Startup Founders’ Favorite Interview Questions to Judge Early Team Fit

At seed-stage startups, especially companies with well-networked founders and investors, finding applicants who can do a job on paper is not overly difficult. The true challenge is to find candidates who will mesh into a small, budding team and culture. As a result, the interview process during the seed stage can feel a bit more meandering to the hiring manager — who is most likely the founder(s) given the size and stage of the company. In short, you need to dig for softer things than past employer brand names or letter-of-the-law skills. To help you more effectively build your early teams, we asked a group of founders to share their favorite interview questions when they build new startup teams. Here’s what we learned…

Hire a Missionary

Ben Rubin, Co-founder & CEO, 10% Happier

What he likes to ask: “What matters most to you as you think about your next gig?”

His ideal answer: Folks who reply with some form of “learning, growth, personal change, professional development” get aces.

What he’s trying to learn: If a candidate, without being prompted, lines up with our mission. Joining a startup can serve many needs (get something out into the world, working closely with a small team you love, financial reward, etc.), but we are looking for folks who live and breath the 10% Happier mission: To help people change their minds and improve their lives through meditation.

(10% Happier is meditation for those allergic to New Age-y nonsense. Built in Boston.)


Look for Tenacity

Eric Berry, Co-founder & CEO, TripleLift

What he likes to ask: “Tell me about a time when you faced some sort of overwhelming challenge at work and how you overcame it.”

His ideal answer: Grit and tenacity are incredibly important — and evidence of these traits is something that makes for a great answer. Also, since startups move quickly and often don’t have everything spelled out on Day 1, people who have experienced some sort of particularly challenging work in the past tend to make a better fit.

What he’s trying to learn: Whether this person will have the perseverance to get the job done in an environment that isn’t always the easiest to work in. Other people [at TripleLift] in the interview process tend to focus more on the skills and abilities, so I’m looking for culture fit in this question.

(TripleLift is native programmatic advertising simple, scalable, and effective on the visual web. Built in New York.)


Discover Their Fulfillments

Sasha Hoffman, Co-founder, Fuzzy Compass

What she likes to ask: “What are your top two favorite work memories?”

Her ideal answer: Ideally one that shows the person likes to be challenged, spend time solving complex problems or gets a high from delivering a really quality product or strong outcome. I’ve heard everything from getting a big bonus to closing a huge deal to leading a team to X goal. Not sure there is a “right” answer but there is one that probably suits your long-term company goals more – whether it shows they can sustain the long haul or are just a great team player and want to make an impact.

What she’s trying to learn: As a manager, it’s very important to understand what motivates people as everyone is motivated differently. This question helps me get at what historically has made an impact on that person’s career and brought them fulfillment. If you can channel an employee correctly to do what they excel at and enjoy, it benefits the whole team. It also tells me if that person is the wrong fit (e.g. just here for the $$$, won’t work in startups).

(Fuzzy Compass connects you directly to the travel influencers behind the world’s most popular travel blogs, websites, and Instagram accounts to plan customized trips. Built in Boston.)


Is Impact or Income Their Motivator?

Ben Forgan, Co-founder & CEO, Konekt

What he likes to ask: “In an ideal world, where money isn’t an issue, what do you see yourself doing?”

His ideal answer: It can vary, but an ideal answer is something related to building impactful products/business/technologies.

What he’s trying to learn: To paraphrase Randy Komisar: It’s the romance, not the finance, that makes entrepreneurship and startups worthwhile. Are they really just looking for a big payout so they can do something else (in which case they probably won’t be happy/intrinsically motivated), or are they on board to try and build something amazing because that’s truly their passion?

(Konekt offers tools to make it easy for anyone to add cellular connectivity to their hardware devices. Think of it like Heroku for cellular-connected hardware. Built in Chicago.)


Let Personality Shine

Zoe Barry, Founder & CEO, ZappRx

What she likes to ask: “What business would you love to start?”

Her ideal answer: Including “ZappRx,” any business idea is fine! But, I’d really like to hear about personal interests – from opening a high end restaurant, to a building a mobile app, to opening a surf shop. The beauty of this question is that it allows an interviewee’s personality to come through. Plus, I can see if they have the creativity and drive needed for entrepreneurship. Working at a startup isn’t for the faint-hearted.

