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Top 10 pitch questions investors ask (from actual investors)

Published:  Feb 1, 2019
Featured expert
Yana Abramova

Founder of Pretiosum Ventures

62d926778667bb377251dad6 Oliver Kicks
Featured expert
Oliver Kicks

Principal at Concept Ventures

Jonny Seaman
Featured expert
Jonny Seaman

Investor Partnerships Manager

Anthony Rose
Featured expert
Anthony Rose

Co-Founder and CEO

You’ve nailed your pitch and you’re finally on the ‘thank you’ slide. Now what? What questions will investors ask you after your pitch?

We’ve spoken to venture capitalists and angel investors to gather the top ten questions to prepare for when you pitch and when you have your first meeting with investors. We’ve also explained why investors ask these questions and how best to answer to make a good impression.

In this article:

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10 questions investors ask when you pitch

The questions investors ask when you pitch will vary, so we’ve listed the most common questions along with some more unusual questions. As part of your preparation, it will be helpful for you to think about the answers to all of these:

1. How do you explain your product to customers?

You know what you do (hopefully) but how good are you at communicating it simply and concisely? It’s common for investors to still feel unclear about what problem a company solves by the end of their pitch. They end up having to ask for a more straightforward explanation after the pitch. That’s because a lot of founders talk about what they’re doing more than the problem they’re solving.

Save your investors’ time and make sure you explain what you’re offering during your pitch as if you’re talking to your potential customers.

Anthony Rose

From the start, explain your company simply: We are X and we solve X problem. And then make it super clear why your customer will want your product. I want to see a pitch presented as if I was a consumer of the product rather than an investor. If I can see you have a compelling consumer proposition then I want in. If you can’t explain it as a consumer might want it then I won’t want to invest because if you can’t explain it to me, you can’t explain it to anyone and no-one will want it. Explaining things easily to a mass audience is very important to make sales.

Anthony Rose

CEO & co-founder,


2. What do you perceive to be your biggest challenge following this raise?

Some of the questions investors ask are aimed at gaining a better understanding of who you are, what your mindset is like and how well you understand your market. Make sure you know what your challenges are and how you plan to solve them.


I like to ask this question because I’m looking for a founder to demonstrate self-awareness and their ability to assess the market they’re operating in. If someone doesn’t think they will have challenges, it usually isn’t a good sign. The best way to answer is to outline some clear issues, and describe, step by step, how you’ll solve them.

Oliver Kicks


Concept Ventures

3. What core assumptions/questions will you test?

This is a pre-seed stage question. When you raise your first round, you’re probably still at the idea stage so you won’t have much proof from the market yet. Investors want to understand what you’ll prove and test with the capital and resources from the raise.

For example, before Airbnb existed, there wasn’t proof that people would rent a room in someone’s house short term (or that owners would agree to host guests in their home). Airbnb needed to test their product in the market to prove that it would be adopted and become lucrative.


Hopefully, once you’ve proven that you’re solving a large and lucrative pain point, the company can raise more capital to bring the product to market. This isn’t achieving product-market fit but is instead proving the business premise. When you’ve proven this, you can raise more money from later-stage investors.

Oliver Kicks


Concept Ventures

4. If everything goes right, where do you see this business in five to seven years?

This is a common question and a tough one to answer because it’s difficult to judge where you’ll be in five to seven years. Things change. You can never be sure. But from the investor’s point of view, it’s not about being sure – it’s about demonstrating that you have a clear vision and goals, understanding that things might shift but you know what you’re trying to achieve.


Here we’re testing the ambitions of a founder, and aiming to understand how they are seeing the future they’re building. There is no right or wrong answer, only a chance for them to tell their story.

Oliver Kicks


Concept Ventures

5. Why do you want to create this company?

Your personal objective is the seed of your company. If you’re fully committed, clear and believe in your solution to a defined problem, it will drive the success of your entire company. Use a question like this as an opportunity to inspire your investors.


I ask this question because it helps me understand the founder better. I want to know what drives them and why they believe in what they’re doing. I want to understand their personal objective.

Yana Abramova

Founder & Managing Partner,

Pretiosum Ventures

6. What’s your biggest weakness?

When they ask about your biggest weakness, the investor wants to know more about who you are and explore whether your values align with theirs. In your answer to this question, think about how you can express self-awareness, humility, who you are and what you value.


For me, this is not a question about weakness but about honesty, integrity, and authenticity.

Yana Abramova

Founder & managing partner,

Pretiosum Ventures

7. How do you hire people?

This is a common question because the people you hire have a massive impact on your company’s success (or failure). Investors want to know they can trust you to hire the right people.


Along with this question, I ask:

– How do you define f a potential employee is a good fit or not?

– Have you already identified people to hire after you’ve raise the round?

Yana Abramova

Founder & Manging Partner,

Pretiosum Ventures

8. What makes your team the best people to do the job?

Investors want to know that they can trust your leadership team to execute your ambitions successfully, especially during early-stage raises before your company has plenty of achievements to show. Make sure you’re prepared to explain the experience, industry knowledge and expertise of your team members. You can also talk about your advisors and mentors and how they are helping you.

Jonny Seaman

I always ask about the team because I want to have a good understanding of the industry knowledge they have. I’m looking for them to demonstrate that the people behind the idea understand their industry and market. It’s important for me to trust a startup’s leadership team to achieve success before I make angel investments, and I know it’s the same for other investors I speak to daily.

Jonny Seaman

Investor Partnerships Manager,


9. What risks does your business face?

It’s important to understand potential risks before you pursue your venture. Investors might want to know about:

  • Legal risks
  • Regulatory risks
  • Product liability

Make sure you understand all the risks your business might face and be prepared to explain how you’d mitigate those risks.

10. Are your documents in order?

Investors might not ask about this when you initially pitch, but by the first meeting, you should be prepared for investors to ask about the following:

Due diligence is when investors collect information about founders and the company to help them make an informed decision about their investment. Investors will want to see legal and financial background information. Read more about due diligence and data room in our article Deal data room: securely share documents with investors.

Targeted questions about your business

Investors will also ask targeted questions about your business. They want to understand if you know your business in fine detail. They’ll ask precise questions about aspects of your business model and question your assumptions. They want to know that you’ve truly thought things through and that you have a deep understanding of your venture. At the pitch or during the first meeting, investors might ask about:

  • your business metrics (for example customer acquisition costs and expected growth rate)
  • how competitive the market is
  • the size of the market
  • what trends you see in the market
  • how you stack up against your competition

5 quick tips to improve your pitch

Getting ready to pitch? We’ve listed our top five tips below. For more detail and unique insights from investors, read our article How to pitch to investors and download our free pitch deck template, which includes tips from experts and step-by-step guidance.


Our top 5 tips to nail your pitch:

  • Tell a story to keep things exciting
  • Focus on the solution you offer – not just what you do
  • Don’t use too many words – bold statements and bullet points are ideal
  • Keep it high-level – don’t give too much detail
  • Use high quality imagery and videos to showcase your product
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Anthony Rose

Anthony Rose

Serial entrepreneur and startup champion, Anthony is our CEO and Co-Founder.
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