Tech companies have had a reputation for throwing curveball questions at job candidates when it comes down to interview time. In the past, a share of firms followed Google and Microsoft’s leads by pelting brainteasers at interviewees in the hopes of jostling them. (For example, I was once asked how many more televisions there were in Texas than in Massachusetts during an interview.)
But job-hunters may encounter fewer riddles and more profound interrogations around Boston. While some startups here may still subject potential hires to “gotcha” puzzles, there seems to be a greater focus on asking questions that cut to the core of each candidate to assess them not only as professionals, but also as human beings.
Here are what five leaders in our tech community deemed to be their go-to question during the hiring process.
Filling in the blanks
Sometimes, people’s professional paths can be patchy, particularly when transitioning from school to the real world. There may be moments of unemployment - forced or by choice. And that’s OK, according to Matthew Bellows, founder and CEO of sales analytics company Yesware. As long as you take something away from that time off, of course.
“In interviews, I like to focus on the gaps between school and jobs ... but I'm not looking for excuses,” said Bellows. “I'm looking for great stories, adventure, learning, traveling, serving the community.”
“People that take advantage of the natural gaps in a professional life by doing something extraordinary are the folks we want at Yesware,” he concluded.
Triggering an existential crisis
If work is the center of your life, it can be hard to separate your profession from yourself. But so many startups are intertwined with personal values and purposefully seek people who will stay true to those same principles. That’s why Ash Ashutosh, founder and CEO of data management firm Actifio, likes to ask,"Who is xxxx?" xxxx would be the name of the candidate here.
“Almost always, xxxx goes on to describe ‘what’ they've done, their career,” Ashutosh began. “I have to stop them and ask them again and, this time, clarify what I am looking for: core of the person, what motivates them, the culture fit.”
“Most of them pause for a while, because this is the first time they've stepped back for self-introspection,” he elaborated. “Many are never able to answer it!”
The importance of being earnest
In that same vein, many startups want to know what drives different candidates. To determine whether a person would be right for a company, as well as a specific role, some interviewers need to hash out his or her main motivators. Matt Lauzon, co-founder and CEO at positive feedback platform Dunwello, doesn’t beat around the bush with this subject.
He’s revealed that he always asks people for a frank conversation about what they really want out of a job: money, fame, power, opportunity, etc.
"There's a reason why so many people are unhappy at work or don't succeed in new roles: a lack of alignment,” Lauzon started to explain. “Both sides are so focused on selling the other party on the fit that they overlook discussing anything that might raise questions.”
“While having frank discussions means it's more likely the company or potential employee say no, it ensures that every single person you hire is starting on a solid foundation for success," he concluded.
Taking a methodical approach
Sometimes, disruptors have the interview process down to a science. They know exactly what they to look for in possible additions to their dream team, pinning down the proper question combo to separate the wheat from the chaff.
Just look at Mike Volpe, former CMO at HubSpot, who put together an all-star marketing team from scratch. From his published deck “How to Build and Manage an Inbound Marketing Team,” which has been polished since his HubSpot days, he laid out the series of questions used to pinpoint competencies.
While Volpe describes three main questions, one that stands out to me is what he calls “the website homepage question,” which seems like a high-pressure role playing scenario. He showed interviewees two rudimentary mockups for a potential website. "The CEO likes version A, the COO likes version B, and the company is evenly divided,” it reads on Volpe’s slide. “Which homepage do you launch?"
This question appears to uncover people’s raw analytical talent, gauge marketing-specific faculties and assess negotiating skills - which would all add up to an ideal addition to a startup marketing team.
Open to interpretation
Startups can also gain more insight into what people subconsciously hold dear by asking a simple, yet extremely broad question. The vagueness of a question can catch someone off-guard, enabling them to disclose more information than they even know.
Tom Coburn, co-founder and CEO of post-click marketing platform Jebbit, told me that his interview question of choice is, "What are you most proud of?" And this query - which could apply to anything that’s ever happened in a person’s life - definitely falls into the category described above.
Coburn continued to explain that he keeps it “intentionally open ended. Doesn't have to just be about work or business.”
So people could reveal that they're a roller derby champion, a published poet or an award-winning LARPer. What better way to get to know someone as a person and determine whether they'd complement company culture?
Images on file.