What she’s trying to learn: I want to hire the best and brightest talent who will shape the direction of ZappRx. But in order to do that, I need a team of people who are entrepreneurs at heart; they’re passionate about building a business from the ground up and are willing to go through the hard work to do so. This is especially important early on when the business direction might pivot and you’re doing all you can to get your name out to investors and early customers.

(ZappRx helps cut out the inefficiencies in specialty prescription orders for health care professionals, pharmacists, and patients. Built in Boston.)


Get to Their True Self

Scott Britton, Co-founder, Troops

What he likes to ask: “What are you most proud of in your career (or life) to date?”

His ideal answer: Something that demonstrates characteristics we’re looking for in a candidate for a particular role that also fits our core company values.

What he’s trying to learn: Whether they posses excellent character and dedication to their craft.

(Troops is smart CRM software that makes work easier. Built in New York.)


Parents (Sometimes) Understand

Jules Pieri, Co-founder, The Grommet

What she likes to ask: “What is a lesson you learned from one of your parents that you still use?”

Her ideal answer: There’s no ideal answer other than one that reflects ownership and maturity regarding life experiences. One person told me about how badly her single mother managed finances and she was determined to build self-sufficiency. Another told me about his father’s work ethic and the trials and tribulations of being raised by an entrepreneur. These gave me deep insights on the person that might have taken me months or years to obtain.

What she’s trying to learn: I am partly looking for original thought and partly looking to disarm the person to share a less professional or polished side of their life experience. It is super important to me that people are moving forward in life deliberately and not following a conventional line of thinking or expected path.

(The Grommet is a platform that launches innovative, undiscovered products and helps them succeed. Built in Boston.)


Keep It Informal, but Understand Your Odds

Adam Brod, VP of Technology and Engineering, BookBub

What he likes to ask: I really try to get to know a person and what their motivations are to make sure we are the right fit for them. The one question I tend to use is, “Let’s say you had an offer from BookBub and Company X — how would you decide on one versus the other?” (I don’t share anything else about the offers.)

What he’s trying to learn: That question tends to get people to share how they evaluate different opportunities and what’s important to them. I believe I was trained to use that question at my first job at Sapient, so I can’t take credit.

(BookBub is e-book discovery for millions of readers and tools to help publishers and authors grow readership. Built in Boston.)


Avoid the Typical Interview Altogether

Samuel Clemens, Co-founder and Chief Product Officer, InsightSquared

If it’s a seed-stage hire, you should already know the person. Think Ocean’s 11.

I have a “keeper list.” When I meet people and think, “I want to work with that person someday,” be it for engineering or sales or customer support or anything, I add them to the list. When you start your company, even if it’s years later, you can then run down this list and see who is available.

(InsightSquared is business intelligence software for sales teams at high growth tech companies. Built in Boston.)


In The End…

Whenever we at NextView speak with founders of seed-stage companies, whether pre-launch or gaining initial traction currently, their personal relationships are far and away the biggest source of talent. Sam’s idea of a keeper list, whether over or implied, appear to be the most important element to effective early-stage hiring. As a result, to get to the nuance of whether someone will be a fit on your early team, it’s far better to know the person over time than to look for a single silver bullet interview question.

Ultimately, like so many parts of an interview, you have to go with the experiences that you as a professional have had. At the same time, it’s critical to be hyper-aware of your own biases and actively try to navigate around them. For instance, for both hiring and for networking in general, be proactive about meeting and learning from a wide array of people — different personal backgrounds, professional skills and experiences, ages, genders, geographies, and so forth. At the seed stage, each and every new hire must be a fit, and that word “fit” implies different pieces to a puzzle — not pieces that all resemble each other.

At any seed-stage startup, it’s easy to joke that growing 300% month over month is a misleading stat. After all, you’re building off a small denominator. But when it comes to team growth, saying “300% team growth” when you’re growing from 2 to 6 to 18 to 54 and beyond is actually understating the impact it will have on your business, for better or worse. We hope the advice above can help ensure it’s for the better as you grow your team. Good luck!