Tricky interview questions



Given our two-speed economy, I figured I should fulfil my promise to table my killer job interview questions sooner rather than later.

You see, if you’re:

  1. Hiring, you need to be more certain than ever you’re getting the right person.
  2. Seeking work, prior knowledge of these questions could be your winning edge.

These queries are neither foolproof nor universally used.

But if you role play them to perfection with colleagues, family and friends, I promise you’ll be ahead of the game.

Question everything

  1. Choose five words to describe yourself.
  2. What are your weaknesses?
  3. If you had to choose, would you rather work alone or in groups? Why?
  4. Why should we hire you over all the other candidates?
  5. What are you going to bring to this company?
  6. You’ve had a lot of jobs in a relatively short time. How do we know you’ll stay with us?
  7. Tell me about a time when you were in conflict with someone at work.
  8. How are you going to balance work and private life in this job?
  9. What is your vision for our industry?
  10. Why do you want to work for us?
  11. What are your three, five and ten year plans for personal and career development?
  12. What made you apply for this job?
  13. What do you do for kicks in your spare time?
  14. What can you tell us about our organisation?
  15. Why do you want to leave your current job?
  16. What are you passionate about?
  17. Why are you in this industry?
  18. What do you like best/worst about your current job?
  19. Describe in detail the best/worst day you’ve ever had at work. What made it so?
  20. If you don’t get this job, what will you do?
  21. What are you afraid of?
  22. If you had to leave this industry, what would you do instead?
  23. If you could have any job (apart from this one), what and where would it be?

Quiz show

For ten years, these questions helped me separate the sheep from the combine harvesters.

They unmasked pretenders, exalted true talent and revealed hidden gems.

The people who answered correctly went on to great things.

Doesn’t that sound nice?


See any questions you like?

How about some you hate?

Got any to add?

I’m in your hands …

Fire away!



| Founder & Senior Writer – The Feisty Empire

  • Q. 24: Did he fire six shots or only five? 😉

  • Great list Paul.

    I’ve always hated the “what are your weaknesses?” question. It usually elicits one of those “Oh..I’m a perfectionist and workaholic – my standards are probably a little too high” kind of answers, or “I can’t start my day without a good cup of coffee and I’m addicted to pretty shoes *titter*”.

    After all, who is going to admit to being cruel to small fluffy animals or having a penchant for stealing company funds?

    • Good point, Anna! You’re dead right about those ‘pat’ answers. As a recruiter, your goal is to winnow out applicants who won’t fit the organisation’s culture. Better to dig a little at the interview than two days after probation has expired!

      As a candidate, your aim is to use this question to showcase those of your (true) traits which, while considered ‘weak’ in some circles, are precisely what the recruiter is after.

      Ironically, having tracked Animals Australia for the last few months, it seems there’s a high demand for people who excel at fluffy animal cruelty. I give such clients a wide berth these days.

      Many thanks for joining us today! :)

      • Wasn’t game to watch the video after reading the transcript :( I love ducks (and not for eating) and it really upsets me watching any animal being treated like a commodity.

        Kind of veering off topic though (there might be another blog in this for you, Paul.)

        Back on topic – I used to love going to interviews just for fun (yep – I’m a freak) to see what I could get away with. I’d try to turn the tables and put the interviewers on the back foot, just shake things up and rock the status quo. Ironically, it often worked in my favour.

        Perhaps I should have taken up needle-work or some other hobby, instead of tormenting interviewers 😉

      • I don’t blame you, Anna. It’s pretty heavy stuff.

        Tormenting interviewers is hands-down one of the weirdest hobbies I’ve heard of.

        Yet it’s the variety of our readers (and their disarming candour) that makes this community so fascinating. :)

  • Can you really ask things like what they do in their spare time, or does that summon the PC police?

    I love the idea of hiring for purpose, so questions like:
    What is your purpose in wanting to work here?
    How will working with us be fullfilling?
    What gives you meaning at work?
    What do you value at work?
    If this was your dream job, what would you be doing that would make it so?

    these can be really challenging for some candidates, but I find that where the job serves their greater personal purpose, they are happier, more successful and more productive. It means that the interviewer also needs to understand the mission and vision of the organisation so they can see if the candidate’s responses match!

    • We’re on the same page, Phil! (And what a fine read it is too … :) )

      You can ask in general what people do for fun, so long as they have the power to decide how much (if anything) to reveal to you. You certainly can’t press them for answers.

      Nor can you ask specific personal questions (like if they’re married, planning a family or into cross-dressing) that aren’t directly relevant to the job.

      This may be why more employers are checking candidate Facebook pages ahead of interview. These days people reveal FAR more private stuff online than I ever had confessed to me in an interview room!

