Hiring is by far the biggest concern we hear from founders. Finding the right people to work at your company is high-stakes. Poor performers can take a catastrophic toll on your success. Most seasoned CEOs say that founders should be spending as much as 50% of their time early on getting the right talent in the door. Yet, the actual hiring process tends to remain more of an art than a science for startups — regardless of all the structure and rubrics they try to impose.
This makes the questions you choose to ask during interviews of paramount importance. You only get a narrow sliver of time with each candidate, so you need to maximize your learning per minute. How do you do that?
Over the years here at the Review, we've collected and aggregated hundreds of interview questions recommended by top leaders in every field. Our goal in this piece is to present the very best questions we've heard for hiring incredible performers — with deep dives into interviewing technical and product candidates in particular. We hope having them all in one place will make your future hiring that much easier.
As Co-founder and CEO of Koru, Kristen Hamilton has long worked to bridge the gap between graduation and employment, and place people in jobs where they’ll excel. Working with candidates who lack real-world experience has had a surprising byproduct — she now has a crystal clear sense of the skills and traits that make people great performers. She's identified seven characteristics that, taken together, best translate into someone killing it at their job. These traits transcend department or career stage, and they apply to entry-level engineers and marketing executives alike:
To test for each of these qualities during a standard interview, Hamilton has curated very specific questions—
For grit, ask:
Tell us about a time in your career that you wanted something so badly that you were unstoppable in pursuing it. What obstacles did you overcome to get there?
As you listen to the answers to those questions, pay close attention to both the tasks and the duration described. “Try to get a sense of how long that person can stick it out. How long are they going to beat their head against a problem?”
For rigor, ask:
Tell us about a time you used data to make a decision.
Look for details about the complexity of the data and how the thinking happened, rather than focusing on them immediately getting to the right answer.
For impact, ask:
1) Tell us about a time you had a measurable (read: quantitative) impact on a job or an organization.
2) Tell us about a person or organization that you admire. Why do you think they have made an important impact?
You’re looking for signs that the candidate understands the larger picture, and that they can speak to the importance of making trade-offs and prioritizing appropriately.
For teamwork, ask:
1) When working on a team, what's hardest for you?
2) What about a time you worked on a difficult team? What was your role and experience? Do you know where the other people involved were coming from? Tell us about the situation from their perspective.
3) What makes you happiest and most effective when working with others?
You want to use their answers to measure EQ and ability to empathize. Are they able to acknowledge and understand the experiences of those around them?
For ownership, ask:
Tell us about a time you experienced what you perceive to be an injustice.
"Regardless of their answer, empathize with the unfairness," Hamilton says. "Say, ‘Are you kidding? That's crazy. What a jerk.’ True owners will immediately respond with something like, ‘Yeah, but I recognized it wasn't worth my time to complain about it.’ They won’t buy in and double down on venting or complaining."
For curiosity, ask:
What's the last thing you really geeked out about?
You're looking for them to say something they then obsessively taught themselves about. "If someone doesn’t have that quality — if they don’t need to learn every single detail of the topic in front of them — they’re probably not going to reflect that level of engagement in their work, either.”
1) See how they handle themselves when you interject or interrupt them in the conversation.
2) Do they send a thank you note shortly after the conversation?
You're looking for calm confidence when they might otherwise be flustered or thrown off their game. Gratitude following an interview indicates humility and a sense of professional standards that will translate into their work.
For more on how to ask these questions and suss out the 7 traits for success, read the rest of Kristen Hamilton's interview here.
As the former Technology VP for both Amazon and Zynga, Neil Roseman's interviewed hundreds of people and believes every phase of the process needs to be meticulously designed to drill deep into skill sets, actual accomplishments, culture fit and leadership potential.
In his opinion, great interview questions focus on specific examples of the candidate’s unique contributions, actions, decisions and impact. Ideally, you want to:
Probe: give me an example…
Dig: who, what, where, when, why and how on every accomplishment or project
Differentiate: we vs. I, good vs. great, exposure vs. expertise, participant vs. owner/leader, 20 yard line vs. 80 yard line
“I look for past projects and accomplishments that seem to have enough weight and depth that I can apply STAR questions — STAR stands for situation, task, actions and results.” Roseman subscribes heavily to an approach called Behavioral Interviewing, in which STAR questions are a staple. They include:
What's the background of what you were working on?
What tasks were you given?
What actions did you take?
What results did you measure?
When it comes to soft skills and culture fit, Roseman is a big fan of one question — he asks everyone, no matter the position: Do you consider yourself lucky?
"I’m looking for the people who embody the phrase ‘fortune favors the prepared,’" says Roseman. "It’s the willingness to be ready and take advantage of every opportunity that presents itself. At a startup, this is particularly valuable.”
For more questions and advice on how to structure interviews from Roseman, read on here.
