6 - Using AI as a Writing Partner — When to Use It, When Not To
I have written emails at two in the morning that I never sent. I have drafted letters in my head during a long drive and then sat down at my keyboard and couldn't get a single sentence right. Writing has always been the place where I get stuck — not because I don't know what I want to say, but because I can't seem to say it the right way. Too much Jill in it. Too much heat, too much history, too much something. What I didn't know until recently is that AI would become the writing partner I never knew I needed — and it changed the way I think about what writing is even for.
The Core Insight: Sometimes the Best Letter Sounds Like No One in Particular
Here's what I discovered: sometimes the best version of what needs to be said is calm, clear, and professional — without your personality all over it. AI does this naturally. It has no history with the person you're writing to. It has no frustration, no backstory, no emotional residue. For certain situations, that's not a limitation. It's exactly what the letter needs.
Example 1: The Resume
When I applied for a new job after fifteen years of not needing a resume, mine was three pages long, badly organized, and full of redundant language. I didn't ask AI to rewrite it — I asked it to reorganize it. Here's what I have; put related things together, cut redundant language, don't invent anything. It came back a page and a half. Better organized than I could have done it. Same facts, much cleaner presentation. And it worked.
Example 2: The Board Member Email
I had to write an email to a fellow board member — someone who reads confrontation into innocuous sentences and tends to respond with real heat. The situation needed to be addressed. But if there was any warmth in the writing, any frustration, any hint of me, it would make things worse. So I told AI the situation, the relationship, the goal. I asked for something neutral, measured, professional, non-confrontational. What it came back with was a little formal, a little robotic — and exactly right. The email worked. The situation got handled.
Example 3: The Resignation Letter
Leaving a job I'd been at for fifteen years was emotionally complicated. But the letter didn't need to go to my boss — it needed to go to HR, in a city I'd never been to, to a person I'd never met. The letter needed to be dignified, professional, and blank. Dates, gratitude for the opportunities, acknowledgment of my supervisor. Nothing embarrassing. AI gave me exactly that in about thirty seconds. Something that would have taken me an hour to write and still might not have been right.
When Not to Use AI for Writing
The closer the relationship and the more the letter is about that relationship, the more it has to come from you. A message to a friend who is grieving. A thank-you note to someone who went out of their way for you. A letter to your child. Those need to sound like you — and increasingly, people can tell when they don't. AI writing has a certain evenness to it, a smoothness, that can feel distant when warmth is what the person needs. The rule I've landed on: the more professional and situational, the more AI can help; the more personal and relational, the more it needs to be you.
How to Check Your Output
Before you send anything AI helped you write, ask yourself: does this sound like a real human wrote it, or does it sound like AI? If something feels stiff, tell AI. "The third paragraph is a little formal — can you make it sound more natural without losing the professional tone?" Ask AI to critique its own output. Surprisingly, it's quite good at this. The back-and-forth is where the best drafts come from.
The Key to Better Output: Context Is Everything
A vague prompt gets you a vague email. If you tell AI who you're writing to, what the relationship is, what happened, what you're trying to achieve, and how you want to sound — you'll get something you might actually want to send. The more specific you are upfront, the less revision you'll need. Think of it as briefing a very competent but very literal assistant who knows nothing about your situation unless you tell them.
Next episode we'll look at using AI for billing disputes, insurance letters, and correspondence where you need something very specific said without needing a lawyer. Thanks for being here.
Jill’s Links
http://jillfromthenorthwoods.com [https://abetterlifeinsmallsteps.com/]
https://www.youtube.com/@startwithsmallsteps [https://www.youtube.com/@startwithsmallsteps]
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https://twitter.com/schmern [https://twitter.com/schmern]
Email the podcast at jill@startwithsmallsteps.com [jill@startwithsmallsteps.com]
By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.
