Founder Resources
How VC funds evaluate and identify strong startup leaders and teams
This article is the second in a series of three articles about building a team that will help you raise $10M+ in Latin America.
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:
“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.
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.
* 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.
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:
During the interview process, your goal is to figure out if a candidate:
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:
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:
Deep-dive interviews: Use deep-dive interviews to get to know the person behind the CV. In long-form interviews, get answers to:
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:
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.
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:
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:
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?
What has been your biggest achievement?
Who was your manager at (insert their last role), and what will they say about you in a reference check?
Why did you leave (insert former position)?
Is there anything I didn’t ask that you want to say?
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.
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:
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?
2. What are your values? What are the core values you bring with you to all different parts of your life (personal, professional, etc.)
3. What would you do in the first 30 days on the job?
4. Walk me through your last project (or job). What should have been different?
5. How are you most likely misunderstood?
6. What life experiences have had the most impact on who you are today?
7. What important truth do very few people agree with you on?
8. Which company cultures did you like and which did you not like, and why?
9. What’s the last awesome thing you learned?
10. What do you think everyone on the team should read?
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.
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
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?
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?
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.
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.
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.
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.
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.