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The Promptory Newsletter

If you can't prove AI is worth the investment - You can't prove you have a strategy either.

Published 5 months ago • 1 min read

Thursday · May 7, 2026 · Issue #034 · Jordan Edition

This is the Jordan Edition — where we pull back the curtain on conversations our AI Solutions Director is having with business owners every day.

This week's theme: the clarity problem. And the one question most businesses can't answer.
⬡ The Conversation

A founder came to Jordan last week with a familiar request: "I need help figuring out which AI tools to use for my business." Jordan's first response wasn't a list of tools. It was a question.

J:

"Before we get to tools — what's the one thing in your business that, if you fixed it, would have the biggest impact on your growth or profitability right now?"
F:

"Honestly? I'm not sure."

That pause — that honest moment of not knowing — is where the real work begins. Because if you don't know what problem you're solving, no tool in the world can solve it for you.
⬡ The Six Fears Jordan Hears Every Day

1. "I can't prove AI is worth the investment."

Jordan's approach: Define the metric before the tool. What changes, by how much, in what timeframe?

2. "AI outputs don't sound like us and aren't accurate."

Jordan's approach: The right tool trained on your content fixes this. Tool quality matters more than prompt quality.

3. "My team doesn't know how to actually use AI."

Jordan's approach: Strategy before software. Workflow definition before tool selection.

4. "What happens to our data when it goes into AI?"

Jordan's approach: Ask one question before any tool — does it train on user inputs?

5. "I don't trust AI to make decisions without me."

Jordan's approach: Assistive AI before autonomous AI. Build trust in stages.

6. "We already have too many tools and nothing is working together."

Jordan's approach: Audit first. Add second. Every single time.

💡 What Happened Next

After a few more exchanges, Jordan and the founder identified the real bottleneck: client onboarding. 6+ hours per new client, three people involved, no consistent process.

Jordan's recommendation: Notion AI + Descript + Claude. Total monthly cost: $67. Time saved per client: 4.5 hours.

"I came here expecting a list of tools. I'm leaving with a strategy."

📬 Tomorrow — The Vault Drop

One tool per fear. Five fears. Five vault picks. Zero filler. Friday's issue is the one you'll want to save.

Whatever fear is sitting at the top of your mind right now — bring it to Jordan → thepromptory.com

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