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What do you do when you want to ask a question so difficult, it won’t cut it to just use someone else’s words? Here’s a technique I use to ask my toughest questions without scaring away my guests: pre-ask the shocking.

I used it when I was invited to interview investors on stage at LAUNCH Festival, the startup conference. After investor Jonathon Triest answered some of my questions about startup advice, I said to him, “You’re a photographer. You weren’t a startup guy. And the money you invested is family money.” Then I asked him what credibility he had telling entrepreneurs how to run companies when he built his business on his family’s money.

It might seem like an unfair question. But when I researched Jonathon, his family’s money and his lack of entrepreneurial experience are what stood out. Anyone who knew him might wonder the same thing and feel that leaving it out was avoiding a big, obvious issue.

The challenge with asking threatening questions like this is that the interviewee can feel so insulted that they stop trying to give helpful, interesting answers. Then the interview becomes painful for the audience to sit through—not to mention you.

But Jonathon didn’t close up. Instead, he looked at the audience as he gestured toward me and said, “He’s a wonderful, wonderful dude.”

Why? Because I tipped him off before the interview started. I explained to him that audience members who looked him up might wonder if he was just a “trust fund kid.” Would he mind if I asked him about it so he could address it? He said he wouldn’t mind at all. He agreed that it was worth bringing up.

And when I asked him onstage, with conference goers watching, he complimented me. Then he explained that he was a photographer, but when he worked for Sports Illustrated, he realized he was “a terrible sports photographer.” That led him to design and to launching a design agency, which gave him entrepreneurial experience. He explained that yes, his first investment fund came out of “the dear generosity of my family.” He went on to say, “I used that fund to learn the ropes, and it was a remarkable leg up. But I had to build a network. And I had to build a brand.” He had the experience. Then he raised an investment fund based on his own experience, network, and credibility.

When I pre-ask the shocking questions before an interview, guests don’t ask me to back off. Because I tell them ahead of time, they trust me more. And by explaining to them why I want to bring up the question, they understand and encourage me to do it.

caution This technique is for topics that could be controversial or potentially damaging to someone’s reputation—and it could be your reputation that’s hurt if you fail to use it. Here’s a quick example of a time I didn’t pre-ask a difficult question and paid the price.

As part of my prep for an interview with an entrepreneur, I read court papers from a lawsuit he had with his ex-girlfriend. I wanted to understand his financial business acumen. The suit was written up in newspapers, so I thought it was okay to ask about it in an interview. When I brought it up, the conversation turned from how he built his business into more of an argument. We went back and forth about whether what I asked was relevant, and I couldn’t get us back on track. Unable to move past it, I thanked him for doing the interview and ended it.

If I’d brought up the lawsuit beforehand and told him why I wanted to cover it, he could have declined. Or we could have come up with guidelines that would have made him feel comfortable enough to give me some useful answers.

At the very least, he wouldn’t have felt blindsided.

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.

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