Useful Questions to Ask a Startup

Okay, so here’s the situation: you’re in tech. You’re in high demand. Not only that, but you’re doing scores of interviews and chatting with lots of companies. What questions should you be asking?

From my time in the startup world, I found a number of questions to be useful when talking with startups. While these questions were developed with startups in mind, you can easily customize them for non-startups. My hope is that you’ll find some use in these questions no matter the type of company you’re talking to. Now, enough preface — on with the show!

Your questions will fall into three buckets: company, team, and individual. Your goal is to collect as much information as you can in these areas.

Company level

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At the company level, you want to know the company’s success likelihood. You want to know the company’s culture and resources. Nominally, anyone from the executive team should be able to answer these questions (e.g., CXOs, SVPs, VPs). In reality, this knowledge may reside in the heads of many people. Find them (e.g., “Oh, you don’t know; do you know someone who could answer this question?”). Now, for the specific questions.

  1. What is the company’s unfair competitive advantage? Why will it be sustained? Obviously, a good answer could explain the what and why of the company’s sustainable unfair competitive advantage. But, you should also note that a good answer could also be that the company has no sustainable competitive advantage (See Rita Gunther McGrath’s HBR article: Transient Advantage). That said, I’ve never heard a company claim to not have a sustainable competitive advantage (at least to a candidate). So, if one does to you, that company likely values candor or is trying to discourage you from joining. You’ll have to use your judgment to know which one.
  2. Is the company pre-revenue? Does it have early customer validation — does it show product market fit? Is the company simply expanding on a working formula? These questions are grasping at a simple fundamental question: how close does the company’s funding round match with the company’s maturity (See the diagram after question #5). If a company’s maturity is lagging its funding, the company is likely sluggish with execution but great with investors. A company whose maturity exceeds its funding level is one likely to have its pick of investors.
  3. Have people left? If so, why? If not, why do you think why not? What would you say the attrition rate is? You’re probing for any systemic issues in the company. This question is one you ideally want to ask in person. You want to watch the person’s overall reaction just as much as their words. It’s similar to the kind of question Elon Musk posed to Ashlee Vance when he asked: “Do you think I’m insane?” Elon didn’t really care about Ashlee’s words; he cared about Ashlee’s reaction.
  4. What are people least excited by? What do they dislike most? Asking about what people are least excited by is important because when you ask a question, people tend to answer your question as posed. This leads them to looking for positive examples which leads to confirmation bias. The antidote for confirmation bias is disconfirming evidence. And, you get disconfirming evidence through asking disconfirming questions. So, asking about what people dislike is critical to getting that disconfirming evidence. You can get at this through many ways. For example, you might ask “how many days in the past month has your job left you energized?” (Jeff Bezos believes this important for “work-life harmony.”)
  5. What are people most excited by? What do they like most? This is the inverse of the above question. In this question and the previous question, you really want to ask this question of as many people as possible. You will really want to see if patterns emerge. If something is being echoed by many different non-colluding people, you can give those responses more credence. Separately, this also gives you a sense of whether or not this is something you could get behind if you became an employee at the company. If people at the company are anything like the people in this global study they’ll likely be excited by innovation, purpose, and flexibility. Those three things are abstract. Your goal is to make them concrete.
Social Capital Slides (Slide 5); Does the maturity level match the funding level of the startup you’re considering?

Team level

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In many startup environments, most of your work will be with team members. Ergo, understanding how you will work with those team members will give you insight into how you will be expected to work. If the team has a system of operating that doesn’t fit your working style, you won’t excel. Better to figure this out before you join versus after your first performance cycle. The person these questions should be aimed at should be your potential manager or tech lead.

