1. On how many boards do you sit?
  2. Do you really have enough time to impact the outcome of this investment through your involvement and engagement?
  3. Is there a culture of providing bridge capital to a series of objective milestones to get to a better point to raise our next round of financing?
  4. Do you have the necessary external relationships to help us build the syndicate for our next round of financing?
  5. What are your return expectations?
  6. Don’t ask for a reference call with a CEO of one of the companies they had to shut down;just cold call them without telling the VC.
  7. How do you feel about truly independent outside board members i.e. those with no affiliation with the firm?
  8. May I talk to one of the CEOs that you had to remove or delegate from their position?
  9. Questions on fund solvency are a must.
  10. what is the size of the fund you would be investing from?
  11. What is the average size of your first round investments?
  12. Don’t ask for a reference call with a portfolio CEO: just cold call them without telling the VC.
  13. Don’t assume that changes in founding CEOs are a bad thing. What you want to find out is how the investor behaved in managing these kinds of transitions.
  14. What was the toughest portfolio company experience you went through? How do you work through these tough situations?
  15. How many times have you been through CEO changes in your companies, and how did you arrive to that change?
  16. Would you consider this as an investment if the right opportunity and team were to present it? Why or why not?
  17. How close does a product need to be to finished before you will consider an investment?