Tip: Write Effective Email Subject Lines with ChatGPT

About this lesson

Transforming Email Subject Lines with ChatGPT

In this training video, Les from Power Up! Training demonstrates how to use ChatGPT to craft compelling email subject lines that grab your boss’s attention. He shares a life hack where ChatGPT rewrites subject lines to make emails more clickable, showcasing its effectiveness with various examples. The video emphasizes the importance of starting a new chat for each email to avoid carrying overtones from previous sessions, ensuring the AI generates contextually appropriate subject lines.

Les walks through multiple scenarios, starting with a straightforward request for a status report and moving to more complex emails with jumbled topics. He shows how ChatGPT can identify key elements and generate suitable subject lines, even when the original email content is chaotic. By asking the AI for alternative suggestions and tweaking the outputs, Les highlights how to refine subject lines to be concise, forceful, and engaging, ensuring they stand out in a crowded inbox.

The video also explores setting the right tone, such as making a subject line sympathetic but professional for a personal request. Les demonstrates how adding context to the prompts improves the results, and he encourages viewers to mix AI suggestions with their creativity. The tutorial showcases ChatGPT as an excellent tool for brainstorming and refining email subject lines, helping users communicate more effectively and increasing the chances of their emails being read.


  • 01:25 Summarize Email Content
  • 05:07 Reset ChatGPT for Each Session
  • 05:36 Bringing Order to Long Emails
  • 08:41 Setting the Tone Just Right
  • 11:56 Start With A Starter Subject Line


Subject AI ChatGPT

Software Compatibility All Email Clients


Course Completed

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ChatGPT Email Subject Lines Transcript

Emails: An evil workplace necessity.

I get so tired of crafting an email that my boss might not even open.

But I have figured out a lifehack for work that will get my boss’ attention:

CHAT GPT rewrites my subject lines to make my emails more clickable.

While the internet has gone over the top with the idea AI chatbots taking over the world or writing Shakespeare sonnets.

“Hey Chat-GPT, Write a limerick about Taylor Swift”

But in my everyday life, I use of GPT in an “exacting” prompt creation mode.

And in return I get a brilliant personal office assistant, for free.

Hi, this is Les from Power Up Training and I am usually showing you how to be better at using Microsoft Office products, but in the last months, Chat GPT has transformed my personal use of Outlook mail for the Office.

Let Power UP on using Chat GPT to effectively improve our email subject lines.

I will walk you through four email subject line rewrites using different strategies that you can employ.  Starting with “creating a subject line based on the email content.”

This will be an easy softball request to Chat GPT to create a subject line for this simple email about requesting a status report and explaining an embarrassing mistake.

I am already logged into OpenAI’s ChatGPT, and if you have not used it before, check out my link to get you going.

Since I am a paid subscriber, I will be using GPT 4 engine Model, but this would work with the older GPT 3.5 or Bing Chat.

So here is my first GPT command prompt: “Write an email subject line. Wait for my input”

Here I am giving the instructions of my goals.  REWRITE AN EMAIL SUBJECT LINE. . . don’t create a new  email message or write a title to a movie, but a create a “subject line” based on the email message . .  that I am about to provide.

Note that I could just have added the email here; but it is clearer for our tutorial to write the COMMAND first and then follow up with the content that we want GPT to examine and transform.

Here I will copy the contents of the email and paste it into Chat GPT prompt box and hit enter.

And there we go  . . . this is a lot of words, but it does summarize the contents of my message for the subject line.

But let me fix the tone; I want it done TODAY; so I modify the results with the command prompt

“make it more forecful”

GPT working in CHAT mode will refer to the earlier response and reworks the output to match my request.

Ok that is a bit better, but I am not sold on this version.  So I ask GPT to show me 5 alternatives.

And now we are getting closer;  and while these capture my intentions with a hint of my displeasure with the timecard fiasco, I worry that LONG subjects will get lost in the sea of other emails; especially if my staff member is looking at their inbox on their phone and the limited screen space to view message headers.

So lets not make it just forceful but use fewer words.

And this is much better.  I like #1 “ACTION: Report & Timecard justification by Tuesday”

This one sums up that an action is required by a Tuesday deadline about not just the status report but also an explanation of the timecard snafu.  Al is captured in seven words with the FORCEFUL “Action” command.

But as always, I add my human creativity to the robots suggestion.  I would insert the word “MISSING” in from of timecard to add just a bit more emphasis.

Me and my AI assistant fixed this subject line.


But before moving to example number two; I want to emphasize the importance of ALWAYS, and I mean ALWAYS, start a new Chat when beginning a new topic.

If you don’t, you risk GPT building on your previous persona (such as make it forceful) which would influence your future results.

Just go to the top left corner of the webpage and click NEW CHT to start from scratch.

The next email is a mess. Can chatGPT save me?

Lets look at it!

