John Nash on AI Workflows for Outreach

Founders don’t need more AI “tricks.” They need clarity. John Nash’s “AI Workflows for Outreach” briefing is about using AI to think better, not to hide behind it.

AI Workflows for Outreach

John Nash covers three low-friction workflows that help you write messages people actually respond to:

How to open an email so a tired reader keeps reading
A quick framing tool to get clear about the ask
A 60-second tone check so your outreach feels human and honest

About the Speaker – John Nash

John Nash is an educational leadership professor and solopreneur who helps builders use AI to produce clearer, faster, more ethical communication. He teaches design thinking and researches applied AI at the University of Kentucky.

More Resources:

Authors Who Influenced the AI With Principles Manifesto

George Lakoff: words shape worldview
Blair Enns: clarity over convincing
Bob Moesta: solve for progress, not preference
Abby Covert: sensemaking is design
Greg McKeown: less, but better
Ray Dalio: clarity, feedback, and reflection
Eddie Schleyner: write to persuade
Jasmin Alic: understand how people read copy
Justin Welch: write to stop the scroll

Notes for “AI That Works: Workflows for Clearer Outreach”

by John B. Nash, Ph.D. / jbnash@gmail.com

Opening Cringe

The Prompt: Write an outreach email to a potential customer asking for a 15-minute meeting to show them my new software platform.
The AI Output (The Cringe):

Subject: Unlocking Synergistic Growth for [Company Name]
Dear [Name],
I hope this email finds you well and that you are navigating the complexities of today’s fast-paced entrepreneurial landscape with agility.
I have been following [Company Name] and am truly impressed by the multifaceted tapestry of innovation you have woven. We have developed a groundbreaking platform designed to help visionary founders like yourself leverage AI to maximize ROI and empower your team.
I would love to hop on a 15-minute deep-dive call next Tuesday to explore how we can collaboratively transform your trajectory.
Best, [Your Name]

What are some issues with this? (The Slop Audit)

The “Party Mask”: Words like “tapestry,” “synergy,” and “leverage” sound like a robot trying to be “professional.”
The Buried Bear: We are two paragraphs in before we know what the sender actually wants.
Sociopathic Flattery: The “I’m impressed by your journey” feels fake because it is.
Zero Service Design: It’s asking for a “deep-dive” that’s more work for the reader, rather than offering a solution.

Most AI emails spend three paragraphs telling you how ‘the earth cooled’—all that fake flattery and ‘I hope this finds you well’ filler.
In this workshop, we use a rule called ‘Start with the Bear.’ When you’re camping and a bear walks into your site, you don’t start by talking about the gear you bought or the drive up the mountain.

You yell, ‘BEAR!’

The Bear is the moment of action that matters most to your customer. Everything else is just throat-clearing that makes a tired reader want to hit delete. If you want to stop the scroll, you lead with the bear.

In your outreach, the ‘Bear’ is the thing that actually matters to your customer. It’s the core problem or the big opportunity. Most of us write emails like we’re telling a long story about the history of the forest. We’re telling founders today: Stop describing the forest. Lead with the Bear. Put the most important, tension-filled, or useful sentence first when possible.

Key Concept: The “Bear First” Rule

The Problem: AI loves to write “Earth Cooling” introductions—long, polite, and boring preambles.
The Solution: Identify the Bear (your actual request or core insight). Move it to the very first sentence.
The Result: You respect the reader’s time and increase your reply rate.

Your reader (a busy customer, an investor, or a teammate) is “scanning for the bear.” They are mentally filtering out the “slop” to find the one sentence that matters. By putting the Bear first, you are practicing Clarity as Kindness. You are saving them the cognitive labor of hunting for your point.

