pitching an idea

3 Questions That Will Stump Almost Every Startup at a Pitch Competition

Mike Sobol Startup Strategy 1 Comment

These questions cut to the core of what it means to be a startup: how you understand risk, how you learn what you need to and how you make choices and take action. They assume that the pitch itself is not the entire “framework” for your business, merely a succinct way to demonstrate you’re on the path to something big.

As we discussed in our last post, the value you gain from a pitch competition depends on how you approach it. Considering questions like these will help you to be the best-prepared participant on the stage.

Of course, you aren’t likely to get questions like these from most judges. They have a lot of information to process in short order, then they have to come up with an improvised performance of their own. They will be tempted to take what you say for granted and merely ask follow ups to fill in some blanks (there are always blanks). They may depend on their own industry or technical knowledge to press you on certain details. They will want you to see further into the future or have better plans than you do (that’s always an easy one for them). Of course, you can only do and learn so much with limited time and resources. Knowing that gives you the power you need to answer these questions effectively:

Question One:

Of all the things you could be working on, instead of practicing this pitch and being here, why is this competition the thing you chose? And what are you putting off? Be specific.

Weak Answer:
I’m trying to raise money. 

Better Answer:
Fair question. Top of my list: [Priority x, priority y, priority z]. I put those things off to be here, and I spent a lot of time preparing to be here because [insert how being here supports those priorities].

Never assume a pitch competition is your highest priority now or maybe ever. You must question everything. The judge who questions your very reason for being there is doing you a favor. If you are thinking every day about how to make your startup successful, a great answer to this question will already be top of mind for you because you’re always aware of the choices you have to make.

Question Two:

What are you probably wrong about? Your pitch is full of assumptions (all pitches are, it’s OK). I want to know which assumptions you just know are most likely to be wildly inaccurate and why. Or, at the very least, which ones are most likely to kill your business?

Weak Answer:
Well, my growth estimates are very aggressive. 10x growth in 18 months will be hard to reach, but even if we hit half of that, we’re doing pretty well.

Better Answer:
We know that [our plans hinge on being right about x]. That’s a big unknown. So is [y]. We have good reason to think we’re right about those things based on [evidence or analog example…], but we’re [taking these specific steps] to validate those things so we can move forward confidently. We feel good about how we’re systematically de-risking our strategy.

Humility is a rare thing on the stage. Demonstrating that you know full well what you’re up against (you should), and being clear-eyed about what’s more or less speculative is just plain smart. If all the answers were already known, your startup wouldn’t be anything new. If you look like you’re sure about everything, judges will be sure you’re on your way to being blindsided.

Question Three:

Tell me about something you’ve had to fight for. It’d be great if it’s related to your startup, but it doesn’t have to be. I want to hear about how you overcame a serious obstacle to getting what you want.

Weak Answer:
I work hard all the time. I graduated top of my class.

Better Answer:
[Some off-the-wall story about how failure looked imminent but you gutted it out. Did your startup run out of money? Did a key team member quit? Did your technology break? Did you pivot?]

This one’s personal and it’s meant to be. Sh*t happens to everyone, but what did you do about it? Millions of other people work hard and are successful, but few people are willing to step into the unknown to do it. Do you have the grit and creativity to handle it when plans break down, assumptions prove to be wrong and the world conspires against you?

Depending on the venue and audience for the pitch, you may never get questions as tough as these. They could seem unfair, even a little embarrassing to ask. That’s fine. But you should be prepared to answer them. Merely describing the problem, your solution, your traction, team and plans is so basic that it has a way of focusing people on whether they really think the idea is any good– that’s not the real point of the pitch.

What you, the judges and the audience really should be focused on is whether you are becoming the kind of startup founder who can make it happen. Ideas are not the constant in your startup. You are.

Comments 1

Leave a Reply