Teaching Students to Write a Good Email in the Age of Artificial Intelligence (and Revising Lesson Plans for AI)

Computer covered with sticky notes

My first How-to-Write an Email lesson plan from a place of grouchy tough love.

A decade of teaching high school English overlapped with thousands of book-related pitch emails: Please read my work. Please help me sell my book to a publisher. Please let me come on your show or podcast and talk about my work. Please, Mr. or Ms. Intern, pass this email on to your boss and don’t just immediately delete it.

Each email had to be just personal enough, just professional enough. It needed enough detail without running too long. The mechanics had to be perfect.

And still, the most common response was no response at all.

This was to be expected; most of these emails went to strangers whose inboxes were overflowing with requests from people like me.

At the same time as I was carefully crafting pitch emails to publishers, I was on the receiving end of emails from my students. The contrast was jarring.

These were good kids, for the most part, with decent communication skills.

But many of their emails seemed almost perfectly engineered to get a negative response.

FROM: ThisEmailAddressRefersToAPartOfMyBody@gmail.com

Subject line: URGENT!!!! CHANGE GRADE!!!

dear teacher i am to lazy to check my spelling and or punctuate my sentences but i want you to spend your weekend time checking on my grade please do that right now i think sending a professional looking email is overrated apparently but i think its important for me to let you know that you made a mistake. YOU MESSED UP! CHANGE MY GRADE NOW!!!!. also, i’m not going to give you any information about the assignment so you can just scroll thru your gradebook and see if you can figure out what i’m talking about. Student name

                                                             This signature line is indented for no particular reason.

I knew most of my students wouldn’t be pitching books to publishers. (Most sane people don’t fling themselves into that particular meat grinder.)

But they would be sending emails their whole lives. These emails could either give them a shot or nail a door shut before it even had a chance to open.

There was so much students needed to learn about how emails land on the receiving end. On a selfish note, I also wanted to get better emails from students.

Emails like the one above damaged my morale.

The original email lesson plan ended with a dramatic homework assignment: I warned students that I’d be creating a made-up assignment in my electronic grade book and giving each of them a zero.

To get the grade changed, they’d have to craft the type of email they’d need to send to a teacher who’d given them an F by mistake.

Their grade would be changed based on the quality of the email they sent.

As ChatGPT hit the scene, it became clear this lesson plan needed some revision.

The homework assignment was the first part of the lesson plan to become outdated.

It didn’t seem likely that students would write the email themselves if a machine could get a higher grade.

And it only took 30 seconds to get this from ChatGPT.

Reading this AI-generate assignment, I realized teachers might never again have to teach students not to write a terrible email. At least–not the old kind of terrible email.

AI can help a writer avoid many of the mechanical problems that make teachers let out a long, discouraged sigh.

AI is good news for people who are self-conscious about their writing abilities, which likely includes some of your students.

A.I. programs like ChatGPT are sometimes described as “democratizing written language.” As much hesitation as I have about some aspects of AI, this definitely feels like an upside. There will be people who find it miraculous to have a machine help them write an on-topic, reasonably-formatted email with no embarrassing mechanical errors.

The bad news? There are still lots of ways email can go wrong. Here are some email-writing principles teachers still need to reinforce with students.

Teachers still have work to do when it comes to helping students write a good email. Specifically, teachers need to reinforce the following. . .

People who get a lot of emails now get a lot more emails.

Getting a constant stream of robo-emails takes a toll. Hiring managers on LinkedIn, for example have complained that they can “just feel” when an application has been written by A.I., especially when they receive a stream of such applications.

It’s usually infuriating to spend more time reading something than the writer spent writing it.

Teachers know this better than anyone.

The response to an email should never be, Does this person think I’m dumb?

AI is likely to make this problem worse.

Writing skills are thinking skills. And both of these still matter.

In the same way that students need to learn long division even if they’ll eventually move onto calculators, they also need to know what makes written communication effective—even if they can now get a machine to do some of the writing.

