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AI Outreach That Doesn’t Sound Like a Bot Wrote It

AI Outreach That Doesn't Sound Like a Bot Wrote It

Guest column from Susan Diaz, host of AI Literacy for Entrepreneurs and Founder of Northlight AI.

You’ve built your business on referrals and reputation. But now you’re staring at a pipeline that needs feeding and a calendar that’s already full.

You know AI could help. You’ve watched peers post their ChatGPT wins on LinkedIn. You’ve downloaded the prompt packs. Maybe you’ve even asked it to draft a bunch of outreach messages.

And they came back sounding like… a robot wearing your blazer.

Generic. Pitchy. Nothing you’d actually send.

AI-driven outreach fails because most people hand AI a vague ask and expect magic. No context. No voice. No system.

So the founder ends up back where she started – writing every message from scratch after hours, or not reaching out at all.

There’s a better way.

The 5-Line Framework

Good outreach respects context. It doesn’t pretend to be intimate. It shows you’ve done the work and makes saying yes to an easy next step effortless.

Every message needs five things:

  1. Context – why you’re reaching out now (not a fake compliment)

  2. Value – the specific benefit they’ll care about

  3. Ask – the smallest possible commitment

  4. Next step – one clear action (a 90-second Loom, two time slots, a short doc)

  5. Grace – an easy out if the timing is wrong

Five lines. Seventy-five words max for DMs. One hundred for email.

Teaching AI your Voice

Give your AI better ingredients.

Build a small library of mix-and-match blocks your AI can pull from:

  • 3 ways to describe who you’re reaching (one clause each – not buzzwords)

  • 3 versions of the friction they actually feel

  • 3 proof points with real numbers or outcomes

  • 3 small, useful offers (never “pick your brain”)

  • 3 CTAs with options (“2 minute Loom or 15 minute chat?”)

Store these alongside notes on your voice and your core offer. Now when you ask AI to draft outreach, it has real material to work with – not a blank page and good intentions.

The 60-Second Check

Before you send: kill the pitchy phrases. (“Synergy.” “Circle back.” You know the ones.) Add one specific line from their feed or website that proves you actually looked.

Then send it. Within 24 hours. Log what happens.

The Real Point

AI should make your outreach clearer, not louder. And it should give you back the hours you’ve been spending on messages that never land.

When your knowledge is organized and your offers are concrete, the tech becomes a quiet amplifier. The conversation becomes the point.

Want to build this system live in Toronto?

I’m running an in-person AI workflow workshop at the Verity Club in Toronto. We’ll build your outreach system step-by-step – your voice blocks, your framework, your actual workflow – so you leave with something ready to use.