The questions that are first on my list to ask are:
- How does the investor valuate my company compared to how I valuate it?
- What will I need to give up in order to complete this raise? (not just talking about equity but also possible micro-managing by the investor if they aren't passive)
- Can the investor bring more assets and value to the table than just capital and how could that have a positive effect on the growth of the company?
There is no guarantee that the questions above will have any impact whatsoever in the fundraising process. I think a bigger problem as I find myself in the position lately of failing to effectively qualify potential investors. You never know what an investor will do when it comes time to write the check, but it seems that the majority of investors (at least those that I have interacted with) are tire kickers that apparently have a great deal of time on their hands to snail through a deal.