After I sold my greeting card company, I moved to Santa Monica and took a few years off work to focus on personal development.
One of the best things I did was go to weekly Toastmasters* meetings to become a better speaker. I was still new there when one of the members invited us all to her house for drinks.
For the first hour, the conversation was stilted, limited to whether our cars could make it to the top of Bear Mountain without snow chains. Elena, one of the other guests, said: “I don’t know if it could make it up a mountain, but I know it could go across the country. After my sister committed suicide, I put all my things in the backseat and drove till I got to California. It didn’t give me any trouble on the way over. I’ve had it for seven years, and it’s always held up.”
Someone asked what type of car it was. By then I already knew how to spot a shoved fact, and how it’s a signal that someone is eager to talk about a topic. So after she answered that she had a Ford Bronco, I asked a more meaningful follow-up.
“Do you feel comfortable saying more about your sister?” I asked. (In the section on double-barreled questions, you’ll understand why I phrased my question this way.)
She paused for a moment, then said, “She was battling depression for years, but my family didn’t talk about it much. We thought it was something she’d just get through as she got older.”
Someone else said, “My aunt went through that too. Back then it was an embarrassing thing to talk about. We thought people would blame us for causing it, or that her depression was contagious and would somehow rub off on them.”
As Elena told us about her family, I asked a few more questions, and she kept opening up. She unburdened herself. The big secret she kept hidden didn’t need to be a secret. It felt good to be accepted and to see she wasn’t alone.
Unlock expert knowledge.
Learn in depth. Get instant, lifetime access to the entire book. Plus online resources and future updates.
Then, as she wound down, she said something that hurt me. She leaned back into the sofa, crossed her legs, and said, “Andrew’s always pumping us for personal information.” I looked at her and saw resentment in her eyes.
I couldn’t understand it. I knew she felt relief from talking. At times she cut me off and cut others off, just so she could keep telling us about her family. Why the hostility?
As I drove home that night, I couldn’t stop thinking about Elena. I realized that as my conversation skills improved, some people felt relief and closeness by talking to me. But I also realized that some people said the same thing Elena did. They felt I was pumping them for information, even though I was tapping into what they were dying to talk about.
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.
So I started talking more about myself. At first, I tried keeping things balanced. I talked as much about myself as my conversation partners talked about themselves. Quickly, I discovered that most people don’t want to listen. They prefer to talk.
What I’ve learned is to include a revealing sentence or two about myself every once in a while, then go back to giving others a chance to talk. That reciprocation is the right balance.
Once I figured that out, I asked Elena if she wanted to take a walk to the Coffee Bean & Tea Leaf for a drink after a Toastmasters session. When we sat down, I said, “I was curious about your sister because my brother dealt with depression in high school. I always wondered what I would do if I had kids who went through it. That’s why I asked you about it the other night.”
She started telling me about how she’s been in therapy and what her family wished they’d done. We talked for two hours. Well, she did most of the talking. I was incredibly curious and loved listening. Every once in a while, I interjected with something personal about myself. When she finished her second cup of tea and was ready to go home, she said, “I like talking with you, Andrew. I feel like you’re the only one who really understands me.”
I reciprocate in interviews too. Robert LoCascio, founder of LivePerson, the $3B customer service software company, told me about the failure of his previous company. He lost almost everything he had, and he told me about how miserable he was, which finally led him to get a therapist. If you listen to that interview, you’ll hear me share stories about my background, and how I was ashamed as a boy when my family’s landline was shut off because we couldn’t pay the bill. My little confessions made me feel relieved, but they also created an atmosphere where Robert could open up about his problems.
When Pablo Fuentes, founder of Proven, the small business hiring company, told me about failing nine times, I told him that one of my most painful worries is that if my business fails, I won’t be able to get a job.
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.
Other good podcasters do it too. Dax Shepard is an actor, director, and host of the hit podcast, Armchair Expert—the most downloaded new show on Apple Podcast in 2018. Shepard says people listen to his show because of the vulnerability of his guests. “I am so often trying to enact vulnerability,” he said as a guest on The Tim Ferriss Show, “which requires me to go first. It’s almost like an [Alcoholics Anonymous] meeting where it’s like, I share first, and then maybe you’re compelled to share back.”
As you get good at using these conversation techniques, you’ll get a deeper understanding of other people’s lives. Make sure to share your life with them too.
“I notice that bloggers, Instagrammers, podcasters, and others use their reach to show how amazing they are. They only show their strengths. Meanwhile, I can’t stop bringing up my weaknesses in my interviews.”
“For example?” he asked.
“Well, just look at the transcript you’re going through right now. Within ten minutes I told my interviewee about one of my flaws. She responded by telling me how amazing she is. So now anyone listening will think of me as weak and her as successful.”
No response. Jeremy kept his head in my transcript. Did he even care? He produced national television. Was helping a flawed interviewer like me so beneath him that my issues weren’t even worth acknowledging?
Then Jeremy said, “Scroll to page 15 of the transcript. That’s where she tells you how her parents were incredibly hard on her and she felt like a failure as a child. Then she tells you how that led her to work harder, to prove herself to her parents. To fight back against what people thought of her.”
I read the passage from the transcript. “Andrew, you shared,” he continued. “You got vulnerable. You can’t expect her to reciprocate instantly. This isn’t a transaction where you trade your story for hers. You’re setting the atmosphere, giving her space to share too. And she did. I’ve read dozens of your transcripts. I can’t think of a single time that didn’t happen … eventually. But you need to be patient and trust.” He was right.
“And you know what?” Jeremy said. “Sometimes the people you’re talking with won’t open up on the first conversation. It might take them years. Others won’t open up at all. You need to be fine with that.”
Today I am fine with that, but only because I saw how often it’s true. If you want people to be open with you, you need to be willing to share first, and to do it without an expectation for immediate reciprocation. Give it time. The depth of your conversations will be worth it.