HR & Leadership

14 SaaS Leaders Share Their Favorite Interview Questions

January 8, 2021

What’s your biggest weakness?

For many folks, the answer might be… asking job candidates good questions. If that feels like a burn, know that we’re right there with you—especially early in our career, we’re guilty of asking questions for the sake of asking questions on more than one occasion. It’s just not productive.

We’ve also been on the other side plenty of times, and “Which animal would you be and why?” takes the cake as the worst question ever. For the record, we’d be an armadillo.

Great interview questions tell you who a person is, what motivates them, how they think and solve problems, and what they’d be like as a teammate. And perhaps more importantly they tell a job candidate who you are. To help us all conduct better interviews, we asked some of the smartest leaders in SaaS to share their favorite questions. Here’s what they said:

“What did your last product do for customers?” It’s kind of amazing, but most people struggle here. Their answer shows whether they understood the value proposition from the vantage point of the customer. It demonstrates empathy. In addition, if the answer is a succinct elevator pitch, you can tell that the candidate has made a habit of this thought process. Whether the role is in Product, Sales, Marketing, or even Support, a candidate should be able to answer this. Bonus points if they name a specific customer in their answer, suggesting that they valued their interactions with customers.”
–Jason Garoutte, VP Growth & Marketing Operations at Twilio


“‘When growing up on the playground, many kids have visions about being doctors, athletes, teachers, etc. No one usually said, “When I grow up, I want to be a salesperson.” What was your career dream when you were younger and how did you find your way into sales? What do you love about what you do today?’ This is a great ice breaker question that allows me to get an initial glimpse into their personality and understand their sales DNA.”
–Leandra Fishman, Chief Revenue Officer at Intercom


“‘Tell me about the last piece of constructive feedback you received and what you did with that feedback.’

This question gives me a window into multiple aspects of a candidate: self-awareness, level of maturity, integrity, growth mindset, ego. A candidate who can’t give me a real answer may not be open to feedback or may lack the humility I want to see on my team.”
–Leela Srinivasan, CMO at SurveyMonkey


“‘If you could go back in time and leave yourself a 30-second voicemail when you started your last role, what advice would you leave for yourself?’ I find that this question tests humility and introspection.”
–David Apple, Head of Customer Success at Notion


“Take two minutes and remember the toughest decision you had to make in your life (at work, ideally, but can be personal, too). What was the situation/decision to be made, how did you make the decision, and what were the learnings from the process?”
–Ashvin Vaidyanathan, Chief Customer Officer at Gainsight


“‘If you asked your boss, a peer and a direct report what your biggest strength and your biggest weakness are, what would each of them say?’ I like this question because it’s easier to talk about these things from a third-party perspective, and I get very direct and honest answers from candidates. Helps you really understand how others see them.”
–Lisa Campbell, CMO, Autodesk


“‘What do you do for fun?’ It tells me a lot about a person and how they spend their time outside of work. If the answer comes out fast, it’s usually their passion. I get the most amazing answers to this question.”
Peter McKay, CEO at Snyk


“‘Tell me about the last time you took a big risk. Why did you take it? What was the outcome? Why?’ I’m looking to understand how they think about risks, and whether they take responsibility and learn.”
–Carol Meyers, Board Director at Zipwhip


“‘What happens if you have 10x the success with customers that you are targeting? 100x?’ Many team members struggle to think ahead about scaling challenges and what to do next. Another approach to the same challenge is resourcing—if a candidate or team member thinks a problem set requires five people to solve, what would they do if you gave them 50? Do they have a perspective on how to ramp investment to deliver outsized results? These questions are helpful in ensuring you’re hiring team members who can deliver value at the current and future stage of the company’s growth vs. just filling a need of the moment.”
–Ross Moser, GM of Surveys at SurveyMonkey


“I have two: 1. ‘Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?’ (Credit to Chad Dickerson, former Etsy CEO). 2. ‘What are the three most important skills to lead this function (or perform this role)? How do you evaluate yourself on these skills, ranking from strongest to least developed?’”
–Brandon Peay, EVP and GM of Skills at Pluralsight


“‘Think back over the last 2–3 years. If I asked someone you worked for during that time what your top development areas are, what would they tell me?’ I love this question because the way in which the candidate answers it tells you as much about them as what they say. For example:

How easy is it for them to come up with an answer? This provides great insight on how much active interest the candidate has in hearing where they can develop and/or how willing the candidate is to be vulnerable in high-stake discussions.

How do they go about answering the question? Are they a curious leader who sees development areas as opportunities for growth and exploration, do they become more defensive and/or do they deflect and decide to tell you about their strengths even though that was not the question?

What do they say their development areas are? How will someone with these development areas fit into the role you have open? Does their answer align with other information you have on the candidate such as commentary from back channel references and/or from the discussions you have had?”
–Yvonne Wassenaar, CEO at Puppet


“‘What scares you about taking on this position?’ This allows me to gain a perspective of the candidate’s capacity for learning new things and taking risks.”
–Rashida Hodge, VP, North America Global Markets at IBM


“I run through a hypothetical experiment and some data, and I ask them to interpret it. It gives me a good sense of data literacy, product intuition, creativity and generally what it would be like to work with them.”
–Jesse Miller, Head of Growth at Postman

More wisdom from SaaS leaders

Managing Editor<br>OpenView

Kristin joined OpenView after spending over four years at InVision managing their Inside Design publication and helping build brand love as chief storyteller, lead producer and editor. Before InVision, she co-founded the digital strategy agency Four Kitchens, spent several years in the restaurant industry as a chef, and was Editor-in-Chief of the nation’s largest college humor publication, the Texas Travesty, as an undergrad at the University of Texas at Austin.