Questions to ask before working at a startup
August 22, 2019 10PM PDT
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.
- Does the product already exist?
- Do you have a working version of the product?
- Have you achieved product/market fit?
- What does your product/engineering roadmap look like
- What advantage does/will your product have over existing ones?
Goal: understand the engineering process and technology stack.
- What is your work schedule?
- What is your tech stack?
- How often do you have meetings?
- What tools do you use for communication
- How do you see the team growing
- Describe your management style
- Is this a technology I like working with?
- Is this an outdated technology / framework / methodology?
- What does your software architecture look like?
Goal: determine if this team is viable.
- What is the current team size
- How many employees are in X department?
- What are your plans for hiring?
- How many remote employees
- How many in-office employees
- Plan to go full-remote?
- Plan to have a distributed team?
- If there are remote people, what time zones are they in?
- What are the core hours?
- Are there any current/past employees?
- ask yourself: are these people I would want to work with?
Cap Table / Capitalization
Goal: gain an understanding of the company equity structure and your upside.
- Show me the cap table.
- When was the last round raised?
- How much money was the last round?
- What was the post-money valuation of the last round?
- Who are your investors?
- Who’s on the board?
- When do you plan to raise again?
- How much dilution has occurred?
- How much runway does the company have?
- Is there a path to profitability?
Goal: figure out the size of the opportunity, how the company plans to monetize and who they're going after.
- How big is the total addressable market?
- Who are the major players in that market?
- Do you have any customers?
- What is the profile of your customers?
- What acquisition channels do you have?
- What is the acquisition cost of your customers?
- What is the churn rate?
- What is your NPS?
Goal: figure out if these are people you want to work with and that you trust.
- How many founders are there?
- Are all the founders currently working on the company?
- How do you resolve conflict between one another?
- Can you provide me with references from your investors?
- What do you view as the biggest risk to the business?
- Is this a lifestyle business? A quick flip? A moonshot?
- ask yourself: is this someone I would want to hang out/spend disproportionate amounts of time with?
- ask yourself: is this someone I can trust?
- ask yourself: does this person seem shady?
Goal: gain an understanding of the total value of your opportunity.
- What is the current fair market valuation of the company?
- Can I have founder shares?
- What is the strike price?
- What percentage of the company are you willing to offer me?
- Acceleration of equity upon acquisition?
- Options or grant?
- What is your vesting schedule?
- How long is your option window (90 days? 5 years? 10 years)
Goal: glean insight into the financial health of the business.
- Show me the financials
- What is the business model?
- How will you make money
- Are you currently profitable
- What is the top-line revenue of the business
- What is your projection for revenue
- How do you do accounting
Vacation / Benefits / work-life balance
Goal: understand if there are safeguards against burnout.
- What do you do for work-life balance?
- How do you manage burnout?
- What is your vacation policy?
- When was the last time you went on vacation?
- How do you track vacation?
- How do you make sure people take vacations?
- Do you offer any sort of employee benefits?
Goal: find out if remote is an option.
- Are you open to a remote team?
- Are there any plans to have remote workers?
- Do you currently employ offshore developers?
- What percentage of your current employees are 100% remote?
Goal: figure out if this is something you want to toil away on day-in, day out.
- Let me see the codebase
- How do you review code?
- What’s your process for releasing to production?
- Do you even test?
Goal: Greed can be good, but do the founders understand when enough is enough?
- What would a meaningful exit look like to you?
- What would be “enough” for you?
- What would a liquidity event look like for current/future employees?
Goal: understand the vision and how long they have been at it
- What’s your vision for growing the company?
- How long has the company been in business?
Goal: see if you are aligned with the founders.
- What, if any, are your values?
- What is your mission?
- [subjective questions probing alignment of your personal values with the founders here]
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.