First of all this email should never be sent . . it meanders and bunches up different comments and requests into chaos

. . Change in schedule . . going on vacation . . . can Rochelle take my place .  . .  lets pick the yellow color theme . . . . but tell me now so I can prepare the powerpoint presentation . . and importantly my phone number has changed. Lastly, does anyone really care about a yummy lunch?

Maybe six different things smashed into a single, rambling email.

As I said, what a mess; but let’s see if ChatGPT gets lost and can’t build a subject title.

I will start with the command prompt to write an email subject line and then drop in the contents of the message.

After submissions, I really, really want the AI robot to tell me that it is an embarrasing email and it would be better to delete it and write five seperarte emails for each topic!

But alas; GPT makes a heroic effort and ends up identifying four key items missing the request to rotate in Rochelle and my new phone number.

These results are amazing, and quite frankly, I had planned for this tutorial example to fail, so I could say GPT does not always work but I am blown away at just how clever ChatGPT can be.

Let’s see five more alternatives to the proposed subject line title.

All following the same lead, but in different wordings and styles.  I kind of like #3, because the subject line emphasizes at the end that I “Need your Input”

Still, all five may be a bit long.  (Subject lines should not be a paragraph in length)

So I tell GPT to use fewer words.

I might go with #1 Zamarotini Concerns: Vacation, Colors.

If my boss’ reputation is tied to the product launch, then the use of CONCERNS add some mystery to the email title and might intrigue my boss to open up the message sooner than later.

However, I probably would go back up to the longer titles, just because this messy email is jam-packed with disparate topics and select #3

Once again, your robot assistant is just giving you alternatives, you MUST be the grown-up human to select the right message.

In example #3, lets work on getting the tone of our message just right.

I have this time off personal request, but I do want to keep a professional, so I create this prompt:

“Write an email subject line for the following request to my boss, and make it sympathetic but professional. Wait for my input.”

Pay attention to how I set the tone with “make it sympathetic but professional” before I even get started.  The more context you can give to GPT up front, the superior the results will be.

And is that even surprising?  If I asked you to pick up groceries and nothing else; what would I get?

But if I added context of get groceries for a salmon and spinach salad dinner; the results would be spot on.

So DO add context up front.

And here is the response.

Okay . . .that might work. . . but I always like choices . .so  I am asking for five, but you could ask for a dozen or more.

Ok, ok, you could choose any of these and be done.  But it doesn’t quite ring true in my sititation as I have a longer-standing professional relationship with my boss and we get along well and I have talked about my family in the past.

So I will try this “make it more personal”

Okay, this may be getting a bit creepy with a AI Robot trying to make me more human. . . . #5 ” A caring hand: time off for mother’s emotional shift to assisted living.”

But GPT is taking on the role that we asked of it.

Now, one last modification. We need this to happen now, so “and add some urgency” to modify the choices.

And there we go

Of the group, I think #3 works best, but I would change it a bit to “Approve Personal Request Today: Urgent Care For my Mother’s move to assisted living.”

The title is a bit long, but it does capature both the urgency and the personal impact.

Do take note that we are NOT turning everything over to the Chat Bot.  I am looking at the ressutls and adding the appropriate modifiers,

In the end, electing to do human editing to get it just right.

But still, what an amazing digital assistant to bounce off new ideas to reenvision our email subject lines.

CHATGPT excels in brainstorming mode


Let’s do one more, where I use my favorite technique of getting the tone just right by writing the subject line myself.  (What? Me do work up front?)

Here is a longer, complex email about a project team having to evaluate and score a collection of Request for Information submissions.

ANd the result is okay; but lets contrast this with a title I composed with no robot help. “ACTION REQUEST: Score the Seven RFI Submissions by Next Tuesday”

I find if I humanly write the title first and then get GPT to offer suggestions, that often I get my best results faster with just a few tweaks along the way.

1st tweak: Hey GPT make them more friendly for my close-knit work team.

Ok, I am not quite hip enough to use emojis in my email titles.  But it might work for you.

Now watch as i EDIT the previousprompt and totally change it by replacing friendly with “EYE CATCHING”

Time’s Ticking.” ?

“score Big” ?

“You be the judge?”

And lastly, who does not want to be MORE CLEVER.”?

<nod, nod, Smile> oh yeah

“Ready Set Score!”

Oh I like that . . let me fix it for me

“Ready, Set Score: Get your RFI Analysis Game On and Reach the Goal Line by Tuesday”

See that!  A marriage of a ChatGPT-inspired idea and me going to the next level.

This is ChatGPT at its best to be your cleaver brainstorming assistant, for free.

Want more ways to be better; go watch my similar tutorial on making better PowerPoint slide titles, which has some relevance to this video where I dig deeper to change the focus to match the intended audience and to change my role as the presenter. (Pretend I am a project manager . . now pretend I am the head accountant). Do yourself a favor and watch.

And for more work lifehacks on Office tools, like and subscribe

Until next time, Go Power Up!