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Roll for persuasion

I've started playing Dungeons & Dragons.

Not something I ever expected to write, but here we are. For those unfamiliar, D&D is this tabletop roleplaying game where a group of people sit around telling stories, rolling dice, and pretending to be fantasy heroes.

My girlfriend got me into it and convinced me to join her family's game night. Now I'm playing a half-elf paladin (think holy warrior with pointy ears), complete with my own set of dice and everything.

And you know what's funny? Between battles with orcs in abandoned fortresses (don't ask), I've noticed some interesting parallels with my copywriting work.

In D&D one person - the Dungeon Master - creates and guides the whole adventure. They describe each scene, control how the story unfolds, and keep players engaged through hours of gameplay. And watching our DM work, I've realized he’s using a lot of the same principles I use when crafting conversion copy for B2B clients.

Take your typical B2B software company who needs website copy. What if instead of leading with features and specs, we'd take a page from our DM's playbook?

He’d build tension before revealing what's behind that ominous dungeon door…

We’d paint a picture of what keeps our prospects up at night. The endless back-and-forth emails, the version control nightmares, the Friday afternoon scramble to figure out who has the latest update. Those moments when a CEO asks for a status update and nobody knows where to find it.

By the time prospects hit the product details, they're already nodding along, seeing themselves in the story. That’s because both D&D storytelling and conversion copy work best when you:

1. Give your audience room to feel the problem. Our DM lets us sweat a bit when we hear those ghoul footsteps getting closer. Similarly, good copy acknowledges the full weight of your prospect's challenges before rushing to fix them.
2. Make it personal. In D&D, when we’re rolling dice, we're making choices that matter to our characters. In copy, when we talk about features, we should show exactly how they transform our prospect's daily work life.
3. Light the path forward. Our DM always gives us clear choices, even in tough spots. Good copy does the same. Whether that's a technical deep-dive for the engineering lead or ROI calculations for the CFO, everyone knows their next move.
4. Keep it relevant to the quest. The DM doesn't waste time describing random taverns our party will never visit. Every detail serves the story. Same goes for copy. Every word should move your prospect closer to seeing themselves using your solution.
5. Know your party members. In D&D, you adjust your strategy and story based on whether you're playing with wizards or warriors or monks etc. In B2B, you craft your message differently for the tech lead who needs API documentation versus the CFO who wants to see ROI projections. Knowing the decision-making unit matters.
6. Create memorable moments. Sure, our DM could just say "you beat the ghost" - but describing how my holy sword blazes with divine light as I land the final blow? That sticks with you. Same principle applies to case studies and testimonials. Don't just tell them you increased revenue, paint a picture of what that success actually looked like.

And it works. Sales demos booked without endless follow-ups. Cold outreach that gets enthusiastic replies. Homepage bounce rates dropping like a stone. Sure, maybe not as exciting as rolling a critical hit in the heat of battle (fellow D&D players, you get me), but watching those metrics climb is its own kind of victory.

I never thought tabletop gaming would give me insights into B2B copy.

But that's the beauty of this work.

Sometimes the best inspiration comes from the most unexpected places. Besides, both us marketers and a dungeon master share the same core goal: guiding people through a journey they actually want to take.

DISCOVERY

Use AI to cut your research time and cost in half

I just published a ~40 minute video where I dive deep into my Empathy Engineering™️ framework for researching customers and writing copy that converts using AI. As I say, AI can write content, but it lacks context. This is how you do it right.

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10-min podcast snack on AI copy? YumYumYum

Yesterday I jumped, almost literally on the Nohacks podcast for a 10-minute, one-question interview. Loved it. And I'm thinking of tweaking the format of my podcast too. More coming soon.

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Conversion Alchemy has grown in 2024, here's how

Most people are afraid to share their numbers. I'm an open book. I just published my annual update on Starter Story. You can check it out here to peek at what we've done last year, and some thoughts on what's up for 2025.

RESONANCE

Dan Koe, The Art of Focus

Have a great weekend!

Cheers,

Chris

Chris Silvestri Founder & conversion alchemist

🙌🏻 Let’s be friends (unless you’re a stalker)​

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