Questions to Ask When Considering Startup Jobs
What to ask yourself, the founders, and others before joining a startup
At dinner the other night, a friend asked me what questions I would ask in a startup job interview. She had recently left her startup operator job to take a brief sabbatical and consult on a freelance basis, but was starting to consider new full-time roles again. She’s reflecting on her most recent role, which was at a startup that was exciting when she joined but whose growth had stagnated and lost momentum while its competitors sped by.
She wanted to know if there’s a way to evaluate whether you’re joining the winning team.
We discussed and agreed that picking winners in early stage startups is unlikely. Most startups fail; risk is a feature, not a bug. Even venture capitalists, whose job it is to predict which startups will succeed, have portfolios comprised of many weak investments subsidized by a few 10x+ winners.
While it’s not likely that startup operators can accurately pick early-stage startup winners, asking for more and better information can help de-risk the decision: by increasing the probability that you’re joining a smart, capable company capable of achieving its lofty goals, and clarifying whether you’re considering the right role for yourself.
We started listing the questions we would ask ourselves before taking a startup job, as well as several questions we would need to ask the founders and other current and former employees before signing on with an early stage company.
Our conversation stuck with me for a few days afterwards, so I reached out to several other friends who have worked as operators and founders to ask: What questions would you ask yourself or others before joining a startup?
Their answers and rationale spanned financial health & strategy, understanding the market and competition, leadership and decision-making, hiring and team dynamics, specific questions for joining international startups, and additional considerations for personal fit and future prospects. While the list of questions is by no means exhaustive, I’ve compiled them below.
Questions to ask founders and/or senior leadership
What’s the biggest cost of doing business today? Startups underestimate their costs and overestimate their path to profitability.
What do they think about their competition? Ask the founder what they think about their competition. The goal is to understand whether they overestimate themselves and underestimate their competition, or if they understand the dynamics of the market (winner-takes-all vs. highly fragmented market with many tiny businesses competing). Red flag if the founder thinks all of the other competitors are stupid. Green flag if they tell you some things they admire or appreciate about competitors, but indicate a path to win. A founder I asked says, “I [underestimated competition] at first; now I try to point out what they did right.”
What was the last decision that was made? How was that decision made? An operator mentioned that this helps them get a sense of how different parts of the business work together, and how much they do (or don’t) use data to inform decisions. It can also indicate how much the CEO or another executive micro-manages vs. delegates.
How does the company spend money? What are their biggest expenses? What is working for them? Where does the budget sit? What have they tried, failed at, and learned not to spend money on?
How are users mostly acquired? What is the cost of acquiring a user? Are there positive unit economics? Are these users organically acquired, or all paid? If paid, what’s the retention like? Are users happy and recommending the product or service to their friends?
What is their strategy around hiring and team construction? Are the people hired *really* useful for something? Or is the startup hiring because they have funding to spend and can increase headcount? During the ZIRP era, headcount was a way to puff chests and indicate that the company was growing and going somewhere. But it depends how early stage the startup is and how close to (or deep into) product-market fit it is. In a smaller, earlier stage startup that’s still finding its way, it’s important to know how hiring decisions are made. You feel the presence (or absence!) of every single person on your team. You want to feel like you’re walking into an environment where the leadership worked hard to assemble a top team, knows why every person is there, and how people can communicate quickly and effectively with each other.
What is the company’s runway? How profitable is the company right now? When was the last fundraise? What was the amount? Round? Circumstances? Rationale? Who were the investors? This one is important to understand the general climate of the company, the equity story, how you fit into the trajectory, and how your equity package might look if you join. If the company has less than one year of runway, are you sure you want to join now? If the company has two years of runway, but is not even close to profitability, are you ready to roll up your sleeves and get there? Or are you hoping for an environment where those battles have already been won?
Have the founder(s) built a company before? One of the biggest factors contributing to startup success or failure is whether the leader is a first-time founder. Second-time founders have an edge with network, capital, team assembly, and decision-making, but also might suffer from overconfidence. Know your team and their mindset before you join.
Is the business forecast realistic? Is it based on optimistic assumptions or conservative ones? This will tell you a lot about how the company perceives itself and its prospects. It will also save you a lot of grief if you learn early on that the leadership is delusional in its optimism, or too conservative to seize the market faster and better than competitors.
Is there a real customer interest or need? An operator gave the following example: “We built a learning app, did a user test after the app was already built, and the people who tested said they wouldn’t pay for it.” I’ll write about this in another piece, but gauging real paid customer interest is often done horribly wrong yet is critically important.
Who is talking to customers? How often? How do these insights spread across the organization? Inform product development? Change existing roadmap? An operator mentioned, “I remember being super annoyed when the product designers made ignorant comments about a feature, very unaware of what our biggest competitors are doing with the same idea.” In a small, early stage startup, everyone should speak to users; this should be a regular practice. Building real solutions for real people’s problems is the point.
What is the company’s runway? How profitable is the company right now? If the company has less than 1 year of runway, are you sure you want to be there? If the company has 2 years of runway, but is not even close to profitability, are you ready to roll up your sleeves and get there? Or are you hoping for an environment where those early battles have already been won?
What values do you look for in employees and what culture are you aiming to build? Do you have policies that speak to this? Culture can mean a lot of things. Diversity is a value. But so is excellence, or velocity, or reliability, or playfulness. These will all attract certain types of employees and management. These values will translate to how customers interact with your team. Unpacking this question can help you decide whether this is a culture you want to be part of.
