Interviewing. 20 Questions That Could Make All The Difference

For all its flaws, the interview is still the best means of assessing individuals for a specific role…..but only if done properly.

Let me start by saying there is no definitively perfect interview. My approach and style HeadHunters - Gary Chaplincertainly isn’t, and thus what you read below is wholly subjective.  However, the way I conduct my interviews, and advise my clients to conduct theirs, is built up over 20 years of experience….and by interviewing, on average, 10-15 people per week for that time.

I touched on Interviewing HERE (an interview on Interviewing), and touched on my personal driver when interviewing HERE (Christmas Chemistry)…..But in brief, my style is more relaxed and less interrogating/intimidating than most of my contemporaries – I seek to really get to know the person to assess Chemistry Fit rather than get all ‘Alpha Male’ and seek to give people a needlessly tough interview which reduces the chance of getting truly candid answers, but buffs the interviewer’s megalomaniacal ego.

That said, my advice to my clients is very different. They do need more structured interviews, and more structured questions from which to gain an insight, but also more means of being able to rapport build, allow personalities to shine and see the person behind the interviewee…..especially as the majority of interviewers are comparatively inexperienced at doing so. But most importantly, interviewers need to remember that interviewing is a two way process – interviewers need to sell as much, and more usually more, than interviewees.

The interview is really just answering three simple questions:

1.    Can he/she do the job?
2.    Will he/she do the job?
3.    Can I work with them?

Question 1 is comparatively easy. You will have read their CV beforehand (I’ll repeat… you will have read their CV beforehand…) and thus the interview is just probing into specific areas of interest and understanding motivations/reasons/thinking/experiences/etc

Question 2 is a lot harder for most. This is where you will have to sell. The interviewee has been sold-to sufficiently to get them interested, and interested enough to come for an interview, but you need to fire and stoke their interest. The old-school approach of a one-sided interrogation is no longer going to work, especially for head-hunted candidates who are not likely to be pro-actively seeking to move role/company and will almost certainly have no specific reason to need to move job.

…but Question 3 is the prime focus of the interview. Understanding if you can work with them, and specifically if they will fit within your business’ culture. This is the biggest area you need to understand. You and other members of senior management will most likely be spending more hours awake with the appointee than you/they do with their husband/wife etc….and majority of people take longer than a couple of 90 minute interviews and a couple of references before walking up the aisle!

The opener – Small talk

This is a critical part of the interview. You need to relax the interviewee (and probably yourself). You don’t want the interviewee to be in ‘interview mode’ too much as they will be overly defensive, act in the manner they think you want to see and certainly not give candid answers to stickier questions. Asking about their journey, recent events, topical issue in/out of business – easy, conversational and mostly importantly open questions to get them talking.

….But there is another reason to start with casual open questions. You will understand how easily they talk, and if they talk too much. By asking an easy open question about their journey to the interview, you will see if they are likely to waffle on, or give very tight closed answers. If describing their journey there takes them 15 minutes to describe and they don’t notice you falling asleep…you are going to have to adopt interview control techniques and maintain charge!

After that, set an informal agenda to manage expectations of content and timescale; and thank them for their time. Don’t fall into the archaic headhunter trap that an old MD of mine insisted on… trying to wrestle power by refusing to thank the interviewee as it is the interviewee that should be thanking the interviewer for their [more valuable] time – it’s horsesh*t, their time is likely to be more valuable, they have likely had far greater inconvenience and you probably have more to lose by not securing the perfect candidate.

The interview.
Jo Nesbo HeadHunters. Gary Chaplin I will always advocate taking an interviewee through their career in reverse chronological order, but there are no hard and fast rules, it is purely subjective. Focus on the why not the what. Let them talk; they them explain, don’t lead them towards the answers you want. Ask direct but open questions. Listen to what they say, question what they say, don’t just focus on a list of questions you want to get through.

Look for the use of ‘we’ rather than ‘I’, disseminate between group/business accomplishments and personal accomplishments, get a detailed picture of direct responsibilities and expected vs actual achievements and don’t be afraid to ask about negatives/weaknesses/mistakes – gone are the days where good people use hidden strengths as weaknesses (“I can be intolerant of people who aren’t as focused as I am…..” etc).

