What speechwriting and dating have in common

When I was dating, instead of filling out a traditional profile I wrote a series of fake testimonials:

"She is the smartest, most beautiful girl in the world." — Anna's mother

"I'd date her." — Anna's ex-boyfriend

Partly to amuse myself. Partly because I was exhausted by profiles about how much everyone enjoys spending time outdoors and/or with family. But mostly because I knew that someone who read my profile and laughed would be a good match.

I've been thinking about that a lot lately, because the speaker-speechwriter relationship works exactly the same way.

You want to work with someone who gets you. Someone who thinks you're smart and funny. Someone you genuinely look forward to talking to.

A woman I'm working with on her keynote said to me recently, "I find myself really looking forward to our sessions. Is that weird?" It's not weird. It's necessary. Trust is what makes it possible to write someone's stories in their voice. And to write jokes that land for them — which, it turns out, requires knowing what makes them laugh in the first place.

The thing no one tells you about working with a speechwriter

Here's something I've noticed again and again in ten years of doing this work: people are very bad at knowing what makes them fascinating. Because it's just their life, right? It seems normal to them.

This has completely shaped how I work. Instead of asking "What do you want your talk to be about?" I'll say, "Whatever you think you want your talk to be about — let's just put that on a shelf and have a conversation." Not just to make you comfortable, but because that conversation is usually where your real talk is hiding.

About a year ago I was working with a journalist who wanted to write a talk about the power of curiosity. She was struggling to find her unique angle on a fairly well-trod subject. Then, midway through our first session, she casually mentioned that when her dad died she learned he'd been in the KGB.

Wait — what?

Of course someone who grew up in a world of secrets, whose phone was tapped from the age of seven, would grow up obsessed with finding the truth. That became the lens for the talk only she could give.

That moment only happened because the relationship was right. Because she trusted me enough to ramble. Because I was listening for the thing she didn't know she was saying.

If you're reading this thinking, "But Anna, I'm not that interesting — no one in my family was in the KGB," I'd say two things. First: are you sure? And second: everyone is fascinating. You just need someone to ask the right questions.

What a speechwriter actually does

My job is to find where your real talk is hiding and write it with you, in your voice. When you slip into "speech voice," I'll stop you and ask what actually happened — because the true version is almost always better than the polished one. We'll throw out the clever lines that are doing less than you think they are, and fiercely protect the strange, specific, true ones that make a room hold its breath.

That's something AI can't do. It can be a great tool — but it can't sit across from you and notice the thing you didn't know you meant. It can't catch the line where your voice cracks and tell you that's your opening. It can't build the relationship.

And the relationship, it turns out, is everything.

So. How do you find the right fit?

Your speechwriter gets to know you in a way almost no one else does — how you think, what words sound right coming out of your mouth, what you're really trying to say underneath what you think you're trying to say. That takes trust. And trust takes fit.

Which means the first conversation matters. Not because it's a sales call — but because it's actually a first date. You're figuring out if you like each other, if you make each other laugh, if this is someone you want to dig into the hard stuff with.

If you have a talk coming up — or have always wanted to give one — let's find out if we're a good match.