How to get better at interviewing so that build a team to help you win

January 17, 2024

August 25, 2022

Most companies are terrible at interviewing

Early-stage startups are even worse. Startups waste a ton of time in what Foundry’s Chris Moody calls “who knows“ interviews. “Who knows” interviews leave both the interviewer and the candidate thinking, “Maybe that person/job was great, who knows?” The recipe for “who knows” interviews is:

Graphic of bad interview: Unprepared interviewer talks most; candidate aims to please, ends in 'Who Knows?

“Who knows” interviews are a horrible use of your time for founders, hiring managers, and candidates. They are a result of an unorganized recruiting process. 

TLDR: Create a process, prepare for interviews, interview better, hire better

  • Interviews aren’t standalone events, they are part of an entire Talent Acquisition (TA) process
  • Use different interview formats for different purposes 
  • Use written communication to test a candidate’s written abilities, understand why they are interested in this role at your company, and why they could be a fit
  • Use short interviews to quickly test if a candidate could do the job and work well with your team
  • Use long interviews to get to know the person behind the application, and assess if they are someone you’d want to work with
  • Always have other team members interview candidates
  • Have a two-way conversation, don’t hog the conversation or oversell the role or your company
  • Block 5 minutes after every interview to write down your initial thoughts, following this guide

Interviews are just one part of the TA process:

As Snowflake CEO Frank Slootman says, interviews are just a “sniff test” that give you a quick glimpse into whether a candidate could be good or not for the job you’re hiring for. Interviews as standalone events give you an incomplete picture, but interviews are not independent events, they are part of an entire Talent Acquisition process, which includes precruiting, interviewing, working with candidates, and referencing them. 

Talent Acquisition Process

Recruitiment process guide: PrecrRecruitiment process guide: Precruiting, interviewing, working with candidates, candidate referencesuiting, interviewing, working with candidates, candidate references

* The 14 questions to answer before recruiting startup executives

** Building a recruitment roadmap to find the right candidate for your startup

*** How to build a “Work With Us” career page to attract top talent

Improving each part of your talent acquisition process helps you build the right team, avoid the costs of firing and re-hiring, and gives you a major competitive advantage. Improve your interview process, and you’ll improve your team.

Never hire alone: Involve your team members in the interview process

Founders should make final decisions for all hires at early-stage startups with ~30 team members or less. However, you shouldn’t be the only one involved in the interview process. 

You are more likely to hire someone who is like you. Introverts are more likely to hire other introverts, fast talkers are more likely to hire other fast talkers. Hiring people like you isn’t always a bad thing, especially when you are trying to build a specific type of culture early on, but only hiring people like you can be a false proxy that makes you miss potentially great candidates. Even if you’re making the final decision on who to hire, you should have other people on your team interview candidates. A general guideline for founders is:

  • When you are 15 people or less, 1 other person should interview candidates. You make the final decision.
  • When you are 15-30 people, 1-2 other people should interview senior candidates, while 1 other person should interview junior candidates. Train your direct reports on how to interview and hire during this time, but still make the final decision.
  • When you are 30-60 people, 2 other people should interview candidates. You can still interview candidates, but unless you are hiring for a senior role, train a direct report of yours to be the final decision-maker.
  • When you have 60+ people, you should only be involved in interviews for senior roles.

Different interviews for different needs: written interviews, short interviews, and deep-dive interviews

During the interview process, your goal is to figure out if a candidate:

  • could do the job well
  • is inspired to work with you on your mission
  • could push your company forward, and 
  • is someone you want to work with

Companies usually schedule calls with any candidate who looks remotely relevant for the role, leading to aimless first calls and wasted time. Avoid this by defining what you want to know about the candidate and choosing the most relevant of these 3 interview formats:

Written interviews: Use email interview questions to filter out candidates who are clearly not a fit for the role. In written communication, get answers to:

  1. Why is the candidate interested in working with us?
  2. Why is the candidate interested in this specific role?
  3. In one sentence, how could this person be a fit? 

Short, 15-minute “YC style” interviews: Use short interviews to quickly test if a candidate could do the job, and if they could fit and add to your team. Use 15-minute interviews to get answers to:

  1. Does this candidate have substance?
  2. Could I picture them on our team?
  3. Do they seem like they fit and could add something we don’t have to our team?

