The questions founders should ask startup investors in the first meeting

I coach founders every week on how to hold more effective investor meetings, and there’s one recurring problem: founders wasting time chasing investors who don’t fit.

Sound familiar?

Success isn’t pitching your startup.

The path to fundraising success starts with making sure the investor is right for you.

You have the right – and responsibility – to qualify investors early on. Asking the right questions isn’t rude; it’s smart. And, it sends a positive signal to investors that *this founder* thinks deeper.

Here’s how to do it politely and efficiently.

TL;DR

• Ask questions like: “What is your cheque size range?” and “Are you currently investing?”
• Qualify investors early to avoid wasting time.
• Request specific introductions at the end of the meeting.
• Send a well-structured warm intro email to make it easy for the investor.

Why Qualifying Investors is Crucial

If you’ve been in the startup world long enough, you’ve probably heard the horror stories.

Example: A founder I know spent 3 months entertaining an angel investor, only to find out that they didn’t have any money to invest. That’s 3 months completely wasted!

These situations are all too common. Asking the right questions early on helps you avoid dead ends and ensures you’re speaking with investors who are serious and a good fit for your startup.

Key Questions to Ask Investors

1. What is your cheque size range?

It’s surprising how many founders skip this. Knowing the investors cheque size from the start prevents massive mismatches later.

Polite phrasing:
“Can you share your typical cheque size range? I want to make sure we’re aligned on funding expectations.”

Example: A client of mine once spent 30+ hours with an investor, only to learn they typically write $10k cheques, while the startup was raising $1.5 million. Imagine that disappointment.

2. When was the last time you invested in a company like ours?

Investors who haven’t invested in startups like yours before or in a long time might be a lot harder to get across the line (if at all).

Polite phrasing:
“Could you tell me about your most recent investment in a company like ours?”

3. Are you currently investing?

With some venture capital funds and angels tight on capital right now, this is a critical question. There is no point pitching to an investor who isn’t currently able to invest.

Polite phrasing:
“Are you actively making investments right now? I’d love to understand where you are in your investment cycle.”

Example: A client of mine spent about 6 months talking to a VC fund, only to find out that the fund didn’t have any cash and therefore couldn’t invest.

4. Are you a wholesale or sophisticated investor?

This is a legal question but important in Australia to ensure the investor is compliant.

Polite phrasing:
“Just to ensure we’re compliant with regulations, are you verified as a wholesale/sophisticated investor?”

5. Do you lead rounds?

Some investors prefer to follow, while others lead. Understanding this helps you structure your round.

Polite phrasing:
“Are you comfortable leading rounds, or do you typically follow? This helps us plan the structure of our round.”

Additional Critical Questions to Ask

6. What’s your decision-making process and timeline?

Investors all have different processes. You need to know how long it will take to get to a “yes” (or “no”).

Polite phrasing:
“Can you walk me through your decision-making process and timeline? I’d love to know what to expect for next steps.”

This helps you go into the process with your eyes wide open and manage expectations.

7. What kind of involvement do you expect post-investment?

You don’t always have time for hands-on investors who want to be heavily involved. And some investors don’t have the context to be as involved as they think they should be.

Polite phrasing:
“How do you typically get involved post-investment? I’d like to know how hands-on or hands-off you are.”

Passive investors can be just as valuable if they trust you to run the business.

Ensuring the investor has the capacity to participate in future rounds is important to your long-term stability.

Polite phrasing:
“How do you approach follow-on funding? I’d love to know how you support startups through multiple rounds.”

9. What does success look like to you in this investment?

You want to be aligned with the investor’s vision of success. If not, there could be conflict later on.

Polite phrasing:
“What does success look like for you in this investment? I want to ensure we’re aligned on long-term goals.”

Why asking hard questions can impress investors

Some founders worry about asking tough questions, thinking it’ll scare investors off. But guess what? It shouldn’t. Thoughtful questions show you’ve done your homework and that you’re serious about finding the right partner.

Follow-up: Requesting introductions

When the investor is enthusiastic and asks how they can help, don’t be shy—ask for introductions.

Polite phrasing:
“Thank you for your interest and support. One way you could help us is by introducing us to investors in your network who might share our vision. We’re especially looking for those passionate about [specific focus].”

If you’ve already researched their connections, ask for specific introductions. Afterward, make it easy by sending a warm intro email for each person they agreed to introduce. This ensures they don’t have to draft anything themselves—just forward it. They’ll appreciate how easy you’ve made it.

Conclusion

Asking the right questions early saves you from wasting time and ensures the investor is a good fit. Remember, it’s a two-way street: Investors get to ask hard questions, and so do you.

Follow up with them, make it easy to help, and you’ll build stronger relationships and increase your chances of a successful round.

Bonus Tip: At the end of the meeting, if the conversation went well, ask if the investor would like to be added to your investor newsletter.

This keeps them updated on your progress and strengthens your relationship for potential future investments.