How to Raise $20 Million in 7 Steps, Lesson 6

How to Handle Hard Questions in a Pitch Meeting

Once you get to the pitch meeting, it means that you’re going to field all sorts of questions about you, your business and your ability to give investors a return on their money. Just as the process unfolds on Shark Tank, these investors are going to have all kinds of questions that they will use to interrogate you. Your ability to answer their questions will determine the success of your pitch. They’ll interrupt you, they’ll push you and they’ll say rude things. You’ve got to be ready for it. Luckily, you can prepare for most of this before the meeting. And even the questions that you can’t foresee, you can prepare for how you’ll deal with them in the moment.


Research hard questions

You won’t be the first person to receive tough questions in a pitch. And you won’t be the last. Take the time to research the kinds of hard questions that investors typically ask and prepare your answers. If you can have a handle on the standard way investors will challenge a founder in a pitch, you’ll be prepared for whatever comes your way. 

Review hard questions you’ve already been asked

There was a reason you took a bunch of notes in all of your pre-meetings. Those notes will provide insight into the questions people had. Review those notes and look for any questions that threw you off guard, or similar questions that multiple people asked. Make sure you have clear and succinct answers prepared for them. 

Practice a Q+A with your team

You want to ensure that you’ve thought of all the hardest questions before your actual pitch. Put really smart people who you trust in a room and don’t just practice your pitch; practice answering their questions. 


Don’t compliment their question

You can say, “What a good question” only once in a pitch. Or don’t say it at all. Investors see through it — and they see it as a stalling tactic. If a question throws you off, you’ve got to remain calm and act unflappable. It’s totally fine to be honest that the question is making you think. But instead, say something like, “That’s a new question for me.” Only say this if it is true, and don’t say it more than once in a meeting. It complements the investor in a different way while showing that it’s not one you’ve heard before. (And a pro tip: Ask the colleague you take with you to the pitch to write down all of the questions! You’ll want to remember them). 

Repeat the question

This will give you a single second to breathe and come up with an answer on the fly. It may seem like it’s no time at all, but it’s enough time to get your mind jogging so you can think on your toes. You’ve got to deliver the answer like you’re confident and sure, and repeating the question will give you a little bit of time to do that. 

Remember your audience

Investors all have a different area of interest, and when you’re answering a question that is difficult, do your best to speak to their needs while you answer it. Even if you don’t nail the delivery, you’ll show that you have their priorities in mind.

Investors all have a different area of interest, and when you’re answering a question that is difficult, do your best to speak to their needs while you answer it. Even if you don’t nail the delivery, you’ll show that you have their priorities in mind.

Ask for clarification or a definition

If you sort of understood them, but not fully, ask. Different words and perspectives can mean different things. By asking this, you’ll get more insight into what they’re actually getting at, and you’ll give yourself more time to think on your feet. Additionally, it shows the investor that you’re not afraid to gather information and use it — something critical to building a company. 

Hedge inappropriate questions

Every once in a while you’ll hear something completely rude or inappropriate. Everyone will deal with this differently. You might decide to call it out, to shoot from the hip, or you can hedge by not answering the question they asked, but by answering the question you want to answer instead. Amy’s strategy is to ask the investor to repeat the question, with a simple: “Could you repeat that? I don’t understand.” Her hope is that in asking the investor to repeat the question, they might see the bias or awkwardness they’re bringing to the situation. It will also give you an extra second to prepare your response. 

Buy yourself more time

If an investor asks you a question that requires further data or requires you to crunch numbers that are not easy to do on the spot, or that requires future modeling of projected numbers, tell them you’d like to spend more time on the ask before giving them an answer. Tell them you’ll get back to them, and actually do so. This will give you a reason to follow up. Remember, you can only really do this if it’s a new set of numbers or projections. If it’s about anything current, you should know your numbers like the back of your hand. (If you do ask for more time, it goes without saying: Follow up! And quickly!) 

Questions in big pitch meetings can be difficult. Do as much work as possible to prepare for the hard ones, and to get comfortable expecting the unknown. Whatever you can do to show up as completely confident and unflappable in your business, do that. It’s important you’re not easily thrown off when challenged. Learn to expect curveballs in meetings, because investors are particularly good at throwing them.

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