The Emails You Keep Putting Off? Hand Them to AI First
There's an email sitting in your drafts right now, isn't there. Or worse, it's not even in your drafts. It's just a thing you know you need to send, floating in the back of your head, taxing you a little every time it surfaces. Mine last month was a price increase to a client I've had for three years. I opened a blank reply four separate times. Wrote nothing. Closed it. Went and did something "more urgent" instead. It took me nine days to send an email that took four minutes to write. Here's the thing I figured out, and it's the reason I'm writing this: the problem was never the writing. It was the starting. And starting is exactly what AI is good at.
Why these emails are so hard
The emails you dread all have one thing in common. They carry a little emotional weight. You're asking for money. Saying no. Delivering bad news. Admitting a mistake. Ending something.
A blank screen plus a hard feeling equals procrastination. Every time.
What AI does, and this is the whole trick, is remove the blank screen. It gives you something to react to. And it turns out reacting to a draft is about ten times easier than creating one from nothing. You go from "what do I even say" to "no, not like that, more like this," which is a much friendlier place for your brain to be.
The simple formula
You don't need clever prompts. You need three things in your request, every time:
- The situation: what happened and who you're writing to.
- The hard part: the thing that makes it awkward, said plainly.
- Your tone: how you actually talk, so it doesn't come out stiff.
That's it. Here's what that looked like for my price-increase email:
The draft it gave me wasn't perfect. It was about 80 percent there. I cut two sentences, changed the opening line to something more me, and sent it. Nine days of dread, gone in four minutes, and the client wrote back "totally fair, thanks for the heads up."
The lesson isn't "AI writes great emails." It's "AI gets you unstuck, and unstuck is the entire battle."
The emails worth handing over first
Not every email needs this. A quick "sounds good, see you Tuesday" you can just send. Save the AI assist for the ones that make you wince. In my experience, these are the usual suspects:
- Chasing an unpaid invoice. You want to be firm without torching the relationship. Hard to strike alone, easy to draft with help.
- Saying no. To a project, a discount, a favor, a "quick call." No is a skill, and a draft makes it easier to be kind and clear at the same time.
- Raising your prices. The one that started this whole post.
- Apologizing for a screwup. When you feel bad, you tend to either grovel or get defensive. A neutral first draft keeps you in the middle where you should be.
- Ending something. Letting a vendor, contractor, or even a client go. Nobody enjoys writing these.
- Following up for the fourth time. When "just checking in" has started to feel pathetic and you need a fresh angle.
If you've got one of those sitting on your conscience, that's the one to try this on today.
How to keep it sounding like you
The number one worry I hear is "but it'll sound like a robot wrote it." Fair. Here's how to avoid that.
Tell it how you talk. Words like "warm," "direct," "casual," "no corporate speak," "short sentences" go a long way. If you curse a little in real life, tell it that. If you're formal, say so.
Feed it a sample. Paste in an email you're proud of and say "match this voice." This is the single biggest upgrade you can make. The AI stops guessing who you are and starts copying who you actually are.
Always do the last pass yourself. Read it out loud. Cut anything you'd never say. Add one specific detail only you would know, a reference to their kid's soccer game, the thing you talked about last time. That one human touch is what makes it land, and it's the one thing AI can't fake because it wasn't there.
Think of it as a first draft from a sharp assistant, not a finished letter from a stranger. You're still the one who hits send, and it should still sound like you when you do.
A few honest limits
I'm not going to pretend this is magic, because overpromising is how people get burned and then swear off AI forever. A few things to keep in mind:
- Don't paste in anything you wouldn't want stored somewhere. Sensitive legal, medical, or financial details deserve caution. When in doubt, keep the specifics vague and add them yourself in the final version.
- It doesn't know your relationships. It's never met this client. The nuance, the history, the inside jokes, the thing you promised in March, that's on you.
- For truly high-stakes messages (a legal dispute, a firing, anything a lawyer should see), use AI to organize your thoughts, then get a real human's eyes on it before it goes out.
Used with a little judgment, though, it turns your most-avoided task into a two-minute one. That's not hype. That's just removing the friction that was never really about the words.
Try this today
Pick the one email you've been avoiding. Just one. Open your AI tool of choice and give it the three ingredients: the situation, the hard part, and your tone. Read what comes back, make it yours, and send it before you can talk yourself out of it.
Worst case, you spend two minutes and delete it. Best case, you clear a thing that's been quietly weighing on you for a week. I'd take that trade every time.
The Price Increase
A three-line prompt (situation, hard part, tone) turned a nine-day-avoided rate-increase email into a four-minute task. The client replied "totally fair."
The Dreaded Six
Unpaid invoices, saying no, price increases, apologies, ending relationships, and fourth follow-ups are the emails worth handing to AI first.
Sounding Like You
Pasting in a sample email you're proud of and saying "match this voice" is the single biggest upgrade, so the draft copies who you actually are.
FAQ
Won't people be able to tell an AI helped write it?
Not if you do the last pass yourself. The tell is when people send the raw draft untouched. Trim it, add a personal detail, and read it out loud, that's all it takes to make it sound like you.
Which AI tool should I use for this?
Any of the major chat assistants handle this well. Use whichever you already have open. The approach matters far more than the brand.
Is it safe to put client details into an AI tool?
Be thoughtful. Keep genuinely sensitive information out of it, or write the email with placeholders and fill in the real specifics yourself at the end. For most everyday emails, general context is fine.
What if the draft is bad?
Then tell it why, "too formal," "too long," "sounds fake," and it'll adjust. Reacting to a bad draft is still easier than starting from nothing, which was the whole point.
The Bottom Line
The emails you keep putting off aren't hard to write, they're hard to start, and starting is exactly what AI is good at. Give it three ingredients (the situation, the hard part, and your tone), react to the draft instead of staring at a blank screen, then do the last pass yourself so it still sounds like you. If you're trying to figure out where AI actually fits into your day-to-day, which annoying tasks are worth handing off and how to do it without losing your own voice, that's exactly what we help people sort out at Humanity AI. Book a free AI strategy session at gethumanity.ai.
Want to talk more?
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