Conducting Interviews? Ask These "Outside The Box" Questions!

business leader entrepreneurship skill interview leadership teams Oct 21, 2021

Alright, so you're ready to expand your team. But there are a lot of things to consider about finding the right team members - and knowing how they are, how trustworthy they are, and whether they'll be a good fit can be tricky if you aren't used to it. It might also not be where your skills are.

However, by asking the right questions (with intention), you might start to get a feeling for if they're the right fit in terms of both character and competency. So we've compiled a list of some really interesting and unique questions you could ask, and how asking them might help you make your hiring decisions.



How do you imagine this role being carried out in the day-to-day? - This shows off any operational experience they might have in similar roles and how much you might need to train them.

Name the top three personal qualities or character traits that are the most important to you? - This should show you if their personal values might align with the organisation. It might also show you if they've actually thought about their character before or what this means. If not, it might not be very important to them (unless you're hiring younger candidates, then you should curb your expectations for obvious reasons).

If you had to have everyone in your life watch the same movie, what would you want it to teach them? - This is actually the reverse of a great question we recommend asking yourself as a leader, which goes "If everyone in your organisation needed to watch a movie as a part of their onboarding, what values would you want it to teach them so that everyone was on the same page?" This will help you understand their values and potentially their soft skills better.

What concerns do you have about this role or this organisation? - This doesn't necessarily need to be something you have a right/wrong answer for, but it can help you understand how you would need to support them if you choose them. It could also help you understand how familiar they are with your organisation, if that feels relevant to you.

If you didn't need to worry about an income, such as by winning the lottery, what would you do with the money and your time? - This can give you an insight into their passions, priorities, and their values. And it's an easier question to use to spot if they're telling a fib of some kind.

Teach me something. - A simple ask, but a difficult task for some. Hubspot apparently likes to ask this question in their interviews. This helps you understand some really important professional skills, such as communication and quick-thinking. It helps you understand if they're good educators, which could hint at them being "management material". For really keen leaders, you might even spot how they think while you listen to them explain it to you - do they think in a way that could be an asset to the organisation?

Describe the colour purple. - You could change this for really any colour. You also shouldn't have an expectation of a right or wrong answer. What you're looking for is mainly how they think outside of the box, and how they deal with being asked such a strange-seeming question.

If you ran a pet-sitting business, would you rather have one dog that is really difficult to take care of or 4 dogs that were really easy to take care of? - There are a lot of renditions of this question you could ask, but it essentially seeks to understand whether the candidate would rather tackle one big task or have multiple smaller ones going at the same time. If you anticipate the role would need one more than the other, this could help you understand if they would be good at working in that kind of role.

What are the first three words your friends would use to describe you? - So essentially, what are the first words that you think would come to your friends' minds about you? This can be tricky for candidates, but shouldn't be taken too seriously, because they will likely need to give answers that we all know are tailored to the professional environment (we all know our close friends might say things about us as a joke that aren't suited to the workplace).

Name as many uses for a brick as you can in one minute. - This question is apparently asked at NVidia's interviews, to help show how creative someone can be, their ingenuity skills, as well as how quickly they can think on their feet.

How would you respond if I suddenly turned into a bird and flew away? - What a strange question! These are useful to ask sometimes, to see how well people respond to being thrown off, and to allow their personality to shine. You probably shouldn't judge their answer for these kinds of questions.

What is your Myer's Briggs personality? - This question is very specific. It would help you understand their personality traits, and there is some thinking in business that, as the hirer, it's your job to ensure a team can work well together - which includes if their personality would suit the rest of a team. We would recommend having them do the test if they don't know, or have them do it before they get to the interview and to not ask it at all during the actual conversation.

If you had a lot of tasks on too tight of a deadline, how would you deal with these? - This question is great for anyone to understand their time management and organisational skills. And for hiring for someone higher up, like a manager, this is probably a must. You can add an activity to this, where you use a one-week timetable task to see how they would prioritise the tasks and get them done. For example, do they delegate? If so, what do they delegate? Do an activity like this at the end of the interview, and give them 10-15 minutes to complete it without you in the room.

Your close friend or family member's birthday is coming up. What do you do to prepare or do for them? - This shows their forward-thinking abilities, their preparation skills, how conscious they are of important dates, and how they treat people who are important to them (if someone didn't treat someone they cared about well, how would they treat a random colleague?)

What mistakes have you learned from the most in the past? What did you learn? - The skill of self-introspection is incredibly important in all individuals and teams!

If a colleague comes to you with a personal issue, how do respond? - This shows their ability to empathise and if they understand how to respond appropriately to difficult and potentially personal situations in a work environment.

How do you choose what companies or roles to apply for? - This helps you understand what they value in a workplace/employer. Do they match up to your company principles? It could also be fairly easy to see if they're lying - for example, if they just wanted this job for money, there's a good chance they wouldn't sound confident with this answer or that they wouldn't talk about their passions, principles, or how they want to professionally grow.

Name one accomplishment you're most proud of? - This helps you understand both their past accomplishments, as well as why they think those accomplishments are important. What could this tell you about their character and their competency? 

From what you know about our company, what would you improve about X [e.g. our office layout, our customer service, our marketing]? - What exactly you ask them to say that they would improve might depend on the role or the nature of your organisation/industry. This might help you see how observant they have been, or how well researched they are.

Where do you think our industry will be in 5-10 years? - This helps establish how well they know your industry. Note that for some roles and experience levels, this won't be necessary and might even be a hindrance. But for really technical roles that require an understanding of how your organisation might need to evolve, being aware of industry projections like this would be crucial.


Please note that this is not an exhaustive list, and we sometimes come back and add to it as we find or try out new ones!

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