Let's say I'm interviewing a person that has likely gone through significant personal hardship. The purpose of the interview is ultimately to provide a short documentary of that person's life experiences leading up to the present.

"The worst thing that's ever happened to them" is relevant to the interview, but asking the question straight out strikes me as possibly insensitive and possibly exploitative. It's not always clear to me what's socially appropriate and why (it seems arbitrary), so I'm curious if there's is a better, perhaps more respectful, way to get at that information ?

The context would be interviewing people from various walks of life, documentary style. For instance, interviewing drug addicts about their life for a documentary. They could come from any walk of life, but somehow ended up dealing with this adverse condition. There were probably a series of unfortunate events that culminated in their addiction, but it seemed like asking about "the worst" event, would give some scope to previous events without having to go through a laundry list of items.

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    I think this may need a little more context. Are you making a documentary about a specific individual? If so why did you choose this individual? Is the worst thing that's happened to them strictly relevant to the documentary?
    – apaul
    Sep 5 '17 at 15:08
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    I agree, the question needs more context, please. Is this social chit-chat? A job interview? College admissions interview? Psychiatric treatment intake? A commercial project of some sort for your personal benefit? A publicity ploy for the interviewee? You will get more useful answers if you explain a bit more about WHY you want to ask this.
    – 1006a
    Sep 5 '17 at 21:22
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    Maybe start by asking them if there's anything they're uncomfortable or unwilling to disclose, to avoid you asking about it? As @apaul34208 says, we need more context. From your description, it seems as though the subject has willingly put themselves in this position, so perhaps they are already expecting and have prepared for your question.
    – ESR
    Sep 6 '17 at 1:48
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    Probably a rude question. In context of a job interview: who cares? I will give an example of a drug abuser (which I have not actually been) - e.g.: If I was on drugs, and my stomach felt woozy, and I decided to get off drugs, great. If my stomach felt woozy, but I overdosed and got hospitalized, and then decided to improve my life, great. Why focus on my time of pain, knowing exactly how bad things were, before improvement came about? Let's focus instead on the fact that I recovered from whatever my life's challenges are, and am here in this good condition now, and what I can do for you now.
    – TOOGAM
    Sep 6 '17 at 12:49
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    @TOOGAM It's not a job interview, so I'm not really sure where you're going with that comment.
    – Catija
    Sep 6 '17 at 16:33

"The worst thing that's ever happened to them" is relevant to the interview...

The worst thing that's ever happened to them might not be relevant to the point of the interview. Maybe they were sexually assaulted by someone they trusted (just an example.)

I think you can ask that question framing it by relevance only to the reason your documenting their history. Maybe,

What do you consider the most discouraging experience you had with regard to x?


What would you say was the low point in your journey?

These might sound like they're splitting hairs, and the interviewee might understand what was meant by the question, but the original question might be one they would feel was irrelevant or too painful to reveal.

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    +100 this. Trust me you do not want to ask what's the worse thing that ever happened. You might be making a documentary about Wal-Mart employees and the person come back with something totally horrible, utterly irrelevant, and very awful. From there it's very hard to recover. In fact it may ruin for ability to be impartial.
    – coteyr
    Sep 6 '17 at 2:45
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    If someone asked it in an interview, I would assume they meant worst thing professionally, obviously clarifying before answering. That being said, I know people who intentionally ask sub-par interview questions with the hopes that interviewees make the necessary clarifications. Not advocating it, but it is a thing.
    – corsiKa
    Sep 6 '17 at 2:50
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    @corsiKa If you were being interviewed for a documentary about your drug use, why would you think this meant professionally?
    – Catija
    Sep 6 '17 at 18:00
  • @Catija It appears I missed that line...
    – corsiKa
    Sep 7 '17 at 15:28

Context is important.

Since you say it is "relevant to the interview" I'd imagine the interviewee wouldn't be too caught off-guard by such a question (I'd hope).

I think the wording is fine in this context, however, prelude the entire interview or this question with something like:

Some questions/the next question touch on sensitive, personal topics. Feel free to ask to skip a question if you do not feel comfortable answering it.

In a personal interview that it seems you're doing, making the interviewee feel safe and secure is important which usually means being upfront about the type of interview and the areas the questions are meant to cover.


Part of my job in casting was occasionally interviewing people for directors who were more interested in stories than in trained actors. They looked for cast who could naturally relate to their characters because they were that person rather than someone imagining what it was like to be that person.

For one of these films we had to interview a bunch of real prostitutes. This was something we had to do very cautiously because (as in most places) prostitution is illegal and many of these ladies are understandably cautious about checking the veracity of unsolicited contact from people.

To prepare for these interviews, my boss often told us "channel your inner Terry Gross". Gross's style of interviewing is extremely low key and open, she's done her research to be familiar with the person that she's interviewing and she really cares about the information she gets. This makes people want to share with her. I strongly recommend you review some of her work, how she asks questions and how she paces interviews.

  1. Create a safe space, physically.
    Really make them comfortable in the space.

    • Minimize the distractions - the fewer people in the room the better.
      If there is only one person they have to tell their story to, they'll be more likely to share.
    • Arrange them so they're looking at you, with the camera just to your left or right, over your shoulder.
      Ignore the camera and focus on having a conversation. You need to forget the camera if you're expecting them to.
  2. Build rapport.

