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I have an upcoming interview with a startup, but don't know what kind of questions I should ask them. I can't do much research on them since they are just now getting off the ground.

  • Please keep us posted about your progress. We'd like to hear your reasons about accepting or declining an offer. – user8365 Sep 8 '12 at 14:01
  • also ask how they score on Joel Test – vartec Sep 10 '12 at 11:44
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    @vartec - a startup may only be able to indicate how they 'intend' to score since they may have nothing built yet. – user8365 Sep 10 '12 at 20:31
  • Consider a short-term paid temporary project, ideally with the team you'd potentially be working on - you and the company will learn a great deal about one another and see if you're likely to be a good fit. It might even be worth taking a bit of vacation time from your current job so you can experience more of their real-world culture. Good luck! – Careerasaurus.com Oct 3 '15 at 9:54
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Beyond basic technology choice questions, here's what I usually want to know:

  • What is their intended business model? (because I don't live in the Bay Area, I expect them to have at least an initial strategy, even though it's always subject to change)
  • How big is the market they're targeting? (not always that important, as everyone will overstate how big a deal the market they are getting into is)
  • What do they think it will take to get to 1.0?
  • For really early-stage, poorly funded ventures: What do they think it will take to achieve ramen profitability (the level it would take to pay people enough to live with roommates and eat cheap food and achieve basic subsistence, or, what it would take for the company to achieve the equivalent of not freaking out about making payroll)?
  • Do they have any customers right now? If not, who is doing business development? Whose job is it to find, market and sell to customers?
  • What does their development team look like right now? I have a slight bias against firms that have done their first round of work with outsourced labor, but I'm not dogmatic about it.
  • What's their current level of funding and how much runway do they have before they burn through all their cash? (In typical scenarios, it's about 6 months; in better funded scenarios, closer to a year). What's the plan to get the next round, assuming it's necessary?
  • What skills do they think are critical to their success?
  • How many people are involved right now? What does hiring look like in the near term? etc.
  • Do they believe in a sustainable development pace? Do they expect death-march mode for the foreseeable future?
  • Assuming fairly long hours, how much flexibility do they have about where the work is done? Can I do 35-40 hours a week in person and spend evenings and weekends home with my family but dealing with the occasional production issue or prepping for a board meeting?
  • What's their development process? Are they practicing a specific methodology or is it all cowboy, all the time? Scrum? Kanban? Egocentric micromanager CEO developing a task list and saying go?
  • Do they have any intellectual property (patent applications, exclusive licenses, etc) that are valuable as assets if the company is sold or auctioned off?

Edited to add:

  • Because I work on a couple of small-scale side projects, I often ask if they have a problem with me doing occasional off-hours work for non-competing projects. It's worth knowing at least because it helps you understand how much they want you to drink the Flavor-aid vs. how much they value entrepreneurial thinking.
  • I also like to know how transparent they will be about their finances once I start working there. When I was at Zillow, we had monthly or at least quarterly meetings showing our cash burn rate, how far off or how close we were to target revenue, and a bunch of other metrics; it made us very aware of how big the hill was that we had to climb, and how much we had to worry about.

Here's what I tend to get told about even without asking:

  • The pedigree of their executives, advisors, board of directors
  • How great the market is for the thing they're trying to do
  • How clever their founder/lead developer/CEO is
  • What they've built so far

An angel investor friend of mine once told me, as a precondition to accepting an offer (obviously only after one has been extended), if you're going to be employee #1-10, it's perfectly reasonable to ask for proof that they've got money in their bank account in roughly the amount they've been funded.

Expect a fair amount of rose-colored glasses salesmanship, coupled with realism about how tough it will be to actually reach their target market.

If you're actually extended an offer, it's fair to go through several rounds of discussion about equity, vesting, vacation, and so on. You probably won't get much leverage on cash compensation except in unusually well funded ventures. You'll probably be paid 30-40% less in salary than a job at a profitable firm, and sometimes worse.

Most of the startups I've interviewed with have pitched offer salaries that I wouldn't have complained about a year or two prior to the pitch, but are below my current going rate. You have to be willing to work for the potential big payoff, but more importantly, ok with the likelier outcome of financial catastrophe, so don't just accept something that you can barely live on because of the promise of stock options. If you're important enough to their initial success, you may even be able to insist on an ownership grant that vests over a certain number of years of service (though this will be taxable to some extent), not just stock options.

  • Thank you for a very well thought out and explained answer! You covered so much, many different areas that I didn't even consider. – Jeremy1026 Sep 8 '12 at 14:10
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I've been burned by jumping head long into a startup before. In my experience, you should ask them and yourself some questions.

Questions for them

  1. Is there a set date for the next major release of the product?
    (If they can't give a specific tangible date/month, trouble)

  2. What areas/technologies/skillsets will they still be lacking after you join their team?
    (If there are too many, chances are they will not meet number 1 above).

  3. Given your resume, do they believe your skills as is, are going to count directly to their bottom line?
    (At the first sign of trouble, the non-essential hands are the first to be cut loose)

  4. Who do they feel their biggest competition is in the space they plan to operate in? How are they mitigating this?
    (you need to look at their competition and evaluate for yourself how feasible it is that they'll be able to get a slice of that market without being crushed)

  5. Are you going to be led/be reporting to a technical person or a business person
    (I can't sing enough about this)

  6. If there is any learning curve to joining this startup, within how long do they expect you to start pulling major weight? Do they have any documentation/wiki/shadowing to help you ease into the process?
    (Zero documentation or at least a whiteboard of what they've been doing will leave you gasping for air most times.)

  7. Is their technology stack cast in stone or are they willing/open to evaluating, possibly including proven tech/apis that will make the development all that much easier?
    (A startup without any form of flexibility with regards to problem solving approach is the antithesis of a startup. They should be open to experiment)

  8. Read the contract properly. How are they tying your hands? Does working for them stop you from working for a competitor for the next 5 year? Are they allowed to can your a@# with 10 minutes notice?

Ask yourself

  1. What do you stand to lose should this experiment go belly up?
  2. Can you afford this experiment?
  • Your point about being lead by a technical person vs a business person is unclear. Which are you suggesting is better? – Burhan Ali Sep 18 '12 at 14:26
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    Techies should be led by techies. The team/tech lead is/should be the technical department's bridge to the business end. Two technical people communicating on an issue/challenge will get more done faster than a tech subordinate trying to articulate the challenge to a non-tech. It's an age-old problem – kolossus Sep 20 '12 at 3:57
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As long as they can demonstrate they can pay a competitive salary (like JasonTrue mentioned), it's not that different from any other job.

However, if a large portion of your compensation is going to come from equity (stock, options), you need to think about this more like a venture capitalist. You may not be investing cash, but you are putting in sweat-equity and providing some expertise.

  1. What qualifies the people starting this venture? Previous experience, skills, etc.
  2. How do they know someone will buy their product? Have they done any testing or is this a feeling about their great idea? Not good enough. Has anyone in this company have any experience selling to this market? Fortune 500 companies don't buy 6-figure software packages off the internet after a 90-day trial period.
  3. Get a lawyer and get things in writing. If they object, something is wrong.

Getting into more details on some of these points may be more appropriate after an offer has been made.

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