13 Best Questions To Ask Startup CEO At Interview


There’s no denying that joining a startup company comes with tons of benefits. However, you need to understand that taking this move also has its issues. Startups typically fail, and apart from that, joining one of these companies means you’ll have to work harder.

One of the few ways to make sure you’re not joining the wrong startup is by asking the company’s CEO the right questions at the interviews. Taking this move comes with tons of benefits; one of them will make the CEO understand you have an interest in the company. Besides, you’ll also find out whether joining the startup company is the right thing for you.

During a startup interview, you can always ask the CEO regarding the company’s vision and values. Apart from that, you can also ask questions that let you understand the startup’s long-term viability. Here’s a good example; what is your current growth rate, and does your company have a product-market fit?

In the rest of this article, you’ll find some of the common interview questions that will let you know if joining a startup is the right move for you.

1. What does “success” mean to the company?

One of the many ways to confirm whether a startup company is worth joining is to ask how the company sees success during an interview with the CEO. Here’s an excellent way to ask the question; what exactly does success look like for your company?

The purpose of asking this question is pretty simple; it’ll help you understand how the founders are driving the startup. Are the founders looking to push the company until it becomes a well-established corporation? Or will they only push the company for some time and then sell it off?

The answer you get from this question will let you understand the company’s long-term viability.

2. Does your company have a product-market fit?

Here’s another question you can ask the CEO during a startup interview – does the company have a product-market fit? If the answer you get is no, then it’s safe to say that the company doesn’t have real money. That’s not all; the probability that the startup will have real money is pretty slim.

However, if the answer is yes, you can proceed and ask this one – what value does the product exactly drive for the target shareholders? One of the reasons you need to understand the value of the company’s product during an interview is that it’ll help you establish the long-term viability of the startup.

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3. How exactly does the company develop talents?

As a talent looking to join a startup, you need to worry about your development. How exactly will the startup company you’re looking to join help you elevate your career? This is one of the many things you need to discuss with the CEO before joining the startup.

That said, during an interview, you can always ask the founders how they help their staff grow to the next level of their careers. The answer you get will certainly make you understand whether or not the startup is proper for you.

4. When is the company expecting cash flow break-even?

During a startup interview, one of the questions you can direct to the CEO is when they expect cash flow break-even? Cash flow break-even is when a company needs to make the right decision on how to meet its fixed costs. It allows the startup to decide whether to go for additional financing or liquidate some of its assets to meet its fixed costs.

Here’s the thing; most investors often shy away from companies in their first level or start from the ground. A fast cash flow break-even can help attract investors to the company, making work easier for everybody. So, knowing when the company is expecting cash flow break-even is an excellent factor to decide whether or not joining the startup is the best decision for you.

5. How does team collaboration look like in the company?

The importance of team collaboration in a startup cannot be overstressed. One of the benefits of this approach is that it enhances employees’ communication skills. Interaction and collaboration in a company help the employees to work more effectively. That’s not all; it also enables corporates to stay competitive.

During a startup interview, one of the questions you can always ask the CEO is how the team collar works in the company. Doing this will make the CEO see you as someone genuinely interested in working at the startup. Besides, this question will also help you understand the type of role you’ll be playing in the startup and how to partner with other employees to get the job functions executed fast.

6. What is the current company’s runaway?

A startup’s runaway represents the number of months a business has to keep operating and driving the company forward before running out of funding. There’s no denying that it often feels uncomfortable talking about money with the CEO. However, asking this question is essential for you to understand how sustainable the business is.

Furthermore, by knowing the startup’s runaway, you’ll understand the strengths and weaknesses of the company’s management team. Here’s the thing; a company with only a few months of runaway left should have a better plan to raise more capital.

That said, you can always ask the CEO regarding their plans to fund the business after reaching runaway. This way, you’ll be able to make a better decision regarding whether or not to join the startup. Without funding, the company might end up not paying your salaries or giving you a pay-cut option.

7. Does the company have an exit strategy?

Startup founders and investors often employ an exit strategy to transfer ownership of their businesses to third-party companies. This move enables an investor or capitalist to get a return on the investment amount.

