Compelling, easy reading for the busy entrepreneur
1 Million Amazing Ideas
98 Articles
50,786 Words

What 4,000+ interviews taught me about the questions to ask
Jan 4, 2017  |  Kenelm Tonkin


Scenario #1
You’re a business owner and need a list of interview questions because your candidate has just arrived. It’s been a busy day and you haven’t had time to prepare for the interview. 

Scenario #2
You’re a candidate sitting nervously in reception fearing you’ll make a mistake. You’d have loved an insider’s guide on how to answer interview questions before you arrived.

Good news! After conducting well over 4,000 interviews since my entrepreneurial life began in August 2000, I've developed a list of handy go-to interview questions.

These don't test the technical skill of a candidate for a particular role. That requires a unique set of questions and exercises particular to a role.

However, these interview questions have served me well in differentiating candidate traits, outlook, intelligence and whether they'd be a good fit for a lean, entrepreneurial outfit.

Anyway, here they are. My 24 Chink Finders. (I'm imagining the candidate as a knight in days of old, with my role to unveil their protective amour, or even just to find the occasional chink.)



Tell me about your biggest professional achievement to date.
Promising Answer: any well-articulated, enumerated contribution.
Red-Flag Answer: waffle, restatement of job description or no reference to KPIs.

What's your biggest strength in this job application?
Promising Answer: a clear, confident response about a commercially-valued skill.
Red-Flag Answer: a string of generic, propagandist, unverifiable or limply-stated traits.




Why are you leaving your current job?
Promising Answer: a reply indicating mastery of that role or desire for professional growth.
Red-Flag Answer: any hint of criticism of the company, it's managers or staff; a job hop for small gain.




Describe the work environment you find most fulfilling.
Promising Answer: a vivid description link environment to fulfilment in cause and effect.
Red-Flag Answer: a reply which doesn't directly offer an analysis of cause and effect.


What ambition does your family have for you?
Promising Answer: one which describes a fully-realised career and family pride in the candidate's achievement should it materialise.
Red-Flag Answer: any response limited to the personal or omitting vision of a fully-realised career.


Everyone experiences stress at work in some form or another. How do you manage yours?
Promising Answer: concise, practised and personalised steps for handling workplace stress.
Red-Flag Answer: a feeble play at perfection such as "I never get stressed!"


What have you learned most about yourself over the last 12 months?
Promising Answer: an unambiguous exploration of the revelation.
Red-Flag Answer: an experience apparently revealing something which should already have been known.


What can you do better for us than the other candidates we're interviewing?
Promising Answer: a confident declaration of superior, rare or unexpected commercial skills, experiences or achievements.
Red-Flag Answer: a sheepish or weak iteration of a job description.


What's your biggest weakness in this job application?
Promising Answer: a reply which embraces rather than mask or hedge, and couples this with confident self-awareness and mitigation.
Red-Flag Answer: propandist redundancies like "I'm a workaholic" or "I'm impatient with incompetence".


Describe the job you’ll be doing five years from today.
Promising Answer: a bold declaration of ambitious, realistic goals.
Red-Flag Answer: any reply which offers a saccharine, lifetime devotion to the job applied for.




Tell me about an experience you had working on a team with a difficult person. Describe it from that person's point of view.
Promising Answer: a reply in which the candidate has the emotional intelligence to be in the shoes of that person.
Red-Flag Answer: a candidate caught in the minutae of the difficulties without seeming able to perceive a break in the deadlock.


Tell me about your least favourite supervisor and why you don't like working for this person.
Promising Answer: a professional response devoid of personal attack; a concise appreciation of what the candidate needs in a boss.
Red-Flag Answer: any comment hinting at personal attack or superiority.


Describe a difficult workplace situation that you faced and that you think you handled well.
Promising Answer: identification of the challenge and analysis of how a solution was achieved.
Red-Flag Answer: any retelling which perpetuates the imbroglio.


Tell me about a workplace situation you don’t think you handled well and what you could have done differently.
Promising Answer: identification of the challenge and analysis of how a solution could have been achieved.
Red-Flag Answer: any retelling which perpetuates the imbroglio.


Describe a company policy you've previously worked under which you found unfair or inconsistent.
Promising Answer: statement of the policy, the challenges it created and a respecting, alternate, non self-serving version.
Red-Flag Answer: complaining without offering a respecting, alternate non self-serving version.


Describe your all-time favourite supervisor and why you like working for this person.
Promising Answer: a crisp exploration of what made the commercial relationship work.
Red-Flag Answer: non-commercial revelations like 'he was my friend', 'she gave me all the gossip' or 'he was my boyfriend.'




Share the time you last obsessively taught yourself something.
Promising Answer: a thoughful outline of the learning experience, plus the motivation and resourcefulness to self-teach.
Red-Flag Answer: a lame offering of something the candidate already knew or gradually learned on-the-job; lacking obsession.


What current trends are you seeing in this industry?
Promising Answer: a sweeping, insightful tour of the industry.
Red-Flag Answer: gossip about current employer or a non-response.


About which important truth do very few people agree with you?
Promising Answer: one which displays thoughfulness about the truth and self-awareness about the lack of support.
Red-Flag Answer: a motherhood 'truth' or a self-serving answer.


You're standing on the surface of Earth. You travel 10km south. Then you move 10km west. Finally, you go 10km north and discover you're standing on the same spot as you started. Where are you standing?
Promising Answer: the North Pole.
Red-Flag Answer: "On the surface of the Earth" or a shrug of the shoulders coupled with "I'm not good with numbers."




How do you define working too hard?
Promising Answer: establishes clear boundaries but not so uncommercial as to disqualify the candidate.
Red-Flag Answer: propagandist answers like "You can never work too hard" or "working any more than 9am to 10pm daily."


What do you think is a frivolous sick leave claim?
Promising Answer: "taking days off when you able to work."
Red-Flag Answer: "if you're sick, you're sick."


Would you be surprised to learn that your referee said you often come to work late or are absent?
Promising Answer: a confident "yes" because they know the referee did not say that.
Red-Flag Answer: difficulty understanding the question; flip-flopping; justification of attendance issues.


This role requires you work from [START TIME] to [END TIME]. What factors prevent you from consistently doing this?
Promising Answer: "None."
Red-Flag Answer: the introduction of any personal circumstances which would impact attendance.



What would be your #25? What's worked for you?

Let me know your thoughts in the comments section below.