A well-written email must strike the correct balance, whether AI helps or not.

Emails still have to be just personal enough and just professional enough. They still need enough detail to be clear without running too long. Bad mechanics can still be a dealbreaker. But now, so can an email that is completely lacking in human touch or one that doesn’t account for the relationship between the sender and the recipient.

It’s still a good idea to lock in a non-embarrassing email address before the end of high school.

An email address is one of the ways immature decisions can haunt students in their professional lives. Take it from me: My first email address contained the phrase foxyroxee; I definitely used it to apply for official purposes at until something forced me to change it. An email lesson is a chance to do this for your students.

Be the change you wish to see in your students’ email addresses.

This was also my first dive into revising a language arts lesson with the help of AI, learning its capabilities and limitations. Here are some of the things I learned.

Sh*tty first drafts serve a purpose. Skip them at your own risk.

You don’t have to be a high school student to wish you could get a robot to your homework. We all hate staring at a blank page, and AI can feel like an easy fix.

With this in mind, my first step was to ask ChatGPT to generate a version of my email lesson plan from scratch.

The result? Professional looking, but underwhelming.

The plan was formatted correctly. It followed the basic logic of a lesson plan. You could turn it in to the main office if you had to. An observer might look at it and check off the necessary box on their checklist.

But the details that got to the heart of the thing? They were cleverly-disguised blank spaces. Perhaps I could have gotten ChatGPT to generate the elements it referred to in the lesson plan. The right prompt might have produced something close to the type of “student email” that frustrated me as a teacher.

When thinking through a concept is an important part of the process, it may be easier to write from scratch than try to edit an AI-generated draft.

Author Anne Lamott wrote a famous essay entitled Sh*tty First Drafts that I’ve loved as both a writer and a writing teacher. Even though this essay was published in 1995, it explains an aspect of first drafts that AI can’t recreate.

Very few writers really know what they are doing until they’ve done it. . . . The first draft is the child’s draft, where you let it all pour out and then let it romp all over the place, knowing that no one is going to see it and that you can shape it later. . . Just get it all down on paper because there may be something great in those six crazy pages that you would never have gotten to by more rational, grown-up means. There may be something in the very last line of the very last paragraph on page six that you just love, that is so beautiful or wild that you now know what you’re supposed to be writing about, more or less, or in what direction you might go — but there was no way to get to this without first getting through the first five and a half pages. . .

Almost all good writing begins with terrible first efforts. You need to start somewhere. Start by getting something — anything — down on paper. A friend of mine says that the first draft is the down draft — you just get it down. The second draft is the up draft — you fix it up. You try to say what you have to say more accurately. And the third draft is the dental draft, where you check every tooth, to see if it’s loose or cramped or decayed, or even, God help us, healthy.

Anne Lamott, “Sh*tty First Drafts,” (from Bird by Bird: Some Instructions on Writing and Life)

A.I. can be a real time-saver in generating examples.

This idea originally came from Ethan Mollick. Mollick is a Wharton business professor whose newsletter, One Useful Thing, has become one of my go-to sources as I step onto the rickety bridge of the AI-assisted future. His piece on Using AI to Make Teaching Easier and More Impactful led me to ask ChatGPT to generate examples for a hypothetical class discussion. And. . . the results were useful! The original version of lesson did set aside time for a class discussion, but I hadn’t included any examples of the comments that might come up. Pre-AI, this was the type of work that didn’t seem worth the time. But after asking ChatGPT to generate about 20 example comments, I was able to include the most helpful ones, putting them into into categories to help teachers guide the class discussion.

An AI version of your work can also serve as a formatting checklist.

While I didn’t take much from the AI-generated draft of the lesson, it wasn’t a total write-off. I matched it up against my original lesson plan and realized I hadn’t included an objective. . . which led me to an even more delightful discovery. . .

AI can match Common Core Standards to your lesson within seconds.

Now there’s a task many teachers won’t miss.

When it comes to the professional-looking busy work requirements of teaching, AI is your friend.

