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19 of the Most Unexpected Questions Investors Will Ask You

Here to help startup founders be prepared are 19 of the toughest questions investors may ask in your next pitch.
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Preparing for a pitch meeting is a crucial first step for any entrepreneur seeking funding. Much like any interview, being able to think on your toes and handle pressure well are vital abilities that an entrepreneur needs.

Before heading into a pitch meeting, you should have defined your goals, such as what you plan to accomplish. A solid business plan is your best friend if you're looking for funding. You'll need to include financial projections, a detailed explanation of how you'll use the funding, and information about your business model and competitors.

Your presentation should be engaging, informative and tell your brand’s story in a clear and compelling manner. Your presentation is your chance to showcase your business's strengths and impress potential investors. Rehearse your presentation to ensure that everything goes smoothly.

Lastly, make sure to anticipate investors' questions. Answering tough questions about your business is probably the most challenging part of a pitch meeting — but preparation is key! As mentioned above, having clear goals plus a strong pitch deck are crucial components of preparing for a tough pitch meeting.

Investors will usually ask about your company or the product or service you're pitching. The "standard" questions may be easy enough to answer, especially if you've gone over your presentation multiple times and know your business well. Every so often, though, you might encounter a tricky question that may rattle you in a high-pressure situation. 

Some investors like to ask scenario-based questions about missteps or even personal questions that might catch you off-guard. These allow them to gauge certain aspects of your leadership style and personality and how you handle certain situations. Again, the key to staying calm under these circumstances is anticipation and preparing as best you can.

Pitch meetings are often always nerve-racking, but taking time to think about possible questions that investors may ask can help you stay prepared. Answering investors’ questions adequately will also let them know that you’re knowledgeable in your field, familiar with your business's specifics, and can hold your own under pressure. 

Aside from the usual questions, we've rounded up some random questions that investors may throw your way. Here are 19 of the most unexpected questions investors may ask you based on interviews with VCs, angel investors, and startups.

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Built to scale with HubSpot for Startups

It takes some time to put together a startup pitch deck that works, but once you’ve nailed your presentation, you can reuse it for multiple pitches with just a few tweaks to update any data or statistics.

HubSpot for Startups helps you track marketing and sales data to make this process easier. New investors can rest easy knowing you’ve got the support of HubSpot’s powerful CRM at your fingertips.

Amazon Web Services

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