What Rewriting a Speech 24 Times Taught Me About Selling With Personal Stories

I have a speech competition this weekend.

The speech?

I wrote it a few months ago. And I’ve delivered it to a few audiences already to test the idea and gauge their reaction.

After the first batch of feedback, I rewrote it.
Then I rewrote it again.
And again.

By the 24th rewrite, I thought I’d nailed it! One of the best speeches I’ve ever written.

It had:

• A clear, powerful message.

• A punchline I repeated enough to stay ingrained in the audience’s mind.

• Personal stories to build connection and avoid sounding generic.

• Vivid imagery that made people see the story, almost as if they were living it.

• A mix of humor and drama, like a binge-worthy show that keeps you hooked.

I thought it was perfect.

But on Tuesday, I did a test run in front of some experienced speakers… and I could feel something was off.

I couldn’t put my finger on it.

Luckily, someone in the audience, a seasoned speaker herself, could.

After my delivery, I asked her for feedback.

“It lacks an emotional connection,” she said.

I stood there, stunned.

I knew exactly what she meant. But I didn’t want to admit it.

For context, the speech revolves around this message:

“To stand for the truth, despite the fear, no matter the cost.”

I framed it as a lesson my grandmother taught me through a story about a man who faced a dilemma: stand for what’s right and risk death, or stay silent and let injustice prevail. He chose the former.

Then I shared three personal stories showing how I carried this lesson with me in my life:

• A lighthearted incident from high school.

• A relatable moment from my first year in college.

• And finally, a recent, deeply personal story where I had to make a tough choice: stand for the truth or stay silent.

That third story was supposed to be the heart of the speech. But as my speaker colleague pointed out, it wasn’t.

“I know you shared personal stories, Mo,” she said, “but it didn’t feel deep enough. I couldn’t feel the struggle you experienced to make that decision.”

And she was right.

I skimmed the surface of my emotions.

I didn’t dig deep enough to make the story resonate.

Here’s a modified snippet from that part of the speech:

========================

“Fast forward to a few months ago…

I was sitting at my desk, overwhelmed by everything life was throwing at me.

So, I picked up a pen, thinking writing would help.

[talk about how the act of journaling was so difficult and how…]

I couldn’t take it anymore, so I started scratching out the words…

I thought I was silencing my fears with all that scratching. But no, no…I was running away from them.

In that moment of fear, I heard my grandmother’s words echo: ‘Stand for the truth, despite the fear, no matter the cost.’ As if by magic, all my fears were washed away.”

[start the conclusion]

========================

Reading it now, it’s clear why it fell short.

It was personal, yes, but it barely scratched the surface. It didn’t heighten the emotional tension or pull the audience in deeply enough.

Instead of connection, it created an emotional riff between me and the audience.

And here’s the thing: we often make the same mistake in selling.

We share personal stories but without enough depth to resonate. Or we avoid sharing them altogether, thinking they’re unnecessary.

But that’s why the best sales pages are long and the most impactful speeches and seminars aren’t 10 minutes, but hours long.

It’s not enough to share a personal story.

Your story needs depth. It needs courage. You have to dig into the emotions driving it, even the ones you’re hesitant to share.

So, here’s my challenge to you:

Find the stories you use to sell your product or offer. Then, go deeper.

Identify the emotions behind those stories.

What makes them real?

What makes them human?

When you hammer down on those emotions, that’s when you create a connection.

As for me? I’ll be rewriting my speech again before the weekend.

I’m not selling anything today. But I’m working on some valuable resources that I’ll share with you soon.

Until then, go dig into your stories.

Mo