I always want to see people who have made mistakes, admit them and learn from them. “The Person Who Never Made A Mistake, Never Tried Anything New” – Albert Einstein

Once you have fully explored, understood and interrogated their career history/background (and reasons for changes), I move on to the role in question. Asking about their understanding will highlight what research, preparation and more importantly, what thought they have put into the opportunity. I allow for unlimited questions (within reason) on the role, me, us, the market….current affairs, meaning of life, etc etc.

Once they have told me everything they know about the role, I will move on to generic questioning, usually less formally. This can be the point where you will really understand the interviewee, get to know them and give you the ammunition to understand if they are a fit or not (or for recruiters to answer your client’s question “What’s he/she like then?” with a little more insight than “They interview well”). Employers/recruiters omit this human side of the interview at their peril!

The Close
Bring the interview to a formal close. I will usually ask interviewees if there is anything else they would like to add. And ask them why they feel I should shortlist them. This is also the opportunity for them to close you.

NB….after the ‘end of the interview’ is also a great time to ask 2 or 3 salient questions when the interviewees defences are lower and candor will be far greater! Use this time to pick up on a couple of specific issue you are uncertain about; reasons for moving on; challenges currently faced or just to get inside the person’s psyche. But remember to leave on a high!

20 of my favourite questions

Non-exhaustive list, used, adapted, sometimes I’ll only use one or two, sometimes all 20 and more. Never read a list, just throw in where relevant.

1.  What circumstance brings you here today?
Great opening question. Candidates can reveal problems with their current employer, lack of personal interest, derailed career, market intelligence, potential insubordination, as well as character traits both positive and negative.

2.  Tell me about yourself?
Another good opening question, or a means of starting a more relaxed/personal discussion after a more intense career interrogation. Great way to see what the individual highlights first and how they draw the answer into their career and the role in question. Look for a blend of business & personal and overall enthusiasm.

3. What is/was the greatest frustration in your current/last job?
A great means of gaining insight into the current role without inviting a direct negative (i.e., not ask what was wrong/unfair/etc). Also a great way of finding out what makes motivates the interviewee and what they stand for.

4. Talk me through a difficult scenario at work and how you dealt with it
Good way to assess the ability to cope under pressure (answering the question AND the scenario chosen/being detailed) as well as providing a relevant example, on the spot and detailing resolutions/resilience/emotional intelligence/etc.

5.  Tell me how you worked effectively under pressure
This provides not only the means of understanding how the interviewee deals with pressure, but the example chosen will give an indicator as to what they consider IS pressure at work.

6.  Describe the hardest decision you have faced in the past 12 months
Again the choice of subject (what they consider hard) as well as the means of managing are two great indicators. Assessing body language and understanding the time interruption in their life becomes very telling.

7. Tell me about our company (or the hiring company). Give your top-line analysis.
Another opportunity to assess what research they have done, but also give them a platform to demonstrate commercial awareness, initiative, analytical ability and understanding/interpreting values as well as being an indicator of their confidence.

8.  What specifically interests you about this job?
Is the interviewee interested in your job or just any job? What have they taken from their own research coupled with your description and their questioning of the role.

9.  What are the biggest strengths you would bring to this organisation?
Better than blindly asking what someone’s key strengths are…and an ideal follow-on to the above, it assesses the interviewee’s perception of how their skills and personality would fit with and help drive the company forward whilst also giving a platform to sell themselves and potentially mentions points that have been previously overlooked.

10.  What are the first 5 things you’d do if you got this position?
Again following on from the above, this gauges what has been understood from the interview, and how the candidate perceives their ability to fit and deliver in the role. You are ideally looking for focus towards chemistry and company culture as well as the job function itself.

11.  What are the 5 things you need to be successful in this position?
Again demonstrates understanding of the role but with a multi-tiered angle as the answer could cover personal attributes, external support/provision as well as raw skills.

12.  What type of work environment do you thrive best within?
By the time you ask this, you should have worked this out but this is a good qualifier and control question to highlight/confirm the candidate’s likely fit, aside from the ability to do the job.

