Daily one-pagers about AI, leadership, technology, and being human.

johnmaconline

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November 1, 2025 2 minute read

How To Talk to AI — Clarity and Ask Me Questions

You want clever output.

However, to get what you’re looking for, your prompt needs to be to the point and specific. Boring, really. Plus, you want the LLM to ask you questions and make it interactive when useful. 

An LLM is very sure of itself. To the point of just making stuff up (hallucinating). Therefore, reminding it that it should ask you about stuff it needs is an important skill of talking to it. 

Sticking with our marketing theme, here’s something that you, as the boss, might need to do.

Boss Directive:

“I started writing the launch email for the new product, but I ran out of time and energy. We’re announcing our new productivity tool for freelancers. I need it finished.”

A useful prompt for asking AI to do it looks like this.

Prompt:

You are a senior marketing copywriter with a background in SaaS and tech product launches. You know how to take a rough draft and turn it into a clear, persuasive email that builds curiosity and drives click-throughs — without making it sound like generic sales copy.

You have a feel for voice and tone, especially in fast-growing startups. You understand how to write like a human: warm, specific, and benefit-focused, but not pushy.

Here’s the rough draft I started. Please complete and polish it. Keep the voice consistent — conversational, smart, and a little punchy. Don’t change the opening unless it really needs help. Make sure the product benefits are clear, and the call-to-action stands out. Suggest alternate subject lines if you have better ones.

START DRAFT:

Hey [First Name],

Ever feel like your calendar is winning and you’re just along for the ride?

We get it. We’ve been there.

That’s why we built SlotRight — your new favorite tool for getting your time (and headspace) back.

END DRAFT

Do not make stuff up! Ask me questions when you need more details on the product, the audience, or past emails.

This prompt follows all of the rules so far: role, goal, structure, verbosity, and now clarity, and ensures it will ask you questions about stuff it needs to know. 

Next up: Ask for Suggestions and Several Versions

October 31, 2025 2 minute read

How to Talk to AI — If You Don’t Say It, It Won’t Know (More Words, Please)

Unlike with humans, where less is more and simplicity is king, AI needs more words from you. 

Brevity doesn’t help. Succinctness doesn’t help. Inference definitely doesn’t help. 

AI doesn’t infer what you meant, only what you typed. Verbosity helps. Overexplaining helps. More data helps. Even rambling on helps (sometimes). 

Boss directive:

“Our Facebook ads for the new coaching program aren’t converting like they should. We need better messaging.”

Here’s how to ask your friendly neighborhood LLM.

Prompt:

“You are a senior direct response copywriter who specializes in Facebook ads. You’ve worked with coaching programs, especially ones that target professionals who are looking to make a meaningful change in their careers.

You understand how to write ads that connect emotionally, build trust fast, and drive action from people who are skeptical or distracted.

We’re marketing a career coaching program for professionals ages 35 to 50 who feel like they’re stuck in their careers. They’re not in crisis, but they know they want something different. Some feel like they’ve missed their window. Others feel like they’ve plateaued. They’re capable, responsible, and looking for clarity.

The coaching program helps them rediscover what they want, regain their confidence, and design a next step that fits their current season of life.

Please write 10 Facebook ad variations. Each one should include a scroll-stopping opening line (hook), a few lines of emotionally resonant copy, and a call to action. Vary the emotional angle (e.g., frustration, hope, ambition, regret, clarity). Avoid buzzwords. Avoid vague promises. Keep it tight, clear, and human.”

More is more. 

Next up: Clarity Over Cleverness

October 30, 2025 2 minute read

How to Talk to AI — Roles, Goals, and Structure

AI works much better if both you and it know who it is —  which role each of you is playing.

The first thing to remember is that you’re the boss. You’re always the boss. To get the most and the best out of an LLM, you have to think and direct as the boss. 

So be the boss.

Here’s an example of a problem that you, the boss might need to solve with the team.

Boss directive:

“We need to win back lapsed customers before Q4. We need to draft some email subject lines to test?”

Then, think of AI as your most promising intern with gallons of coffee at its disposal. Smart, can-do attitude, ridiculously book-smart, quick, literal, and tireless. 

But like any intern, it only performs well with clear direction, including its goals and the structure of how you’re trying to accomplish the task. 

So here’s what the boss directive looks like when you translate it to an effective LLM prompt.

Prompt:

“You are a digital marketing associate at an outdoor gear brand. Craft three email subject lines aimed at previous buyers who haven’t purchased in 6 months. Tone: friendly but urgent. Keep each to 50 characters.”

