Why Bizarre Interview Questions Are Asked and How to Handle Them 

What Makes an Interview Question a Good Insightful Question? 

Resources to help you self-direct your WorkLife learning
Learning Resources From School of WorkLife. Resources to help you self-direct your WorkLife learning.

Part of a series of stories of weird questions people were asked at interviews, how they answered them, and what the interviewer may have been looking for in asking these questions. This series also considers what makes a question, a good question from the point of view of being an insightful question.

How Would You Count the Hairs on a Cat?

William was asked this question when he was interviewing for a project management role at an investment bank in the City of London. He was given a pen and paper, and calculator to work it out! He was thankful for this because it gave him time to gather his thoughts, and while he didn’t calculate, he did scribble down a few thoughts.

His answer was: “I’d weigh one hair, then shave the cat and weigh all the hair I shaved off, I’d then divide the overall hair weight by the individual hair weight to get the number of hairs on the cat.” He got the job!

What the interviewers were looking for was a candidate who could demonstrate their ability to think on the spot, showing creativity and intuitiveness as well as logical and practical thinking, including how they would go about solving difficult and even unusual challenges that might arise, and also to have conviction in their answer and the confidence to communicate this. The interviewers were more interested in how candidates got to an answer, as opposed to what the answer might be.

Such challenging questions are becoming ever more commonplace in interviews it seems, as employers seek to get past the polish to hire the best candidate. With so many self-help websites, candidates can be quite polished on standard interview questions, making it difficult for people to stand out if they ask the routine questions. So doing things differently will help them get to the best candidate, or so the thinking goes.

I asked William how easy it was for him to know how to answer this type of question, and if there’s anything he does to help him prepare. He told me that he loves to think about things in different ways and to explore the hidden side of everything. He went on to share this:

Book Wisdom

The book Freakonomics by Steven D. Levitt & Stephen J. Dubner is described as a rogue economist exploring the hidden side of everything, saying it’s all about using information about the world around us to get to the heart of what’s really happening under the surface of everyday life.

They talk about building the chapters around admittedly freakish questions, such as: “What do schoolteachers and sumo wrestlers have in common?”  They say: “If you ask enough questions, strange as they seem at the time, you may eventually learn something worthwhile.”

They go on to say: “The first trick of asking questions is to determine if your question is a good one. Just because a question has never been asked does not make it good. Smart people have been asking questions for quite a few centuries now, so many of the questions that haven’t been asked are bound to yield some uninteresting answers.

“But if you can question something that people really care about and find an answer that may surprise them — that is, if you can overturn the conventional wisdom — then you may have some luck.”

In researching this story, and as part of my ongoing research into considering what makes a question an insightful question, I came across these:

Words of Wisdom

If you’re on the other side of the table (the interviewee) you’ll need an arsenal of questions, too. Because at some point you’ll be asked: Do you have any questions for me? Lori Goler, VP of People at Facebook.

Goler goes on to share the following:

Sage Wisdom

The question “What is your biggest problem and can I help solve it?” is a question she posed when she cold-called Sheryl Sandberg. She was hoping to land a job, any job at Facebook. When Sheryl responded “Recruiting, we have amazing people, and we want to continue to build the team.” Despite never having worked as a recruiter, Goler jumped at the opportunity; and after a few months working as a recruiter, when the head of HR moved to a different team, Goler moved into the role. She has been Facebook’s head of Recruiting and HR ever since.


William’s interview was some years ago now. A more recent HubSpot blog post, says: “Hiring managers have heard about using these curveball questions to identify the best candidates. Fortunately, for intelligent and qualified candidates everywhere, studies have found that the brainteaser interview questions made famous by Silicon Valley and Wall Street are just as silly as they sound.” It goes on to say: “There’s a need to get creative in asking questions to understand if, for example, a candidate is a team player.”

Because of my interest in insightful questions, this is a subject I’ll come back to again.

Today I leave you with the question:

What is an important question for you to have in your arsenal of questions to get your foot in the door of a company you aspire to work at?

Use the self-feedback that comes to you through reflecting on this question, to build your arsenal of questions for all of the opportunities you want to pursue in your WorkLife.

Today’s featured book is: Freakonomics by Steven D. Levitt & Stephen J. Dubner

WorkLife Book Wisdom Stories:

The intention of the stories I share is to inspire you through people’s stories of their WorkLife experiences. Through these stories, you will learn about people’s dreams and ambitions, along with the challenges, obstacles, failures and successes they encountered along the road of their WorkLife journey. And how they used the power of book wisdom to help them find the inspiration and guidance to navigate their path to live their WorkLife with passion, purpose and pride.

My hope is that these book wisdom stories will help you throughout the chapters of your WorkLife Story.

I believe stories are a powerful mechanism for teaching, a powerful medium to learn through, and a powerful way to communicate who you are and what you stand for.



This story was originally published on 16/6/21. I needed to republish it to add updates and also to tell you 

… The Continuing Story …

The pandemic brought about a change in my WorkLife from delivering in-person individual coaching sessions and group workshops to creating resources to help people self direct their WorkLife learning.

In the last three years, I’ve published 30 books and over 200 stories.

Each book and each story is based on real life struggles and successes that people have encountered in their WorkLife. They also detail the exercises that helped navigate through these situations, which are set as assignments for readers to adapt to their WorkLife situations and learning needs.

I believe stories are a powerful mechanism for teaching, a powerful medium to learn through, and a powerful way to communicate who you are and what you stand for.

My inspiration for creating my work comes from a lifelong passion for learning. My work has taught me that the one thing in life that can never be taken away from you is your learning. 

School of WorkLife Guiding Statement: To create resources that are helpful, insightful and inspiring in helping people to pursue their WorkLives with greater clarity, purpose, passion and pride by creating continuous WorkLife learning programmes and resources that are accessible to everyone.

The resources I create will help you take ownership of self directing your learning in your own space and in your own time.


School of WorkLife helps you self-direct your WorkLife learning through resources that have been created to help you to take ownership of your learning in your own space and in your own time. 

What is Self Directed Learning? 

Self-Directed Learning is when an individual is motivated to take the initiative and responsibility on decisions related to their own learning. It is a series of independent actions and judgements free from external control and constraint. 

Resources to Help You Self-Direct Your Learning 

You may find the books below from The School of WorkLife Book Series helpful in meeting your learning needs as a self directed learner. Tap the book title to see a preview of what’s inside each book.

How To Self-Coach, Direct and Lead Effectively 

How To Be Creative in Your Thinking  

How To Let Curiosity Be Your Driving Force   

Tap The School of WorkLife Book Series to view the complete collection of books. From here, you can tap on each individual title to see a preview of what’s inside each book.

Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning
Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning

Founder of School of WorkLife, Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning.  These include a Collection of Books which originated from her first book, Your WorkLife Your Way and a  Learn Through Reading Series of Case Studies.  which originated from her latest book WorkLife Book Club. 

That’s the power of writing (and reading, which is an integral part of the craft for writers). It helps you find, develop and tell the right story at the right time in all WorkLife situations – in day-to-day communication: WorkLife and feedback conversations, presentations, talks, and negotiations, at interviews, and when socialising and networking in building and maintaining good relationships. The practice of writing helps you to tell the stories that express who you are in an interesting and engaging way.

Published by Carmel O' Reilly

I'm Carmel O’ Reilly. I'm a writer and learning practitioner. My books and learning resources are designed to help you self-direct your WorkLife learning. As founder of School of WorkLife, my guiding statement is to help people pursue their WorkLives with greater clarity, passion, purpose and pride by creating continuous WorkLife learning programmes that are accessible to everyone.