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Questions to ask when joining a startup

Questions to ask when joining a startup

Knowing which startup to join is all about asking the right questions

Joining a startup can be an exhilarating thrill ride, or a crazy horror show. At least for me, it’s easy to get overly excited about a company during the interview, even if there are some nagging doubts in my mind. That’s why I’ve prepared a list of questions that I ask myself during the interview process, before I join a company.

Some of these questions may seem obvious, and some may appear completely out of left field. All of them are important. I use them to try to determine whether the startup meets my three criteria for a company that I would be willing to work at:

  • I like the people

  • The customers are in love with the product

  • If I could, I would invest in the company

You’ll notice that money (and stock options) come last on that list. I’ll explain why later…

Figuring out if I can work with the people at a startup

I cannot emphasize it enough: the people make the place! Way before I am thinking about how much I am getting paid, or contemplating what my commute would look like, I am wondering if I can work with the other people at this startup. Here are some questions I ask to try to figure that out.

  1. Am I treated with respect by EVERYONE on my interview loop? This is obvious, but I believe everyone, at every level, should be respectful to everyone else. It’s just common human decency, and a baseline expectation for any workplace.

  2. Do my interviewers ask me questions about my working style, and the working environment that I am most successful in? If they don’t, then how could they determine if I would be a good fit or not?

  3. Were the interviewers trying to make me fail, or hoping for me to succeed? I find that the tone of a question betrays a great deal about the type of company it is. Sometimes, interviewers devise trick questions to trip me up, or they dig and dig into every facet of my response to find fault. I understand some scrutiny, but I also realize that these are the people I am going to work with, and their attitude won’t suddenly change when I start working there.

  4. Did I actually get to talk? Sometimes, the people I am interviewing talk and talk and talk and talk. I had one interview at a startup (where I was actually given a very nice offer), and I probably only spoke for 40 minutes out of nearly a day of interviews. No one could shut up about how awesome everything they were doing was. I’m sure it WAS awesome, but I don’t want to work for arrogant windbags.

  5. Are they excited about the customers and the product? Anyone can be excited to have stock options in a successful startup. But, the companies that are built to last have employees that love the product, and love their customers.

  6. Do they say nice things about one another? I always ask them about their colleagues. Who is their favorite person to work with? Who is the hardest person to work with? They’re awkward questions, in a way, but the answers are priceless morsels.

Do the customers love the product?

Why does this matter, you might think. Well, the truth is that there isn’t any way to find out if a startup will fail or succeed, but a startup with unhappy, disenfranchised, and moody customers probably isn’t long for this world. Happy customers aren’t a guarantee for success, but they are definitely a very very positive indicator.

  1. Does the company have customer references? These should be on the website, or at least available upon request as either a PDF or an introduction (for very early companies). If not? I RUN.

  2. Are the customer references GLOWING? A happy review is easy to come by. Even the crappiest of companies can find one customer to say something nice about them. Finding a customer that is GLOWING with excitement is much more difficult. Customers who gush about a product, and go into detail about how it has changed their lives, are a rare and powerful asset.

  3. Are review sites favorable? Although I don’t put too much stock into Yelp, G2Crowd, or Gartner Peer Insights I will admit that having some sort of review is better than nothing. It’s worth a read.

Is this company a good investment?

I have said it before: I will only work if I get a piece of the equity. Life is to short to be a wage slave, so I have promised myself that no matter what I am doing I will own at least a piece of the company I am working for. Naturally, this requirement lends itself to startups, which almost always give Incentive Stock Option grants to their employees.

Even then, not just any startup will do. I also need to find someplace where those options might be worth something! I need to find a company where I would actually WANT to invest my own money, because by working there I am investing my very valuable time. Here are some of the questions I like to ask to find that out:

  1. Does it pass the 1 in 10 test? If I intend to work for a company, I need to know that they have the potential… the likelihood even… of driving at least $1b in annual sales over the next 10 years. It’s fine if it is a tiny company, but a tiny company in a tiny market will just never be worth it.

  2. Does the product solve an problem someone would pay to get rid of? If the product doesn’t alleviate some sort of pain, then it’s not likely to sell very much.

  3. Does the product exist in an established industry? Although it is hard to break into existing markets, it’s much easier than creating a new one entirely. I always look for companies that are disrupting an existing market.

  4. Am I getting a material stock option grant? If I am working for stock, then there needs to be potential for that stock to be valuable. This could either be because I have an outrageous amount of stock in a company with moderate prospects, or I have a tiny amount of stock in a company that is a sure thing. Either way, it needs to be something worth working for!

Obviously, knowing whether or not the employees are good and the customers are loyal are important factors in evaluating the company as an investment, which is why I put this section last! If I don’t get to the investment section, then it doesn’t matter anyway.


What are the questions that you ask before joining a company? These are really just starter questions for a longer discussion, but I think they are pretty good!

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