Investor meetings and pitching live
How do I handle tough questions during an investor pitch?
Short answer
Prepare for them before the meeting. Write down the 30 or so hardest questions an investor could ask about your deal, then draft honest answers from your pitch deck. In the room, answer directly, say so when you do not know, and follow up in writing. A question you have already practiced is easier to answer calmly.
Most tough questions are predictable
When a question catches you off guard, it is usually because you never wrote it down. Sophisticated investors ask about the same things again and again. They ask about risk, about your track record, about how you get paid, and about what happens if the plan goes wrong.
I tell people to treat this as homework. Before you ever sit down with an investor, list every question you hope they will not ask. Those are the ones to answer first.
Build your own due diligence questionnaire
Here is what we recommend at Family Office Club. Create a questionnaire of about 30 questions that any investor should be asking you. Most investors do not know what to ask, especially if your niche is something like storage, healthcare or fintech. So you write the questions for them.
"If you're raising capital, we always recommend you have a due diligence questionnaire, like 30 questions that every investor should be asking you, but they don't know what to ask you."
This does two things. It forces you to find the weak spots in your own deal. It also shows the investor that you have thought about the hard parts before they did.
This clip shows how to turn a pitch deck into a list of sharp investor questions and first-draft answers.
I talk about using AI for this in the clip. You upload your pitch deck and ask for the top 30 questions a sophisticated investor would ask. Then you ask it to answer them using your deck. Copy the result into a document and edit the answers until they are accurate and in your own words. The first draft is just a starting point. You still have to check every fact.
What to do in the room
- Listen to the whole question before you answer.
- Answer the question that was asked, not the one you wish was asked.
- If you do not know, say so and promise a written answer.
- Send that written answer quickly, ideally with supporting documents.
- Keep a log of every question you get so your questionnaire improves.
Honesty matters more than polish. Investors talk to many sponsors. They can often tell when someone is guessing. A clear answer of "I do not know, I will confirm and send it today" can build more trust than a vague answer that sounds confident.
Remember that investors prepare too
Some investors now run your materials through their own tools before the call. Some send you questions by email before they agree to meet. If you cannot answer those questions well, they may not take the meeting.
Also keep your data room ready. Documents that support your answers, such as financials, track record and legal materials, should be easy to share. Many sponsors talk to a securities attorney about how to communicate with investors.
More from my talks
Two habits matter once you are in the room. Stay calm, because getting emotional or defensive about a hard question tells the investor more than your answer does, and reply quickly so nothing sits unanswered for weeks. Also, do not walk through your pitch deck page by page and only then ask if there are questions. I think that is the wrong way to go. Let the investor's questions steer the meeting, so you spend your time on what they actually care about.
"One thing is to make sure that you are ready for tough questions. You don't get emotional or defensive about it and that you're able to respond very quickly."
"So I like, "Oh great, we get a chance to pitch, let's go through our pitch deck page by page, and then we'll see if there's questions." And I think it's the wrong way to go."
Facts from this talk
- We recommend raisers keep a due diligence questionnaire of about 30 questions that every investor should be asking.
- An investor can upload a 60-page pitch deck to an AI tool and get questions to email the sponsor before agreeing to a meeting.
- The AI advisory board tool includes seven personalities, drawing on a thousand plus investors who have spoken on stage.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Mental Models, AI, And Investor Edge: How To Think Differently And Raise Smarter Capital. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.
General education only. Not legal, tax or investment advice.
Talk to a securities attorney to explore options around investor communications, offering documents and pre-meeting disclosures. Do not use AI to write your own legal agreements.
Next moves
- List the 30 hardest questions an investor could ask about your deal.
- Draft honest answers from your pitch deck and check every fact.
- Practice the answers out loud with someone who will push back.
- Prepare a data room so you can send support quickly.
- After each meeting, add any new questions to your list.
Follow-up questions
What if I do not know the answer to an investor's question?
Say so plainly and promise to follow up. Then send a written answer soon after the meeting. Guessing in the room can hurt your credibility.
Can AI help me prepare for investor questions?
Yes, it can draft a list of likely questions and first answers from your pitch deck. You need to review and correct everything before you use it.
Should I send answers to investors before the meeting?
A prepared questionnaire can help, since many investors do not know what to ask in your niche. Many sponsors talk to a securities attorney about what to share before a meeting.
Related questions
- How do I pitch investors over Zoom effectively?Treat the Zoom call as the first meeting and aim to earn a second one.
- How do I explain my startup idea to investors?Start with the customer problem, then explain in plain language how your startup addresses it.
- How do you pitch an investor for the first time?I would pitch an investor for the first time by keeping the conversation short, relevant, and focused on their interests.
- How should I follow up with an investor after a meeting?I follow up with investors by listening carefully, documenting what matters to them, and contacting them when I have something genuinely valuable to share.
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