A Mistake Most Interviewers Make

A Mistake Most Interviewers Make post image

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.

Screen Shot 2017-03-03 at 2.58.36 PM

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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Published on 03.14.17
  • Really interesting point. Would you have recommended phrasing the original question in a different way? Or just shutting up after asking it and waiting for the interviewee to come up with an answer?

    Also, what are your thoughts on giving interviewees the questions (or general discussion topics) beforehand? I love being asked the tough questions as well, but often if one is sprung on me by surprise, I tend to say the first thing that pops into my head, which may not have been the best answer or the one I would have given if I’d had time to reflect.

    Especially if it’s something I’m not really thinking about regularly – ex) ask me anything about how I do e-mail marketing and I can answer that instantly; but ask a meta-question like “what’s your biggest weakness as an entrepreneur” and I’m not going to have a good answer immediately because it requires more thought and is not at the forefront of my mind all the time.

  • “Would you have recommended phrasing the original question in a different way?” Nope. Just shutting up. The question are hard so it might take some time to generate an answer. The reason I made this mistake earlier in podcasting (often) was that I was trying to keep the conversation “flowing” or the banter going back and forth, or that I was trying to soften a hard question for the guest. Now I just give it space because their perspective is more interesting than both of those concerns.

    “Also, what are your thoughts on giving interviewees the questions (or general discussion topics) beforehand? I love being asked the tough questions as well, but often if one is sprung on me by surprise, I tend to say the first thing that pops into my head, which may not have been the best answer or the one I would have given if I’d had time to reflect.”

    Our policy is to give general ideas, particularly if they need to remember a story or a particular time in their life, but not the specific questions. The reason is because the prepped answers generally aren’t better than the off the cuff ones. They may be if you’re asking someone to talk about what they think about something (like their analysis) but it’s rare that interviewees are adept at that (btw, I think that’s why your first episode on TMBA was so remarkable was that your analysis of your own business activities was so clear http://www.tropicalmba.com/espressoenglish/)

    On the point about asking about email marketing vs. biggest weakness, yeah most people will give a bad answer for ‘biggest weakness’ even if they have a lot of time to think about it. Better question: “what are you anxious about when you check your email in the morning?” or “what don’t you want to see…” follow up: “does that happen often?” so you can find other ways to drive at the same topic but potentially will get more interesting insights that don’t require them to plan out answers.

    Principle: when possible, ask them about what they do and not about what they think about what they do.

  • The problem with giving people questions ahead of time is that the person’s answers can be too heady. I noticed I tend to do this when in groups where we go around and share something and I’m not close to the first one to go. I rehearse my answer too much and can sound robotic.

    If a question is asked on the spot, the recipient doesn’t really have time to get into their head and is more likely to speak from their heart. This is exactly what you want when asking a question about emotions (which are some of the hardest questions IMO) like from the example.

  • That makes sense to me.

    One common constraint I think many podcasters have to asking these types of questions is that they ‘can’ be stumbling blocks… they can derail the conversation occassionally, so they can require more editing that the standard ‘talking points’ interview. That said, I think there’s a balance you can find if you don’t want to edit to heck every interview you do. There’s ways to help that don’t involve feeding answers, you can feed ‘types of answers’ Bill Simmons is good at this– he answers the question from his perspective and by doing so shows the guest how they could share similarly

  • Johnny

    Great point. At the pause, I thought great question then interviewer answered the question. Ugh. Maybe the interviewer felt that he put him on the spot a little to much. Maybe he lost his footing and sympathized with him about such a crucial game loss.

    If questions are written out in front of you when doing the interview maybe INSERT a note to self. Something like, ” Dont answer this question. Let him take time to feel the question.Wait its worth the few seconds of dead air,” etc. Just a thought.

    Next. I never understood the giving the questions before hand. I mean its sn interviewer that is live. It should be spontaneous. Questions beforehand is really an jnterview that can be printed. I feel it lacks intensity if answers are pre asked. It would be okay to give an outline so the interviewee can prepare by focusing on the type and time frame of questions.

    Nonetheless this was an interesting post

  • Thanks yep, I think the motivation comes from a good place (compassion) but through some practice I’ve realized that if you really care about the question, and you’re subject/interviewee, it’s best to give it the space/respect it deserves. I’ve even thought that perhaps I got this habit from in-person conversations, but perhaps especially in person it makes sense to give people space. Also worth noting I think there’s a meaningful distinction between asking a good / ‘real’ question and simply “putting someone on the spot.”

    Agree with too much prepping the guest beforehand.

  • Johnny

    Definitely worth noting it is never good to put a person on the spot, so it is pertinent to be sure the question is worded with compassion. it would be horrible to have an interview backfire because the interviewee felt threatened. I guess there is always this risk and could be a reason why people are reluctant to agree with an interview.

  • “Principle: when possible, ask them about what they do and not about what they think about what they do”

    Nice! I like it :-)

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