      Thank you very much for playing. :)

  • Hi Paul.

    Interesting post. I am a big fan of well considered questions.

    Reading through your list there are several that I wonder for someone being interviewed, is there a right answer? Right for them or right for the interviewer?

    Why do you want to work here? – Frankly for many the real answer is probably something like “I have been sending applications out and this is one of the interviews that I managed to secure and most of the others I didn’t even get an acknowledgement for and I really am worried about how I am going to pay next month’s mortgage and now the kid needs braces and I don’t know what I am going to do if I don’t get this job.”

    That’s probably not what the interviewer is wanting to hear. Or is it? What is the purpose of this interview? I the applicant doesn’t need the job, is that a better signal? If they have a job already (seems to be popular way to tell someone is an attractive proposition) the does that mean someone who doesn’t already have a job has been asked to the interview with no real prospect of consideration?

    Some questions like these seem to want to have the applicant dress up like a dog at the circus and dance around in their tutu for the amusement of the audience. Is it necessary? Is the interview meant to get the applicant to perform? And if so … how does that tell you about the competency of the individual when it comes to working in the role on offer? In some cases it may have some bearing but in many it may have little or none. Some people are excellent at interviews. And crap at working or sharing a space with day in and day out.

    What is purpose behind the questions? What is the intention of the interviewer in asking these questions? How should the candidate approach answering questions that are geared to elicit staged responses and require a response that has no way to be verified and seem to lead the applicant in the direction of pandering to what they can only guess the interviewer wants to hear.

    Then we come to some of the questions that to me frankly are way out of line and are intrusive and really neither useful nor appropriate. “What are you afraid of?” What is that? What business is that of some person I don’t know, but who is in a position to have something that I need, in an already stressful environment, asking me about my internal processing? That’s right up there with asking for my FB login details. It’s none of their business but the interviewer could get one of several responses. One could be a lie. Or my greatest fear may be having my privacy violated without thought. I’m now both out of a good answer that will be welcomed by the interviewer and feeling even more lousy than when I walked in the door.

    “Why should we hire you above all the other candidates?”

    I’d love to know what the “right” answer to that is. Is the answer to speak to why for the candidate or why for you the employer? Again, is this supposed to be to make the employer feel good? It reads like a trap.

    Asking good questions is hard!

    Catching someone blind is often not really telling us much that is useful. Getting a rehearsed response is encouraging a charade. I doubt that is very useful either.

    Thanks for raising the topic Paul. It is worth some reflection.

    This might be a good fit here. .

    • Thanks so much for crossing over from Facebook, Lindy. And for posing such fab questions yourself!

      My reason for using these questions was to reveal enough truth to decide whether both parties would form a long, happy and mutually prosperous employment relationship.

      So, the ‘right’ answers were those that moved us closer to this goal.

      ‘Correct’ lies were useless. As were ‘incorrect’ truths.

      I came across several hungry souls in my career. I understood they’d rather feed their kids than elevate the company.

      Our quest was to see if we could meet in the middle to serve both our purposes.

      I used interviews to expand resumes.

      I rarely interviewed candidates who didn’t need the job. Probably because my job ads and pre-screening tools were pretty robust.

      The few who considered themselves ‘above’ the job didn’t do well.

      That said, people with jobs – passive job seekers – are generally better candidates. That’s why they always have work.

      My task was to find great people who sought something … more.

      I find interviews exhausting. Running one for the sake of appearances is anathema, but I was forced by senior management to do just that a few times.

      I can’t speak for other interviewers, but I hear stories. I left HR because I found it a progressively grubby business.

      Some interviewers (usually business owners, rather than qualified HR professionals) use interviews as power trip. They offer nothing and demand everything. Yet in the act of ‘winning’ they lose.

      When I found a person who looked good on paper but was crap at interviews, I strove to make them relax and be themselves – provided being crap at interviews was not a barrier to doing the job.

      After several hundred interviews, you can spot a ‘staged’ response. They’re a waste of time for all parties.

      Re verification, I’d cross-check answers by asking similar questions from different angles. Those with nothing to hide shone.

      ‘What are you afraid of?’ is a very revealing question.

      The most common answer was ‘Not getting this job’. That was my cue to probe their motivations for applying. Not because I was a mongrel, but because I had to be sure the job could meet the candidate’s needs.

      The worst outcome for me was to have to repeat the whole interview process due to a poor fit.

      If you chose not to answer that question, I’d ask why not, and you could tell me where to shove it (and perhaps reveal valuable negotiation skills ideal for the role!)