Deep-dive interviews: Use deep-dive interviews to get to know the person behind the CV. In long-form interviews, get answers to: 

  1. What motivates the candidate?
  2. What are the candidate’s core values? 
  3. Is this someone I want to work on difficult things with? 
  4. Am I confident they could do the job on day one?
  5. Does the candidate have all the information they need about us?

Written interviews:

Most companies jump from reviewing CVs to a first call with candidates. Use written communication to filter as many candidates as possible and avoid getting on calls with mismatched candidates. Many candidates will filter themselves in written communication, by either giving little thought into their responses, responding in a way not aligned with your company’s mission or values, or by not responding at all. You can usually filter around half of your candidate pool with written questions. The goal of the written stage is to add a quick gut-check filter, not to add an unnecessarily big hurdle to the process which could make good candidates pass. Ask only the questions you need to know, don’t force candidates to write an essay back to you.

What to look for in written communication: Writing is an important meta-skill for any role you are hiring for. Look for clear and concise written communication. It’s a yellow flag if the candidate’s responses are indirect or unclear. 

What types of hires should I use written communication for? Use written communication with candidates for all types of roles. It becomes more important when you are recruiting for more junior roles, or looking to hire high-slope people. Only schedule calls with candidates when you can answer the following questions:

  1. Why is the candidate interested in working with us?
  2. Why is the candidate interested in this specific role?
  3. In one sentence, how could this person be a fit? 

What types of hires should I not use written communication for? If you can already answer the 3 questions above, you should schedule a call with the candidate. If someone you trust recommends a senior candidate for an important role and you already know the answers to the three questions above, set up a call.

Recommended structure: Email the candidate your follow-up questions directly. Whether you have one question or six, ask them all in one email clearly to avoid unnecessary back and forth. Be clear with the questions you ask and set the standard for clear written communication at your company.

Short, 15-minute “YC style” interviews:

YC is famous for its 10 minute zoom interviews with startups. In 10 minutes, founders need to explain what their company does, why their team will win, and talk about their traction. YC looks for clarity and direct communication, and discards startups that ramble and use jargon.

You can use short interviews to do a quick first assessment of candidates as well. Scheduling 15-minute interviews is a feature, not a bug. By putting a time constraint on the interview, you test if the candidate is direct, clear, and nimble. You also show the candidate that your company rewards clear communication, values its time, and moves fast. 

In a 15-minute interview, you can cover all important experiences the candidate has had, ask any follow-up questions, and allow time for the candidate to ask you one or two questions. 

What to look for in 15-minute YC-style interviews: Look for clear and direct candidates who give authentic answers and don’t ramble. Your goal is to get clear answers to:

  1. Does this candidate have substance?
  2. Could I picture them on our team?
  3. Do they seem like they fit and could add something we don’t have to our team?

When to use 15-minute interviews: Instead of 30-minute first-round interviews, opt for 15-minute ones. 30 minutes is too short for depth but too long for a quick assessment, often leading to disorganized, time-wasting conversations. 

With few exceptions, first-round interviews should be 15-minutes long. This works well for junior roles when you’re looking to hire looking to hire high-slope people. Once you’ve screened junior applicants through written communication, have a 15-minute interview with them. 

Recommended structure: 

  • Before the interview: Set expectations with the candidate. Tell them the guidelines over email first, something like: “This is a 15-minute interview, we value clear communication in our company and we’re looking for concise and clear answers to make sure we can cover everything we need to in 15 minutes. Looking forward to our conversation.” 
  • During the interview: Start by introducing yourself. Then, repeat the expectations of the interview, the same details you put in the email. Avoid extended small talk, while not being rude.

Some questions I like to ask: Start with some of these questions, then ask follow-up questions for more clarity. Keep the conversation lively. Use these questions as a general guide, not a checklist.

Tell me about yourself, why are you interested in working with us, and in this role?

  • Candidates tend to ramble on this one. The more clear and concise the answer, the better. If the person is talking for more than 3 minutes, remind them that you only have 15 minutes. Ask any follow-up questions you have. Look for candidates who show they are genuinely interested in your company, and not giving boilerplate answers.