“AI With Principles” Manifesto

Prompting Isn’t the Skill. Thinking Is.
Generative AI can write for you, but it can’t think for you.
If your ideas are unfocused, unkind, or unclear, AI will just amplify the mess.
Tools Are Fast.
Speed means nothing if you’re producing more of what’s forgettable, confusing, or misaligned.
Principles Keep You Honest.
Principles give your work shape, heart, and purpose.
Your First Prompt Is a Mirror.
If the response feels flat, it’s often because the prompt reflected your uncertainty.
Pause.
Zoom out.
Ask: What’s the real job I’m trying to do here?
Good Output Feels Alive.
It hooks attention.
It moves someone.
It builds trust.
It respects the reader.
AI can do that, but only if you ask it with care and craft.
AI Done Well Is Service Design
Every prompt is a design act.
It either helps someone do what they care about or adds noise to their day.
Choose wisely.
The Goal Isn’t Better Prompts. It’s Better Work.
A better prompt is not the point.
A better message is.
A better client experience.
A better decision.
A better outcome.
That’s the point.

Five Principles That Make Prompts Work

What’s the Job -> Don’t describe the task—describe the change.
Hook, Then Help -> Start with a spark, not a throat-clearing.
Clarity Is Kindness -> Confusion isn’t a vibe—it’s a failure.
Write for Action, Not Ego -> Strip the show-off stuff.
Make Them Feel Something -> Speak to pride, fear, hope, belonging.

How I Arrived at This Manifesto

Working Iteratively and Reflectively
I built my way here by: Prototyping newsletter formats, workshop prompts, and messaging
Diagnosing potential failures (“Do a pre-mortem on this”)
Testing framings in governance, teaching, coaching, and design contexts
Using AI as a collaborator, not a crutch

I Kept Asking Better Questions: I didn’t just want content that “sounded good.” I wanted it to work. I consistently asked:

“Why doesn’t this land?”
“What’s the actual outcome I want here?”
“Would someone know what to do next?”
“How would this feel to
- A tired customer?
- A doctoral student?
- A colleague under pressure?
- A neurodivergent learner”

I use AI as co-design, not a shortcut.

Studying—and Applying—Timeless Ideas

I didn’t start from AI hype. I started from foundations that existed long before LLMs:

George Lakoff: words shape worldview
Blair Enns: clarity over convincing
Bob Moesta: solve for progress, not preference
Abby Covert: sensemaking is design
Greg McKeown: less, but better
Ray Dalio: clarity, feedback, and reflection
Eddie Schleyner: write to persuade
Jasmin Alic: understand how people read copy
Justin Welch: write to stop the scroll

Staying Ruthlessly Outcome-Focused

I say things like:

“Make it easier to read.”
“Sound like a real person.”
“Match the tone to the reader’s state of mind.”
“Make this useful in 60 seconds or less.”

I treated every prompt as a tool to create clarity, drive action, or uncover insight. Never do I say, “Make this longer,” or “Add fluff.”

Five Principles You Can Use Now

I built my way here by working iteratively and reflecting on outcomes and what I learned:

Prototyping newsletter formats, workshop prompts, and messaging
Diagnosing potential failures (“Do a pre-mortem on this”)
Testing framings in governance, teaching, coaching, and design contexts
Using AI as a collaborator, not a crutch

PRINCIPLE 1: What’s the Job?

(Bob Moesta / JTBD)
Rule-of-Thumb: Write your prompt as if you’re helping someone make progress, not just get a task done.
Prompt Tip:“Instead of asking for a 15-minute screen share, write a message that helps the reader feel like they are finally reclaiming control of their scattered follow-ups. Focus on the ‘switch’ from feeling overwhelmed to feeling organized.
Red Flag: If your output could apply to any meeting or audience, you haven’t nailed the job.

PRINCIPLE 2: Hook, Then Help

(Eddie Schleyner / Jasmin “Jay” Alic / Justin Welsh)
Rule-of-Thumb: Don’t start with background—start with tension, curiosity, or a meaningful question.
Prompt Tip:“Give me a headline that makes someone stop scrolling. Then explain what’s in it for them.”
Red Flag: If the first sentence starts with “We are pleased to…”—you’ve lost them already.

PRINCIPLE 3: Clarity Is Kindness

(Abby Covert)
Rule-of-Thumb: If someone has to work hard to understand your message, they probably won’t.
Prompt Tip:
“Rewrite this for a 10th-grade reading level. Make the action and meaning obvious in the first sentence.”
Red Flag: If it sounds smart but makes people pause to reread, it’s not actually clear.

