Svane, the founder of customer service software, Zendesk, we talked about the challenges of his early days in business. Then I tried to get more personal. Me: Is it inappropriate for me to ask you if you’re still with your wife? Mikkel: Yes, it’s highly inappropriate.

‍

• 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.
• 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.
• If you want people to be open with you, you need to be willing to share first, and to do it without an expectation of immediate reciprocation. Give it time. The depth of your conversations will be worth it.
• 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?”
• Our job as interviewers is to encourage them to do it. The dramatic lowball does that. In fact, the dramatic lowball is so effective that I try not to use it in interviews. I don’t edit my interviews, and I don’t want to trick anyone into publicly releasing something they’re not ready to share.
• 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.”
• Here are a few other examples of how I phrase criticism through other people’s words: What do you say to someone who’s listening to us and thinking …? What would you say to someone who thought …? I imagine someone listening to us thinking … What would you say to that?
• 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?”
• 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.

‍

So stop asking questions. Start leading your guests through better conversations.