My Favorite Startup Job Interview Questions

Originally Posted in The Startup on Medium

Hiring well is among the greatest challenges for early-stage startups with limited resources — and also one of the best predictors of success. The stakes are high, and that’s why it’s important to throw out the list of interview questions you brought with you from your “big tech” role.

While traditional tech job interview questions might work for most roles, roles at early-stage startup companies are not like most roles. These roles require passion for the mission, can be more demanding, and usually force people to lean on a wider array of personal and professional skills.

Here are three interview questions I’ve asked or been asked — they may be a little off-kilter but in my experience, they lead to meaningful conversations during an interview and ultimately, healthier and more productive working relationships.

Have you used our product?

This is more about the follow-up than it is about the initial “yes” or “no.”

If the person has used the product, ask for feedback and pay close attention to the parts of the experience they emphasize or detail. If it’s relevant to the role, drill down on specifics and ask how they might handle the roll-out of revisions or updates.

As a member of the team at ChangeNOW recently reminded me, don’t write off people who have not used your product. Instead, figure out why. ChangeNOW staff prioritize learning how people are solving the problem without their multi-chain bridge solution, for example, and figure out what it would take to get them (as an end-user) to switch. This offers the rare opportunity to do direct user research. You may find that your value proposition needs adjustment or your on-boarding flow is broken in ways you weren’t previously aware.

What’s the job after this job?

Here’s an opportunity to demonstrate that you give a care about this potential employee’s development and begin your relationship from a place of understanding and alignment.

This is where you might learn, for example, this person is leaving the safe confines of big tech for an earlier-stage startup because they’re interested in starting their own company someday. If you’re a good and thoughtful leader, you’ll tailor their work experience to serve their long-term goals — and if you show that you care about them, you’re more likely to have a dedicated and engaged employee.

What’s your most unpopular opinion?

Understand this can be a challenging question for your potential employee — and you should not judge their response. Instead, evaluate their ability to sell the opinion. Are they leading with an emotional appeal or a data-centric approach? Are they bringing you along? This question can be useful well beyond sales roles — this can help give you a sneak peak of how the employee can handle a disagreement on their team.

The Right Interview Questions Lead to the Right Hire

It’s often said startup operators should hire slow and fire fast, something that many struggle with: when a company has a need, it’s often glaring and can be difficult to resist plugging the hole as soon as possible. That can lead to a rushed decision and a bad hire that you’ll come to regret.

These questions (and other creative questions with an eye on getting a full view of an individual’s approach and adaptability) will help companies shorten that path and find greater success in their startup hiring process.