by Brian DeChesare Comments (2)

Public Service Announcement: Please Stop Using ChatGPT for Email

ChatGPT for Email

Normally on this site, I write about a mix of careers, sectors within finance, financial modeling topics, and current events.

This week, though, I am posting a public service announcement.

Please stop using ChatGPT for email – or learn to use it correctly so you don’t write horrible emails that sink your career.

Over the past few months, I’ve seen an uptick in AI-generated messages from students, customers, suppliers, and random people asking me for favors on LinkedIn.

In ~99% of cases, I can tell within 1 second that these messages are AI-generated because tools like ChatGPT add useless words and awkward phrases that no human would ever use.

The tone is also completely inappropriate and sometimes borders on comical.

If you send these emails to bankers in your networking/recruiting efforts, they will notice, and your chances of winning interviews and job offers will decrease.

Also, if you send short emails – which you should in any networking effort – these AI tools are pointless because they barely save you time.

I will make a few recommendations here, but I’ll start with the fun part and show you some examples of clearly AI-generated messages:

ChatGPT for Email: Horrible Examples

I’ve deleted names and email addresses from these examples for privacy.

And to ensure I wasn’t going insane, I plugged each message into Copyleaks (the most accurate free detection tool) to verify that it was AI-generated.

Example #1: How to Write 1 Page When 2 Sentences Would Do

Here’s a long email from a student that is obviously AI-generated.

In case you cannot bear to read it to the end, I’ve summarized his question below:

ChatGPT for Email 01 - Upgrade Request

His Question: “Can I purchase just Module 1 of your Real Estate course?”

This one baffles me because it probably took several sentences to prompt ChatGPT to write this message, given its details.

In the time it took to enter these prompts and tweak the message, he could have written a 2-sentence email to ask the same question:

“I’ve found your courses helpful. Is it possible to sign up for just Module 1 of the Real Estate course or to upgrade to the course at a lower price since I already have courses X and Y?”

Example #2: An Email Even with More Fluff Than the Average Cat

This one isn’t quite as bad, but it’s still clearly AI-generated:

ChatGPT for Email 02 - Study Plan Recommendations

Again, this person could have asked the same question in 2 sentences:

“Thanks for sending me the quick reference guides. I have an upcoming technical/modeling-based interview at the same real estate firm, and I wanted to know if you had any suggestions on the case studies I should complete to prepare for this.”

Example #3: The Student Who Requires “Assistance” from the Teacher

This one is short but also the worst example because of the tone.

If a professor, MD, or client got this type of message, they would reconsider their relationship with you:

ChatGPT for Email 03 - Student Teacher Request

Not only is this too wordy, but the last paragraph is nonsensical.

Have you, as a human, ever written “aligns with your query”?

Oh, and why would a student ask if the teacher needs “further assistance”?

Again, you could ask this same question in 2 sentences:

“Quick question – with the financing fees, you’re not factoring in the refinanced debt if the acquirer repays and replaces the target’s debt. Do you need to do that, or is it a simplification in this version of the model?”

What’s Wrong with ChatGPT for Email?

I’d sum up the main issues as follows:

  1. Overly Verbose – These AI tools add way too many useless words to messages, and they use awkward, robotic phrases.
  2. Tone/Style – The tone in these messages is inappropriate. If you already know someone, you communicate one way, but if you don’t, you say things differently. You also communicate differently with co-workers vs. clients vs. bosses.

ChatGPT for Email: What Should You Do Instead?

I do understand why you might want to use AI tools for emails.

Maybe English is not your first language, or you’re writing in another language you’re not 100% comfortable with.

Or maybe you feel intimidated by any writing, and a blank screen is the equivalent of Thanos.

But the problem is that most AI tools are bad at writing.

It goes back to what I stated in my article about ChatGPT and investment banking in January: it’s good for summarizing code/documents and can sometimes help with writing code.

If you use AI to generate code or write a formula, it just needs to work correctly.

The “style” and length don’t matter because clients will not see your code or formulas; they just need the correct output.

But as soon as you use AI to communicate with a real human, you’re gambling that it will use the correct words, length, and tone.

Here’s what I recommend instead:

  1. Short Messages – Do not bother with these tools if you can ask a question in 1-2 sentences. They’ll cost you time because you’ll need to refine your prompts until you get a shorter message.
  2. Longer Messages – If you need help with longer messages or documents, please take the time to learn how to use AI tools properly. You can find online guides, but you need to get comfortable with prompting them, reviewing their output, asking them to fix it, and continuing until you get what you want.
  3. Get Better References and Help from Friends – If you’re unsure about an important email you just wrote, ask a native speaker friend to review it. If you don’t have time for this, find some good templates (see our cold email templates and informational interview templates) and learn how to modify them to fit your needs.
  4. Always Personalize Your Networking Emails – Even before ChatGPT, plenty of students copied and pasted the same message in hundreds of emails. This is a terrible idea that will yield almost no responses. You need to spend at least 15 minutes reviewing the person’s background on LinkedIn to customize your message.
  5. Improve Your Communication Skills – Finally, if you want to advance in industries like investment banking and private equity, you must improve your communication skills.

These industries are built on personal relationships.

No AI tool will ever let a banker skip 10 years of relationship-building and win a pitch just because their second sentence was strong.

If you have no interest in improving your communication skills or building relationships with clients and executives, you should rethink your career goals.

Quant finance, prop trading, or certain types of hedge funds might be a better fit for you.

ChatGPT for Email: What Next?

Networking channels such as LinkedIn and email may become less effective because of the flood of “content” generated by these AI tools.

The phone, Zoom, and in-person meetings and sessions could become more important as the only way to “prove” that you are human.

I also predict that bankers will become increasingly hostile toward AI-generated emails.

They already get flooded with terrible emails written by students who don’t know what they’re doing, and now they’re getting flooded with even more terrible emails.

And these AI-generated ones are even worse because they’re longer and full of useless words.

But if you can learn to communicate effectively and write specific, personalized messages that show you’re a real human, these developments might be good news for you.

After all, if a banker gets an average of 99 terrible emails per week, you can stand out quite easily by sending one non-terrible message.

And if you don’t want to learn how to write simple, personalized emails, please ask ChatGPT to limit your messages to 1-2 sentences the next time you use it.

Additional Reading

You might be interested in Will ChatGPT and AI Kill the Investment Banking Industry and Other “Knowledge Worker” Jobs?.

About the Author

Brian DeChesare is the Founder of Mergers & Inquisitions and Breaking Into Wall Street. In his spare time, he enjoys lifting weights, running, traveling, obsessively watching TV shows, and defeating Sauron.

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  1. Oleksandr

    Great article, Brian!
    I would suggest you create a crush course on Outlook. When I entered a profession mastering Excel and Powerpoint skills was easy, but Outlook I learned the hard way.

    1. Thanks. I can’t tell if your comment is sarcastic, but I have no idea what a course on Outlook would cover or why it is more difficult than Excel/PowerPoint. Outlook is… sending email. It’s intended for a mass audience, including brain-dead corporate drones who can barely do arithmetic, so it can’t possibly be that hard.

      By contrast, Excel can get fairly tricky when you get into more advanced features and functions and it does require specific training in most cases.

      So, we’re probably never going to do an Outlook training course, but thanks for the suggestion.

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