Get Guarded People to Open Up

6 minutes

Holloway Editione1.1.1

Updated September 14, 2022
Stop Asking Questions

You’re reading an excerpt of Stop Asking Questions, by Andrew Warner, a veteran podcast host of 2000+ episodes. The book explains how to lead high-impact interviews and learn anything from anyone. Master the craft of interviewing with this complete digital package. Purchase now for lifetime access to the book and extensive audio and video resources.

I wasn’t being a jerk when I pushed Jason Fried to tell me about his failures. I acknowledged and admired how he bootstrapped Basecamp into a project management tool that was bringing in millions of dollars a year in profits.

Still, I wanted to hear about his failures. I learn a lot about growing a business by understanding how people overcome failures. But if I’m honest, I was also hoping to see that he was like me: a human being with failures I could relate to.

So I pushed. And pushed. And pushed. Finally, he looked right at his webcam—on a video call, the closest thing to looking someone in the eye—and told me that it’s not helpful to even think about failures or look back.

Years later, when I hired Jeremy Kareken, an interview coach, I brought up this interview as an example of a big problem I have. In conversations, pushing harder for a goal often leads me further away from the goal.

“Ah,” he said. “Join the resistance, Andrew.”

He explained that he learned this technique from his therapist, who encountered similar types of resistance. In couple’s therapy, when she pushed male patients to be open—to use their time as an opportunity to bring up problems and work through them—the men would resist with comments like, “I don’t have any problems.”

The therapist used to push back. She tried explaining that everyone has problems, that the reason a patient was in her office week after week was that he obviously had challenges to work through. None of it worked.

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.”

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That did it. “Easy?” her patient would ask in shock. “You don’t know how hard things really are. Just this week …” And suddenly, the conversation was productive.

To see how powerful this technique is in interviews, let me tell you about the next interview I did with Jason after I’d learned it.

We talked about how he had a massive hit with HEY, his new email service and software. Within 30 days, HEY had 170K people on its waitlist and generated $5M in revenue. His approach was to start from scratch, ignoring how email had worked since its inception. He simply asked himself and his team what they wanted from email. That’s how they decided to create a gatekeeper section, which doesn’t allow anyone to reach users’ inboxes without prior permission.

After hearing about what went well, I brought out my new technique. “Everything seems to work for you,” I said, referring to the products he’d launched over the years. “Great for you.”

This got Jason’s attention. He started listing software he’d created that didn’t go nearly as well as his big successes. Campfire, for example, was a business chat software, like Slack. Slack ended up becoming a multibillion-dollar, publicly traded company. Campfire was sunsetted. His list went on.

Still, these setbacks didn’t damage his company because he didn’t bet the business on them. Business books often recommend that founders become like the general who storms the beach and burns his soldiers’ boats behind him. With no option but to win, the soldiers are said to be forced into invincibility. Entrepreneurs are also told to take big risks that keep them from backing out.

What I learned from Jason was that it’s sometimes preferable to take smaller risks. It’s OK to close a business, even if others would consider it a massive failure. What Jason learned from creating Campfire informed the chat feature in Basecamp, his massively successful project management software.

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.”

Did I trick Jason into sharing his failures? Am I telling you to use “join the resistance” to make people reveal their secrets to you?

I’ve interviewed Jason seven times in the past decade. He keeps returning even though he knows I’m going to push him to be open. He returns because he trusts me.

I have a recording of the first time I used the “join the resistance" technique. If you watch carefully, you’ll see him doing something that others have done when I encouraged them to be open. He peeks up at his computer screen to see my face. He’s checking me out to see if he should trust me, if I’m being sincere, if it’s safe to talk.

caution If you have bad intentions, you might trick someone once, but they’ll resent you for it. And they won’t want to talk to you again. If your motives are grounded in a need to get real understanding, they’ll appreciate that you helped them open up.

Listen: Join the Resistance

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