Blog > Startup Culture

Five Questions to Prepare for Your Next Startup Interview with Eight Sleep's Co-Founder & CEO Matteo Franceschetti

Eight Sleep is the world’s first sleep fitness company, on a mission to fuel human potential through optimal sleep. Founded in 2014, Eight Sleep leverages 51 million hours of sleep intelligence data to design products, content, and tools to restore individuals to their peak energy and achieve sleep fitness. 

Eight Sleep has raised over $160M from top investors, like Y Combinator, Khosla Ventures, Founder’s Fund, Naval Ravikant, and our very own Anthony Pompliano. 

Eight Sleep was named one of the World’s 50 Most Innovative Companies of 2023 by Fast Company, alongside companies like OpenAI, Canva, and Google DeepMind. Eight Sleep was also recognized twice by TIME’s Best Inventions of 2018 and 2019

Eight Sleep Co-Founder Matteo Franceschetti went on The Twenty Minute VC (20VC) Podcast, hosted by Harry Stebbings, where he shared a ton of valuable advice on building a team and funding a startup. 

Matteo runs the exact same interview playbook for everyone he interviews. He’s now used this playbook to interview thousands of candidates, which allows him to identify “red flags” very quickly.

In the interview, Matteo goes through each of the candidate's previous jobs and asks them five questions about each of their previous roles. 

How did you find your previous job and what did they hire you for? 

It’s helpful for Matteo to understand how someone found their job because he can see if the candidate was recommended by someone, like their previous manager. 

Although it’s not a “red flag” if someone didn’t land their previous role via recommendation, seeing that other people are willing to stick their neck out for a recommendation is a great sign.

What is your biggest achievement? 

Although Matteo calls this a “stupid question,” he says it’s one of the greatest questions. The best people respond to this question with hard data.

For example, a good answer is something like, “I improved the website's conversion rate from 8% to 9.2% by doing A, B, and C.”

A bad answer lacks hard data and has a lot of “fluff,” like “I bonded with my teammates.” An answer like this shows that the candidate likely did not have meaningful achievements or hasn’t adequately reflected on their past contributions.

What has been your lowest point? 

When asked this question, many people will start complaining, and Matteo is able to see what they complain about.

Responses like, “My manager never gave me the right task,” or “I wasn’t given enough freedom to operate,” provide valuable insight into a person’s agency and how they deal with problems.

Who is your manager, and what are they going to say about you when I do your reference check? 

Including the phrase “in your next reference check” forces people to tell the truth about their relationship with their manager.

Some people become rigid when asked this question. This indicates that they likely did not have a great relationship with their previous manager, and it’s probably helpful to look into this more deeply.

If someone describes an excellent working relationship with their previous manager, they are likely being honest since they know Matteo will follow through with a reference check.

Why did you leave? 

This is a soft way to understand why the person left. Were they pushed out? Were they laid off? Did they leave to explore other opportunities?

The reason the candidate left the role provides valuable information and may differ from role to role.

You start seeing patterns when you run through these questions for 5-6 jobs.

Matteo takes notes during the interview, so when he goes back to a candidate, his feedback is not based on opinion. He’s able to make data-based statements like, “I saw “x number of red flags,” based on the candidate's responses. At that point, the candidate trusts Matteo’s feedback.

For great people, it only takes 20-25 minutes to ask these questions for all of their previous roles. 

Another big red flag is when it takes candidates 20-30 minutes to provide responses for two or three of their previous roles.

How you can use Matteo’s framework to prep for your next startup interview. 

As you’re preparing for your next startup interview, walk through your resume and use Matteo’s playbook to prepare. Go through all of your previous roles and write out answers to the questions to think through Matteo’s questions.

Then, go back through your answers and honestly assess how many "red flags" pop up and how many "signs of greatness" you display. 

Interested in working at Eight Sleep? 

Use this link to explore Eight Sleep’s open roles.

Watch Matteo's responses below: