Nine Interview Questions for Hiring Top Senior Engineers

Engineering managers from Google, Oscar Health, Giphy & more share their favorite interview questions

Captured by Denali Tietjen

Last week, we hosted our latest working session with Alan Warren, CTO of GC-backed Oscar Health and former VP Engineering at Google. Two dozen senior engineering leaders from high-growth startups Giphy, ClassPass, ZocDoc and more joined us for discussion, which centered around structuring engineering teams, making senior hires, and identifying junior talent with management potential (More on that here).

As part of the discussion, attendees shared their favorite interview question or best practice. Each takes their own approach to evaluating candidates (some cherish highly-technical questions, others collect personal anecdotes), filtering for fit and quality.

“Find out how well the candidate matches the values of a company. You can hire people who are very smart engineers and proven leaders, but if they don’t match your values, they just struggle. The most successful candidates match the most of those values best.”— Camille Fournier, former CTO, Rent the Runway

“As you get more senior, design becomes more important, and the ambiguity of dealing with complexity and unknowns becomes more important. To get at that, I typically start with ‘design Citi Bike.’ I want to see how they think about a large problem and break it down into basic components that we can address.” — Serkan Kutan, Head of Engineering, ZocDoc

“My favorite question is ‘Design a multi-player mobile game.’ I like this question because yes, there are technical considerations, but there’s also an opportunity to push the boundaries of what someone knows. Where they start is indicative of what they’re comfortable with. Backend engineers typically start with the backend. See where they go from there. — Teresa Brooks, Head of Engineering, Elysium

“Have a rubric. Not many interviewers go in with rubrics of what they’re trying to assess. This is particularly important when you have multiple interviewers interviewing candidates. If you don’t have the same criteria, it’s difficult to calibrate how someone did compared to the last candidate. Be disciplined in what questions you’re asking and how you assess the responses.” — Tracy Chou, former Software Engineer, Pinterest

“Most good engineering leaders were strong software engineers at some point in their life. I try to look for people who are reluctant leaders — they want to code, but realize they could have more impact on the company by being a great leader. To get at that, I ask about that transition.Anthony Johnson, CTO, Giphy

“One thing that correlates with experience is how much failure you’ve been through so I tend to ask about a project that failed. What I’m looking for is 1) Are you able to identify why it failed without just pointing fingers? and 2) Do you recognize what you could have done to make it more successful?” Adam Marcus, CTO, B12

“On the leadership side, I look for leaders who don’t lead for the title but because of the people they want to empower. So to get at that, I ask them to tell me about someone that they’ve grown to the next level how they made them successful.” — Steven Okano, VP Engineering, Mark 43

“I try to figure out how they deal with competing priorities. The specific question I ask is “You’ve been given two projects. They both have to get done, both super high-priority. How do you deal with that?In their answer, I get to understand how they delegate things and adjust resources and get a sense of how they manage their time.” — Todd Sundsted, CTO, SumAll

“When I think about problems or challenges in the past, I tend to think more personal rather than a project. The question I ask is ‘What design decision did you make that you would like to go back and have over again?’ How they talk through that and how honest they are in their communication is really telling.” — Alan Warren, CTO, Oscar Health