Early-stage hiring / The questions startups should be asking in interviews

7m read

Now that you’ve had a taste of what the interview process is like , the question comes up of what exactly you should be asking candidates. If you’ve ever applied for a job yourself, you might already have an intuitive sense of what kinds of questions you thought worked well and which ones didn’t. You might even disagree with many of the questions you’ve been asked. More likely, the questions have become so ingrained that you don’t question their validity.When candidates are strung along for 3, 4, even 6+ interviews, that can be attributed to not being strategic and instead veering off into conversations that over-index on perhaps one aspect of assessing candidate fit (i.e. personality) and not enough on the others. When you don’t have a strategic plan for each stage/interview, especially as a founder who's got a million other things to do, you may end up having conducted the interviews like clockwork but end up on the other side feeling like you still don’t have enough information to choose one candidate over another in what feels like hiring limbo. In order to design an effective candidate experience, you should spend time thinking about your goals for each step in the interview process , and what questions will help you assess the answer in relation to those goals. So instead of a prescriptive list of must-ask questions, here are three categories that you should incorporate into your interviews, with examples of questions you can pull from. 1. Assessing for overall startup fit“The first hires should all be “startup people” — they are good with ambiguity, have an innate ability to execute, aren’t afraid to take risks and fail, and are willing to roll up sleeves to help find solutions to problems as they arise.” —Gale Wilkinson, VC As mentioned in our article on what makes a good startup employee , there are specific traits and qualities that lend themselves to people who are more likely to thrive in a startup environment. Part of your interview process should involve trying to assess for these traits with questions like: What do you value in a job? What was your last failure and what did you learn from it? Which parts of your current position bring you the most stress? Where would you like your career with ___ to take you? (An updated version of “Where would you like to be in five years?” with the added bonus of relating specifically to your company and understanding their drive and motivation.) Think about something you deeply love. Take a few minutes to prepare and teach it to me in a few minutes. (Chamath Palihapitiya, CEO of Social Capital with a blurb on why this kind of question, which Google also uses a version of, can be effective) Out-of-the-box questions like this last one are great for assessing overall startup fit because they allow you to gain actual insight into a person’s personality, thought process, and ability to think on their feet—among other things like self-awareness, creativity, and grit. Here are a few creative ideas collected from across the Twitterverse and beyond: What question should we ask you that we haven’t asked? (@jereshiahawk) What experience do you think you can get here that you can’t get elsewhere? (@MrPeopleOps) What secret project or idea are you working on or thinking about that not many people would know about you? (@SALBshow) A screwdriver and a screw together cost $2.20. The screwdriver costs $2 more than the screw. How much does the screw cost? (Mark Anderson, CEO of Complete Express Foods. Give this one a try yourself: it assesses critical thinking and active listening skills.) Tell me about a time you saved the day. (@Pam_Rubin1) Through the interview process, you should also aim to uncover whether or not they’re a doer, someone who really enjoys building and isn’t just intellectually interested in the idea of growth. They may be future leaders at your startup, but for now, they need to execute. What you’re really looking for is proof of this ability to execute. So, for example, when you ask them what they value, do you get the sense that they really like to do and build things and not just sit around talking strategy? Andrew Chen writes here about not hiring anyone more senior than a team leader or director for this reason. 2. Assessing for values matchYour early employees not only impact culture, they very much shape it. And while culture evolves over time, values are the core of any company and brand. Values are what differentiate one company from another, and a strong reflection of values will be evident throughout the product itself, stewarded by you and your early employees. Here are a few general questions that help you assess for a values match, to start: Tell me your life story. (Shopify, with an explanation of how this conversational approach lends itself to getting to know you, your values, and how you might fit into their values of impact, readiness, trust, engagement, and self-awareness.) What stood out about our company that led you to apply? (Listen closely: do they mention the things your company actually cares about, or do they mostly refer to surface-level things?) To get more up close and personal, work backwards from your company values, then engineer your questions. Examples: When have you worked with a group of diverse people? What do you think are the 3-5 most important steps to establishing a relationship and building credibility with a new team/team member? Please share an example of how you were able to build credibility with a new group. (Unity, with a great article on why they ask this and how it helps them assess for the company’s core value of building relationships.) How would you go about building that? (Airbnb, to help them identify candidates that fit into their “builder-not-maintainer” value, also great to help assess for that startup star quality mentioned above.) What feedback do you have for our interview process? (An example of a great question to ask if your company values trust, feedback, growth, and transparency.) Tell me about a time you gave your boss critical feedback. What was it and how did you approach it? (Jeff Tetz, CEO of Results. Another example of a great question to ask if you’re trying to assess the ability to be constructive and kind, something that isn’t easy for many people.) 3. Assessing for role matchThis is where companies tend to focus the majority of their interviews, especially with behavior and situation-based questions that usually sound something like this:Tell me about a time when you did ___.These types of questions help companies learn from what someone has already done. You should include a few of these but keep in mind that they tend to rely on strong memory; and a well-prepped candidate may perform better. Preparation counts for something but in the startup world, it certainly doesn’t count for everything.Here are examples of other questions that assess what behavior-based questions aim to, while providing a more well-rounded view of how they might actually be suited to the role you’re hiring for—along with the results of any skills tests, of course. What stood about the role that led you to apply? Tell me about one of your favorite projects that you’ve worked on? Questions that reveal their thought process specifically when it comes to challenging questions and topics related to the role or industry. An example: How do you think we can attract an even larger customer base? (From Netflix, who is currently faced with the challenge of a declining subscriber base.) Questions that reveal their depth of knowledge and strategic and analytical abilities when it comes to their industry. For example: What brands do you think are doing a great job at _ and why? What not to askWhile the following are considered standard interview questions, they tend to be filler questions that most people expect and have a well rehearsed answer to that may or may not be the truth but is most likely just a rendition of what they think you want to hear. For example: What’s your biggest weakness? (Cue “I’m a perfectionist” or “I care too much about my work”) Do you like working alone or in a team? (Cue “It depends! I genuinely enjoy both.”) Instead, think about whatever you’re trying to learn about them and work backwards to discover the answer as part of the flow of an authentic conversation. This typically comes from asking open-ended questions, or being a skilled interviewer. For example, if the role is highly independent and you really need someone who can manage themselves and work alone, instead of asking “Can you work by yourself?” where the signal of what you are looking for is evident in how you’ve framed the question, you can ask, “What does an ideal work day look like for you?” Going a bit further to keep the question grounded in reality, you can ask a variation: “Think about your best day at work. What was happening and why was it your best day?” You’ve disarmed the candidate with a question that has a positive association, and encouraged a response that is hard to fake because you’ve asked them to remember something good; when they do, under the pressure of an interview, it’s really difficult to not say the truth—and that’s what you want. You’re looking for real insights, not perfectly rehearsed responses. "Instead of hitting your candidates with the same old, 'What are your strengths?' question, this is a more organic way to uncover their strengths." —Darren Bounds, CEO of Breezy HR

