The Top 10 Questions You Should Be Asking at your Startup Interview

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Are you a professional seeking to join a young and growing startup? If you’re reading this, you probably are! I have been in the startup world as an entrepreneur for the past 5+ years and have interviewed over 100 applicants from the United States and abroad. Through these interactions, I’ve learned a tremendous amount about the differences between startups and corporations and the questions that job seekers should be asking to ensure that they are getting what they desire.

In this article, you’ll learn the top 10 questions that you should be asking in your startup interview so that you leave the room with the information you need to make a smart career decision. These questions will not only inform you, but they will also impress the individuals you are interviewing with.

Keep in mind that startups are radically different from major corporations where interviewing and hiring standards have been set years in the past. Startups may not always have all of their ducks in a row when it comes to the role, employee benefits, and future potential. It’s not because they don’t want to…it’s merely because they are still in the process of getting it all organized on top of everything else that is on their to do list.

While you don’t want to hold it against them, you want to make sure that you are joining a startup that has long term potential as well as job security in the short run.

I’ve split the 10 questions into four key areas that you should be focused on as you enter your startup interview.

The Role

The job description on Indeed.com briefly outlines the role that the startup is seeking, but it’s your job to get into the nitty gritty details of what you’ll actually be doing. As a startup owner, I’ve witnessed strategies that are used to make one’s job posting appear more attractive while not giving a descriptive overview of the actual position. Make sure that you fully understand the role and are confident you will be happy in the role before moving forward.

Question #1: What are the major goals for this position? How will I be contributing to the growth of the company?

With this question, you can get a better understanding of what the company wants out of this person and their contribution. Knowing where you will make the greatest impact will prepare you better for the position.

Question #2: How many hours am I expected to work within the position?

Startups have endless lists of tasks to complete and not enough manpower to make it all become a reality. Oftentimes, startups expect their employees to work hours longer than the normal 9 to 5 answering emails in the evenings and on weekends. Make sure that you understand the expectations while discussing the role with the employer.

Question #3: What teams does this role work most closely with?

Learn about who you will be working with at the company and how you will contribute to their individual and team goals. If there is a lot of team work and collaboration, that demonstrates that you may have the opportunity to learn other areas of the business outside your expertise. If there is little teamwork involved in your role, you must make a decision whether that is best for you or not.

The Company

Startups tend to be between 0 and 3 years old before they begin to shed the association with being a young startup. In these defining years, the founders of the company tend to be the lifeblood of the culture and future growth of the company. When applying to work at a startup, you want to understand who the founders are and why they decided to start the company. This information can give you better judgement on whether the startup is destined for success.

Question #4: What are the goals for the company over the next 2 years?

When working with a startup, you want to make sure that there are leaders that have a strategy for the growth of the company. If someone in the company cannot answer this question, seriously consider whether this is the best long term option for you. If they have an amazing answer that lights a passionate fire in your body, it may indicate this is a great opportunity for you.

Question #5: What does the company value most in its employees? Who is an ideal candidate for this position?

Test the interviewer to see if they know who their ideal employee is. If they can answer this question without issues and they create a picture of who you are as an employee, this could be a great fit. If their company values drastically differ from your personal values, determine if it will be an issue when working in their company culture.

The Benefits

Startups are different from established corporations. One of the biggest differences is employee benefits. For young startups, they may not be able to afford all of the employee benefits that most employees are used to. It’s important to review these aspects of the position with the interviewers before you get into the final stages of the interview process.

Question #6: How does the company handle health insurance and retirement account contributions?

It’s important to know if the startup covers any portion of health insurance payments and what providers they currently work with. It’s also important to know if the startup offers any retirement accounts, i.e. 401k, for you to invest in your future. Off of that, you want to know if the startup matches any of your retirement contributions at a certain point after working with the company for so long.

Question #7: How does the company handle vacation, sick days, personal days, and federal holidays?

Most startups are much more flexible and handle days off differently. Make sure that you understand their vacation policy and when it becomes effective for you. If the company states that they have an Open Vacation Policy, ask them how they interpret that and how many days employees typically take off.

Question #8:  What is the starting salary for this position? How do raises, bonuses, and promotions work?

Learn about the starting salary for the position that you are applying for or confirm what was presented on the job posting. Ask the interviewer about how the company handles raises, bonuses, and promotions so you understand what you should be working towards. If the company doesn’t have a plan for these areas of people management, it may be a sign that they do not plan to give raises, bonuses, or promotions. Be wary of situations like this.

The Future Potential

Last, but certainly not least is the future potential of the company. As a potential employee for this startup, you want to understand how you can grow within it and where the founders see the company going.

Question #9: Where do you see my role going within the company over the next year?

If this is a company you see yourself with for the next 2+ years, make sure that the leadership team sees it the same way. Ask them this question to understand how you can grow within your role and within the company as you dedicate more and more of your time.

Question #10: Are there opportunities to grow into a management or leadership role within the company?

If the position you are applying for does not entail any leadership or management, ask the interviewer how you could eventually make it a part of your role. If there are set tracks to grow into a specialized expert or leadership role, it is clear that there is room for growth within the company. If there seem to be any dead ends within the growth structure for employees, take note of that and ask more questions.

End Goal: Leave the Room Informed

Using these 10 questions should give you a much better understanding of what you may be getting yourself into if the company is interested in hiring you. With startups, it’s important to have all of the information before you make a final decision. The time to learn that information is in the interview process.

At the end of every interview, or perhaps even within the interview, the interviewer should ask you if you have any questions. Take this time to dive deeper into the information that they have already provided with the 10 questions above. Show that you are serious about their answers by asking to take notes. Don’t leave the interview until you have clarification on the four areas I’ve outlined above.

With a clear understanding of the role, the company, the benefits, and the future potential, you will be able to make an educated decision as to whether the position is attractive for the short and long term growth as a startup professional.

I hope that this information helps in some manner as you work your way through the startup interview and hiring process. If there are any additional questions that you would like to add to the list or if I can provide clarification on any of the top 10 that I outlined, please reply in the comments below. Best of luck to everyone reading this article!

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About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

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