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9 Creative Interview Questions To Help You Find the Right Talent For Your Startup

Interviewing for and finding the right talent is without a doubt the most important task at hand when you’re trying to scale up your startup. While much of job seeking is opportunistic and driven by our perceived chemistry with the candidate, asking the right questions can make all the difference in helping you identify who the right person is for your team.

As HR trends go, even startups have steered away from the popular brain teaser type questions of previous years (e.g. how many soccer balls are in the state of California? How many cars cross the Brooklyn bridge everyday?), but this doesn’t mean you can’t ask creative questions to uncover how a candidate thinks, what their values are, and how they’ll fare in your company’s culture. Read on as we list some of our favourites, and what type of answers to look for.


WHAT DO YOU HOPE TO LEARN IN YOUR FIRST YEAR IN THIS POSITION?

What this question reveals: Whether the candidate understand what this position entails, and whether she / he is truly interested in taking on and gaining from the required skill-set.

What answer to look for: Someone who can specifically list both short and long term goals, or skills they hope to gain.

IF YOU COULD START YOUR CAREER OVER, WHAT WOULD YOU CHANGE?

What this question reveals: This person’s perspective on decision-making, especially in relation to something as important as their career path.

What answer to look for: Someone who is able to learn from, but not dwell on, the past.

DESCRIBE THE BEST (AND WORST) SUPERVISOR YOU’VE WORKED FOR, AND WHY YOU FELT THIS WAY.

What this question reveals: This individual’s personality, especially as it relates to workplace relationships.

What answer to look for: Simply someone who is honest, and able to work in a close-knit team environment.

HOW WOULD YOU SELL [YOUR COMPANY’S PRODUCT]?

What this question reveals: How much homework the candidate has done to understand your company, which is especially significant when this concerns a novel idea or product.

What answer to look for: Someone who has a solid understanding of the selling points, and how to effectively communicate these ideas.

IS IT BETTER TO BE A SLOW PERFECTIONIST, OR SOMEONE WHO IS JUST APT BUT TIMELY?

What this question reveals: The candidate’s style of working.

What answer to look for: As most managers would agree, if one had to choose, the latter is more preferable for the long-term sustainability of the company, which is especially true in the time-sensitive world of startups.

WHERE DO YOU SEE YOURSELF IN 5 YEARS, AND WHAT SKILLS ARE YOU HOPING TO GAIN TO GET YOU THERE?

What this question reveals: This is a basic, must-ask question not because of what this person says, but how this person says it.

What answer to look for: An ambitious person who sees the position they’re applying for as an essential stepping stone to the goals they ultimately hope to accomplish.

TELL ME ABOUT THE MOST SIGNIFICANT PROJECT YOU’VE WORKED ON IN YOUR CAREER, AND HOW YOU WENT ABOUT ACCOMPLISHING IT, AND HOW YOU MEASURED ITS SUCCESS.

What this question reveals: The candidate’s work ethic, the confidence they have in their work, and ability in recognising the help of others.

What answer to look for: Someone who takes ownership of their work, and who is able to objectively measure the outcome of a project, as independence is extremely important for startups.

WHAT IS A WORK EXPERIENCE YOU’VE LEARNED FROM, BUT WOULD NOT WANT TO REPEAT?

What this question reveals: How the candidate deals with doing work they’re not completely happy doing.

What answer to look for: Someone who understands that it’s a fact of life to have to do things you don’t want to do, and the need to treat every experience as one to learn from, which is something that is inevitable in a startup environment.

WHAT IS ONE QUESTION I HAVEN’T ASKED YOU BUT SHOULD? AND, OF COURSE, PLEASE ANSWER THIS QUESTION. 

What this question reveals: This person’s self-awareness with regards to her / his own abilities.

What answer to look for: An answer that’s not too generic (i.e. what is your biggest flaw?) to show that this person is creative and eager to show off a unique skill.

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