Follow page

The questions startups should be asking in interviews

Now that you’ve had a taste of what the interview process is like , the question comes up of what exactly you should be asking candidates. If you’ve ever applied for a job yourself, you might already have an intuitive sense of what kinds of questions you thought worked well and which ones didn’t. You might even disagree with many of the questions you’ve been asked. More likely, the questions have become so ingrained that you don’t question their validity.

When candidates are strung along for 3, 4, even 6+ interviews, that can be attributed to not being strategic and instead veering off into conversations that over-index on perhaps one aspect of assessing candidate fit (i.e. personality) and not enough on the others. When you don’t have a strategic plan for each stage/interview, especially as a founder who's got a million other things to do, you may end up having conducted the interviews like clockwork but end up on the other side feeling like you still don’t have enough information to choose one candidate over another in what feels like hiring limbo.

In order to design an effective candidate experience, you should spend time thinking about your goals for each step in the interview process , and what questions will help you assess the answer in relation to those goals.

So instead of a prescriptive list of must-ask questions, here are three categories that you should incorporate into your interviews, with examples of questions you can pull from.

1. Assessing for overall startup fit

“The first hires should all be “startup people” — they are good with ambiguity, have an innate ability to execute, aren’t afraid to take risks and fail, and are willing to roll up sleeves to help find solutions to problems as they arise.” —Gale Wilkinson, VC

As mentioned in our article on what makes a good startup employee , there are specific traits and qualities that lend themselves to people who are more likely to thrive in a startup environment. Part of your interview process should involve trying to assess for these traits with questions like:

What do you value in a job?
What was your last failure and what did you learn from it?
Which parts of your current position bring you the most stress?
Where would you like your career with ___ to take you? (An updated version of “Where would you like to be in five years?” with the added bonus of relating specifically to your company and understanding their drive and motivation.)
Think about something you deeply love. Take a few minutes to prepare and teach it to me in a few minutes. (Chamath Palihapitiya, CEO of Social Capital with a blurb on why this kind of question, which Google also uses a version of, can be effective)

Out-of-the-box questions like this last one are great for assessing overall startup fit because they allow you to gain actual insight into a person’s personality, thought process, and ability to think on their feet—among other things like self-awareness, creativity, and grit. Here are a few creative ideas collected from across the Twitterverse and beyond:

What question should we ask you that we haven’t asked? (@jereshiahawk)
What experience do you think you can get here that you can’t get elsewhere? (@MrPeopleOps)
What secret project or idea are you working on or thinking about that not many people would know about you? (@SALBshow)
A screwdriver and a screw together cost $2.20. The screwdriver costs $2 more than the screw. How much does the screw cost? (Mark Anderson, CEO of Complete Express Foods. Give this one a try yourself: it assesses critical thinking and active listening skills.)
Tell me about a time you saved the day. (@Pam_Rubin1)

Through the interview process, you should also aim to uncover whether or not they’re a doer, someone who really enjoys building and isn’t just intellectually interested in the idea of growth. They may be future leaders at your startup, but for now, they need to execute. What you’re really looking for is proof of this ability to execute. So, for example, when you ask them what they value, do you get the sense that they really like to do and build things and not just sit around talking strategy? Andrew Chen writes here about not hiring anyone more senior than a team leader or director for this reason.

2. Assessing for values match

Your early employees not only impact culture, they very much shape it. And while culture evolves over time, values are the core of any company and brand. Values are what differentiate one company from another, and a strong reflection of values will be evident throughout the product itself, stewarded by you and your early employees. Here are a few general questions that help you assess for a values match, to start:

Tell me your life story. (Shopify, with an explanation of how this conversational approach lends itself to getting to know you, your values, and how you might fit into their values of impact, readiness, trust, engagement, and self-awareness.)
What stood out about our company that led you to apply? (Listen closely: do they mention the things your company actually cares about, or do they mostly refer to surface-level things?)

To get more up close and personal, work backwards from your company values, then engineer your questions. Examples:

When have you worked with a group of diverse people?
What do you think are the 3-5 most important steps to establishing a relationship and building credibility with a new team/team member? Please share an example of how you were able to build credibility with a new group. (Unity, with a great article on why they ask this and how it helps them assess for the company’s core value of building relationships.)
How would you go about building that? (Airbnb, to help them identify candidates that fit into their “builder-not-maintainer” value, also great to help assess for that startup star quality mentioned above.)
What feedback do you have for our interview process? (An example of a great question to ask if your company values trust, feedback, growth, and transparency.)
Tell me about a time you gave your boss critical feedback. What was it and how did you approach it? (Jeff Tetz, CEO of Results. Another example of a great question to ask if you’re trying to assess the ability to be constructive and kind, something that isn’t easy for many people.)

3. Assessing for role match

This is where companies tend to focus the majority of their interviews, especially with behavior and situation-based questions that usually sound something like this:

Tell me about a time when you did ___.

These types of questions help companies learn from what someone has already done. You should include a few of these but keep in mind that they tend to rely on strong memory; and a well-prepped candidate may perform better. Preparation counts for something but in the startup world, it certainly doesn’t count for everything.

Here are examples of other questions that assess what behavior-based questions aim to, while providing a more well-rounded view of how they might actually be suited to the role you’re hiring for—along with the results of any skills tests, of course.

What stood about the role that led you to apply?
Tell me about one of your favorite projects that you’ve worked on?
Questions that reveal their thought process specifically when it comes to challenging questions and topics related to the role or industry. An example: How do you think we can attract an even larger customer base? (From Netflix, who is currently faced with the challenge of a declining subscriber base.)
Questions that reveal their depth of knowledge and strategic and analytical abilities when it comes to their industry. For example: What brands do you think are doing a great job at _ and why?

What not to ask

While the following are considered standard interview questions, they tend to be filler questions that most people expect and have a well rehearsed answer to that may or may not be the truth but is most likely just a rendition of what they think you want to hear. For example:

What’s your biggest weakness? (Cue “I’m a perfectionist” or “I care too much about my work”)
Do you like working alone or in a team? (Cue “It depends! I genuinely enjoy both.”)

Instead, think about whatever you’re trying to learn about them and work backwards to discover the answer as part of the flow of an authentic conversation. This typically comes from asking open-ended questions, or being a skilled interviewer.

For example, if the role is highly independent and you really need someone who can manage themselves and work alone, instead of asking “Can you work by yourself?” where the signal of what you are looking for is evident in how you’ve framed the question, you can ask, “What does an ideal work day look like for you?” Going a bit further to keep the question grounded in reality, you can ask a variation: “Think about your best day at work. What was happening and why was it your best day?” You’ve disarmed the candidate with a question that has a positive association, and encouraged a response that is hard to fake because you’ve asked them to remember something good; when they do, under the pressure of an interview, it’s really difficult to not say the truth—and that’s what you want. You’re looking for real insights, not perfectly rehearsed responses.

"Instead of hitting your candidates with the same old, 'What are your strengths?' question, this is a more organic way to uncover their strengths." —Darren Bounds, CEO of Breezy HR

Suggested