      ‘Why should we hire you above all the other candidates?’ is merely a device to get shy or modest people to ‘blow their own trumpet’. In that way it is a trap. But some candidates are so frozen with terror, you have to help them reveal their true, excellent natures.

      Many of my hires were in automotive manufacturing. This is not a kind sector. I did sensitive types a favour by catching them ‘blind’. In the end, it was me who turned out to be too sensitive. Which is why I left.

      I love that video, Lindy. And I hope I’ve addressed at least some of your excellent points to your satisfaction.

      Once again, thank you! :)

      • Thanks Paul. I suspected that there would be more up your sleeve than just these questions. Delivery is key and someone reading this list would do well to delve into your reply here and consider some of the back issues that you have mentioned.

        It’s true what you say, I am sure some employers do see it as an opportunity to use an interview as a power trip. I would guess that many are just as awkward going in to the interview as some candidates. That probably also underlies the real problem with some of these occasions and that is trying to do things outside your own expertise. Many times small business would do better to consider their method for recruiting and develop a proper working system for who and what and how they recruit, not just panic when they suddenly find they have to replace someone and have not thought it through. Using a recruiter can be a good idea but that depends on the quality of the recruiter – and finding a good one is not so easy either.

        Thanks for the mental workout 😉


  • You’re welcome, Lindy. I could write loads on each of these questions, but I was keen to let readers like you decide what they wanted to probe.

    I totally take your point re delivery, and perhaps should have covered that in my post.

    Many of interviewers who joined me on panels said they were more scared than the candidates. It’s an odd interaction to be sure.

    I agree that systemising one’s approach and outsourcing to a recruiter are great ideas, though there are some real cowboys out there. I can, however, recommend this chap with complete confidence:

    Thank YOU! :)

  • Can I just say I am soooo glad I don’t worry about interviews and jobs anymore? That juggling between ‘impressing’ the employer and telling the truth while wondering if I really do want that job – too mich like ahrd work and you’re not even getting paid yet!

    The last few times I’ve interviewed anyone I had some specific skills-based questions of course, but mostly chatted with the people to see what they’re like and how their personalities fitted the need. If both can enjoy the chat, the odds of being able to work together are much higher. Not always possible as a technique for big companies or recruiting firms, but works in SMBs.

    • You sure can, Tash! It’s always nice to reflect on a positive aspect of working for yourself.

      I like your approach, too. As I struggle with in-person chatting, I’d love to study an analysis of all your chats to see if you covered any common topics.

      If, for instance, talking about pets is a 40% better compatibility indicator than discussing the weather, we could be onto something! 😀

  • HI

    Finding a good recruiter is similar to finding the right employee. It takes time to determine, usually through performance, if the recruiter is genuine and has your best interests at heart. The cowboys that Paul is referring to are recruiters that are interested in placing people but not necessarily standing behind their product, human beings. As with any product it’s important to know it and your market so as to avoid returns.

    When discussing expectations and strategy with our candidates we always suggest that they find two or three recruiters that they feel they can trust. Its the same for an employer. Essentially you interview the recruiter. Find out what they know about your industry. If you get that feeling you may have had when you were perhaps purchasing your last car then it is highly likely that this isn’t the recruiter for you. However, if it is an enjoyable experience go with it and let performance sort out the rest.

    Cost is a big deterrent to using a recruiting service. I know for myself, that the time spent looking for staff is actually better spent on other tasks. Having someone else take down a job brief, write the ad, post the ad, vet the responses, search the database, make the calls, conduct the initial interview, do the reference check, present the options, set up first and second interviews, assist in the offer and acceptance stage….

    Aside from being quite a lot of work it’s a lot of time saved particularly if it doesn’t work out.

    For people looking for a new work experience interviews are tricky things – determining a future job opportunity in 30 to 45 minutes – darn near impossible. But being prepared will certainly help you relax in the interview. Remember you need to be assessing interview panel as well. If the responses to your questions lack lustre then….

    One trick that works for me is to treat the interview situation as if it were a catch up with someone you know well but haven’t spoken to for a while. Have fun.

    • Dear Andrew, I’m thrilled to bits that you made the time to table your expert views on this topic. Thank you for laying it out so beautifully for us.

      I’ve been working with you for more years than I can recall, and I’ve always seen you operate with the absolute integrity you recommend. I agree it’s the only way.

      I do hope you’ll visit us again soon! P. :)

  • How’s THIS for some inspired further reading from Lindy?!

    I don’t usually give out elephant stamps, but this one gets a great big purple one. Thank you, Lindy! :)

  • G’Day Paul,
    In the best HR tradition ,I want to say a couple of things………….!

