Issue #1: Writing & Judgement
AI-generated image of a woman sitting at a desk using a laptop, surrounded by plants and colorful shapes, with an “AI” speech bubble indicating she’s interacting with artificial intelligence.
Written by Jay McGrane with an assist from Paula
How has AI changed the writing game? (aka are you ready for Judgement Day?)
Paula and I can’t stop using the word “judgement” to describe how to write with AI.
Yep, you’re the judge, jury, and master-deleter.
Gone are the days of being the master wordsmith carefully piecing together the most perfect analogy known to man. (Or, sitting in front of a blank screen drinking yet more coffee.)
AI has given you a new job. You’re now the hot shot editor managing your new chatbot reporter. You give the AI the brief, edit the work, and publish the final piece.
Which leads us to the ultimate question today…
What skills will make you a master AI writer…umm editor?
Somewhat counterintuitively, since we’re both writers, Paula and I decided the best way to wrestle with this question was through a zoom call.
I thought about writing you an essay, then I realized that what we need most right now is human connection. So today, I’m inviting you to join our conversation with some carefully curated excerpts. (Psst: write back to us and let me know if that’s annoying or fun to read. It’s an experiment!)
Here’s what our conversation actually sounded like:
1️⃣ Connection makes writing human.
Jay: "I don't know exactly what counts as creative anymore. Maybe it doesn't matter. Maybe creativity is less about what's created, and more about where it comes from—those small, personal moments."
Paula: "That might be exactly it. AI can produce the words, but it can't capture the little human moments of connection—like leaving a poem for someone after a long night at work. There's intimacy there that's uniquely human."
(Jay here → True story, my husband had a co-worker that used to write a poem at the end of an on-call. When he switched to AI poems, my husband felt that something had been lost.)
2️⃣ Editorial skills are more important than ever before
Jay: "Effective AI writing requires strong editorial instincts and deep knowledge of your own voice. If the AI is writing alongside me and the voice feels off, it takes me about ten seconds to notice."
Paula: “Yeah, me too - I can quickly tell when the voice is wrong. Writing with AI means knowing your voice, setting clear standards, and being able to quickly evaluate if the AI is meeting them."
3️⃣ AI is kinda dumb, especially when researching 😗
Paula: "Evaluating information quickly is now an essential skill. If we don't explicitly teach students how to rapidly judge source quality, we’re doing them a disservice. Relying on AI alone can easily mislead."
Jay: “Yes! I asked AI for a quick fact-check. I instantly knew the sources it gave were weak. Sure, it agreed with me, but the sources were ridiculous. You’d fail an assignment if you cited those in school."
4️⃣ Writers’ block still matters (maybe even more)
Paula: "Struggling helps us internalize deep concepts. With AI, if the struggle disappears entirely, we might lose something critical—our ability to truly internalize knowledge and form our own thoughts.”
Jay: “I think the real skill now might be deciding when to embrace struggle. Writing with AI means knowing when you need quiet, when you need friction, and when you need the smooth path that AI provides.”
5️⃣ The struggle needs protection.
Jay: “The tension is knowing when struggle actually helps us learn versus when it's unnecessary friction. I think a core skill is deciding which battles we still need to fight ourselves.”
Paula: “I feel strongly that certain tasks—like writing a business plan—should still involve genuine struggle. AI can support us, but the struggle is how we internalize and truly understand important concepts.”
We hope this excerpt helps you think through what parts of writing need to remain uniquely human. For us, we know there will always be a place for 100% human writing. However, we still use AI to help us create content on a daily basis.
How do I write more strategically with AI?
Most of us learned how to write by drafting. We put pen to paper and wrote. Simple. Sure, we might have an outline or research notes, but writing was an individual activity.
The writing equation looked like the one below:
1 Brain + 1 Paper + 1 Coffee = ♾️ Thoughts
AI short circuits this equation. The chatbot can create endless textual permutations. Now, you’re no longer the writer in the room. You’re the editor.
Enter Publishing Standards.
In this analogy, your job is to manage your AI chatbot. Your chatbot functions as your reporter. You need to give them the brief, edit their work, and publish it.
Most AI writing how-tos focus on prompting. This step is essentially giving your “AI reporter” the brief.” However, it misses the forest for the trees. Yes, you need a clear prompt. But you can only evaluate the AI output with clear editorial guidelines. Otherwise how will you even know when the AI writing has reached the goal?
Here are a few things you could consider when beginning to train your AI on your writing needs:
Style and Voice Guidelines
Audience Personas
Textual Structure (article, blog, poem etc.)
Editorial Mission Statements
Checklist or Rubric to Assess Work
Content Brief