Questions to Ask before Joining a Startup

In most of my experience with startups, I’ve been either a founder, an advisor to the founding team or an employee joining in executive level.  As such, I’ve generally been on the hiring/recruiting side of the equation.  It continues to amaze me how often people fail to ask the really important questions before joining a startup.  They get a lot of the basics (compensation, benefits, vesting, roles/responsibilities, etc.) right – but often fail to hit some of the important topics that are peculiar to startups.   

The reasons people don’t ask the critical questions can be broadly categorized as:  “I didn’t even to think to ask that” or “I would have liked to know, but didn’t think it was appropriate to ask”. 

Here are the things that I think all individuals looking to join a startup should know about the startup before joining – but are in many cases, not asking.  I’m going to stay away from the standard questions that most people already know to ask and focus instead on the questions that often go unasked.  Note:  I’m not suggesting that you ask these questions “point blank”.  I’m trying to really just surface the areas that should be covered in your discussion.

1. What's the vision?
2. What is the Organization structure?
3. Strategy for competition and growth strategies
4. What do they expect from you to achieve and get it done?
5. What are the biggest problems? What do they want you to fix first?
6. What's exit plan?
7. What's Employee engagement strategies?
8. Can they tolerate aggressive push in order to generate results?
9. Will they allow crazy experiments like unlimited annual leave?
10. What is the purpose of the startup? Why not other startups?