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I've been asked 'what was most challenging about my last job/project' in all the interviews I had.

What types of information are the interviewers looking for when they ask this question?

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    I edited this to keep it on topic and avoid it being an opinion poll. – enderland Mar 12 '17 at 22:38
  • I've never been able to come up with a good answer to that question. It is on my list of interview questions that I don't think tells the interviewer anything and tells me they read a book on "how to interview someone". Usually any answer I would give comes with so much background and context for it to make any sense, they get bored before I get to the actual answer, or it requires me to disclose proprietary/classified information. – bluegreen Mar 13 '17 at 11:51
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    @bluegreen you just need an editor. Try telling the story to yourself once out loud. Then drop details until you reach the core. Make yourself the hero. Show how you approach things (attitude) and that you won at least once. Nobody cares about the background or the context. – Kate Gregory Mar 13 '17 at 16:16
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This popular question elicits two kinds of very valuable answers:

  • I found it very hard to [something you need to do in this job] because [I really kind of suck at that and don't like it]
  • I was really challenged by [insanely hard thing that anyone would be challenged by] and I had to work really hard but I did it and [story of technical excellence that is directly relevant to the job at hand]

along with others that are less valuable:

  • I found it hard or unpleasant to [something you don't need to do in this job] and that's one of the reasons I'm applying for this kind of job
  • I was really challenged by [insanely hard thing that anyone would be challenged by] and I never did manage to do it but if I face it again, I'll try again

and finally this sort of thing:

  • nothing challenges me, I do everything on the first try, all jobs are easy when you're as smart as me
  • blank stare
  • [clearly made up story]

Do not tell a story that matches the first answer. If you have a story that matches the second answer, get good at telling it. No matter how small the thing, a story where you're the hero is the best. But avoid

  • I was really challenged by [simple easy thing that is required for the job] and I had to work really hard but I did it and [story of everyday ordinariness presented as heroic excellence]

Running these stories past your peers may reveal if you think you're presenting the second one, but are actually presenting the last one and excluding yourself from consideration.

  • "Do not tell a story that matches the first answer" - which answer? – Brandin Mar 13 '17 at 11:27
  • @Brandin " found it very hard to [something you need to do in this job] because [I really kind of suck at that and don't like it]" – Kate Gregory Mar 13 '17 at 12:51
  • So what you're saying is only to use the second option? It doesn't seem quite clear... – Weckar E. Mar 13 '17 at 14:02
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    The unclear part was how you list the first two stories as "very valuable" but then later you say not to use the first one. (Is it still valuable?) The first story could probably also be fixed by rephrashing the last part, e.g. "I found it very hard to [do something] because of an initial lack of experience. But with hard work and my colleagues' support I succeeded". – Brandin Mar 13 '17 at 16:04
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    @Brandin the first one is insanely valuable to the interviewer because it makes it easy to rule you out, no-hire. It's the sort of answer that inspires the question. Understand, you're there to get the job. The interviewer has different priorities. What is valuable to an interviewer drives what they ask. You need to know what they value, but never think that the only things they find valuable are things that make you look great. And unaware candidates do cheerfully say "I find [thing that is vital to this job] very challenging because [I really don't understand it]" – Kate Gregory Mar 13 '17 at 16:12
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I usually go with a very radical and unorthodox approach:

The Truth

I know it's not what one thinks of when trying to get through an interview, but honesty really is the best policy.

  • Almost everyone has "tells" when they're not being truthful
  • It's easy to remember
  • It withstands the scrutiny of follow up questions

There are cliche questions like "what is your greatest weakness" but this one doesn't qualify. You're typically safe in being honest as long as you also use tact. It's like if your wife says "How does this dress look on me?" you can reply with "like a circus tent" or "it's not very flattering, the blue one looks better I think." Both have the benefit of being true but one is insulting.

