- Frank OBrien

If you asked me to sum up my approach to writing with AI, I’d put it this way: Don’t use AI to create for you. Use it as a modest editor to help evaluate what you’ve created. And don’t use AI to think for you. Use it as a way to stress test your thinking.

It isn’t about not using AI. It’s about using it the right way at the right points in the process. One example: It can be really helpful to use AI as a modest editor of the original copy you’ve written. Just don’t go overboard. Treat AI as a junior editor, not an oracle. And stick with what my copywriting friend Madeleine Nance calls “bite-sized” edits like shortening a too long paragraph or cleaning up a clunky sentence you’ve been staring at for too long.

And if you do use AI as an editor, you want to do it in the strongest way possible. That’s where prompting comes in.

You don’t have to get carried away with “prompt engineering.” There is no magically worded prompt that will transform your life. But the fact remains, basic, mediocre prompts generate basic, mediocre output. And well-designed prompts help produce far more on-point and useful results.

Let me illustrate using an example of what I call a Persuasion Pivot – those moves that take your message from one that misses the mark to one that really drives persuasion. Below are three versions of the writing:

a rough first draft which I’ve intentionally written in a suboptimal way
an AI rewrite based on a simple “make it better” prompt
an AI rewrite based on a much more detailed and strategic prompt

I used Claude because it is preferred over other LLMs by most writers including me.

EXAMPLE: Attention Economy Strategies

Rough First Draft: In the attention economy, it’s not enough to just attract people’s attention, you have to attract it in ways that you can hold onto it and funnel it into long-term engagement. But that’s too confining to be the standard for every effort to gain attention. It just has to be the long-term impact of your overall attention strategy.

Basic Prompt: “Make the following statement more clear, compelling and persuasive.”

Claude (Opus 4.7) After Basic Prompt: In the attention economy, getting noticed is the table stakes, not the win. The real test is whether you can hold that attention long enough to turn it into something that matters — belief, action, loyalty, a movement. Now, that’s an unfair burden to put on any single post or headline; not every piece has to do all that work. But your attention strategy as a whole? That bar is non-negotiable.

Commentary: This one is a mixed bag. There’s some language I would pick up. For example, “that’s an unfair burden to put on any single post or headline; not every piece has to do all that work.” is stronger than “that’s too confining to be the standard for every effort to gain attention.” But “getting noticed is the table stakes, not the win.” and “that bar is non-negotiable” is AI language, not Frank language. So, like a human junior editor, AI’s suggestions are hit or miss.

But what happens if we give Claude more to work with:

More Strategic and Detailed Prompt: I need a stronger version of the statement below that delivers strong advice in the voice of a nonprofit messaging expert – confident, professional, but also conversational. This is for an audience of nonprofit communicators who range from industry experts to people just beginning their careers. What matters to them is an enhanced ability to gain attention, build trust, and drive impact with their audiences. Success means providing concrete, hands-on advice that they can really use, not just pithy observations that they can’t do anything with. Focus on being clear, honest and compelling. Avoid sounding like an arrogant expert. The readers should come away saying to themselves “Now I understand this better and have a clearer roadmap on how to proceed. This was really practical and helpful.”

NOTE: I want to give credit where it’s due. The structure of the above prompt is drawn from a model by the How to Prompt platform (they post regularly on LinkedIn). Here’s the format:

Primary Goal: I need [output type] that [accomplishes what]
Context: This is for [audience/domain] where [what matters]
Performance: Success means [specific observable outcome] not [what failure looks like]
Constraints: Focus on [priority] avoid [anti-priority]
Outcome: The reader should [what they’ll be able to do afterward]

Claude (Opus 4.7) After More Strategic Prompt: In the attention economy, attracting eyeballs isn’t the win. Holding attention long enough to convert it into engagement, action, and loyalty is the win. But here’s where a lot of communicators get tangled up: that doesn’t mean every single post, ad, or email has to do all of that work. A funny meme can earn its keep just by getting noticed. A breaking-news alert can succeed simply by being read. The standard you’re aiming for isn’t “did this one piece deepen the relationship?” — it’s “is my overall attention strategy moving people from a glance, to a read, to a click, to a gift?” Judge individual pieces by what they’re built to do. Judge your strategy by whether the pieces add up.

Commentary: Much more to work with here.

Because of the more in-depth info I provided, there is less AI-sounding text (“from a glance, to a read, to a click, to a gift?” is borderline at best).
There’s some wonderful, conversational language. (The more detailed prompt’s “here’s where a lot of communicators get tangled up: that doesn’t mean every single post, ad, or email has to do all of that work.” is a giant step better than the simple prompt’s “that bar is non-negotiable.”
There are concrete examples which bring the advice to life. (Remember my prompt said “Success means providing concrete, hands-on advice that they can really use, not just pithy observations that they can’t do anything with.”).

Remember, for a serious piece of writing, human first drafts are always a better option than AI first drafts.
But AI can help with research, modest editing, and stress testing your thinking.
Use AI as a modest editor taking on bite-sized edits and treat it like a junior editor, not an oracle.
Don’t forget this rule: Basic mediocre prompts produce basic, mediocre output.
If your prompts are more detailed and strategic, the edits AI proposes will be more on point, more useful, and less prone to AI speak.
Better still, the more you prime your LLM about your style, context, and writing samples, the stronger the AI feedback on your drafts. (More on this front in my June 1^st post.)