What is the end game for them as they build the company out? Then, how far along do they think they are in achieving this? Are they trying to build a generational company? A generational product? Do they imagine IPOing? Are they imagining M&A opportunities? Are they winging it and seeing what happens? What does success look like for the founders?
Questions to ask people who joined the company (not founders)
Founder responses are helpful, but only the deputies and other employees at the company can testify to whether those visions are implemented on the ground.
How would you describe the company culture? What are the traditions that make the company special and different? What are the annoying processes that make people roll their eyes? This can help you determine whether it’s the right fit for you.
Why did you join the company? What made the decision easier? Job selection is a two-way street. Understanding what appealed to someone about the opportunity and what clinched the deal can tell you a lot about the organization you’re deciding to join.
When was the last time there was a conflict on the team or with a big decision? What are the factors that go into making big decisions? When the stakes are high, how do processes degrade? Emotions? How are decisions delegated or centralized?
How do they handle failures? This one applies for people as it does to companies. Shit happens. Things go wrong. Failures are part of existing and trying new things. But are there lessons learned from these failures? How are they incorporated into the future operations of the business and decision-making?
How present or not present is executive leadership? Are their calendars busy? Are they cramming energy drinks? Are they in the office? Are they absentee? What are they doing with their time? One friend described their CEO as “never there.” Another’s is ever-present, even on slide design. Another described theirs as available only to press but rarely to the team. What kind of behavior are you expecting from leadership? What is the frequency and quality of the interaction you’re expecting to have? Trusting and respecting your team matters, so if their leadership style doesn’t jive with yours, you should factor it in.
What’s the relationship between the founders? Do they get along? When they disagree, what do they disagree about? After not finding product-market fit, cofounder infighting is one of the leading causes of startup failure. People can go from best friends to bitter enemies once they are in the trenches together. It’s normal to witness relationship expectations evolving over time, but if you have the ability to speak to someone who is already working there, ask what they observe in the relationship.
What are the personalities of the founders? This one should likely be asked to a deputy who left the company already. They often have the best insight and nothing to lose by helping you out. A lot of the startup’s culture and how happy you’ll be working there comes down to personalities of the founders. Do they follow trends whichever way the wind blows? Are they highly pragmatic? You should know.
Questions to ask when joining a startup outside of the US
Have the founders worked outside of the HQ country before? There are several reasons this one is important. One of them is an understanding of the company culture and whether you’ll feel welcome and understood. The other, which is crucial for a startup in the Silicon Valley mold, is that it can increase chances of success and big ambitions (unless the startup is really focused on the local market). In France, for example, the population is ~66M. At some point on a global expansion tear, startups in France expand to the US—a unified market (in terms of language and regulations) of ~330M who are accustomed to adopting new products and services as individual consumers and on the B2B side. If that’s the case and your startup eventually needs to expand there, will yours be able to do so effectively? Will it be able to raise capital in the US or UK if needed? Many companies in Europe, if they exit, list on the NYSE or get purchased by US or UK companies. Will your founders be able to connect there?
How international is the team? What is the dominant language of the office? If you’re not from the headquarter country, it’s important for you to feel like you gel with the team. It also makes a difference if the company plans to expand beyond its home country.
Does the company offer a good equity package? In many European startups, compared to the US, employee ownership is offered less consistently and at lower levels. If you are looking for a great equity package is a meaningful part of your incentives for joining the team, it’s worth asking so you can understand this better.
Questions to ask yourself
Does the topic or sector genuinely interest you? Have you tried the product yourself? Do you believe in the product? Do you believe in the space? Are you okay making that part of the next year or more of your professional career? You’ll be working on this, with close to max effort for marathon timeframes, with part of your comp deferred to equity, and failing a lot, for a while. If you’re not interested, you’ll burnout quickly. Being passionate about the topic, sector, mission or product really helps.
What can I learn from the company? Does it fit in the career story I’m trying to tell (i.e., Is there room for growth? Will I be learning?)? Finding the right role is about a mutual fit and you need to make sure it makes sense with your values and ambitions. What are you hoping to learn in your next role? Will you learn it there? Can you learn it somewhere else? If the company tanks, will you be satisfied with what you learned?
Will this company be alive in a couple of years? There are never any guarantees but given the info you know about runway, how this company earns and spends money, macro-economic risk, and the personalities of the founders, will you find yourself looking for a job again in a few months? In a year? Two years? Three? Five? Depending on your risk and stability tolerance, certain realistic timeframes may be more or less attractive to you.
Will the market evolve enough for us to add value at scale? A very talented operator I know asked this one because many startups begin by targeting a niche and saturating it. Assume that this works—and the startup shows early success here. Can it expand? Pragmatically, by how much?
The most important questions
If I were an investor, would I invest in this business? You’re investing your time and expertise, and there’s an opportunity cost, so it’s worth trying on this point of view before you sign on.
Would I still take this job if all of my equity went to zero? The fact is that most startups fail. If you are taking a startup job assuming it’ll make you rich, that’s incredibly optimistic. But we also have a saying in the US: prepare for the worst, hope for the best. If the worst happens…, would you be happy with this job? Are you comfortable with your exit options? Would you rather work with a different team? Learn from different people? Learn about a different sector or job function? Will this role help get you where you want to go?
What questions would you ask? What did we miss? Leave them in the comments!
Amazing checklist, thanks for sharing these tips!