Give it a role, a goal, and structure. You’re not just asking for ideas. You’re about to unleash the greatest intern. 

Next up: If You Don’t Say It, It Won’t Know

October 29, 2025 1 minute read

How to Talk to AI to Get What You Want (A Series)

AI can be both the most brilliant teammate or the worst. 

It all comes down to how you talk to it. 

Talk to it? Yes. ChatGPT, Claude, and Gemini are Large Language Models (LLM). They understand language (maybe like humans, maybe not, the jury is still out), or at least, they “work” with language.

Regardless, you gotta talk to it. 

So here is a series on how to talk to AI to get what you want out of it. The common vernacular is “prompt engineering.” 

The theme throughout this mini-tutorial is work and specifically marketing. I’ll walk you through how you can use an LLM (any of the above will work) to do some professional tasks.

Each article will tackle one key principle, paired with a real-world scenario and a prompt for you to use.

Getting what you want is not just about what you ask. It’s about how you ask.

Tomorrow: Roles, Goals, and structure.

October 28, 2025 1 minute read

More is More with AI

With humans, less is more. 

Less description. Less narrative. Less words. 

Less is more because our brains work better with simple. KISS. Simple is more coherent. Simple is easier to understand. Simple reaches more people. Simple is more memorable. 

Humans are limited in both memory and brainpower. 

But the opposite is true for LLM AI. 

AI doesn’t have a memory problem. AI doesn’t have a brainpower problem. But it does have a human problem. It has no context. No story. It’s never been there or done that. It can’t feel. 

Therefore, when prompting, more is better. 

More description. More narrative. More questions. More rambling. More brain dumping. More tangents. More run-on sentences. More interjections. More spurious thoughts. More procedure. More steps. More rules. More words.

When asking an LLM AI to help you, more is more. 

October 27, 2025 1 minute read

The Echo Chamber

It used to be just the “Yes” men, but now it’s pretty much any media channel. 

If you want to, you can find and plug into the echo chamber from any number of outlets. The digital age has supercharged it. Target audiences plus algorithms working together to keep you captured. 

But the echo chamber is a trap. Opinions get reinforced. New information is irrelevant. Doubts get silenced. Disagreements feel like betrayals. 

Back in the “Yes” men days, the smart thing to do was to bring in a skeptic. Someone who asks the hard questions and says, “Are you sure?” and “What about…”

Creative tension and friction were the tools.

As it turns out, those are still the tools. You don’t have to abandon your beliefs, but you can use these tools to test them. To morph them when appropriate. To stretch your mind. Maybe to change it.

Sometimes, the most important sound is the one that doesn’t echo back. 

October 26, 2025 1 minute read

The Spinning Compass

You’ve seen it in cartoons, maybe a movie or two. 

The compass that spins round and round. Uh oh. 

Which way are we going? Which way should we go? Which way is north? 

Too many opinions. Competing priorities. Competing pressures. Too much noise. Fear, doubt, and even your own ambition. 

If you force a direction blindly, you may end up even further from your destination.

Pause. What can you control? Take a step and then pause again. Where are you now? What can you control? Is this towards better?

Settle the compass. It’s the only way to move in the right direction. 

October 25, 2025 1 minute read

The Crooked Frame

You notice it right away, and it drives you nuts. 

The picture frame is crooked. Not a lot. But definitely not level. 

Maybe not everyone sees it. But you do. It keeps drawing your eyes. It’s distracting. You can’t unsee it. You can’t ignore it. 

The best thing to do is walk right over there and straighten it up. Adjust expectations? Have a hard conversation? Change direction? Quit? 

You’ll feel it when it’s right.

And then you can focus on the picture again.

October 24, 2025 1 minute read

The Wobbly Table

I can’t handle a wobbly table. 

If it’s my table, no big deal. I have all the time and resources to fix it myself. And I do. I can’t move on without making it stable.

But what about the wobbly table at the restaurant or in the office? 

Well, I certainly try, but I might not have the ability. Can I adjust the foot? Can I put a coaster under it? Can we move it slightly? Can someone else help?

Maybe. But maybe not.

Sometimes you just gotta find a new table. 

October 23, 2025 1 minute read

New Roads

Maybe the old road you were on just dead-ended. 
Maybe the bridge is out. 
Maybe it’s closed due to weather or an accident. 

Whatever the reason, you need a new road. A new direction. 

If you’ve been committed to a particular road, it can be hard to change your thinking. You were focused. You were sure. It’s emotional, every bit as intellectual. 

But new roads have something that old roads don’t — possibilities. Including the freedom to choose again.

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