How to Handle Unexpected Questions During Your Pitch

If you’re the kind of person who typically plans everything in advance, chances are you’re also the kind of person that will rehearse your pitch until you know it by heart.

A polished pitch presented with confidence is what every CEO seeking the support of collaborators, partners, and investors hopes to deliver.

The only challenge?

There’s only so much you can prepare for the questions that you’ll receive from your audience.

So what do you do when you’re asked a question you can’t answer by someone who has the resources that could help you take your business to the next level?

In this week’s video, I reveal my very best strategies for keeping your cool and thinking on your feet, plus a surprise tactic to help you use unexpected questions to your advantage.

Watch it now!

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I'm Kelly Keenan Trumpbour, angel investor and venture capitalist. And in this video, I'll talk to you about how to keep your cool with those unexpected questions that pop up during your pitch.

So if you've ever watched Shark Tank or Dragon's Den, as it's known overseas, you see a lot of entrepreneurs going in front of the show and their pitches seem so well put together. Sometimes there's a few curve balls for drama, but mostly the show keeps rolling along.

But sometimes when you pitch, things come out of left field. So what do you do when you get a question you weren't expecting and you're thrown off your game. Being able to field questions that feel way out of your league, is the way you set yourself apart. Because thinking on your feet like that shows real command of your business and the expertise you bring to it. Don't be afraid of these questions. And don't be afraid if you don't know exactly what to do. The real art is just being able to field them and come back with something that's useful for the investors.

Tempting as it may be, don't try to fake it. Many of the investors in the room will be able to call you out on it. Also, you don't want to say something that just isn't true, and have that come back to be the reason you're denied an investment. Sometimes an investor asks a question, and you don't really know what they're asking. The impulse might be to just pretend like you do, but sometimes the wise course is to ask for clarification. Sometimes the investor just doesn't word the question very well and it is confusing. Other times you may not really know what they're talking about, but it's still better to come off as someone willing to learn, and to take the steps necessary to get the right information to the investor, than to either make up an answer, or pretend you knew what they were talking about when you really don't.

There are times where you're going to be just stumped by a question. That's okay. In those instances, ask the investor if you can follow up. Is there a time after the meeting where you can get them that information? Sometimes this is a great strategy because if you show the investor that you know they're asking something important, but you want to learn more, you might trigger a mentor reflex in them. They may want to give you more time and advise you more so that you can take your business to the next level. It's a win win.

So what happens when you get a question that is so weird and so out there, that you're really wondering if it's worth your time to answer it. My advice is always show interest. Why? It may not be you who's really stumped, maybe the investor completely misheard your presentation as just off on a tangent. If that's the case, don't let that person be embarrassed. You don't have to make up for their fault. But if you just show professionalism and some degree of interest, it'll show the other investors in the room that you're willing to roll with the punches.

On the other hand, maybe the investor is really on to something and they're trying to point you in the direction of something you missed. So if that's the case, showing interest shows that you're willing to learn a little bit more, and at least get curious enough to find out what you have to do to really answer the question.

If you get a question that you didn't think you handled as well as you could, it can be useful after the meeting, in a conversation or a follow-up email, to ask the investor to clarify. There's actually a surprise tactic in here. If you want to be remembered as someone who's worth an investment, even if it's down the line, asking the investor to clarify what they meant, and to show that you're really interested in learning more about that concept, shows that you're on a trajectory of learning more about your industry, finding out what investors need, and taking your business to the next level. It may even awake a sense of mentorship in that investor, and they'll want to help you more than they already have.

Just remember, when you get a curve ball question, in my world, investors aren't trying to be malicious, they're really trying to get to the bottom of what you know and what's at the core of your business. So where you can roll with their questions, show an interest to learn more, and ask for clarification. It can only help you in the long run.

Another temptation is to guesstimate. If you get a question where they're trying to pin down specific numbers, make sure the answer you give back is either based in reality or is something that you can go back and prove. Never put a number out there that's just patently false, it's going to come back and bite you. Investors will absolutely research that information, or call you out when they know conflicting information.

There are always going to be things that you should be able to answer without losing your cool. You have to be able to talk about profit margins, your trajectory for what's happening in the next three to five years in your business. How are you going to scale? Why should investors like us invest in you? What's your ask, and what's the exit strategy? All of these ... you have to be able to talk about them and not get flustered. But sometimes, no matter how much you prepare, you cannot expect all the questions you'll get. It's okay, you don't have to have it perfect, you just have to be able to roll with it enough to show that you're the person worth following and betting on in the future.

If you’ve found this video valuable, go ahead and like it and share it with your friends.

Until next week


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