Questions to ask before working at a startup

Shane F.

Here at Interview Query, we focus a lot on questions and take-homes that are asked of you during the data science interview process at top technology companies, but today we’re going to focus on questions you should ask.

Working at a startup can be a fun (and sometimes lucrative) experience, but not everyone has a great framework for how to evaluate one company from another. Below is a list of things I try to suss out when I’m evaluating an opportunity at a company. Compensation (cash and equity) plays a huge part in choice to join a company but there are many other factors that are at work when you're part of a small team with a big idea.

While by no means exhaustive, this interrogative set should give you a good amount of information with which to inform your decision. Not all of these apply to every company, but you can use this list to kick the tires and find inconsistencies in any statements to try to discern the truth from the sales pitch. Getting the answers to some of these questions is as important as creating a model for yourself of your potential outcome in working for a given company and measuring your opportunity cost.


Goal: discern if this business has a legitamate product, or the opportunity to create one.


Goal: understand the engineering process and technology stack.


Goal: determine if this team is viable.

Cap Table / Capitalization

Goal: gain an understanding of the company equity structure and your upside.


Goal: figure out the size of the opportunity, how the company plans to monetize and who they're going after.


Goal: figure out if these are people you want to work with and that you trust.


Goal: gain an understanding of the total value of your opportunity.


Goal: glean insight into the financial health of the business.

Vacation / Benefits / work-life balance

Goal: understand if there are safeguards against burnout.

Remote Work

Goal: find out if remote is an option.


Goal: figure out if this is something you want to toil away on day-in, day out.


Goal: Greed can be good, but do the founders understand when enough is enough?


Goal: understand the vision and how long they have been at it


Goal: see if you are aligned with the founders.

In early stage companies, interviewing is essentially a two-sided interrogation by which two parties mutually due-diligence each other and relentlessly backchannel. Founders generally have the upper hand, so hopefully this tips the scales a bit back into your favor.

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