According to Anne Dwane, former CEO of Zinch, CBO of Chegg and now Co-founder of Village Global, the most important quality any startup leader (current or aspiring) can have is adaptability. And the most defining attribute of adaptable leaders is who they surround themselves with. They are often on teams with other flexible, resourceful, innovative people. Whether now or in the future, Dwane recommends a certain hiring framework to help you identify self-motivated individuals who will enrich your team’s aptitude for learning.
“The most powerful way to construct a job description is to clearly communicate that unyielding, consistent learning is a core part of the job,” she says.
After making introductions, Dwane begins with a pointed two-part question: What motivates you and what do you want to do next?
Most candidates deflect the question by repeating their resume. “They try to add to it but it doesn’t demonstrate what I’m looking for which is: active listening, the ability to answer the question, and self-awareness."
She then asks these questions to identify whether a candidate is an adaptable learner:
What have you started?
How would you describe yourself in your own words?
How would a colleague describe you in three adjectives?
What current trends are you seeing in your profession?
What new things have you tried recently?
The last two questions are strong indicators that your candidate is self-motivated to explore and embrace new trends, routines, and technology. Take note of this as a critical demonstration of self-learning in your interview. Dwane advises probing more about the new process he or she introduced, why it intrigued them, and the results of implementing it.
As for homework: “I love to give people an opportunity to give a compelling presentation on a topic they care about,” Dwane says. “That’s the game. If they look pained while they are doing it or don’t enjoy the assignment, then you know someone isn’t going to have a gameful approach. You want someone who is going to enjoy talking about the topic and putting the presentation together.”
For more on how to spot, hire and nurture adaptable leaders, read more from Dwane here.
As VP of Engineering at Airbnb with an impressive track record behind him, Mike Curtis has seen the dire impact that bureaucracy can have on a company. In his experience, hiring well to begin with is one of the most powerful antidotes to paralyzing bureaucracy. You want to recruit and onboard people you know you can trust, so you that you don't have to set up a bunch of newfangled process just to ensure productivity and quality.
To hire specifically for this type of trustworthiness, Curtis recommends allocating at least 45 minutes to an interview that is entirely about culture and character. Diversity of backgrounds and opinions is championed at Airbnb, so ‘Culture fit’ is about finding people who share the high-performance work ethic and belief in the company’s mission. If people don’t share your conviction in your company’s success, they aren’t a fit.
At Airbnb, Curtis found that these four moves truly extract the most value out of this type of interview:
Let them shine first. For the first 15 minutes of your culture interview, let a candidate describe a project they’re particularly proud of. The idea here is to get a sense of what excites them — is it technical challenges, for example, or perhaps personal interactions? “Try to suss out what gives this person energy,” Curtis says.
Then make them uncomfortable. The other side of that coin is that you want to learn how candidates react when they’re not excited, too. Ask them about difficult experiences, or moments when they were somehow not in control. Some of Curtis’s go-to questions are:“Describe a time you really disagreed with management on something. What happened?” and “Think of a time you had to cut corners on a project in a way you weren’t proud of to make a deadline. How did you handle it?” This exercise is all about reactions. “Does the candidate start pointing fingers and say, ‘This is why I couldn't get my job done, this is why this company is so screwed up’? Or do they start talking about how they understood another person's point of view and collaborated on a solution?”
Calibrate your results. It’s easy to see if someone nailed a coding challenge. It’s a lot harder to get comparable reads on candidates when you’re working with a group of different interviewers. It takes time to get on the same page, but you can help the process along. “We get all our interviewers together in a room and have them review several packets at the same time to help expedite the process of getting to some kind of calibration on what’s important to us,” Curtis says. Essentially, try to make the subjective as objective as you can.
Watch out for signs of coaching. If a candidate seems to have uncanny command of your internal language, take note. The public domain is exploding with tips and tricks from past interviewees and journalists. “Especially as your company starts getting more popular or well-known, there's going to be a lot of stuff about you out on the Internet. If people start quoting things to you that they obviously read in an article or something that is your own internal language, they were probably coached. They either read something or they talked to somebody who works at the company,” Curtis says. That’s not to say you should reject them immediately, just don't let yourself be swayed.
For more from Curtis on not only how to hire, but onboard and train new employees to head bureaucracy off at the pass, read more of our interview with him here.
