Millionaire CEO Shares The 5 Questions He Asks Every Job Applicant & What He Expects From Each Answer

He explained that for each job applicant, he asks them the same questions to identify any red flags.

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A CEO has revealed some of the important questions he makes sure to ask anyone applying for a job at his company.

In a TikTok video, Matteo Franceschetti, the CEO of a $550 million business called Eight Sleep, a smart mattress and sleep fitness technology company, shared that for all interviews he conducted, he had the same "playbook" so that he could "identify red flags faster."

He shared the 5 questions he asked all job applicants and what answers he expected from them.

In an interview on the podcast "The Twenty Minute VC (20VC): Venture Capital" with Harry Stebbings, Franceschetti explained that he would go through all the previous jobs that an applicant had before, and ask them five questions pertaining to them. 

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1. 'How did you find the job and what did they hire you for?'

"That helps you because in how you find the job if they had five or six jobs, you want to see if they were recommended by anyone or the previous managers. That's a great sign, right? If it never happens, it's not a red flag but it's not a positive sign," Franceschetti said. 

   

   

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2. 'What is your second biggest achievement?'

For the second question, Franceschetti explained that he always asked applicants about their "second biggest achievement" or contribution that they made during their last job.

Whether it was improving the numbers and statistics of a company or improving the mission statement, Franceschetti pointed out that his interest was in personal achievements not achievements made as a team.

3 & 4. 'What has been your lowest point?' and 'Who was your last manager and what are they going to say about you in the next reference check?'

"This is another great one because a lot of people, they start complaining and you see what they complain about," he continued. 

Franceschetti claimed that when he asked this question, applicants would often rant about their last manager withholding tasks or not giving them the freedom to operate, but when he asked who their last manager was and what they'd say in the next reference check, many applicants would immediately change their tune.

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"You immediately see certain people becoming rigid," he said.

millionaire CEO shares 5 questions he asks every job applicant Photo: fizkes from Getty Images / Canva Pro

5. 'Why did you leave?'

For the last question, Franceschetti said he asked applicants why they left their last job, which he claimed was a "soft way" to know if they were either pushed out or something else happened.

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"When you start doing five, six jobs, you start seeing patterns," he pointed out.

People offered their opinions on Franceschetti's interview questions. "This is called Topgrading and it works. The most important part is asking the SAME questions about each job. It’s the pattern that matters!" one TikTok user wrote.

   

   

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Another user added, "This is a great way to interview. Most people can do a job or learn but if they bring toxicity to the team they’re doing a disservice." A third user chimed in, "Best way to interview someone is to let them guide you through a problem they would encounter if they had the job. It's authentic and shows expertise."

Job hunting can often feel like a vast abyss, and by throwing your resume out there, you hope at least one company will catch it and find an interest in you. This often translates to a lot of interviews, and most of the time, they can feel overwhelming.

2022 survey from hiring software company Greenhouse found that 60% of job seekers were “unimpressed by time-consuming recruitment processes.”

   

   

Becca Carnahan, the founder of Next Chapter Careers, told Vox that many companies may use multiple interviews and diverse questions as a way to make the hiring process fair, and to find the best applicant to join their team.

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"It can reduce bias in the hiring process when you’re actually looking at a candidate’s abilities rather than their past accomplishments," Carnahan told the publication.

In the evolving world of job interviews, most job seekers and applicants only really want one thing: Employers and hiring managers use a balanced and fair hiring process to evaluate not only their skills but also if they will be a cultural fit for any workplace environment.

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Nia Tipton is a Chicago-based entertainment, news, and lifestyle writer whose work delves into modern-day issues and experiences.