Questions to Ask in an Interview That Don't Suck – Boring Startup Stuff

Questions to Ask in an Interview That Don't Suck

Interviews are a time for candidates to talk about themselves, their achievements, and their hopes for the role that they are interviewing for. However, interviews shouldn’t be one-sided. They can serve as a tool for figuring out if the job and the people at the company are the right fit for you.

There are questions that you need to ask before joining a startup that provide more insight beyond the job description. At a startup, you have to consider other factors like risk, company culture, and the future trajectory of the business.  

Here are some questions we like to ask before joining a startup:

  1. Where is the company now, and what direction do you see the company going in the long term?

Startups operate in a very dynamic space. The team, as well as the product, can go down completely different and unexpected paths within a short period of time. It is important to establish a clear sense of where the company is today (in terms of funding, growth, product roadmap, team, leadership, etc.) and where it  plans to be in the future. While all plans are subject to change, this question allows you to understand what you might be getting yourself into and how this plays into your future career trajectory.

  1. What motivates your team?

People’s belief in their own product is crucial to gauge before joining a startup.  It is essential to be around people who are forward-thinking and self-motivated against all odds. This question can provide insight into the culture of the company and what types of people are running and supporting the work being done. Are people motivated by the same ideas, or are they driven by personal motives that just happen to move the needle on the same end goal?

  1. What are the current challenges the company faces? And how will this new role address those challenges?

It is important to know about the positive growth companies are experiencing, but it is also essential to understand the shortfalls and struggles of the company.. You cannot understand a company’s challenges simply by looking at their website, so this question explicitly brings to light what still needs to be worked on. Plus, people who work at startups wear a lot of different hats, so this question forces the interviewer to provide a specific perspective on their expectations for someone in your potential position. 

  1. What are the biggest risks involved in this company and how do current employees reduce those risks?

Working at a startup is risky. Transparency about  potential risks (financial, career etc.) are all the more necessary when joining a startup. Risks take on different forms and some might not be as observable to employees as others. Spelling out what risks you should expect can help you prepare for uncertainties that lie ahead. Additionally, learning about how current employees interpret those risks provides an idea of the type of environment you will operate in. Are people constantly working to make sure everything is in line? Are people always ready to pick up extra work when things take a turn for the worse?

  1. Where do you guys typically hang out for lunch?

Despite the risks, challenges, and structure of the company you are interviewing for, you are ultimately going to be working and extensively interacting with the set of people who are currently there. Learning about small, but fundamental interactions such as lunch breaks can allow you to understand more of the culture that the firm operates on and the types of people you will be spending at least eight hours of your day with. Do people generally bring their own food to eat on their own time? Or is there more of a collaborative community where people go out and find places to eat together?




Once you reach the “do you have any questions to ask me?” stage of the interview, it is important to ask unique, hard-hitting interview questions to your prospective employer. Not only can tough questions provide you the answers you need to make a decision about the role, they also set you apart from other candidates.



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