Improve your interviews with a single question

Interviews > Cardinal sins > Double-barrelled questions

The New York Times political reporter was reaching the end of an interview that would air on one of the country’s most listened-to podcasts, and he wanted to put a tidy bow on the Q&A.

“My last question is to look ahead,” said Astead Herndon, “What are the markers that you’re looking for for the campaign to continue the upward trajectory that I think we both know it needs?”

It was a good question. If only he’d stopped there.

However, he did not stop there.

“And then, a follow-up question I have,” Herndon continued, “If it does end up being Biden vs. Trump again, do you know what you would do? Would you donate? Would you vote Trump? Do you know?”

Ohhh noooooooooooooo! He just fell victim to one of the classic blunders. The most famous is never get involved in a land war in Asia, but only slightly less well known is this: Never ask a double-barrelled question if you’re hoping to actually get a good answer.

OK. Perhaps I’m being overly dramatic. It is a tactical mistake, though. One that is so incredibly common that I feel like I’m picking on Herndon when the only reason I encountered this example is because I love his work so damn much on the “Run Up” that I tune in to listen when he’s on other podcasts, too.

The mistake of multiple questions is so common that John Sawatsky came up with a name for it: the double-barrelled question. Sawatsky is a Canadian investigative reporter who for a long time he served as ESPN’s in-house interview coach. He’s the first person I heard single out this particular mistake, and now I can’t stop hearing it. In fact, I believe that simply asking one question at a time produces a bigger payoff than anything else you do in an interview.

• Fix: Ask one question at a time. Always.

• Reason: Stacking questions one on top of the other will never improve your interview, and it will almost always worsen it.

  In a best-case scenario, the subject faces the confusion of having to choose which one to answer. In a less-ideal situation, the subject gets an out and chooses the less difficult question, which means you missed an opportunity.

Case study No. 1 

Let’s go back to the podcast episode I mentioned to start this article. It was from a January 2024 episode of “The Daily” — The New York Times podcast. Herndon was interviewing Tim Draper, a venture capitalist who had donated to Nikki Haley’s campaign for the Republican nomination. This was before Haley dropped out of the race. If you want to listen to the audio, it’s at the 21:00 minute mark of the episode. Here’s the transcript of what Herndon asked:

OK. That’s more than two questions, so let’s break it down to the two topics. First, Herndon asks the donor what he’s looking for to determine if Haley has a viable path to the nomination. Second, he asks the donor — a venture capitalist named Tim Draper — what he’ll do if Trump is the nominee.

Draper ignored the first question entirely, which is the most frequent response when someone is asked a double-barrelled question. The subject tends to address what was asked last.

However, in this case, Draper doesn’t really answer the second question either, saying he doesn’t think it will happen and he expects Haley to be not just the nominee. However, because the initial question gets lost in the shuffle, Draper doesn’t reveal any of the markers that he would be looking for to see if that’s possible.

Asking one question at a time is always preferable for two reasons.

1. The subject is clear on exactly what they’re being asked instead of having to choose which question to answer;

2. The interviewer gets a chance to hear the answer, and their ensuing question can be informed by what the subject has just said.

In this case, if Herndon had asked Draper what he would do if it’s Biden vs. Trump again, and Draper answered he thought it would be Haley, then Herndon can follow-up by asking what markers he would look for to believe she has a viable path to the nomination.

Case Study No. 2

This one shows how a double-barreled question can provide a subject — especially someone who is uncooperative or disinterested — with an out. After all, they get to pick which question they’re going to answer.

Several years ago, Canadian hockey reporter Jim Matheson asked Leon Draisaitl, a player for the Edmonton Oilers, a question during a press conference.

Matheson: “Lots of reasons for why the Oilers are playing the way they are, in terms of winning and losing. What do you think is the number one reason for the losses now? Is there one thing, in your own mind, that you’re saying, ‘We’ve got to get better at that’? ”

Oops. Matheson is asking for the biggest reason for the recent losses, and then the one thing the team must improve on. But unlike Herndon — who had a cooperative subject — Matheson has someone who is … well … less than enthused to address his question.

Draisaitl: “Yeah. We have to get better at everything.”

Matheson: “Would you like to expand on that?”

Draisaitl: “Nope. You can do that. You know everything.”

It gets even more awkward after that, and given that I’m a very shallow person who really enjoys messy personal exchanges, the whole exchange is absolute catnip for me.

Matheson: “Why are you so pissy, Leon?”

Draisaitl: “Hmm?”

Matheson: “Why are you so pissy?”

Draisaitl: “I’m not.”

Matheson: “Yeah, you are. Whenever I ask you a question.”

Draisaitl: “I gave you an answer.”

Matheson: “Not a very good one.”

Matheson is right, Draisaitl was absolutely being pissy. Draisaitl is correct, too. He did — in a technical sense — answer the question.

Honestly, I’m not sure if there was a question that Matheson could have asked that would have gotten Draisaitl to provide a thoughtful answer.

However, the fact that second question was tacked onto the first gave Draisaitl an easy out and showed why you’re better off asking just one question at a time.