13.  What’s the biggest mistake you’ve made in your life and how have you overcome it?
Good candidates welcome, and are proud of their mistakes….in particular the lessons it gave them. By asking a direct questions, the interviewee is forced to open up and be honest. It also provides the interviewer with an opportunity to explore how the candidate handles challenges.

14.  Talk about a time that you took a risk and failed, and one where you took a risk and succeeded. What was the difference?
Almost the second part to the above question. Psychologists and businesses coaches will state that people who take risks are generally more successful than those who do not….but only in the right role in the right organisation. The ensuing discussion from this question can reveal everything you need to know about the persons true fit for your role. Follow up asking what the biggest risk taken is.

15. Tell me about one of your proudest moments at work.
This is a great tool to gauge personal vs team preferred working style and give the means to assess interviewee drive & personal motivators.

16.  When I call your old boss what will they say about you? And what would your husband/wife say?
This asserts that you will be taking references, but it also requires the interviewee to think about how they are perceived in and out of work – and the differences therein. It also assesses their ability to think on the hop and ideally align the answer to the job they are interviewing for.

17.  What are you (most) passionate about?
Unusually, the answer isn’t really important (within reason) it is the way the interviewee answers that is vital in this one. The best candidates will respond quickly and their body language & demeanor will heighten. You will also be able to contrast their style in answering this question to that used to describe roles/work-based-achievements. A useful way to spot genuine passion in the workplace. Above all…. never hire anyone without a passion for at least something.

18.  What accomplishment in your life are you most proud of?
Great open question that can lead to 1000 others. Everyone has at least one achievement so this question identifies motivations and passion.

19.  What is your ‘end-game’ or career goal? How does this role support that?
This is partly a means to understand likely tenure in this role (or any role) but also reaffirms passion, motivation and where the interviewee sees their strengths. The Corporate Controller interviewee stating he wants to be a Commercial CEO within 5 years may ring alarm bells.

20.  Describe someone outside your field of interest who inspires you and why?
The speed of response is likewise telling with this question, but it gives a great insight into how an individual sees themselves, who influences them and identifies motivations.

7 Unusual questions that can work…sometimes even better:

1.  Which five people would you most like to invite to a dinner party?
Provides insight into the interviewee’s personality. Whilst some will opt for safe options, others may be more risky and ‘left-field’. Provides opportunity to demonstrate intellect, cultural exposure and humour ….or closet interests!

2.  Which famous person would you most like to see play you in a film?
Great insight into the candidate’s confidence, self-analytical position as well as providing a great exploratory topic of conversation.

3.  What’s your favourite animal and why?
Sounds like a joke question, but this question is typically answered by the sub-conscious, and most people consider an animal they believe most accurately personifies them.  Becomes a very good means of identifying personality traits.

4.  If you could be anyone else who would it be?
Aside from highlighting latent (or not so latent) extra-curricula interests, this question provides the opportunity for further analysis of personality traits and creativity.

5.  My partner and I are planning a holiday, where would you recommend?
This and dozens of other questions like it allows the interviewee to escape from ‘interview mode’ and speak about a topic away from career/business which can help break down barriers and exploring the candidate’s ‘non-interview’ personality. The choices will also give an insight into their private life, the importance they play on holiday…..and you may get some great tips!

6.  If you inherited an acre of land what would you do with it?
Another question that provides a platform to explore the interviewee’s personality and creativity.

7.  Why do giraffes have such long necks?
The factual truth behind this question is incidental, but it is a great way to explore the interviewee’s creativity, logical thought process or natural history knowledge! (incidentally, there is conjecture over whether it’s for fighting/defensive advantages or to reach food)

……..and finally:

21 frankly bizarre, but real life questions

1.  “If you were to win £1m what would you do with the money?” 
- Asked at PwC

2.  “How many golf balls can fit in a school bus?” – Asked at Google

3.  “What makes you happy about work on a Friday evening?” 
- Asked at Tesco

4.  “How do you fit a giraffe in a fridge?” 
- Asked at UBS

5.  “If Germans were the tallest people in the world, how would you prove it?” – Asked at Hewlett-Packard

