‘Could You Beat George Bush in a Fistfight?’ and 4 Other Questions to Ask When an Interviewee Clams Up

This post originally appeared on The Content Strategist’s sister site, The Freelancer.

In a writing career that now spans many more moons than I would care to remember, I’ve had the great fortune of interviewing hundreds of people, a number of whom are celebrities.

I’ve interviewed Halle Berry, Mariah Carey, Beyoncé, Sheryl Crow, Metallica, Sarah Jessica Parker, Michael Madsen, Ricky Gervais, and other people whose names I naturally drop into conversation at parties in the slender hope that this will make me seem more interesting.

What it actually does is make me look like a bit of an ass, but that’s a different story.

The point of this article is to share a few tips about interviewing celebrities—specifically, difficult ones. The kind of people you thought were going to be lovely because you’d seen them on TV, but who instead turned out to be as helpful and communicative as a robbery suspect.

While I never actually studied journalism at a university—I started writing for a local newspaper when I was 18—I subscribe to what are probably considered best practices when it comes to interviewing people. And the most fundamental rule is to keep questions open, which means don’t ask anything that can be answered with a simple yes or no.

To seasoned interviewers this is all embarrassingly obvious, but for newcomers perhaps a word of explanation is necessary. Instead of saying, “Did you enjoy working on your new movie?” you might ask, “What can you tell me about working on your new movie?” or “What were the highs and lows of working on your new movie?”

While I absolutely do not profess to be some kind of celebrity interview ninja, I have acquired a number of go-to questions and techniques over the years which continue to serve me well. I offer them to you here as a kind of bag of emergency tricks for when things aren’t quite going to plan.

They also come with a caveat that absolutely none of them are guaranteed to work—as I once found out when interviewing Chris Rock. My opening gambit was about him having landed the presenting gig at the Oscars, and I quipped that Billy Crystal must have phoned in sick. I can’t remember which monosyllabic response Rock offered as a reply, but it set the tone for a pretty miserable experience that haunts me to this day.

But, hey, celebrity interviews are supposed to be fun. And my five top tips, to be tweaked as you see fit, should hopefully bring a little extra to your arsenal the next time you’re asking a stranger questions.

1. What’s your best story about a funeral, gun, or injury?

Or, if your interviewee is a slightly more delicate flower, “What’s your best story about a holiday disaster, a birthday surprise, or an encounter with a fan?”

This is the ultimate “open” question, and will hopefully be received as a light-hearted icebreaker if delivered in the right tone. It also offers three good options for an answer, meaning even the most boring celebrities should be able to come up with something.

2. I was talking to a reader about this interview the other day and he really wanted to know…

What this does is take the emphasis off you as the interviewer. Celebrity interviewees often tire of probing personal questions and can quickly grow weary of the meddlesome journalist sitting across from them.

This question also comes with the added bonus of making the interviewee feel special because, for one, you claim to have been talking about the interview in advance, and two, a potentially interested fan is asking the question. Lies, yes, but white ones.

3. We had a long debate in the office yesterday about [newsworthy topic]. What’s your take on it?

Like the second question, this is intended to make the interviewee feel like they are contributing to a lively debate rather than just being grilled by another infernal hack. Throw in a line like, “Some of us thought X, some of us thought Y” for added realism.

4. One of our favorite films in the office here is Anger Management because it seems that not a day goes by without one of us flying off the handle. When was the last time you lost it, and who was your victim?

This question mixes up the dynamic a little, making the question seem valid and culturally relevant.

Simply change the movie title to whatever works for you: “One of our favorite films in the office here is The Wolf of Wall Street because we’re obsessed with the idea of making easy money…” There are a whole number of questions along these lines that you’ll be able to think up if you set aside 30 minutes before your next interview.

Your goal is to be interesting, upbeat, and different (but not annoyingly so), and to make the interviewee feel like they’ve having a conversation.

5. Finally, could you beat George Bush in a fistfight?

I once asked Al Gore this question. Silly questions can make for a great finale, and—as an exception to what I wrote earlier—are one of the few “closed” questions you actually want to bring up. It’s smart to one up your sleeve that has been tailored to whomever you are interviewing, but keep in mind the intention is not to insult or annoy.

All you’re hoping for is a simple “no” that will make for a fun ending to the article. The mild impertinence of the question also helps end things on a bit of a high.

If you’re interested, Mr. Gore actually had more to offer than just “no.” He looked up, smiled, and said, “Well it’s certainly tempting to contemplate that question, but I think, as the vernacular would have it, I’m going to not go there.” Just that one line made for a very memorable addition to the article, and I’m glad I asked him.

A final thought: Make sure you adapt all of this advice to fit the tone of the publication you’re working for. Question five, for example, should not be plucked from the hat during an interview focusing on sensitive topics.

But there is, I hope, food for thought here no matter the circumstance. With a bit of effort we can all do better than hitting our poor interviewees with predictable and uninspiring questions. Additionally, a cheerful, friendly manner will usually help create a temporary bond between you and the bored millionaire on the other side of the table.

Trust me, with a smile on your face, you can get away with asking most questions.