One of the unwritten rules of teaching is that there are some aspects of the job that aren’t the best uses of your best effort. When it comes to paperwork that will prove you paid attention in a professional development session, or will stay untouched in a dusty binder until the end of time, AI might be able to knock these things out for you so you can focus on the parts of your job that best serve students.

My favorite discovery of all: A.I. can provide feedback to your students on their writing!

Grading papers was always my least favorite part of teaching language arts.

More specifically: Writing detailed feedback was always my least favorite part of teaching language arts.

Especially when there was so much to comment on that I didn’t know where to begin.

Especially when one of the things I desperately wanted to comment on was how little effort a student had put into the assignment in the first place, sometimes so little that writing the comment would mean I’d spent more time on the student’s assignment than they did. (Much more on this in the Grading Work without Hating Work chapter of See Me After Class.)

With all that in mind, one of my favorite moments in the lesson revision rabbit-hole happened when I plugged in the example emails from my original rubric.

This was ChatGPT’s response to the example of an A email.

The encouraging comment before the response was a nice touch. It’s the same type of comment teachers often try to write on a good paper, but find exhausting over time.

The rewrite of the email also included some helpful elements that a student might choose to use–most high school students don’t use the word “discrepancy,” but it’s a good term to learn in this context!

My favorite discovery, however was that, with the right prompt, ChatGPT will explain what it did to improve the email.

Again, this is very encouraging, but also detailed enough to be helpful to a student.

This made me wonder how A.I. might handle the type of email I found most frustrating to comment on–the type of email that made me create this whole lesson plan in the first place.
The verdict? Not bad!

ChatGPT was able to get some usable information from the sample email and create something useful. And, unlike the first email, it didn’t say the original email was good.

Here was the feedback ChatGPT added at the end of the “D” level email.

This is probably the feedback an English teacher would feel like giving if that English teacher only had to spend a few seconds reading and responding.

And there’s a lot here that would be useful to the student. If they’re paying attention.

Then again, if they’re not, they probably wouldn’t read the feedback from the teacher, either.

Yet another reason it’s good to have a bot on your side.

Experimenting with AI’s capabilities is a little bit like playing a game of Battleship.

Sometimes, a prompt leads such a direct hit that you feel the room spinning.

On your next prompt, AI just doesn’t seem to get what you’re asking, even though it’s something a human would understand in seconds.

It’s hard to know where the hits and misses are until you’ve played.

This is the part of the where I’m supposed to conclude with a Testament to the Human Spirit, perhaps some reassurance that “our humanity is what will save us in the end.” Unfortunately, I accidentally prompted AI to pump out Testaments to the Human Spirit in the voices of many of my favorite writers–including me.

This started as part of my original micro-challenge for educators nervous about A.I., but quickly got weird.

Lots to unpack here, but that’s for another post.

Apparently, however, AI thinks I’m pretty hopeful about how humans are going to weather this storm! Here’s how AI “Roxanna Elden” ended her passage.

AI “Zadie Smith” ended her passage on a similarly hopeful note.

AI “Dave Barry” was similarly confident in the power of humanity.

And AI “Benjamin Lorr” was downright inspiring. . .

Not a dry robo-eye in the house!

Then again, we might as well believe humanity is our superpower, because the other choices aren’t so hot.

Closing on a note of hope and possibility is a writing style choice, but it’s also a lifestyle choice.

And it’s a choice I’m trying to make more often, especially when dealing with overwhelming new subjects like this one. Starting the day with a brisk, 30-minute rant about our tech-bro overlords has not worked out well for me.

So, sure! Keep trying to make AI your employee rather than your boss. And teach your students to do the same.

Here’s the revised email assignment on TPT, with all the human and machine work that’s now gone into it.

The lesson plan will help you walk students through the thinking process that goes into writing a good email from scratch. It also offers a buffet of opportunities for students to practice in class, and later with the help of AI.

I hope it helps you and your students move forward on all of this together.

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