Bestselling author and Wharton professor Adam Grant has spent years researching and interviewing people he refers to as 'originals.' In his book of same name, he shows how to identify, foster and nurture nonconformists — and the brilliant benefits they bring to their work and the organizations they join. Here are the questions he suggests asking to recognize and recruit them in a startup setting:
Tell me about the last time that you encountered a rule in an organization that you thought made no sense. What was the rule? What did you do and what was the result? “You’re not excited about candidates who just let it go. But you also don’t want somebody who says, ‘Yeah I saw this rule, marched into my boss’ office, argued and quit over it,” says Grant. “What you're looking for is somebody who says, ‘I saw this rule that I thought didn't make sense. I first did some research to figure out how it was created and why it was this way. I spoke to a couple of people who’d been at the organization longer than I had, asking if they knew what it was initially set out to do. If they didn’t know, I reached out to some people who have influence and sought their advice on ways forward to improve the rule and made a few suggestions on how. I got tasked to lead the committee to change the rule. We made a change and here's the evidence that we had an impact.’ That’s an original who’s learned to be a tempered radical.”
Why shouldn’t I hire you? “In Originals, I talk about founder Rufus Griscom, who pitched his startup Babble to investors by listing three reasons not to invest in his business. Sarah Robb O’Hagan once opened her job application the same way, describing why she shouldn’t be hired. In one breath, she outlined which qualifications she didn’t meet, but also why she was suited to do it anyway,” says Grant. “She challenges the job description and shows that she can bring something different than what a company thinks it needs. Part of why this worked is that, in one fell swoop, she shows extreme awareness: not only of her abilities, but also of the proposed requirements — and why some don’t really matter.”
It’s your first few months on the job. What questions would you first ask and to whom? Presidential candidates are often asked what they plan to accomplish in their first 100 days in office, and hiring managers tend to evaluate candidates for leadership positions similarly. “This idea came from one of my collaborators, Reb Rebele, an applied positive psychology expert who leads many of our hiring projects,” says Grant. “He observed that when new people are coming in, their first few months should be as much about learning as doing. Originals distinguish themselves by asking questions that no one else has thought to ask, and posing them to people who have fresh perspectives to offer. Ask candidates what questions they’d want to ask in their first two months on the job, and who their ideal sources would be. Listen for examples of open-ended questions — rather than just yes/no or testing-my-own-thinking styles of inquiry — as well as a willingness to draw from and challenge many sources of information.”
How would you improve our interview process? “I find this question powerful for a couple of reasons. One, it's an opportunity to see if they’re willing to speak up. Two, it's a window into their thinking process. When they encounter something that they don't like, do they have the instinct not only to raise why it may be broken but also suggest how it can be better?” asks Grant. “It's a chance to learn about their tendency to share opinions that might be unpopular but beneficial. It gives you a little bit of perspective on their ability and inclination to improve their environment.”
For more on fostering an environment where original talents can truly thrive, read more of our exclusive interview with Adam Grant.
Todd Jackson has led product organizations across some of the best companies in tech, from Google to Facebook to Twitter. Now VP of Product at Dropbox, he’s worked with hundreds of product managers — and hired dozens — over the course of his career. In every product manager interview, he recommends making sure a candidate fits the following criteria:
Effectiveness within the company culture
Knows what users want
Below, Jackson lists the questions he’s found to be the most valuable when interviewing product management candidates in person, what he believes good answers sound like, and the responses that should give you pause.
QUESTION 1 (Product Sense): Name a product that you think is exceptionally well-designed – ideally a non-electronic product. Tell me what makes it well-designed. (Testing intellectual ability, communication, and whether they know what customers want.)
WEAK ANSWER: Something superficial or cliché. “If they don’t go into a lot of detail and say something fluffy like, ‘My electric toothbrush is so great, it’s won a bunch of design awards,’ that’s a strike against them.”
GOOD ANSWER: First, the candidate will get excited to talk about a product they admire, and it will show. “One of the best answers I heard was about the Micro Kickboard scooter for kids – I remember the candidate getting really excited telling me all the details: ‘I recently noticed how thoughtfully designed my niece’s scooter is. It’s the mini scooter that you see a lot of kids riding lately. It’s got two big polyurethane wheels in front and a third small one in the back, so it goes over cracks and bumps smoothly and prevents faceplants. Also, instead of handlebars that turn, it has a ‘lean-to-steer’ design which is really intuitive for kids, teaching them how to steer by shifting their weight. And it’s also just super easy to assemble and disassemble—basically just two parts that click together.’”
Particularly strong candidates will look at the product from the user’s perspective and talk about the problem it solves. In the above example, “the candidate spoke about how the users of the product (kids) are actually different than the customers of the product (parents) and all the product design and marketing ramifications of that, which I though was quite insightful.” The candidate will have a lot to say and will be very enthusiastic as they speak, especially about the very small details that provide a finished and delightful experience. “That’s how you know the difference between a passionate product person and someone who just wants a job.”
To take it up a notch, you can follow up with the question: “What would you improve about it?” or “If you were the CEO of the company that produced this product, and you wanted to sell 10X as many, what would you do?” Look for educated guesses or reasonable assumptions about the market for the product, who the target buyer is, how the market could expand, the constraints of production, etc. Those are the components that should drive the next best step for the product, it shouldn’t just be a random idea.
