How To Tell Better Stories In Your Pitch

As part of the various accelerators and incubators I’m involved in, I get to help a lot of businesses sharpen their pitches ahead of Showcase Day/Demo Day.
There are a tonne of good articles and talks online about why storytelling is so powerful, and I think at this point everyone agrees that an interesting story beats dull slides.
The question is, how do you make a story better?
Here are some principles that I’ve seen work consistently, try them out for yourself…

The Lightbulb Moment
Every good startup story is built around a “Lightbulb Moment”, the magic point where you suddenly see why this is an exciting business.
There was a moment where you didn’t understand why Spotify would be a good idea, why Uber was better than a taxi, or why a Keep Cup was better than a takeaway cup.
Then something changed, and in an instant you “got it”.
It might have been an example, a tagline, seeing someone you like using a service, but whatever is was, it was a turning point.
If you’re going to win new fans for your business, you need to help people experience that moment for themselves – the moment they understand your cause and your value proposition.
The way to improve your stories is to deliberately design these lightbulb moments, and build your conversations around them.

If you don’t feel like you know what these look like, my suggestion is to watch Shark Tank or Dragons Den.
Look for the key moments, phrases, examples or answers to questions that impress you, or at least impress the Sharks/Dragons.
The camera will cut to these reactions, or if they look unimpressed, you know that something about the story hasn’t triggered the Lightbulb.
Once you start, you’ll see these moments everywhere.

If you tell a story that makes people laugh or sit upright, but doesn’t trigger a Lightbulb Moment, you’ll attract compliments on your speaking but not win new customers for your business.
Compliments are nice, but pitching is all about persuading someone to take action.

Before and After
The number one mistake people make is putting good details in at the wrong point.
Most of the time, their story doesn’t need to be cut, but rather re-arranged.
Specifically, re-arranged into “Things to say in order to trigger the lightbulb” and “Things to say once the lightbulb has lit up”.
For example, your name and your company name go at the start, so does a description of what business you’re in, and an overview of what investment you’re looking for.
Your pricing strategy, partnerships, social impact metrics, growth plans; these only matter once the audience understands what makes your business interesting.

Know Your Story Assets
There is no single script for this, and for good reason: it’s best to build your pitch around your strengths.
I call these “Story Assets”, the elements that prompt the Lightbulb Moment.
For example:
·      A founder’s personal connection to the cause
·      A founder scratching their own itch with their product
·      Demonstrations of the difference your product makes
·      Photos of beautifully designed products and services
·      A physical prototype that the audience can see for themselves
·      Quotes from happy customers
·      Social proof, such as famous customers or partners or investors
·      Validation and traction figures

I recommend building stories around these assets – if you don’t have one of them, don’t bother faking it.
Pitch envy is real, just because someone else has a heartfelt origin story doesn’t mean you should try and spin your own.
We’ve had some of our Indigenous businesses open with a traditional song and dance, the men shirtless and in traditional paints.
The atmosphere is electric, and I guarantee you nobody in that room looked at their phone for the entire time.
Who cares what Silicon Valley says about how to structure slides?
Anyone in their right mind can see that this is the way to start your story.
You want to identify your assets, and shuffle everything else accordingly.

Reason vs Emotion
They say “Reason leads to conclusions, emotions lead to action”.
In other words, you can use facts and figures to create a case, but without emotion it won’t lead to your audience taking action, and action is what will help grow your business.
The best points to add emotion are:
·      What prompted you to start/join the business
·      Why you care about the cause
·      How it feels to have this problem today
·      How much of a relief it is to have a solution today
·      Real customer stories, using individual examples
·      Testimonials from funders or partners

Turning The Knife
There’s a great book called Do More Faster written by the TechStars team and alumni.
They use a storytelling technique called “Turning The Knife” which they describe here:

“Describing the pain is usually quite natural, but many people forget to finish the job.
Think of describing the pain as sticking the knife in.
Your job is not done.
You have to really make me feel it.
You do this by twisting the knife slowly, deliberately, and repeatedly.
SendGrid, one of the TechStars Boulder 2009 companies, does an excellent job of turning the knife.
Their product improves the deliverability, scalability, accountability, and reliability of software-generated e-mail.
Sounds like a real problem, right?
The following is how they turn the knife.
"Twenty percent of legitimate e-mails sent by software companies to their customers will end up in spam folders."
Ouch.
"A large e-commerce company determined that if just 1 percent of their annual e-mail notifications aren't delivered, it costs them fourteen million dollars in lost sales."
Stop it!
"This same company figured out that at least 7 percent of their e-mail is ending up being marked as spam. This problem is literally costing them a hundred million dollars ...”

I love this principle – remember that the audience does not intuitively understand the problems faced in your industry, nor can they quantify the consequences.
By turning the knife, you make the pain points clear, and therefore your solution will seem like sweet relief.

Test Out Your Lightbulbs
You are not your audience, and so you’re not the judge of what constitutes a good sentence in your stories.
The audience is the judge, and we’ll do whatever it takes to lead them to the Lightbulb Moment.
That means the test of a story isn’t “Do I like it?” but rather “Does it work?”.
If you like a particular detail but it doesn’t work, we need to move it or cut it.
If you don’t love it but it works, let’s keep it until we find a better replacement.

Different people have different Lightbulb Moments, so you want to have 6 or 7 options up your sleeve, which you can throw in until one of them lights up.
The way to find 6 or 7 lightbulbs is to draft 50 of them, and you’ve probably been doing this subconsciously over the last few months.
Your brain tracks which lines did or didn’t get a reaction, which guides you towards or away from particular phrases, jokes or examples in the future.
My suggestion is to try out different versions of your stories with different audiences, and ask them what they remember at the end.
People don’t forget the moment the lightbulb lit up for them, so if there are elements that are consistently not remembered, you know where you need to put in more work.

I do this at my workshops; during the breaks I look to see what people wrote in their notebooks.
By learning which phrases and examples they write down (and which ones they overlooked), I’ve been able to drop out the duds, and test out new variants without fear.

Reduce Your Word Count
The way to make your stories more vivid is to remove any sentence that doesn’t contribute towards a Lightbulb Moment.
Filler words, details of where you went, repetition, unnecessary citations – write the story down and cross these out.
I’d say on average you can cut 20-30% of your words, and not only will you not lose anything, you’ll make your strengths even more obvious.
It also helps to use strategic pauses after your strongest lines, giving them time to sink in.

You Won’t Be Nervous Once It’s Working
People tell themselves they hate public speaking, but I propose that this isn’t quite true:
I think people are terrified of public speaking with unproven material.
When they know their joke is a winner, or when they tell personal stories that they know have emotion behind them, all the fear and stuttering goes away.
Vice versa, seasoned speakers get nervous when they are trying something out for the first time, like how comedians do out of town previews when developing a new show.
That means instead of trying to overcome average material with better body language, it might be more effective to get your Lightbulb Moments validated, then you’ll naturally speak with confidence.

The Next Step Can’t Be Learned From An Article
Practice comes from dialogue – reading people’s expressions to see which parts of the story kept them engaged, and which parts lost momentum.
Try talk to 3 different advisors or friends, making adjustments after each time, to double down on what makes your audience pay attention and to save the extra details for questions at the end.

Good luck with your presentation!

For more on pitch structures, have a look at Pitching To Different Audiences.
For tips on slides, read The Art Of The Start 2.0 by Guy Kawasaki.
For great advice on the psychology of pitching, read Pitch Anything by Oren Klaff.