What has been your biggest achievement? 

  • This question allows the candidate to talk about what they are passionate about. The best answers are clear and authentic. The worst are unclear, rambling, and unfocused. 

Who was your manager at (insert their last role), and what will they say about you in a reference check?

  • Phrasing the question this way pushes people to answer honestly, and helps you understand exactly how senior the candidate was in their previous role, which is sometimes hard to tell on paper.

Why did you leave (insert former position)?

  • If they are still at their current job, ask them why they left their previous role.

Is there anything I didn’t ask that you want to say? 

  • Always give candidates a chance to say something important that you didn’t ask.

We have (x minutes) left, do you have any questions for me?

Use these six questions to spark conversation, and tailor your follow-ups to their answers. Depending on what you’re looking for, you can ask different or additional questions, like the one’s included in this article.

“But this feels short!” Many people feel 15 minutes is too short for a first interview and prefer 30-minute first calls. You need to become a good interviewer to master the 15-minute interview. If you've always done 30-minute interviews, you can work your way gradually to 15-minute interviews by trimming them down to 25 minutes, then to 20. With practice, you’ll be able to lead great 15-minute first interviews. 

Deep dive interviews 

After written interviews and short interviews, you should have a shortlist of candidates. Now is the time to invest in a longer, 50-minute conversation.

Deep-dive interviews are built for you and the candidate to get to know each other fast and see if you’d want to work with each other. Get a sense of who the candidate is, what drives them, and their values, and see if they are the type of person you’d want to work with. You are hiring the person, not the CV, and deep-dive interviews are for getting to know the person behind the CV. 

Deep dive interviews should be 1:1 interviews for early-stage startups. In later-stage startups, you can start to use panels of 2-3 people to interview a candidate. 

What to look for in deep-dive interviews: You’ll find out a lot about the person during deep-dive interviews. At a minimum, you should be able to answer: 

  1. What motivates the candidate?
  2. What are the candidate’s core values? 
  3. Is this someone I want to work on difficult things with? 
  4. Am I confident they could do the job on day one?
  5. Does the candidate have all the information they need about us?

Who you should use deep-dive interviews with: Have deep-dive interviews with no more than 5 candidates and ideally 3-4 in a first group, adding more people only if you don’t have certainty on existing candidates. Deep-dive interviews can be panels with 2-3 people from your team, or 1:1 conversations. 

Some questions I like to ask: You’ll need to ask role-specific questions to get a feel for a candidate's ability to do the job. I haven’t included role-specific questions here, as those will be specific to the role you are hiring for, which you will have answered in your 14 questions to answer before recruiting startup executives.

It’s ok to have more small talk with the candidates at the start of deep-dive interviews. Small talk can help you get to know the candidate, so it’s ok to start with a couple minutes of it at the top of the interview.

The following questions help you break through the usual interview stiffness and quickly get to know someone better. Don’t ask every one of these questions in every long-form interview you do. I recommend copying this list of questions and saving it as a document that you can reference before or during interviews.

1. If you and (your company) don’t work out, and either you decide to leave, or we decide to let you go in 3 months, what do you think would be the reason?

  • Why you should ask it: This is a “pre-mortem question” used to identify any major risks in hiring the person. Some VCs ask a similar question to startups to suss out potential risks in investments. Hiring someone is a key investment for you, which is why it’s worth asking candidates. Don’t rush to fill the air space after asking this question, the candidate usually needs time to think. 
  • What to look for: 2 things:
  • Is the candidate thoughtful enough to give you a real answer? If they say, “I don’t see any way that this wouldn’t work,” they are either being dishonest or aren’t introspective enough to see their weak points. 
  • If you hire the candidate, their answer to this question gives you a list of potential pitfalls that you can actively avoid from day one. For example, if the candidate says, “I could see there being frustration from both of us if after 3 months my objectives aren’t clear and we don’t have clear expectations for what success looks like in my role,” you know that clarifying objectives and expectations is your number 1 priority as their manager. This helps you aggressively integrate the candidate once you’ve hired them.

