How to Tell a Story That Persuades Someone to Buy

Good Morning. An AI researcher quit his job at Anthropic this week after saying the AI labs are “gambling with our lives,” while another Anthropic researcher casually estimated there’s a 10%+ chance AI kills everyone within the next decade. Which, I guess, puts missing quota into perspective. But if the robots are coming for us anyway, you might as well squeeze in a few more quarters at 110%. Now, let’s get into today’s Follow Up. (:

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“Stories are remembered up to 22 times more than facts alone.”

That’s according to Jennifer Aaker, a Stanford marketing professor who teaches how stories persuade people.

If you’ve worked in sales for more than a day, you’ve probably heard the advice that great salespeople are great storytellers.

But telling a sales rep to “just tell a story” is a lot like handing someone a mic and saying, “Go ahead and spit me a freestyle.”

It's not gonna go well.

So today we’re breaking down how to find a story worth telling, give it some structure, and use it in a sales conversation.

This is the part where you act like a therapist and do a lot of listening.

You want to find out the things they’re worried about, or why they think the problem they’re dealing with is unique.

They might be worried about getting their team to use another tool. Or about getting burned by another vendor, because it happened to them before.

Each gives you a reason to tell a different story.

Then introduce the story through their own words: “You mentioned how hard it was to get the team using your last tool. That came up with a company we spoke to recently.”

Now the story has a job. Keep it focused on the concern that was brought up, and how another company overcame that same concern.

Before we get into some storytelling methods, let’s define what we’re talking about.

For sales, your own experience and your company’s history give you material to pull from.

This is where experience and tenure come in. The longer you’ve been selling the same product, the more you’ve seen deals stall, customers succeed, and crazy things happen that make for great stories.

But if you’re new to a company or industry, you can also borrow stories from people who’ve been there longer.

Ask people on your team about buyers who had the same concern or solved a similar problem. Get the details: What did the person want? What happened? What did they try? How did it end?

You’ll want all of those details when you’re constructing your story.

Aaron Sorkin is the writer behind The West Wing and The Social Network. And he’s one of the greatest storytellers you can learn from.

He teaches intention and obstacle as the starting point of any good story.

Someone wants something. Something stands in their way.

For a sales conversation, build on that with five beats: goal, obstacle, stakes, choice, outcome.

Here’s a fictional example for a prospect who’s comfortable with their current process:

“An operations manager at a dog treat company wanted to handle more orders with the same team. But every new order of dog treats needed someone to copy details between their two systems. Then they had a video on Instagram go viral, and volume picked up. So their backlog grew, and customers started asking where their orders were. She automated that handoff between the two systems so her team could clear the queue without adding another person.”

If you read through that story carefully, you’ll find the main character’s goal, obstacle, stakes, choice, and outcome. All of the 5 ingredients of a good story.

But if you instead changed that story to “She had a problem with orders, so they bought our product, and everything got better,” you’d skip all of the details that bring out emotions and make someone remember the story.

A story can be used to address a very specific concern.

Here’s an example you could use on someone who’s concerned about their team adopting a new tool:

“A sales leader wanted to help her reps get better at sales calls. But her reps were afraid that she’d use the call recordings to catch their mistakes. So she asked who wanted to volunteer to try it first. Those reps picked the calls and chose which skills to work on. That gave them a say in how they used the tool.”

And sometimes, the story ends with you being unable to help. Here’s an example:

“A buyer needed reports for a board meeting. We checked what they needed and found our tool couldn’t use some of their data. We told them before they signed, and they chose another option.”

Then offer a next step: “Let’s check that our tool works with your data before we go any further.”

I know… it sounds crazy to use a story to tell a prospect they might not be a good fit. But if you’re fully honest with your prospect (even when it means you could lose a sale), they’ll trust you more when you tell them you can actually help with their issue.

After a story, give them room to talk: “How does that compare with what’s happening on your side?”

Listen to the answer. They may point out a key difference or tell you something new.

All of that feedback gives you more opportunities to tell a story that helps persuade your prospect.

Check out The Follow Up Guy on LinkedIn.