When meeting with investors, you have to ask the right questions. It shows you've done your homework and helps you find out more about investor interest and fit. Here are the critical questions to ask:

First, show that you’ve done your research – mention the specific fund that the investor is a part of, citing a similar deal they’ve done. Or ask them how they view your industry and how they see its future. Not only will you show you’ve done your homework, but you’ll also gain some valuable insight into their perspective. 

• Where are you in your VC fund life cycle?

• How much of the fund is reserved for primary vs. follow-on investments?

• What is your follow-on strategy?

• How often do you make follow-on investments?

Second, ask them precise, concrete questions about their investment process – and use their answer to get at the details of timeline and criteria.

• How fast do you make decisions?

• How many meetings are typically held before a decision is made?

• What is your due diligence process?

• Are you interested in leading the deal?

• Who else needs to be involved to make the decision to invest?

• Do you typically take board seats?

Research into VCs existing portfolio can provide insights into their expertise, network, and potential synergies. Additionally, digging into the VC’s track record of success, failure, and lessons learned can learn more about their performance in nurturing portfolio startups. 

• What’s the last company you’ve backed and why?

• Are there any potential conflicts with your other portfolio companies?

• What is information sharing like with founders and within your portfolio companies?

• How have you helped other companies that you’ve invested in?

• Aside from capital, what value-add or support can you provide?

• Do you have a network, and can I use it to connect with new clients?

Get some feedback about your pitch. Avoid asking outright whether they’d be willing to invest. Instead, ask for their feedback on your business and your pitch. If and when they show interest, ask what would build conviction for them. If they say no, ask what you could do to make your project more appealing.

• What aspects of our business or pitch resonated most with you?

• What concerns or reservations do you have about our business model?

• What additional information would you need to build conviction in our company?

• What are the key factors you consider when deciding to lead/follow an investment?

•  Based on what you’ve heard so far, what do you see as our biggest strengths and weaknesses?

• How would you compare our pitch to other startups you've invested in or are considering?

Finally, make sure that you stay on their radar. Ask if it is OK to stay in touch and let them know that you’ll be following up with an investor newsletter. This maintains the warmth in the relationship and lets them know you’re making progress. 

• May I also send quarterly updates to keep you posted on our progress?

• Is there something that we should be tracking or a milestone that you’d like to see in the next several months?

• Do you mind if I email or call you for advice or feedback as we achieve project milestones?