2. What are your values? What are the core values you bring with you to all different parts of your life (personal, professional, etc.)

  • Why you should ask it: This question lets you connect with the interviewee as a person, not just a candidate, and see if their values align with yours.
  • What to look for: There are 2 things to look for:
  • “Cultural fit.” Are the candidate’s values aligned with your company's values? They don’t have to be identical, but they can’t be opposed.
  • Do they have a clear answer? If someone isn’t clear with what drives them, how can you be sure that they will be driven to work on your startup’s mission?

3. What would you do in the first 30 days on the job?

  • Why you should ask it: This shows how good someone is at prioritization. You can only do so much in 30 days, and prioritization and focus are key.
  • What to look for: Realistic and clear goals. If the candidate answers with too many ideas, they may struggle to prioritize and finish what they start.

4. Walk me through your last project (or job). What should have been different?

  • Why you should ask it: This question intentionally avoids the direct question “what should you have done differently?” This intentional ambiguity lets the candidate choose to talk about things the company could have done differently, or what they could have done differently.
  • What to look for: Look for someone who answers this question by saying “I could have done X differently, which would have had Y effect.” If the candidate deflects blame onto others, they’ll likely do the same when something goes wrong in your startup.

5. How are you most likely misunderstood?

  • Why you should ask it: This is a hard question for most people to answer. If you don’t get a good answer from questions 1 or 3, ask this one.
  • What to look for: Look for genuine answers that show how well a person knows themselves, and also how they may be perceived during stressful situations.

6. What life experiences have had the most impact on who you are today?

  • Why you should ask it: if you are hiring for very senior positions, and feel the candidate is comfortable being honest with you, this question helps you quickly get to know the person. 
  • What to look for: This question usually gives you the best insight into who the person is. When someone asks you about the candidate, their answer to this question will most likely be the first thing that pops into your head.

7. What important truth do very few people agree with you on?

  • Why you should ask it: This is Peter Thiel’s favorite question to ask. This question can help you get to know a person that you’ll be working on hard stuff with.
  • What to look for: Unique answers that very few people truly agree with. 

8. Which company cultures did you like and which did you not like, and why?

  • Why you should ask it: It allows you to see how the candidate talks about the company and the people they have worked with.
  • What to look for: Candidates should have some positive examples of company cultures, and some negative examples. If they only give positive examples, they are probably lying. If they give only negative examples, they are probably going to think your startup culture is bad too. Listen to what they liked and didn’t like and you’ll get an idea of if they are going to be a cultural fit.

9. What’s the last awesome thing you learned?

  • Why you should ask it: Their answer shows if they are genuinely interested in learning new things. Startups need people who are constantly growing and learning new things. 
  • What to look for:  There’s always stuff to learn in startups, and high-slope people will always have interesting answers. 

10. What do you think everyone on the team should read?

  • Why you should ask it: This question shows you what the candidate is passionate about, helping you get to know them better.
  • What to look for:  Look for a passionate answer, with a strong opinion, and a good “why.”

Wrapping up the interview: Always leave 5-10 minutes at the end of the interview for the candidate to ask you questions. The question section is often the most important part of the interview both for you and the candidate.

  • Why you should do it: It gives the candidate a chance to lead the conversation, and a chance for you to answer questions directly, and get the candidate excited about the chance to work with you on your mission. 
  • What to look for: The best candidates ask tough questions that they genuinely care about the answer to. If a candidate has no questions, or only asks about compensation or perks, this is a red flag. You want candidates to ask questions about the business and the role, including the tough questions.

This list of questions isn't extensive, but it is a good starting point. There are other good resources like Lenny Rachitsky's How to learn the most about a candidate from a single interview question

The post-interview checklist

Block 5-10 minutes after every short and deep-dive interview you have to write down your thoughts while they are fresh on your mind. Immediately after you leave the video call, or leave the candidate in person, write down your first impressions. I suggest the following format:

1. Could the candidate be a good fit?

  • Hell yes! (We have to hire them)
  • They could be. (My hunch says yes)
  • I’m not sure (I didn’t get clarity)

2. Rate the candidate 1-10 without using 7:

3. Describe the candidate in 3 adjectives:

4. Is the candidate someone I think I’d like to work with?

  • Yes
  • No 

5. First impressions:

Answer these questions immediately after every interview you have. Then, you can run to your next meeting or put out a fire happening somewhere else in your startup. 99% of the time when you come back to your checklist later, you’ll be able to decide clearly if you want to continue or not with the candidate.

