A Mistake Most Interviewers Make

Interviewing people is hard. But it is also incredibly rewarding when you get it right, or even nearly get it right!

While listening to Zach Lowe’s podcast last night, I noticed him make a small mistake that most questioners of all types make. Sometimes, this mistake is made intentionally for deceitful purposes (see if you can spot the use case). I wanted to take some time to talk about it because asking good questions is a skill that has application well beyond creating quality podcasts.

I’m only using Zach’s show because I love it. I’ve made this mistake countless times, and sometimes still do.

A year ago, I didn’t even know it existed. Now, after some time being mentored by our producer Jane, I can’t help but notice it everywhere.

This particular example is from a conversation with DeMar DeRozen, who is one of the NBA’s best basketball players.


I’ve cut a clip out of the interview so you can see if you can spot the problem.

An important piece of context: DeMar’s answers up until this point in the interview hadn’t been particularly long or detailed. He doesn’t elaborate on stories, anecdotes or ideas. He seems to lack a little bit of confidence in his speaking voice. This can make an interviewer’s job hard.

Here’s the clip of the question I had a problem with. See if you can identify the issue.

Did you hear it?

Let’s take a look at the transcript:


ZACH LOWE: “Go back a year. You guys are a second seed in the east.

Lots of hype, great season. The playoff track record is what it is [read: they traditionally underperform] .

We don’t have to get into it.

You lose game one at home against Indiana.

What is the mood like after that game?


Okay. Let’s stop here. The actual question is this:

“What is the mood like after that game?”

That’s a tough question. He’s asking DeMar about one of his greatest sports disappointments.

Here’s where the mistake starts.

Zach begins to give DeMar options on how to answer the question.


Is… just… what was.. The mood like…

were you guys confident?

were you worried?


So DeMar does what most of us do: instead of having to find a way to express how he felt after losing (hard), he agreed with the interviewer (easy).


DEMAR:  “umm… well, we were confident”

The most difficult, and potentially most interesting, question of the whole interview ended up getting diffused at the outset.

After Demar repeats back the option Zach gave him — “we were confident” — he moves from processing the emotions and instead tells a story that everyone already knew:


DEMAR “…because the previous two playoff series I think we lost game one as well… [we had home court advantage], then to lose the first game ya know it sucks, but it kinda gives you that sense of urgency for game two. It sucked. It was a long night.

ZACH: Yeah, what did you do after the game, did you guys go out and talk about it…?”

DEMAR: [No, I rewatched the game…]


Perhaps you are thinking, this is really nitpicking Dan!

Here’s why this is important: DeMar DeRozen is a really difficult guy to get an interview with. He’s one of the best basketball players in the world and an Olympic gold medalist. If you have a chance to speak with someone you are interested in, and who’s had such interesting experiences, why not challenge them to answer the questions you really have?

When I discussed this with our producer, Jane, she said “the best people always want to be asked the toughest questions .. because those are the ones they are grappling with in their heads. You have to put yourself on the line so others will feel they can do the same.”

I know it’s a lofty ideal for a conversation about basketball, but I think this small idea can be instructive in all conversations.

Let’s call this the “giving your interviewee a soft landing” cop-out.

Soft landings are the innocent ‘options’ we give people after asking a difficult question (often, out of a feeling of compassion). [Aside: this is the same technique that interrogators use to get the answers they want].

My sense is most conversations would be improved if we just cut them out. And once you can spot them, it’s pretty easy to do.



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