6.  “If you were the Head of Barclays Corporate what would your strategy be with the recent European Crisis?”
– Asked at Barclays

7.  “How much does a 747 weigh?” – Asked at Microsoft

8.  “Would Mahatma Gandhi have made a good software engineer?” – Asked at Deloitte

9.  “If your friend was seriously injured and you had to get him to a hospital, would you speed and go through a red light?” 
– Asked at Barlow Lyde & Gilbert (Law firm)

10.  “Would you rather fight a horse-sized duck or 100 duck-sized horses?” – Asked at BHP Billiton

11.  “How would you cure world hunger?” – Asked at

12.  “What are the three words that your parents would describe you with?” 
– Asked at YO! Sushi

13.  “Just entertain me for five minutes; I’m not going to talk” – Asked at Acosta

14.  “Why is 99pc not good enough?” 
– Asked at Parcelforce Worldwide

15.  “Pepsi or Coke? And why?” – Asked at United Health Group

16.  “How many ways can you get a needle out of a haystack?” 
– Asked at Macquarie Bank

17.  “Does life fascinate you?” – Asked at Ernst & Young

18.  “How would you explain Facebook to your Grandma?” 
– Asked at Huddle

19.  “Can you spell ‘diverticulitis” – Asked at Morgan Stanley (The candidate answered “No.” and passed)

20.  “In a fight between a lion and a tiger, who would win & why?” 
– Asked at Capco

21.  “Rate yourself on a scale of 1 to 10 on how weird you are” – Asked at Capital One

21 Comments on “Interviewing. 20 Questions That Could Make All The Difference”

  1. Great blog again Gary, nice to see you back sharing your knowledge. I hate interviewing and you have just crystallised that position by pointing out how poor I must be as I do just about everything you say not to do and would never really even think to ask much of what you suggest.

    Great piece. Thanks and well done.


  2. Brilliant tips. I’ve done several different HR training courses on interviewing and none have given the insight you have. Where do you stand on asking the awkward questions that might lead to accusations of discrimination?

  3. Some good tips here but not sure if I agree with the two-way process. I’m in the same profession you are but slightly lower down the food chain. I need to be assertive and almost aggressive to keep control and stop my candidates from treating me like just the little girl. If i get too chatty they just don’t take me seriously or will wrestle control from me. My manager is always telling us to be very strict and very formal, you seem to suggest the opposite?

  4. Great tips Gary. Do you really use the dinner party/actor type questions? And if so, what level or type of person would you use them with?

  5. Great blog Gary with some fantastic tips. I’ve used point 3 a few times and it works so well and tells you so much more than you realise. I also love the question that lead to massive discussions. Little wonder you make the waves you do, great approach.

    Thanks for sharing.

  6. Reading this after our meeting last week was fascinating Gary. I can see how so much of the chat was actually subversive analysis, yet I enjoyed our 90mins like if was catching up with an old friend over a drink by the fireside. Your approach is great and even more impressive having read the above.

    Thanks again for your time, I look forward to hooking up when I’m back in the UK at the end of Jan.


    ps i assume you can see my identity from my email – i don’t want to publicise our meeting on a open forum.

  7. Brilliant blog Gary, great questions. I’ve got to ask. Which would you choose – the horse sized duck or 10 duck sized horses?

    Well done.

  8. Great blog Gary, great list of questions. Planning to print out and leave on my managers desk. She is crap at interviewing and even worse at training to to interview. Good to get tips from someone with proper experience.

  9. Great share from Recruiter and great tips Gary. Love your narrative on your approach to interviewing even more than the questions.

    What answers do you get from the horse/duck and the facebook questions?

  10. Great article. Really useful tips and questions. Never have been able to understand why so many view interviews as a power struggle and refuse to be jovial or conversational. The notion of interviews being an interrogation is highly destructive. Your point about a 2 way flow of information is something that is highly accurate. Well done on another great blog Gary.

  11. Great blog and really unusual questions. Love the approach to interviewing, very different from anything I’ve ever seen or encountered. If you could only ask one question, what would it be?

  12. I agree with the many other contributors, this is a really well written and informative article. Few people out there would not benefit from this.

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