22 Questions to Ask Founders Before You Join Their Startup
Be shameless about asking what you want to know. Don’t let awkwardness get in the way of knowledge.
This is part 2 of a 3 part series. If you haven’t read part 1 yet, I recommend starting there.
A knowledge gap exists between job seekers and founders of startups. I'm writing this to equip you, as a job seeker, with good questions to ask a founder. This may seem odd on the surface. You likely already have some of your own questions in mind. But I'm listing these here so you know that they’re okay questions to ask. Some may seem too bold or might make you cringe to think about asking them. But you have the right – I’d say even the responsibility – to ask them when choosing a new role at a startup.
It’s a big list. Don’t plow through it during your first conversation with someone like some sort of inquisition. When to address each question varies. Consider the stage of the company, seniority of the role, and how serious the discussion is getting between you and the company.
VCs and founders discuss questions like these all the time - even on weekends. It's like a hobby or a sport to them. But as a job seeker, you probably evaluate a new startup opportunity only once every 2-6 years – not nearly as frequently as investors. So you're at a disadvantage compared to people who discuss these questions daily. But here's a simple secret to empower yourself: you deserve to learn everything that can be known about the company you’re considering joining – so be shameless about asking what you want to know.
You could skip all the hassle and awkwardness of asking these questions, but in many cases the difference between joining startup A or startup B could be the difference of millions of dollars in your pocket.
One unintuitive thing about asking these kinds of questions is that they automatically uplevel you in the eyes of your prospective employer. They indicate that you are well-researched and you care about being informed in order to make this high stakes decision. They can also give you valuable information that may improve your ability to negotiate compensation and role in case you decide to do so later.
Let’s get to the questions. I’ll break them down into a few high level categories. For now, just focus on gathering as much information as possible. We’ll talk about how to use this information as part of an evaluation framework in the next post.
Vision and execution
“If everything goes right, what does this become?”
“What do you see as the primary risks to that success?”
“Do you believe the success of the company is primarily dependent upon technical breakthroughs, engineering execution, sales or something else?”
“What advantages does this startup have relative to the broader market?”
Startup Traction
“What inspired you to work on this problem?”
“Do you consider this startup pre-PMF or post-PMF?”, follow-up if post-PMF: “What evidence convinces you this is the case?”
“How do people find out about the product/service today?”, follow-up: “How do you think that might change in the future and what are you doing to explore those new avenues of customer discovery?”, “If you currently have a small number of customers, how did you get them?”
“Can you share specifics of customer, user, revenue, and retention numbers?”
“I’d like to learn more about the current revenue.”
“Is it signed revenue, verbally committed revenue, likely revenue, or expansion opportunity revenue?”
“Is it mostly recurring or one-time purchases?”
“What is the median purchase size of current customers?
“Is there a revenue dependence on a few large customers that drives the product development process?”
“Do you believe there are ‘land/expand’ opportunities with the existing customers? In what directions do you expect to expand?”
Milestones and timing
“What are the next milestones for the company and when do you expect to achieve them?”
“What is the current hiring plan across the org?”
Financing history/future
“Can you give me an overview of the financing history of the company? On what dates were outside capital raised? What were the form/terms of the financings? i.e. SAFE/equity, valuation, liquidation preferences, participating preferred, special investor rights?”
“What is the current runway available before the next financing is required?”
“How much additional capital do you think will need to be raised to get to profitability? Within what timeframe do you expect to achieve this milestone?”
Decision-making process
“How are decisions made at the company?”
“Do co-founders have equal weight in making decisions? How do you break ties in decision-making?”
“Are there any forward-looking topics that the board is encouraging you to explore?”
Role/impact
“Who does this role report to?”
“How do you evaluate the success of this role/team?”
“As the org grows, how will this role grow? Is a senior leader likely to be hired to layer-in or would this role build/lead the team as the company grows?”
Reference calls
“I’d like to hear more color from angels, investors, and board members about how they view this company and the market? Can you connect me for some conversations?”
These are the kinds of questions an investor might ask. If you join a company you are making a very concentrated investment in the future of that company. Investors build diversified portfolios of investments, but full-time employees make single concentrated investments. As a job seeker you should be doing more diligence than a typical VC. It helps to have a community to learn with. That’s why we organize Founders You Should Know.
What do you do once you’ve gathered all this information? In the next article of this 3-piece series I’ll share some frameworks for evaluating the answers you collect. I’ll also be going deeper on the questions raised here in future newsletter posts.
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