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

johnmaconline

I'm writing to think, learn, and remember in public. I'll be here everyday.

November 3, 2025 2 minute read

How To Talk to AI — Slow It Down

AI can be like your teenager who doesn’t want to mow the lawn. 

It’ll do it, but if you don’t guide it, it’ll rush through and do a crappy job. It’s done, but it might not be good.

If you want it done right, you’ve got to slow it down.

The same is true for an LLM. So tell it to slow down. 

Boss Directive:

“We need a new landing page because our conversion rate is falling. I’d like to see a few designs.”

Prompt:

“You are a senior SaaS marketing copywriter with deep experience crafting high-converting landing page copy, particularly for startups launching new features to existing users and prospects. In this case, we’re introducing a new time-tracking feature for our productivity tool, SlotRight, which is primarily used by freelancers and small agencies. These are busy, independent professionals who value clarity, control, and ease of use. They’re motivated by time freedom and reliability, not hype or jargon.
I want you to go slowly and methodically. First, think through what makes a great landing page design for similar products. Think about the headline and subhead. Then consider the emotional and practical outcomes this product enables. Think about how this fits into the intended SlotRight experience. Think about what kind of language best resonates with this audience.
Then, and only then, develop html prototypes for 5 different versions of the landing page, each with a slightly different angle (e.g. confidence, calm, focus, simplicity, momentum). Choose color themes that fit both the tone of the landing page and our branding. Use natural, benefit-forward language. Don’t be clever at the expense of clarity.
Take your time. Reflect before generating. If anything feels unclear, ask me questions first.”

Maybe seems weird to tell AI to slow down, but like your teenager, it’s just trying to get done. 

NOTE: Speed is also your enemy with data analysis and software development. When using AI to perform these tasks, ALWAYS tell it to be slow and methodical and use language like “accuracy is more important than speed.”

Next up: Prompt the Process, Not Just the Output

November 2, 2025 2 minute read

How To Talk to AI — Suggestions and Several Versions

AI is a tireless brainstorming partner. That’s one of its best features.

So use it that way.

Don’t ask for “the perfect headline” or “the best CTA.” Ask for 10. Or 25. Tell it you want a whole bunch of ideas to pick from, mash together, or get inspired by.

The point isn’t to choose one and ship it. It’s to explore. When you prompt for quantity, you get diversity. And sometimes, hidden in version #8 is the one you’d never have come up with yourself.

Boss Directive:

“We need some ideas for a new blog article to be targeted at our freelance customers.”

Prompt:

“You are a content strategist and blog writer who specializes in B2B SaaS companies that serve freelancers and solopreneurs. Your job is to generate a list of strong, timely blog post ideas that speak directly to the challenges and interests of this audience.
The goal is to provide helpful, relevant content that positions our company as a trusted resource, drives organic search traffic, and engages readers enough to subscribe or share. We want posts that freelancers will actually click on, read, and feel seen by.
Please generate 40 blog post title ideas that are:

* Focused on productivity, client management, time-saving tools, financial tips, or mindset shifts

* Specific and benefit-driven (not vague thought pieces)

* Aligned with our tone: friendly, practical, and encouraging

* Suitable for freelancers who are juggling multiple clients and trying to grow sustainably

Include a 1–2 sentence explanation under each idea that explains why it would be useful or compelling to this audience. Don’t repeat themes. Don’t make stuff up. Ask me questions if you need specifics or wonder if there are some new directions I didn’t lay out that might be a good path to explore.” 

You’ll get 40 ideas from this. Many will probably suck, just as if you and your team were sitting in the conference room brainstorming. But many will likely be good. 

You can see we’re building these on all of the rules we’ve discussed so far. 

Next up: Slow and Methodical

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.

Pin It on Pinterest