Asking These 3 Questions Will Make You a Pro at Pitching Startups

This simple framework can help you learn to give a perfect pitch every time.

A buddy of mine runs a startup accelerator. He recently invited me to speak to his cohort and meet, individually, with its 12 current companies. Despite the fact that both my buddy and I explicitly explained I was there as a startup advisor and not an investor, all but one of the startups pitched me and asked for money.

To be fair, of course they did. Ask any entrepreneur what they wish they had more of, and most of them will tell you they need more money. After all, they need to build products, hire people, get more sales, and so on and so forth. Since those things all cost money, their jobs would presumably be much easier and their chances of startup success much higher if only they had more cash.

However, as all these desperate entrepreneurs gave their best effort to get cash from someone who had no plans of writing a check, I couldn’t help but wonder why they were wasting their time. Did they genuinely think if they pitched well enough, I’d magically find a million dollars to give them?

I doubt it. Instead, most of them just didn’t spend enough time considering who they were talking with and why. This is a common mistake entrepreneurs make when they pitch their startups, but it’s one that can easily be avoided with a basic framework built around asking yourself three simple questions before, during, and after every pitch.

Why entrepreneurs need a pitch framework

Before sharing the framework, I should provide some context.

First, I’ll mention that I’m not opposed to constantly pitching anyone and everyone. Heck, I’ve been building startups for 20 years, and most of those 20 years I adhered to the mantra: always be pitching. Whether I was meeting a venture capitalist, a prospective customers, a potential employee, or even just the exterminator doing his quarterly pest control service on my house, I, like most experienced entrepreneurs, understood two important things about pitching:

You can never have too much practice explaining your startup; and,
You never know how someone might be able to help you startup.

Hence… always be pitching. But the always be pitching mantra has a disadvantage, too, and it’s one that gets harder to see the more you pitch. Specifically, when pitching becomes something entrepreneurs do habitually, they sometimes forget to consider why they’re giving a particular pitch.

Think about it like driving a car and using turn signals. You’re driving down the road, and the jackass in front of you hits his brakes without warning. A couple seconds later, he flips on his signal and turns into a shopping center.

That driver probably thinks he’s a good driver. After all, he used his turn signal. He followed the law!

But he didn’t use his turn signal properly because he wasn’t thinking about the purpose of a turn signal. For him, the turn signal was something he was obligated to do. He forgot that turn signals aren’t obligations. Turn signals are meant to help the people in cars around him know what he’s doing before he does it. If he was actually a good driver, he would have engaged his turn signal before braking, not after.

The same is true for good entrepreneurs giving pitches. Pitching shouldn’t be viewed as an obligatory part of entrepreneurship. It’s not a turn signal to be flipped because someone made us. Pitching is how entrepreneurs take all the complex, messy, expensive, time-consuming work we’ve put into building our startups and convey it to others in ways that make our purpose and value understandable and appreciable so people can help.

Unfortunately, the more entrepreneurs pitch, the more they tend to forget why they’re pitching. Like with turn signals, pitching becomes a rote habit… a sort of after-thought they do more because they know they’re supposed to than because it helps the people around them better understand how they can help.

The pitch framework entrepreneurs need to learn

The entrepreneurs at the accelerator I was visiting were struggling with this problem of forgetting why they were pitching. Rather than helping me understand how, with my particular set of experiences and expertise, I might be able to help them, they were focused on pitching me like I was an investor. In other words, they were operating on a sort of pitching autopilot, which meant they weren’t taking any time to think about who they were talking with and why.

Don’t be an entrepreneur who pitches on autopilot. When you pitch on autopilot, you’re not able to extract the full value of talking with someone because you’re giving a pitch that may or may not be relevant.

Instead, use the following framework of three questions to ask yourself before, during, and after a pitch. It’ll train you how to extract maximum value from every pitch opportunity.

Question #1: The pre-pitch question

What does this person already know about why we’re meeting?

The word “pitch” gets used by entrepreneurs to describe lots of different types of meetings: fundraising pitches, sales pitches, stage pitches, etc. However, even though the same word gets used, every pitch is different. At the very least, the people being pitched have different contexts related to why they’re meeting.

Good entrepreneurs understand this and, as a result, they spend time thinking about what the people they’re about to pitch already know before a pitch even starts. This helps savvy entrepreneurs customize their pitches, which, in turn, makes the pitches more successful.

Question #2: The during-pitch question:

Am I talking too much?

Even though pitch meetings seem like opportunities for entrepreneurs to talk about themselves and their companies, that’s actually not the purpose of a pitch. Pitches are meant to connect the work an entrepreneur is doing with the people they’re pitching.

Because of this, a good pitch should never be one-sided. It should be a conversation and a discussion.

To ensure a productive conversation, constantly ask yourself during a pitch whether you’re talking too much. If the answer is ever “yes,” intentionally stop yourself and ask a question. Doing so will get the other person re-engaged.

Question #3: After-pitch question:

What will help this person take the next step I’d like for them to take?

A great pitch is just the beginning of a relationship. Ideally, if the pitch goes well, more conversations (and actions) need to happen after, and that work requires entrepreneurs to follow-up.

As a result, once you’ve finished meeting with someone — a meeting where it’s become clear that the person you’re pitching can clearly bring value to your venture and is excited about doing so — immediately ask yourself what steps you should take next in order to extract meaningful value. Learning to identify and then take the next important step after a productive conversation is key to turning what otherwise would have just been a simple meeting into a successful pitch.