What questions to ask before joining a startup?

Joining a startup can be a very exciting journey, especially if it is your first job experience.

That being said, joining a startup can also be a very challenging path, and may not come with the job security that big companies offer.

Here are a few questions you should ask yourself (and probably even the interviewer) before you decide to join a startup.

• What does the startup expect from you?
  
• What will you learn from your journey in the startup?
• Who will you work with? (Who the boss/supervisor is and what their background is)
• What is your longer term goal and how will joining a startup bring you closer to your longer term goal? 
• What sort of work do you enjoy doing? While there are many things you may have an interest in, what is something you wish to master/specialize in? Can this startup give it to you or help you learn it quicker?
• How big is the team? In smaller teams, the opportunity to have a more hands-on experience is greater, but it may also be more stressful. In larger teams, you may be able to broaden your network quicker and potentially even gain experience in other areas beyond your work scope.

These are just some at the top of my head, there's definitely more.

Fundamentally, my advice would be to work backwards from what you want at the end of the day, and then work for a leader in a company who can bring you closer to that goal of yours.

In my opinion, it is always better to join a startup as your SECOND company (or later).

One should start off by working in a big company (corporate) first, as it helps you gain a broader understanding of how a company is run - corporate culture, processes, and a sense of hierarchy.

It is also a good place to meet some very good connections.

Once you've absorbed enough over there (and feel bored enough to want to leave), then by all means try out startup life.

When entering a startup, fundamentally the most important things are:

• Who will lead you.
  
• What you'll learn.
• Who you'll meet.

And for yourself on a personal scale, you should be clear on:

• Where you'd like to be in 5 years 
  
• What you love doing and want to keep doing for the next few years
• Who you enjoy spending time with (or want to have around you)

Everything else is secondary.

Hence, formulate your questions around these areas listed above, and you will never go wrong.

This may seem pretty selfish, but this is what I'd ask myself:

• Do you really want to spend the next 2 - 3 years of your life working here? 
  
• What will you gain out of it in the next 2 - 3 years in this company?
• Am I passionate about this space / work?
• Do I really need to move to a startup to attain the experience/contacts/skills to what I want to achieve?
• Is there any career progression?

You need to know what you want to achieve in walking this journey, then you know the questions better than anyone else.