  1. What are the different roles on the team? You want to know that you will serve a meaningful role on the team. One of the worst things you can do is join a team and then find out that you have to go off and twiddle your thumbs in the corner as they figure out what you have to do. Some companies have too much money and over hire and then after a while have to over fire. You don’t want to find yourself in that situation. Another benefit of asking this question is that it helps you understand whether your manager understands the team’s dynamic. An inability to explain each role and how they help the team succeeds is a bad signal.
  2. What does collaboration look like? How does the team collaborate with each other? How about with other departments/teams? A company full of siloed teams will be far less able to cross-pollinate and in many cases realize its full potential. In a startup environment, siloing is a bad look. While a big company may be able to get away this, small companies are too small to get away with this kind of behavior for very long. If you’re the type of person that really enjoys working across teams, and you learn that this team doesn’t really do that, you may want to think carefully before joining this team.
  3. How is the team managed? You want to know whether the manager’s working style will match yours. If the manager is fairly hands on, and you know you do your best work when you’re largely left alone, you know you may have a red flag on your hands. If possible, you should cross reference this manager’s explanation with someone that the manager manages — to see if the explanations match.
  4. What are the biggest challenges for the team? Knowing what a team deems hard helps you calibrate your difficulty meter. If the team’s difficulty meter and your difficulty meter are wildly different, there’s probably a mismatch. An inability to articulate what is hard about their work is a bad sign. It suggests the team hasn’t thought deeply enough about their work. Separately, if they tell you what is difficult about their work and you think it’s trivial and they are unable to explain why it’s non-trivial, again you may be a bad match.
  5. What’s the attrition rate? Why? How long has this team existed? How long have you been a part of this team? Everything from the Company section above holds here. In addition to that, the latter questions here will help you understand how to weigh the person’s responses. If he hasn’t been on the team very long, his perspective should be calibrated appropriately with someone else who’s been around longer.
  6. What’s been the biggest accomplishment of the team to date? You want to get a sense of what types of things the team is able to do together. If what they’re able to do sounds like something you’d be proud of, then it might be a good sign. If the team has been around for years, you’d want to know if there are multiple instances of this or was this just a fluke experience for the team.

Individual level

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You want to know how your role will be. After these questions, you should be able to imagine the critical parts of your job. You’re trying to highlight any blockades that may prevent you from being as excellent as you can be as a individual contributor (or as a manager, if that’s the role you’re aiming for). Ideally, these questions would be with the person (or persons) you’d be reporting to.

  1. How are priorities determined? How do we agree on them? It’s incredibly important to understand how work will get done. I think many people think that engineers are simply told what to do and they just go off and do them mindlessly. In many cases, the set of options are large and there’s a fair amount of flexibility in how the work gets done. If the company is run like it’s supposed to, nobody will “tell” you to do anything. Managers/colleagues will try to convince you that a task is the best/most important thing for you to be working on to help move the company forward. If you find out that something else is more important, and you’re able to make your case, you should be allowed to work on that more important thing. To suss out if stuff like this happens, ask if this has ever happened. If it’s never happened, you should ask if people have ever pushed back on working on an assigned task. Work tasks you accept should be work you believe in, not just what some higher up believes in.
  2. How do we determine if I’m getting the right job done? How is feedback provided? Some companies have biweekly, and quarterly retrospectives. Others simply have annual reviews. Some simply have ad-hoc feedback. Others still, have no feedback. You want to know what you’re walking into. Also, you want to know who ultimately decides the quality of your work. Is it your peers, your manager, some combination thereof?
  3. What does success look like in my role? This will help you determine if this is the type of individual you want to be. If the person described is someone that is working nights and weekends and you were looking for a role that allowed you peace of mind on nights and weekends, then this may be a big red flag for you.
  4. What is the biggest challenge for my role? You are hired to solve particular problems. And whether it’s problems you’re working on, or obstacles that make solving your problem difficult you want to understand the nature of them. Your biggest problem will likely take up a meaningful proportion of your life and so you want to get as much of a heads up on this as you can.
  5. What are examples of the type of problems I’d solve? This will help you imagine doing your job. If you can simulate the experience of working there, then you know you have enough examples. Often times, people give candidates abstract scenarios that make it difficult to imagine the work. The antidote to this is a concrete example. If it’s possible for them to discuss something from their actual work because you’ve signed an NDA please have them do that.
  6. Why was it determined that this position should exist? This helps you understand how the organization is thinking about hiring. If you get a bad answer to this (“we just want as many good people as we can get!”), you probably are dealing with someone that isn’t properly prepared to talk with candidates. Or, you might be in a situation where the team is over hiring and may eventually be over firing. Be wary.

These are a lot of questions. However, they’re few when compared to the amount of time and energy you’re considering handing over when you accept an offer. The interview process is usually longer than one day. So, if you don’t remember all these questions when you’re onsite, you can always follow up with phone calls and reaching out to your recruiter or the specific people you spoke with. If you ask the above questions wherever you’re interviewing, I’m confident you’ll be significantly more prepared than most candidates walking into a tech startup interview situation.

Good luck!

(What are other questions, you’ve found useful to ask startups? Share in the comments.)

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