Did you know, pitching might not be your secret weapon after all. Instead, pitch less , and ask your investors better questions.
This article is part two in our three part-series helping startup founders prepare for major startup- and investor conferences. Read also part II and part III.
You’re heading to Web Summit — or any major investor conference. You’ve got your deck polished, your financials modeled, your slides tight. That’s what most founders spend their prep time on. We call that the internal lens.
Smart founders do something different. They prepare for the investors they’re going to meet.
Here’s how. If you know which investors will be at the event — and for most major conferences, you can find out in advance — feed their names into your AI tool of choice (Claude works great for this) and ask it to write a one-page profile on each investor. Then, based on each profile, generate five key questions you should ask them specifically. Highly targeted. Highly effective. This will show you’ve done your prep work.
But what if you don’t know who you’re meeting? Cold contacts. New faces. You have no idea who’s going to walk up and hand you a card.
That’s what these 15 questions are for. Use them as written. Use them as inspiration. Flex and experiment. But go in prepared.
Part 1: The Easy Questions
These are your openers. Softball, yes — but notice they’re all open-ended. Every single one invites a conversation, not a yes or a no.
1. What are you typically looking for? Simple. Broad. Let them talk. You’ll learn more from this one question than from ten minutes of pitching.
2. What are the metrics you want to see before you invest? Get specific early. Every investor has a mental model. This question surfaces it.
3. What stages do you typically invest at? Don’t waste their time or yours. Know where you fit before you go deeper.
4. What investment instruments do you commonly use? SAFEs, convertible notes, priced rounds — know what they’re comfortable with.
5. What does your investment process look like? Set your expectations. Understand the journey before you start it.
Part 2: The Intermediate Questions
You’ve broken the ice. Now you go deeper. These questions are designed to reveal how they actually operate — not just what they say they do.
6. Can you walk me through your investment process from first contact to close? First meeting, term sheet, due diligence, round structure, closing. What does that typically look like, and what timeline do you prefer to work within?
7. Talk me through your due diligence process. What are you looking for? What makes a company easy to diligence? How can we best prepare so you get exactly what you need?
8. Walk me through some of your most recent investments. What did you like about them? Why did you pull the trigger? What are the key insights from your most recent deal? This is where you learn what actually excites them — not what’s in their deck.
9. Once you’ve invested, how do you typically work with your portfolio companies? Board seats, advisory support, introductions, hands-on or hands-off — what’s your typical engagement model?
10. Who are the co-investors you most like to work with? Any strong preferences on who else is at the table? Any names we should know?
Part 3: The Advanced Questions
These aren’t openers. Don’t lead with these. These are for the second conversation — over a beer, over dinner, when you’ve earned a real seat at the table. This is where relationships are actually built.
11. Walk me through your most successful investments ever. From the very first touchpoint, through the scaling journey, through the exit. How did you work together? What did the outcome look like — including the financial outcome? What made those relationships work? What was your MOIC?
12. We know the next two rounds will be critical. How would you typically work with us to get there? We’re not just raising this round. We’re thinking about the full journey. What does that partnership look like?
13. Let’s talk fund math. What’s your fund size, and what does the math look like for us to deliver a fund returner for you? We want to make sure that if you come onto our cap table, we have complete alignment on what success looks like — for you and for us. What numbers do we need to hit together to make you look great, and make your next fund a guaranteed raise?
14. Let’s talk exits. Given the current market, how are you thinking about liquidity? What’s your preferred timeline, and what mechanisms do you like to see? How do you structure your liquidity strategy?
15. If we were your single most successful investment ever — what would that look like? What would we need to deliver? What would we need to build together to make it, without any question, the best deal you’ve ever done across any of your funds? That’s the conversation we want to have. And we hope you want to have it too.
The Bottom Line
Fifteen questions. Entry level, intermediate, advanced.
Use them as examples. Use them as a starting point. But when you walk into Web Summit, remember this: you’re not there to pitch. You’re there to engage. You’re building a relationship with a long-term business partner — someone who might be in your corner for the next decade.
The founders who close the best rounds aren’t the ones with the slickest decks. They’re the ones who ask the best questions.
Go prepared.
This article is the second in a three piece series to help founders prepare for key conferences. Part I: The Founder’s Web Summit Checklist: 10 Things You Need to Prepare. Read it here. Part II: Meeting the Investors? Here’s what they’ll ask. Read it here.
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