During a startup interview, asking the founders regarding their exit strategy will allow you to understand whether or not the company’s goals and objectives align with your timeline. If not, joining the startup may not be the best decision for you, and that’s so because a quick exit may affect your job functions.

8. Has anybody left the startup in the past?

Understanding whether or not anybody has left the company in the past is another way to check whether or not joining a startup is worthwhile for you. This question can help you find out and understand how sustainable the company is.

Here’s the thing; turnover at a startup could be a result of several factors. One of them is no payment of employee salaries. It could also be that the employees were given a pay-cut option because the company doesn’t have enough money to run the business.

No doubt, asking this kind of question may be awkward. However, you’ll get to understand a lot of things when you ask about it. Interestingly, you might even find out why the post you’re looking to occupy is empty. This could be because the previous person is left, or it’s just a new role.

9. What is the greatest risk of the company?

Startup founders, to drive their company forward, need to make decisions from time to time. No doubt, with the right approach, funding, and team, founders can always drive their companies to success. However, you need to understand that all companies will face obstacles as they try to push their businesses to success.

The startup CEO certainly understands what the obstacles are for the company. So, by asking the question – “what is the greatest risk if the company” – you can better picture how the company’s future will look like.

10. Does the company have a self-serve product?

Self-serve products are the ones a company has when customers are allowed to go through the entire product experience on their own. These products are the ones the users can always start using without having to interact with another person.

According to Super Office, companies that offer self-serve to their customers often save up to $3 million per year. Even with that, it’s unfortunate that not all companies embrace this strategy.

That said, during an interview, getting the correct answer from the CEO regarding the company’s self-serve product is a great way to decide whether or not joining the startup is good for you.

Start by asking if the company has a self-serve product? If the answer is no, you can always ask why the company doesn’t have one.

Here’s the thing, providing the customers with self-serve products comes with tons of benefits. So, if the CEO says they are just considering using the approach, you might want to ask why now – why is the company just looking into that?

11. Does the company have short-term and long-term distribution strategies?

In business, distribution is an essential strategy for all companies, and it allows them to get their products right into the hands of their customers. During the interview, you can always ask the CEO regarding the startup company’s long-term and short-term distribution strategies.

The truth is that a great product isn’t all that matters to a startup. A company needs a good distribution strategy to be able to get its products to the target audience. Understanding the short-term and long-term strategies that the startup has in place to distribute its products will give you a better idea regarding whether or not to join.

12. What exactly is the 30-60-90-day hiring plan for your role?

For those who don’t know, a 30-60-90-day hiring plan is a document that companies use to set goals and strategize how your first three months in a new job will look like. During the interview, it’s essential to ask the CEO about the 30-60-90-day hiring plan for the role you’re looking to occupy. By doing this, you’ll better understand how the company sees your job role and what exactly is expected of you.

Furthermore, knowing about the 30-60-90-day hiring plan for your role is also an excellent way to understand what you need to bring to the table when you finally join the company. It’ll allow you to get familiar with your priorities and understand whether there’s a chance of personal growth in the company.

13. How much money can you make?

Figuring out how much money you can make when you join a startup is one of the most critical questions you need to get the CEO to address during the interview. I’m sure you don’t want to end up working for a company that pays less or hardly pays bonuses to its workers.

So, during the interview, you may start by asking about the salary range for the role you’re looking to occupy. Of course, the answer you get from here is enough to understand whether or not joining the company is for you.

But that shouldn’t be all; you need to also ask about how bonuses work in the company. It would help if you also asked how the company calculates raises for its employees. Once you get a range of salary and bonuses the company will be paying, you can always compare with the industry standard and see whether or not working for the startup is worthwhile.


The questions above are a few of the many questions you can always ask a startup CEO during an interview. Of course, you don’t need to ask these questions during the interview; and instead, pick the ones that matter to your role and find out if joining the startup is worthwhile for you.

Many job seekers focus on the size of the company when considering whether to apply for a position. However, the industry type of startup can also be an important factor to consider.

industry type of startup
The information technology services industry is one of the fastest-growing startup industries in America. One reason for this growth can be attributed to high flyer companies that are well specialized and equipped with innovative ideas which help them reach new heights among their competitors.
13 Questions in Interview 150P

Quick Answers To Frequently Asked Questions

Was Steve Jobs a data scientist?

Steve Jobs did not have a background in data science. However, he did have insight into both how to set up an engine for self-learning and how to build a product that would change the world, so his views on this matter are indeed worth hearing out.

What is the best entrepreneur interview question?

The ideal entrepreneurial interview question gives you a window into the qualities and ideals of the entrepreneur stepping into your company. Whether it be what they’ll do if they fail or how to communicate with someone who speaks a different language than them, exciting and diverse questions allow you to learn not only about an individual’s professional ambitions but also about their interpersonal skills.

A good beginning is to ask an open-ended question like “What do you think will happen?” or “What was your favorite project?” These starting points can lead entrepreneurs down many paths to describe experiences that have shaped their past and future aspirations.

How to be the best data science candidate?

Make sure you have a strong mathematics background – if not, take a course. Along with good grades in math and statistics courses, high scores on the quantitative section of any college admissions exams will stand out as well as occasional data analysis projects that demonstrate your ability to think critically about statistical results. Most importantly, have fun with it! Learning about data science can be very exciting and enjoyable.

Does silicon valley have a different interview process?

Yes. Silicon Valley companies typically only do one interview per company, whereas, in other places, employers can use up to 10 interviews before making a decision.

Are Facebook, Twitter, and Reddit suitable for potential hire?

One of the most valuable skills employers are looking for is well-versed in popping up on social media sites. It’s rarely a question these days whether an employer will check your Facebook profile. Still, if they have time to verify other materials you submit with references and resumes, they’ll pop over there too.

Is a coding interview similar to a job interview?

The most crucial difference is that the person who conducts a coding interview is usually not in HR and not in charge of making hiring decisions. Instead, someone from engineering or technical recruiting will conduct the interviews.

Is it better for a hiring manager to do an onsite interview?

This depends on what you’re looking for in a hiring manager. An onsite interview will allow the hiring manager to get a better feel for the candidate by seeing how they react to tricky questions and stressful situations that might arise.

Can you use machine learning or artificial intelligence to find potential employees?

It’s important to note that the way machine learning works will limit who it can find. Generally, it is programmed by humans, with human biases baked into what the algorithm looks for. The programmers of these programs are often unconsciously biased about certain classes of people/persons/outcomes-bias is pervasive in hiring processes.

This means finding a diverse group of qualified employees might rely on manually understanding what bias exists in existing data sets and programming machines accordingly. AI is helpful, but it’s not an alternative to conscious deliberation on the algorithm used. Understanding how current biases are perpetuated will allow any company to use machine learning algorithms to identify common ways people are overlooked or disadvantaged within hiring practices.

What soft skills to look for in a chief executive officer interview?

With your questions, essential qualities to look for in a chief executive officer job candidate are leadership skills, business management skills, broad knowledge of issues affecting the company’s success. The perfect candidate will have strong personal values that are well-matched to yours.

Employers favorite interview question at a phone interview?

This is a tricky question to answer as employers ask many different interview questions at a phone interview. Some of the most common interview questions that I have been invited as an employer could be found in any good book on interviewing techniques, “Tell me about yourself.”

Top 3 behavioral interview questions for an interviewer?

1) What is your proudest professional accomplishment?
2) Why do you want this position?
3) Give me an example of a time when you solved a problem creatively.

Good answers to these questions could be as follows: 
1) My proudest professional accomplishment was getting my Masters’s degree in the specialty I wanted and helping to organize the department I work for now. 
2) This will help me grow both personally and professionally.
3) Be honest.

How do you know a potential candidate is a good fit for company culture?

To know a candidate is a good fit for company culture, employers should look at the company’s values and see if they match up with what you want in an employee. For example, if you care about equality and fairness to all, then looking for candidates from diverse backgrounds would be helpful so that everyone feels welcome.

What is the best question to find the empathy level of a startup founder?

What new technology is going to be a game-changer in the next ten years?

It’s a bit of a risk for founders to answer this question since it’s hard to know what will have the most significant impact before it does. But if you want some excellent guesses from some data, look at who is being funded heavily and where VCs are putting their money.

Is past experience necessary for a technical interview?

Past experience is not necessarily necessary for a technical interview, as most companies value the skills gained through their work and how those set them apart from other applicants. However, the experience can noticeably help those who come into an interview understand the different languages and tools they may be working on. Depending on what’s more important to you as a potential employee, it may be worth it to go out to look for some internships or volunteer projects in programming.

Do I need to know VC firm analytics for a startup interview?

You might need to know VC firm analytics for a startup interview if you apply for a CEO or founder position. If that’s not the case, then it is safe to say that you can feel free from worry from those sorts of questions.

Should I mention my team member was a business analyst at a job interview?

Maybe. It depends on what type of job you’re interviewing for, the level of experience you have, and if it’s relevant.

Is a venture backed startup more likely to succeed in San Francisco?

When it comes to the potential investor, startups in San Francisco have a distinct advantage. The city is home to some of the world’s most influential venture capitalists, and these investors are always on the lookout for the next big thing. 

As a result, early stage companies in San Francisco often have access to more capital than their counterparts in other parts of the country. In addition, the startup environment in San Francisco is highly competitive, which can push companies to reach new levels of success. While there are no guarantees in the world of startups, a venture backed startup in San Francisco is more likely to succeed than one that is not.

How can the young entrepreneur council help the early stage startup?

The Young Entrepreneur Council (YEC) is a leadership style that can be applied to an early stage startup to create a culture fit and help the applicant become more successful. 

The YEC is based on the belief that young people are the best source of new ideas and that they should be given the opportunity to develop their business skill. 

The council provides mentorship, resources, and networking opportunities to help young entrepreneurs turn their ideas into successful businesses. In addition, the YEC also offers a range of programs and services designed to support early stage startups. These include incubators, accelerators, and investment funds. By providing access to these resources, the YEC can help the early stage startup grow and become more successful.

What is the best startup hiring process for prospective employees?

When it comes to hiring new employees, startups need to be strategic in order to find qualified candidates. The best way to do this is by asking specific questions that relate to the job description and required skills. For example, rather than simply asking “What are your strengths and weaknesses?”, a startup might ask “How would you handle a situation where you had to meet a tight deadline?” The specific question is best to identify certain criteria also startups can get a better sense of whether or not a candidate is qualified for the job. Additionally, startups should always keep their job descriptions up-to-date so that they can attract qualified candidates. By following these tips, startups can streamline their hiring process and ensure that they’re only hiring the best of the best.

What is the most important thing to remember at a startup interview?

When you’re interviewing at a startup, customer service is key. Remember that the customer is always right, and always be respectful of their time. If you’re not sure how to handle a customer service issue, ask your interviewer for guidance. They’ll be impressed by your willingness to learn and your commitment to customer service. 

Additionally, startups tend to be fast-paced environments, so it’s important to be able to adapt to change. Be prepared to answer questions about your ability to handle change and take on new challenges. 

Finally, remember that rights reserved trademark and copyright laws still apply to startups regarding personal information. If you’re not sure how to properly use or cite someone’s work, ask your interviewer for guidance. They’ll appreciate your commitment to legality and compliance. Asking a good question shows that you’re engaged in the interview process and that you’re eager to learn about the company. 

Some good questions to ask include: “What are the company’s values?” “What is the company’s mission statement?” “What are the company’s plans for growth?” Asking questions shows that you’re invested in the company and its success and that you’re excited about the opportunity to join the team.

Another important thing to remember at a startup interview is human resources. This is because human resources are responsible for hiring and firing employees. Therefore, it is essential that the company’s human resources department is able to handle the hiring and firing of employees in a professional and efficient manner.

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Wasim Jabbar

Hi, I'm Wasim - a startup founder and proud dad of two sons. With 15 years of experience building startups, I'd like to share my secret to achieving business success - quality marketing leads. Signup today to gain access to over 52 million leads worldwide.

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