    Firstly, the interview is not the most important part of the selection process
    Next, you should interview as few people as possible.
    You should only interview people who have proven, to your satisfaction, that they could do the job. Put bluntly; test skills before interviewing
    You cannot tell what people dan do merely by talking to them. Sorry, that’s the fact.
    The key to successful staff selection is an output centred job analysis. If your job analysis is poor, so will be your selection
    Don’t ask for resumes and written applications . They are the greatest single cause of poor selection decisions.
    Ignore any written reference provided by the candidate.

    As far as the interview goes….
    The prime purpose of the interview is to assess “fit”
    Never ask questions that start with “what would you do if” or that require the candidate to speculate and that cannot be answered based on the candidate’s actual experience.
    Do ask about “weaknesses.’ But phrase the question along these lines “Mr Pulse, you’d clearly bring many strengths to this vacancy. But we both know that “perfect” or “ideal” candidates only exist in textbooks. From what you now know about the job here are there any limitations in your background and experience
    that might influence your successful performance in the job?” Be very suspicious of any candidate who answers “No” to that question.

    Prepare a description of the major pressure points or difficulties in the job. Build questions around those issues. e.g. “Mr Pulse, in this job you have to deal daily with our best customers. They can be very demanding. What experience do you have with working with customers who are both difficult and demanding but absolutely essential to the continued success of the business?”

    Paul, this beats the pants off the typical “What would you do if” type question. But you mustn’t allow the candidate to speculate. If they haven’t had that experience, leave it and get to the next question. That’s why you need a few prepared.

    Finally, write down all of the answers each candidate provides. That’s the only reasonable way to compare candidates after interviews. As you’re only interviewing two or three people, it shouldn’t be a problem. And remember….

    The greatest single impediment to successful selection is that it turns into a self fulfilling prophecy based on a resume written by a complete stranger- a resume writer- about another complete stranger—- the candidate. You’re the buyer. Candidates are sellers.If you wouldn’t do it when buying a new car, don’t do it when buying a new employee.

    Hope this helps

    Best Wishes

    • Hi, Leon! I was starting to wonder whether you’d join us. Given your patent experiene, I’m very glad you did.

      We certainly have been spoilt rotten with fabulous comments on this topic. Your approach, while obviously differing to mine, is beautifully articulated and a valuable alternative path.

      It’s now obvious to me that my tools may be a bit too spiky for some. So thank you for showing us another side of this multi-faceted topic.

      Your hope is fulfilled: you’ve helped a LOT! With best regards for a fine weekend, P. :)

      • I was looking for the Like button for some of these comments – including Leon’s. Nice job.


        PS. Thanks for the elephant stamp. 😉

      • Leon’s a keeper alright. A Like button would be a wonderful addition. I’ll make a votive offering of persimmons to The System tonight. You never know … 😉

  • Thanks Paul, these questions are gold, real gold, for me!

    You see lately I’ve been talking to lots of year 10 students on behalf of the Beacon Foundation who have a goal to assist young people into maximising their opportunities at school and in finding satisfying careers. Obviously job seeking and interviewing skills are of huge importance and these questions will be useful to the many supporters who assist in mock job interviewing roles with the students.

    Thanks heaps!

    P.S. I notice if I don’t write a comment your article on the day, within hours of it appearing, I’m almost dead meat.

  • Fantastic, Winston! I get such a lift when I hear you find my stuff useful. :)

    You can tell those kids from me that getting a grip on these questions early will help them right through life.

    Our comment stream is indeed going well. Not only are our precious regulars still pitching, we’re enticing valued new players to the fray.

    The more the merrier, I say!

    That Beacon Foundation looks like a fine outfit. I’ve started following them on Twitter. Next time they need a bit more reach, let me know and I’ll retweet their message.

    Thanks so much for dropping by, Winston. Best regards, P. :)

    • By the way, Winston, the one demographic we don’t often hear from in here is teens. So if any of the fine young people who cross your path feel like saying their piece, please let them know we’d warmly welcome their comments here. :)

      • Yes, I get the point in regard to younger people. This article sheds some light

      • It sure does! Thanks for that article, Winston.

        I was reflecting last night that I haven’t been a teen for around 30 years, and that I’m way out of touch with that demographic.

        Though I’m at least keeping tabs via my brilliant client Naomi Oakley:

        Unfortunately, Naomi gets to see young people at less than their best. I’m hoping we can provide a forum for them to show us the other side of their coin.

        In fact, if there are any young people reading this who’ve been reluctant to comment, tell me what you’d like to read in here and I’ll see what I can do! 😀

        PS. I used to have a mobile disco business, if that counts … :)

    • Thanks Paul! Love what you are doing, great work.

      I’m sure that Beacon will appreciate your occasional kindnesses.