All the questions you need to ask before joining an early stage startup
Generally, the earlier stage startup you join, the greater risk you’re taking on. However, there are a series of conversations you can (and should!) have prior to joining that can de-risk the decision.
The following are a series of questions I’ve asked companies both throughout the interview process as well as between receiving an offer and accepting/rejecting it.
For some, these questions may seem sensitive/invasive (and you should use common sense as to when is the right point in the interview process to ask them), but if founders aren’t willing to answer them even after they’ve extended an offer and have expressed a strong desire to bring you onto the team, you shouldn’t join the team.
Founder dynamics
At early stage companies, CEOs will play the role of filling whatever gaps exist. It’s important to have an understanding of what kind of work the CEO currently does and how they see their role evolving in the future.
What is the role of the CEO?
How would you describe your founder(s) and how you work with one another? (Ask each founder this. Separately, if possible)
What is out of scope and in scope for each founder’s responsibilities?
How does each founder envision their role evolving over the next year and as the organization grows?
In the past year, what areas of responsibility have you stepped away from and delegated?
How do you see your responsibilities evolving after hiring a “head of product” (dig into what they want to continue to be involved with vs. step away from)
How do you guys resolve conflict? What’s an example of a time where you disagreed?
Business health and financials
What is the ARR, burn rate, LTV, CAC, net retention, and NPS?
What are the different channels of customer acquisition? How do you see this mix changing over time?
What are the key assumptions underlying the business? Do research here first yourself and question them on specific assumptions the company is based on.
What happens if you’re wrong? How do you mitigate that risk?
What are the most common reasons you’re winning and losing deals today?
What does a successful exit look like to you?
Product
This section is the most company-specific section so I’d first recommend just having them give you an in-depth product demo and then asking about why they made certain product decisions and pushing them on their thinking behind them
What are the user problems that x solves today? What new user problems do you envision x addressing a year from now?
What is the top-line product metric that x company cares most about?
Go through and understand how they think about standard product metrics as well as how their product is currently performing.
Why is the product defensible?
What audience is the product catering to? Is the audience that the business is going after long term or do you need it to change to hit longer-term (3-5 years out) revenue goals? If so, what features make up the gap between the current product and the product that addresses this future audience’s needs?
What was a feature you guys shipped that you shouldn’t have? What happened?
How has the product evolved over the time the company has existed?
How do you currently prioritize feature work?
What is your 6 month, 1-3 year, and 5 year product vision?
The Future
Let’s say X company doesn’t exist 2 years from now. What happened?
Let’s say X company has a successful exit 5 years from now? What are the top three things that contributed to this happening? What organizational habits do you have in place that facilitated this?
Culture
What are X company’s cultural values? Give an example where two values have had tension with one another? How did you navigate that?
What mechanisms do you have in place to facilitate goal setting and accountability? (i.e. do they do OKRs?)
Should strategy be top down or bottoms up? (answers to this should be nuanced and not binary)
Dig into diversity and how they think about that from a recruiting, employee retention, and issue resolution perspective. If they lack diversity in a certain area, press them to understand why and see if they are defensive here or approach the topic constructively.