Don’t Let AI Write your Cold Messages Like a Desperate Intern
You've built your business on referrals and word of mouth. Your reputation does the heavy lifting. But now you're looking at a pipeline that needs filling and a calendar that's already maxed out.
You know AI could help. You've seen the LinkedIn humblebrag posts - "Just used ChatGPT to land three discovery calls!" You've downloaded the prompt packs. Maybe you've even fed it a request for outreach messages.
And what came back sounded like... a robot cosplaying as you.
Stiff.
Salesy.
The kind of message you'd delete without reading if it landed in your own inbox.
Why Most AI Outreach Falls Flat
Most people give AI a lazy brief and expect brilliance. No context about who they're reaching out to. No examples of how they actually talk. No system for what good outreach even looks like.
So the AI does what it does best - produces something average. And the founder ends up back at square one, writing every message manually at 10pm, or quietly abandoning outreach altogether.
There's a better way. And it starts with giving AI something real to work with.
The 5-Line Framework
Effective outreach respects the other person's time. It doesn't fake intimacy. It shows you've done your homework and makes the next step feel effortless.
Every message needs five elements:
Context - Why you're reaching out now (not a hollow compliment)
Value - The specific benefit they'll actually care about
Ask - The smallest possible commitment
Next step - One clear action (watch a 90-second Loom, choose from two time slots, or access a short resource)
Grace - An easy out if the timing doesn't work
That's it. Five lines. Seventy-five words max for DMs. A hundred for email. Anything longer and you're writing for yourself, not them.
How to Teach AI your Voice
The secret is better inputs.
Build a small reference library of mix-and-match components your AI can draw from:
3 ways to describe your ideal client (one clause each - skip the jargon)
3 versions of the real friction they experience (their words, not yours)
3 proof points with actual numbers or outcomes
3 small, useful offers (never "pick your brain")
3 CTAs with options ("Two-minute Loom or fifteen-minute call?")
Save these alongside notes on your tone and your core offer. Now when you ask AI to draft outreach, it has raw material - not a blank page and vague hope.
The 60-Second Pre-Send Check
Before anything goes out: kill the corporate filler. ("Synergy." "Loop back." "Touch base." You know the culprits.)
Add one specific detail from their recent content or website - something that proves you actually looked. It takes thirty seconds and separates you from the flood of copy-paste messages they're ignoring.
Then send it. Within 24 hours. Track what happens.
The Real Point
AI should make your outreach sharper, not louder. It should hand you back the hours you've been burning on messages that go nowhere.
When your knowledge is organized and your offers are specific, the technology becomes a quiet amplifier. The conversation - the actual human connection - becomes the point.
That's the game. Not automating your personality out of existence. Using AI to clear the path so you can show up as yourself, more often, to more of the right people.
Want to build this system with me - live, in person?
I'm running an AI workflow workshop at the vibey Verity Club in Toronto.
We'll construct your outreach system step by step: your voice blocks, your framework, the actual workflow you'll use the next morning. You'll leave with something ready to deploy, not another set of notes to revisit someday.
