How to Ask Questions You Shouldn’t Ask

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 have a simple way to get relative strangers to talk to me about their parents, sex lives, and other personal topics.

I can almost hear you say, “That seems inappropriate, Andrew.” So first I need you to understand why I do it. Then I’ll show you how.

Years ago, I pressed Alexis Ohanian, co-founder of Reddit, to help me understand the business rationale behind selling his company so early. Today Reddit is worth over $6B, but he sold it for $10M–$20M.

Despite my efforts, I couldn’t get an answer that made sense to me.

Then, sometime after my interview, Alexis wrote a blog post where he shared the truth. There were family issues that influenced his decision to sell Reddit. I finally understood. Not all business decisions are made for business reasons. We’re human. The personal side matters.

But how could I ask about the personal side without sounding nosy or unprofessional?

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.

Ask a politician in a tight race, “Should people burn the American flag, and would you put them in jail for doing it?” and they might launch into why burning the flag is wrong and completely ignore the thornier issue of punishing people who do it.

As I thought about it, I realized double-barreled questions could be my key to bringing up personal issues.

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?”

Break that down, and you’ll see I’m actually asking two questions:

1. Are you divorced?
2. Do you feel comfortable talking about it?

People who don’t feel comfortable answering the divorce question will answer the easy question: no, I do not feel comfortable.

Here are a few actual examples from my interviews:

Example One: Is it inappropriate for me to ask you if you’re a millionaire now because of this business?

Answer: I didn’t become a millionaire from the business.

Example Two: Is it inappropriate to ask if [your partner] gets half of this business?

Answer: He doesn’t own half my business.

Example Three: Is it inappropriate for me to ask you who you’re dating these days?

Answer: I’m dating my business ideas and my fifty-six thousand books.

The double-barreled question is so transformational that I use them outside of interviews often. When I’m out with my wife and she hears a double-barreled question come out of my mouth, she smiles. She knows there’s a good chance the stranger we just met will share a personal experience they hardly ever share. And with that, the stranger will instantly become a close friend.

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.

Here’s an example of when an interviewee didn’t want to get personal. Toward the end of my conversation with Mikkel 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.

So I didn’t press. We moved on.

Instead, I shared something personal from my life about the difficulty of working hard after college while others my age were having fun. Then I quickly shifted the conversation to a book he mentioned he liked.

When I watch the video of that conversation years later, I can see discomfort in his face when I tried to talk about his family. When I shifted to my story, he smiled a bit, and when I switched to the book discussion, his face lit up. It all happened in under 60 seconds because I didn’t linger on a topic he told me to avoid.

That’s what this technique is about. We want to give people a way to get personal if they’re comfortable doing it, but also give them a graceful way to move past it if they aren’t.