Note: It can be easy for PM candidates to prepare for this question. You can make sure they’re thinking on their feet by constraining the space they choose from. For instance, the example must be a physical or non-electronic product or one they have at home.
QUESTION 2 (Technical Skill): In as much detail as possible, tell me what happens when I type yahoo.com into my browser and hit enter. (Testing intellectual ability, communication skills and technical background.)
WEAK ANSWER: Their response might be rudimentary or confused. You could get an answer like, “I see the Yahoo homepage, right?”
The strongest candidates can answer this question in good detail, taking about five minutes to walk you through the process. This is a good level-setting question for product managers so you can see where they stand technically. They don’t have to hit every single action that happens. Watch out especially for candidates who say they’ve programmed in the last few years but are clueless about this question. That’s definitely a red flag.
If you think that candidates may have prepared for this type of question, you can mix it up by drilling them on specifics at various junctures of their response. Or you can ask them similar questions about the fundamentals of iOS or Android programming if they have a lot of mobile experience.
QUESTION 3 (Leadership): Tell me about a time when you disagreed with engineers and designers on your team. What did you do? (Tests communication, leadership and effectiveness within the company culture)
WEAK ANSWER: There will be allusion to finger-pointing, or mention of blame. The tone of their response will be generally negative, and you might see a dip in self awareness, complemented by a spike in defensiveness. They’ll be more concerned with smoothing over their role in the confrontation than sticking to the facts.
GOOD ANSWER: They’ll demonstrate leadership by diagnosing root causes of the conflict. They’ll show humility. “One candidate told me she couldn’t agree with her engineering and design team on one feature — they all wanted to build it and she didn’t. She said, ‘Okay let’s time-bound it. We’ll do the idea, but if it doesn’t pay off in four weeks, we’re going to change it to this other idea.’ I thought that was a great solution to avoid gridlock.” The candidate knew when to push back and when to disagree and commit.
A candidate who ends their response by saying what they learned from the situation and how they applied these lessons going forward should get serious bonus points.
QUESTION 4: What are all the implications of self-driving cars? (Tests strategic and analytical thinking and entrepreneurial spirit.)
WEAK ANSWER: A response that is boring, cursory, or disorganized. They might throw out some obvious answers, like unemployment for taxi drivers, or self-driving big rigs. But they won’t go deeper into the ripple effects in other industries that will create a whole new wave of businesses. They’ll stay in the inner ring of cause and effect.
GOOD ANSWER: Showing vision and imagination, they’ll paint you a picture of what could happen. Maybe car seats will be arranged in a circle around a coffee table! No one will own cars anymore, which means no one will have garages anymore. “I got an amazing answer to this one the other day: ‘Google will open-source the software for self-driving cars so that any manufacturer can build them, the way they offer Android,’” says Jackson. “I have no idea if that will be true or not, but I thought it was pretty creative.”
Most importantly, the answer should come packaged in some sort of organizational framework. Maybe they’ll say how life will change for drivers, and then the auto industry, and then urban planning. Ideas should be presented within themes, not as a free-association jumble.
QUESTION 5: What aspect of product management do you find the least interesting?
WEAK ANSWER: A PM who complains about doing nitty gritty work (e.g. taking notes, scheduling meetings) and implies that these things are beneath them.
GOOD ANSWER: A great PM understands that they need to lead from the back, and they relish their role as an unsung hero. The candidate doesn’t have to say they love the tough nitty-gritty stuff, but they should get points for acknowledging the grungy parts of PM work and why it’s important to be in service to the team and mission their supporting.
QUESTION 6: Why do you want to work at this company or on this product?
WEAK ANSWER: “X industry/company is getting a lot of buzz. Everyone is talking about it. It’s really hot right now.”
GOOD ANSWER: Clearly passionate about the industry, company or project. Look for specific ideas and plans for what they’d want to do and how they want to make things better. This indicates that they really did their homework and have thought deeply about the company. In particular, keep your eyes peeled for long-term thinking, which indicates commitment to the industry or type of product. For example, is the person talking about what robots or drones will look like in 5 or 10 years? Or do they just talk about how robots and drones are exciting now? Here are some examples:
I’ve always wanted to work in X industry, I’ve done Y and Z in the last couple years to really prepare for this career move.
Company X has a huge competitive advantage because of Y.
I have been using product X for a while, and I really like feature Y. I think feature Z could really improve growth/engagement/monetization and here’s why...
You want people who are excited about the space, not just this one opportunity.
For more on finding, vetting and closing the best product management candidates, read more from Todd Jackson here.
First Round Review is committed to giving you, our amazing audience, all the tools you need to hire the best team for your company. So please stay tuned for more stories about interviewing and hiring. We promise to keep you posted on the best new questions, thinking and exercises leaders across the industry are using to recruit winning talent.
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