And so it is with talking about difficulties at past employers. I try to be honest but I dial back on the bluntness. Some actual things I've said in response to this question (which are true):

  • My manager, while a brilliant programmer, had the rather unorthodox project task management technique which was about 60 tiny Post-It notes on his office window and nowhere else. (I then described how I overcame that without insulting my manager)
  • The fact that in spite of having no C++ on my resume, I was still expected to primarily work on a C++ codebase.
  • No version control, no formal testing or deployment process beyond "copy an executable to the server."

And in every case I would explain how I overcame or compensated for that difficulty. They're not looking for what you found difficult as much as they are in you explaining how you approached a problem and how you were able to overcome it. As long as you're not insulting or badmouthing, you can be pretty honest.

Nobody expects you to have 100% positive things to say about your last project. They don't want you trashing it necessarily, but every project has difficulties.

In other words, Be honest but be tactful and respectful.

It probably doesn't need be mentioned (but I will) that one underlying purpose of any question in any interview is to make sure you're not an idiot, lacking basic social skills, or a potential HR problem. While they may also have other reasons for specific question, they're always looking out for people who may have any of the following answers to "what you found most challenging":

  • Having a female boss
  • Working with [insert race or religion here]
  • Staying awake, haha. (don't make jokes)
  • Security policies
  • Nobody could take a joke

When not to be honest

If you have any legal issues with your former employer, keep it to yourself. I realize that being sexually harassed might be your greatest difficulty, but bringing up any issues involving HR might make them consider you too much a risk. In those cases, choose your second-most difficult problem.

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    In certain cases they COULD be looking what you found difficult, in particular if they are trying to gauge whether you'll be encountering similar difficulties in the prospective job. – Weckar E. Mar 13 '17 at 14:00
  • Perhaps, but even then they'd likely still be primarily interested in how you'd overcome it there. – Chris E Mar 13 '17 at 14:03
  • So... What if you didn't overcome it? If it is partially the reason for the job move, for example? – Weckar E. Mar 13 '17 at 14:09
  • I like that your examples include not just the base work (programming, in your case) but also working with colleagues, and procedures. All of these can provide challenges, and depending on OP's history and personality, some may have been more difficult than others. – Llewellyn Mar 13 '17 at 19:50
  • +1 for that wife example: It sums up "How to answer every boss that you meet in lifetime?" – jainashish Dec 11 '18 at 0:02
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When an employer asks questions like "most challenging project/task", interpret it as "an interesting and challening project/task". They really want to hear a story. Give them the story. We all know, story shouldn't be boring.

Don't get caught up in trying to think about the actual most challenging thing you did, just pick something that was difficult. Pick something you succeeded at in the end, and make sure it isn't boring: interesting is a keyword here.

When an employer ask such questions they are looking for some specific details as well (relevant to the job). Explaining the full stack of an app isn't interesting. Pick a tough part and describe what you did.

For example, when asked said question, One could respond:

I worked on a financial trading system. We had several computers spread across various exchanges and needed to coordinate messages on multiple networks. The user needed a UI that responded quickly with many instruments open.

yawn says nothing, compare to:

On a finance project we had a real problem with writing tests. Multiple networks, and erratic markets, lead to some absolutely crazy scenarios. I had no choice but to somehow simulate this world in our tests. This lead to a YAML+M4 driven domain specific language that could create exchanges, behave as a user, and simulate acausal network activity (yes, that actually happened!).

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Usually what the employer is looking for when they ask this question is proof that you can overcome a tough challenge.

For you, it's a time to bring up a real accomplishment - something that was very challenging that you figured out how to do. If you aren't sure if you did anything that was 'really challenging', try asking your co-workers. Chances are if you had a good working relationship with them, you helped them with something challenging at some point.

And if you truly can't think of anything that challenging, then be honest - but try to put it in a positive light. Say that you never really encountered a great deal of hardship on your previous job, but also explain why you never did - say that you were always really keen and could find answers to your problems very quickly, or that you were often the person people came to for help on difficult tasks (but only if this is true - I'm just giving these as examples).

The most important thing to make out of any interview is a good impression of yourself - so take this as an opportunity, and try to present yourself as someone who can handle 'challenging' tasks.

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