PRINCIPLE 4: Write for Action, Not Ego

(Blair Enns / Justin Welsh)
Rule-of-Thumb: Don’t write to prove you’re clever—write to help people move.
Prompt Tip: “Remove any sentence that exists just to sound professional. Focus on what the reader needs to know to act.”
Red Flag: If it reads like a résumé, a grant proposal, or a thesis—it’s probably ego writing.

PRINCIPLE 5: Make Them Feel Something

(George Lakoff / Richard Moore)
Rule-of-Thumb: Facts don’t move people—feelings do. Frame around shared values and emotional stakes.
Prompt Tip:“Frame this message to make readers feel a sense of belonging, pride, or urgency—not just get information.”
Red Flag: If your writing is technically accurate but forgettable, it’s missing emotional resonance.

Lab “AI Workflows for Outreach”

Lab: https://docs.google.com/document/d/1tQFJQD9Jpy4zrNOp78B39-ClTQxeLt-EbDjco6dohEY/edit?tab=t.0

We’re moving from listening to doing. Pull up that LinkedIn DM or cold email you’ve been avoiding. We are going to run it through the gauntlet using the principles we just covered.”

The Lab
Goal: Transform a ‘Meh’ outreach message into a ‘Principled’ one.
The Rule: Focus on achieving a better outcome, not just a better prompt.
The Process:

Diagnose (The Mirror)
Constrain (Use Principles)
Prompt (The Instruction)
Final Scan (Quality Control)

Step 1: The Mirror Test
Before you touch the AI, answer these three:
The Reader: What is their current state of mind? (e.g., Tired, skeptical, busy)
The Bear: What is the actual request? (e.g., A 15-min screen share)
The Job: What progress are you helping them make? (e.g., Regaining control of follow-ups)
If your AI output feels flat, it’s a mirror of your uncertainty. If you can’t answer these three, the AI definitely can’t. Take 60 seconds to name your Bear and your Job right now.”

Step 2: Choose Constraints

Eddie Shleyner (Precision) “Apply the Shleyner filter: Strip every adjective that doesn’t add value. Make the sentence structure rhythmic and punchy. Lead with the benefit.”
Blair Enns (Authority) “Focus on clarity over convincing. Speak as a calm expert offering a solution, not a salesman pleading for a meeting.”
Abby Covert (Clarity) “Act as an Information Architect. Reorganize this message so a tired reader can find the call-to-action in under 10 seconds.”
Bob Moesta (Progress) “Focus entirely on the ‘Progress’ the reader is trying to make today. Frame the message around the ‘switch’ from their current friction to a new state of relief.”

Step 3: The Principled Prompt
Use Constraints, Not Requests
Write a short outreach email.
Direct Lead: State in the first sentence [job to be done].
No Preamble: Do not use ‘I hope this finds you well’ or fake flattery.
Constraint: Use Principle #3 (Clarity is Kindness). Strip all marketing adjectives.
Action: Propose a 15-minute pressure test (no pitch deck).
Notice I’m not asking the AI to ‘be creative.’ I’m giving it an Instruction Set. I’m telling it to lead with the Bear and explicitly banning ‘Workslop’ like ‘unlock’ or ‘synergy’.

The Final Scan (Quality Control)
The 60-Second “Party Mask” Check
The “Out Loud” Test: Would I say this at Cafe Borrone?
The “Slop” Scan: Delete: Tapestry, Unlock, Palpable, Synergy.
The 10-Word Rule: Is the Bear in the first 10 words?
The Kindness Check: Is the CTA dated and timed?
AI loves to wear a ‘Party Mask’—that overly formal, fake-polite robotic voice. This final scan is your ‘Service Design’ check. Is this message a kindness to a tired reader, or is it just more noise?

Moral of the Story: Better Work, Not Better Prompts

Prompting isn’t the skill. Thinking is.
Clarity is Kindness.
Start with The Bear.
Ship with Integrity.
The goal of today wasn’t to make you ‘Prompt Engineers.’ It was to help you use AI to scale your humanity and your clarity. Go ship that message.

SKMurphy Take

This is a fantastic briefing on how to do effective outreach. John Nash stresses brevity, empathy, and a clear focus on helping your prospect make progress against their goals. His reading list is well-researched and supports the principles on which he builds his “AI Workflows for Outreach”process.

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