Go-to Interview Questions from 6 Startup Founders

Leaders of six fast-growing tech companies share the unexpected questions they like to ask when interviewing candidates.

Founders have to dig deeper beyond a candidate’s hard skills and previous work experience in job interviews to determine whether someone is suited to thrive in the unique, rapidly shifting environment of a fast-growing startup. Crucial qualities like passion, flexibility, and ambition are a bit tricky to gauge in an interview setting so oftentimes, this means founders ask some pretty out-there questions…

To get a sense of how founders determine whether candidates are the right fit for their company, we asked six founders their favorite questions to ask in an interview. Some of their answers definitely surprised us! They also explain what exactly the question reveals about a candidate and share their favorite response to date.

Psst…most of the companies featured below are hiring! Find open roles at these startups and more of Australia’s fastest-growing tech companies on Innovation Bay’s new jobs board.

1. Melissa Widner, Lighter Capital

Melissa is the CEO of Lighter Capital, a revenue-based financing lender that specializes in providing financial capital to small technology companies.

Favorite interview question?

While I’ve never asked this one myself, a recruiter we often worked with in Seattle would record all his initial interviews with candidates and then provide the recordings to the hiring committee (usually the board). We could then watch his interviews on our own time. The last question he asked each candidate was, “what kind of car do you drive?”

What does it reveal about the candidate?

It’s surprising how much this reveals about the candidate, and it has very little to do with the actual make/model of the car but rather how the person answers the question. First, they are always a bit surprised because the question comes at the end of an interview which is focused mostly on topics relevant to the company and position.

Best response you’ve heard?

I’ll never forget the candidate who described his 11-year-old Subaru wagon that he had been driving since he finished grad school. He was interviewing for a CEO position and his background was sales leadership, so one could assume that he would drive a flash car, but it was just the opposite. He really lit up talking about the Subaru, why he loved it and couldn’t imagine selling it. It gave me more insight into his personality than the rest of the interview.

View open roles at Lighter Capital here.

2. Keaton Okkonen, black.ai

Keaton is technical co-founder and CEO of Melbourne-based Black.ai, an AI startup working in supermarket and industrial automation.

Favorite interview question?

A) What’s the most complicated idea or concept that you have a deep understanding of?

B) Can you explain it to me as someone with no background or experience in that area?

What does it reveal about the candidate?

I ask this question as I believe clear communication ability is one of the most important things to hire for. We try to bring on people that are smarter than we are, with skills that don’t completely intersect with the team [the new hire] would sit in. We also try to give people as much freedom and autonomy in their work as possible, so the ability to explain why you should work on what you want to work on is super valuable.

Best response you’ve heard?

Hamish Clark explained gravitational lensing and how the Einstein Cross works, in a way that even my 12-year-old brother would understand. We hired him!

View open roles at black.ai here.

3. Joe Forbes, Biarri

Joe is the co-founder of Biarri, a company using mathematical modeling to build decision-making tools.

Favorite interview question?

What do you do when you are not working?

What does it reveal about the candidate?

It provides a broader view of the person and gets them to relax for the follow-up question about their biggest professional mistake.

Best response you’ve heard?

“When I am not coding I am the lead guitarist in a death metal band.”

Biarri currently does not have any open roles but you can check out their LinkedIn here.

4. Silvia Pfeiffer, Coviu

Silvia is the co-founder and CEO of Coviu, a telehealth software company that has helped thousands of healthcare businesses offer video consultations during the COVID-19 crisis and delivered over 1m video visits in 2020 in Australia.

Favorite interview question?

What business would you like to start if you had the chance?

What does it reveal about the candidate?

I like it because it brings out what drives the candidate and what they really care about. It also brings out if they care about anything at all, i.e. are they startup material.

Best response you’ve heard?

“Oyster mushroom growing” by a SRE — it was so left field!

Coviu currently does not have any open roles but you can check out their LinkedIn here.

5. Jason Hosking, Hivery

Jason is the co-founder and CEO of Hivery, a company that is pioneering hyper-local retailing by combining artificial intelligence, operations research, and human-centered design to help consumer goods companies and retailers generate a return on physical space investments.

Favorite interview question?

I always like to ask, ‘“on a scale of 1–10 how weird are you and why?”

What does it reveal about the candidate?

I like to see how the candidate responds. It usually breaks the ice too and if someone is nervous this can get them to laugh and relax a bit. The answers can be pretty telling too! We like a bit of quirk at Hivery, we call it the H factor and it’s one of our values — about creating a safe place for everyone to be comfortable being themselves. If someone scores themselves too low, they may be a little boring. If there are too high also it could be a red flag. It’s usually an opportunity for the candidate to divulge something about themselves and it usually kicks off a whole new conversation.

Best response you’ve heard?

There have been many great responses! Some a little out there. But one female engineer, who was a little shy and nervous, gave herself an 8. I probed on why and uncovered a whole new side of her. She had a passion for swimwear and had actually set up her own business designing swimwear and a quite successful e-commerce store selling them. And that’s the point, I uncovered more to her background, interests, and a strength and hidden tenacity — far beyond just her python skills!

View open roles at Hivery here.

6. Cibby Pulikkaseril, Baraja

Cibby is the co-founder and CTO of Baraja, a rapidly growing start-up, with a revolutionary LiDAR for self-driving vehicles.

Favorite interview question?

I like to ask “What do you spend your time on outside of work?”

What does it reveal about the candidate?

I like to ask it because it can really show you if people have the “ability” to be passionate about something they care about. Generally, most people say things like family, gardening, etc. Those are not distinguishing answers, and not what I’m looking for. What really intrigues me is when people have a hobby, or a group, or something they really show passion for. One lady was really into painting, her face lit up when she showed us pictures on her phone. We hired her, and that tenacity and work ethic made her a success at Baraja.

Best response you’ve heard?

I’ve just interviewed a guy that makes replicas of the original Star Wars models, down to figuring out which army toys that George Lucas used to assemble the Star Wars vehicles!

View open roles at Baraja here.

What is the best, most unexpected, or weirdest question you have ever been asked in an interview? Let us know in the comments 💬👇

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