Questions to ask before joining a startup

Hiring for Cubeit, I have done dozens of interviews. I am left frustrated at the end because most people don’t know what questions to ask. Questions I can’t possibly have answers to or questions I haven’t even ever thought about.

Joining a startup is not a regular job, it is probably the most brutal, exhausting and plain painful experiences you can go through. The questions you ask regular companies are not ones you should be asking before joining a startup. Asking about the future is simply liking asking for a crystal ball. What you should ask about is the present and history and do your own extrapolation. In asking these questions, you should put yourself in the shoes of an investor, you are investing a couple of years of your life and you have the right to get answers. Here are a few suggested questions.

1. What is the history of your idea, how has it evolved into what it is today: This question helps you understand probably everything about the company. This is the most useful indicator of what the future of the company is going to look like.
2. Who will use the product, What is the problem you are looking to solve: this question gives you the best sense of how the product is going to be used and is that users problem of interest to you.
3. Who are the companies you consider as competition: Are other people in the space getting traction, is a lot of action happening. How fast is the market growing.
4. Who are the investors and why did you pick the investors: Deep insight into what motivates the founders to start the company and how do they feel about it. You only split a pie with people you like. If you are willing to split it with just anybody, you don’t care about the pie.
5. How long before you run out of cash at the current burn rate: Important to know when you might be out of a job. Prepare for the inevitability.
6. What is the founders salary: Getting the answer to the question is not important. How do they respond to this questions will help you understand what motivates the founders. Also the lower the number the more passionate the entrepreneur. Every cheque an entrepreneur takes is a step closer to running out of money.
7. What is the immediate goal for the company: A vague answer to this questions is a huge red flag.
8. What do you consider as core values of the company: Will you fit in to the work culture.
9. What are you looking for in me: This sets the expectations for what you will be expected to do once you join. Don’t join unless you can meet the expectation. If they expect too much, you will be the first one to be let go off because you can’t do your job well. On the flip side, don’t take a job where the expectations are limited, you won’t get a chance to grow. Exponential growth in your career is expected with exponential growth in the startup.
10. If I join what is the first thing I would work on: Don’t join unless you get a very concrete answer to this question. If the answer is vague, there isn’t enough work for you. You shouldn’t join a startup that is nothing for you to do. Joining a startup and not doing anything is counter intuitive.
11. How can I impact the startup: If you cannot find your place under the sun in the startup you will be miserable. If the founders don’t allow you to have your say, might as well work at a larger company.
12. Who was the last person you hired and why: Tells you a lot about who are the kind of people you are going to work with. What is the kind of the problems the startup is currently facing.
13. These are my career goals, do they align with what your vision: Important to know, more important to point out.
14. What will I gain out of working with you: It would help you understand how well the entrepreneur can make everyone win if the startup succeeds.
15. Finally the kicker. What would you do if this idea doesn’t work out: Contrary to popular belief, if you get a good answer to this question: don’t join, run like hell! The only acceptable answer is something you know the guy just made up.

Join a startup because you really believe the product or service the startup is building is meaningful to you. Your time is probably of more value than anything else, don’t waste it building something you don’t believe in.

Famously Brian Chesky Founder of Airbnb asked candidates, “would you work at Airbnb if you only had one year left to live?”