How to sell the best candidates to join your startup

The best talent can choose to work anywhere they’d like. Your job is to convince them to join your mission and your team on your quest to solve the problem you’ve set out to solve. When founders interview a “hell yes” candidate, they typically go into selling mode. 

Overselling a candidate on a role usually backfires. Top talent wants to trust you as a leader, believe in your mission, and know that you’re the best place for them to work for the next few years, not an over the top sales pitch. Give top candidates as much clarity as possible, answer their questions directly, and be honest and upfront with them about your company and the role. 

Investing in pre-work helps do the selling for you. Answer the 14 questions you need to know before recruiting and you’ll be able to give clear and direct answers for what you need from the candidate. Let your work with us page show the candidate what your culture is like. Build a team of A players and high slope people that top candidates will want to work alongside.  

Tips for video or in-person interviews

  • Show up on time. Show up late and you show candidates that you are disorganized  
  • Turn your camera on. If you’re doing a video interview, turn your camera on
  • Avoid rescheduling at the last minute. Reschedule 5 minutes before the interview and you’re telling candidates that they aren’t important
  • Show up prepared. Review the candidate’s application, any written communication that you’ve had with them, and any notes from other people who have interviewed that candidate before the interview
  • Talk less. Anna Papalia, CEO and author of Interviewology, says that on average, interviewers do 80% of the talking during interviews. You are there to interview and have a two-way conversation, not to give a speech. Don’t talk at the candidate
  • Don’t ask leading questions, don’t hint at a “correct answer.” Often, interviewers tilt their hand and suggest the answers they want, leading candidates to answer with what they think is the “correct” answer. You want authentic and honest answers.
  • Leave moments of silence. The best interviews are thoughtful conversations. Give the person you are interviewing time to think. Breathe, it’s ok to have moments of silence. 
  • Block 5-10 minutes after the call for yourself to write notes. Write down your impressions immediately after the interview. Regardless of whether you had the interview in person or virtually, make sure to write down your thoughts while they are fresh on your mind, at a minimum filling out the post-interview checklist 
  • Give feedback to all candidates you interview, never ghost them. Close the loop with every candidate who applies to your company. The more time you’ve spent with the candidate, the more thoughtful your feedback should be for the candidate. 
  • Upload all of your notes into whatever software you use, whether you have an ATS, or you’re just uploading notes into a shared Google drive. Your team and future self will thank you.

What do I do after a long-form interview?

Following these tips will lead to a more successful process of interviewing candidates. After finishing interviews, you should work with the person before you make a full-time hire.

Interviews aren’t just for assessing candidates, they help reinforce your culture and improve employee branding 

Give candidates a positive experience, whether you hire them or not. You want candidates to leave the interview process and be excited about your company and your mission. Don’t be lazy or unfocused with your interviews. As Ring Nishioka of BigDoor and HRNasty says:

“Interviewing sets the tone of the culture to everyone that comes into the company… If you want a culture of teamwork, reinforce that during the interview process. If you want a culture of “always closing” reinforce that.” 

Your interviews should be a microcosm of what working with you is like. Don’t sugarcoat things, you should openly talk about the things that some candidates might think are downsides. Levels Cofounder and CEO Sam Corcos says he “shares a lot of information during the interview process of all of the reasons why you probably won’t want to work here.” Being upfront about what you expect from team members helps candidates self-select out of the process if they realize they aren’t going to fit.

Regardless of how the candidate performs in the interview, you want them to leave with a clear understanding of what it would be like to work with you.

Interview better to build a better team

It’s almost impossible to build a great company without a great team. Interviews are an important part of the talent acquisition process that most companies get wrong. 

You won’t become a perfect interviewer overnight, but if you start to use some of the tips in this article, over time you and your company will create a purposeful and intentional interview process. Start interviewing better and you’ll start hiring better and building the team that can help your startup level up.