrassing stories.
• In the more than ten years I’ve been interviewing, I’ve rarely had a month without at least five guests booked in advance. That’s how I keep getting past my inner doubt and continue improving.
• I missed having a drink in person with friends while our city was in lockdown, but in many ways, the hour I spent in an interview was better. Only experienced interviewers know how true that is. Regular conversations are full of small talk, fillers, and distractions. In an interview, you can avoid all that and focus on what you really care about.