Tips for pitching your story


Picture a baseball game. You’re the pitcher. Your goal? To get that ball into the catcher’s glove. To push past the hitter’s swing.

Your delivery mechanics? You set up, carefully. You take your time. Each move is deliberate. Each second has its purpose. You step and pivot, your leg lifts, you drive down the hill and land. Simultaneously, your arm swings back, comes forward, and follows through.

What appears to be a one-second move, can actually be broken down into a series of critical components, all carefully crafted and planned, yet invisible to the untrained eye.

The best pitches are so flawless that the hitter doesn’t even try to swing. The secret is to throw with control and throw with conviction.

Traditionally, this is the approach that has been advocated for pitching your story to investors, or whomever else. To be measured, to be convincing, to be prepared.

And while being measured, convincing, and prepared provides value to your message, it also lacks in something that is simply more human: vulnerability.

When you’re pitching your company, you’re pitching both the tangible and intangible.

Tangibly, you’re showcasing opportunities for traction, for success, for impact. These things can usually be measured and represented with graphs, charts, and numbers.

Intangibly, you’re showcasing yourself, your values, your beliefs, and your mission. This is all much more vulnerable and can be represented through a dynamic story.

Understanding your story

In order to tell a convincing story, you need to have a solid understanding of your purpose. And this is much harder than it might seem because your purpose might be different today than when you first decided to take on this venture. Your purpose is a living, evolving aspect that may change as you and your organization grow. This is normal -- don’t let anyone tell you otherwise.

But the fact of the matter is that people want to understand why you’re doing what you’re doing. Most of them have either read or listened to Simon Sinek. You have most likely read or listened to Simon Sinek.

So get real with yourself—in this moment, why are you doing this? Who are you? Why you? What’s the problem you could no longer ignore, and what’s the vision that motivates you to move forward?

Don’t expect this information to just come to you. You will need to put in the work to dig deep and get vulnerable with yourself. If you need tools, there are countless ones available online, from logic models to theory of change tools, you can find one that works for you. At Last Draft, we like to use DIY Toolkit’s Theory of Change matrix.

Telling Your story

The landscape of work is, thankfully, changing. Many work environments are becoming increasingly diverse, and are bringing together an array of people with different backgrounds, interests, values, and traits. Let’s leave the Mad Men bravado behind, shall we?

If you want to get real when you’re pitching, lean into some vulnerability. Unlike the tired performativity of putting yourself on your own pedestal, honesty takes courage. And the truth is, if you combine a compelling story with an honest storyteller, your audience will connect with you, and more than that, they’ll trust you.

Finally, as you work through the process of humanizing yourself, you may be pleasantly surprised to find yourself humanizing the people who are listening to you. Yes, they may be investors, or potential partners, or whatever other impressive titles you can think of, but first and foremost, they are people. Try to understand what they care about. Be curious, and be flexible enough to interact with them in a dance that can be likened to an evolving game of theatre improvisation far more than it can to a stiff baseball pitch.