    • Don't immediately go to the heart of the situation and get straight to the deep stuff... start off with some softball questions.
      When we would audition kids, we'd always start off asking them questions like "what's your favorite color" or "do you have a pet? What's its name/what type of animal is it?". These questions are easy to answer. A kid who was scared of the person running the audition will relax and do a better job in their performance. You don't need to use these questions for adults but a similar collection of easy-to-answer, slightly personal but not too personal questions will give you a start to build some rapport.
    • Really listen, don't judge what they say.
      When people feel like they're being judged, they stop talking. Let them know that you respect them and you're taking them seriously.
    • Take your time.
      We only had 15-30 minutes in our auditions but two or three people and a camera in a room can get pretty comfortable quickly. If you can, give it an hour or two.
  3. Ask the right questions.
    There are two main types of questions closed ended and open ended.

    • Closed ended are generally yes/no questions.
      You'll need some of these to know what open ended questions to ask but they tend to not give you much more than a one-word answer, which isn't very useful for a documentary.
    • Open ended questions are the 5 Ws (who, when, what, where, why) and How.
      These questions require more than a one-word answer and start a dialogue. Focus on these open questions. You're already working with a "what" question but I think this is too broad. You need to get to know them a bit first and then tailor this question to their specific story.

Assuming they know why you're talking to them (hopefully you've set up a time to meet in a place that you've prepared), start out asking them about themselves - general questions, ask about their childhood - a good memory. You're about to walk them through some very troubling parts of their lives, start with a happy one. Then, when they seem more comfortable, ask for them to tell you about their first experience with a substance, ask some follow-up questions about that and how they felt at the beginning, then ask them to talk about their descent and when they knew they'd reached bottom and how things were different at that point. I don't think you can really cut corners and just ask them to tell you about the worst part without worrying that they won't be honest about their experience.

Being open to someone changes what they say. If you just sit them down and ask "So, tell me about the worst thing that happened to you in relation to your drug use", they're going to balk. They're not going to be in the right frame of mind. You have to work them there to get the good stuff, the valuable stuff. They may try but it's not going to be the same.

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    "Channel your inner Terry Gross." +1 I love her interviewing style. Sep 6 '17 at 18:08

"The worst thing that's ever happened to you" is a sloppy, unclear, inappropriate request.

Change "the worst thing that's ever happened to you" to "a negative experience that you've had". By asking for "the worst", you may seem to be asking them to survey all their negative experiences and tell you the absolute worst thing. Not only is "worst" subjective, but many people have had some awful experiences which are unreasonable and inappropriate to discuss in almost all professional interview contexts. Such topics are generally irrelevant to the interview, and interviewees have a reasonable expectation to not be required to reconsider and describe them to people they've just met. Particularly not in interview situations, where they also might have a reasonable expectation that bringing up very bad situations might reflect badly on the impression they make on the interviewer.

The question strikes me as a serious violation of privacy and professional boundaries. Asking for a bio summary may be appropriate, but they should be clearly allowed to relate what they chose and to omit what they don't want to share.

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    Couldn't agree more: As stated, it's an extremely inappropriate question in a professional setting. If an interviewer asked me this I would tell them so. Sep 6 '17 at 10:23
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    @ChrisHatton It's not a professional setting... "interview" doesn't mean job interview here.
    – Catija
    Sep 6 '17 at 17:52

Try turning the question around:

What is the hardest challenge you had to overcome?

Assuming you are interviewing this person because you are interested in them, you should consider not only what happened to them, but also their response to what happened. How an event shapes a person depends not only on the event, but also on how the person reacted to the event.

There are two reasons why this question is better:

1) It creates a more interesting interview! True, what happened is relevant to their story, but how they dealt with it is important as well. Overcoming a difficult challenge brings the best from a person, and how a challenge is faced varies from person to person. It lets them talk about their emotions and thoughts. This question would help illustrate some traits potentially unique to the person being interviewed.

2) This one depends on the outcome of the event. It gives the interviewed person a chance to focus on something more positive. What happened is expected to be a very negative experience (as the question stated, "the worst"). If the outcome of this challenge was positive or had positive consequences, it gives them the chance to talk about it.


Whether or not it is important to the context of the interview doesn't actually matter - the right to volunteer this information is, and should always be, in their hands.

Even if this 'interview' is for the sake of therapy, to personally help the person with life problems, you cannot force them to share this information - and attempting to will only further alienate you from that person.

If you absolutely need this information, you need to establish trust with the person first - not just a written contract, but an understanding between you and the person that the information will not be shared with anyone else, because that information could be extremely personal. And if you do intend to share it with others, then the trust between you and this person needs to be even stronger.

You can always ask first - be upfront about what you intend to do with this information, and if they refuse, you can continue with the interview and get back to it later, to see if they have changed their mind.

But if the person refuses to share this information at all - you need to respect that, and find another way to conduct this interview. Ultimately, it is their own choice whether or not it is something you should know.


I would formulate it as

What is the worst experience in your life you are inclined to share?

With this sentence, you acknowledge that there may be personal matters which the interviewee wants to keep private, and indicate that you don't plan to snoop on them. Also, you give some context to your request (it is intended for sharing) which both increases trust in the conversation, and allows the other person to properly interpret your question and give you an answer which is best suited to your purpose, in this case for building a narrative.

Of course this means that sometimes the person will hold back something. This is not only in their interest, but also in yours - you don't want to hear a poignant story in a personal interview, build your documentary around it, and then have the person tell you "I am uncomfortable making it public, please don't include it in the movie".

This answer assumes that your interview is a personal interview held in preparation for the documentary. If you are talking about an interview that is actually to be filmed, there is no problem wording the question as you see fit, as long as you have previously cleared up with the interviewee what the answer will be.

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