How to write a cover letter (with and without ChatGPT)

Cover letters are a job application document that accomplishes two things: are you a person I want to work with? And can you write?

Those are the two questions anyone reviewing your cover letter is asking themselves.

Like all documents, cover letters have standards and constraints. They are expected to be formatted as a letter (your info top, then date, then their address, greeting, body–most of the doc, closing, signature, typed name)

(If you don’t know what a letter is, it’s basically what we used to send through the mail before there was email.)

What I hear most from job applicants is “Why are we still writing these things?” And that’s fair.

But the reason we are still writing them is because people still need a way of deciding who to interview, and companies still need people who have basic communication skills–you will need to write and communicate with your coworkers at least.

So, to answer the question about whether you are a person that the hiring folks want to work with, you will need to tell some good stories about what kind of employee you are. And that’s the goal of the cover letter. Not to make big generalizations about who you are or what you can do–that’s what makes a cover letter bad.

No, don’t fill it with grandiose assertions about how amazing you are (some people think that’s what cover letters are about and it makes them uncomfortable. They aren’t.) Just tell a few good, brief anecdotes about who you are as a worker.

And if you are a student who hasn’t had a job yet, then tell a story about school.

A story is basically just “One time x situation happened, and I fixed it.”

Think of a time where you faced a challenge: this could be with a customer, a client, a coworker, a professor or class–pretty much any instance of challenge where you come out looking pretty good. It’s even better if the problem and solution directly illustrate some of your skills related to the job you are applying for. If they want attention to detail, talk about a time when something was a mess and you found the problem and solved it. If they want an innovator, talk about a time when something wasn’t working and you figured out an ingenious way to make it work. If they want a good communicator, talk about when something wasn’t coming across clearly and then explain how you changed the language to make it make sense.

The goal is to tell two stories that illustrate your best qualities. 

If you tell two good stories illustrating your best qualities, they will want to work with you *and* they will think that you are a decent enough writer to communicate your ideas and merit an interview.

Here’s a rough framework for any cover letter:

Paragraph 1

1st sentence = "I'm applying for ___[Job Title]________.

Next 1-3 sentences say what you like about the company--values, goals, projects, anything you know about what they do, what makes them stand out, and where you connect with them.

You can use AI to help you research the company.

Paragraph 2

3-4 sentences: Tell a story about who you are as an employee that illustrates some of the qualities in the job description. 

You can use AI to help you craft the story and proofread it, but don’t have it write the story for you.

Paragraph 3

3-4 sentences: Tell another story that reinforces the same qualities or illustrates additional qualities in the job description. 

Again, AI can help with moving a rough draft forward and making sure the final version is correct, but don’t let AI writing it for you–it’ll end up sounding weird and like someone else.

Paragraph 4

1st sentence = assert that as the stories demonstrate, you have the skills to succeed in this job. You can make this grandiose if you want, or humble. 

You can use AI to help you workshop this sentence, but it should confidently state that you can do the job.

2nd sentence = State that you are eager to do the job and look forward to an interview. Include your email and/or phone number in the last sentence–many old school hirers look for your contact info in that location (Yes, it’s on your resume and seven other places in the application. I don’t know why they don’t look in those other places. Just do this for the old people.)

Once you have the basics, you can use AI to help you check grammar and make sure the stories are clear. I would ask AI questions like “What else would you need to know to hire me?” Or “What should I add to get an interview?” It will automatically offer to revise your writing for you. Decline. Or ignore whatever it produces as much as you can.

Remember, AI writing is creating based on the average, so it will change your language to match what everyone else has said out in the world–those people are not you and most of them did not get a job. Also, most people are not great writers, so AI’s recommendation are a reflection of other average writers’ writing. 

Your cover letter should be as true to who you are as it can be. That means using *your own words* because the language you use gives people so much information about who you are and what you are like. Your language is as unique to you as your fingerprints. Don’t throw away what makes you special so you can have correct language that makes you sound like anyone else. 

Hiring committees want to hire individuals who can really offer something special to their team. You are special. AI’s language is not. Use it to *support* your writing, not to make you sound like everyone else. Everyone else isn’t getting hired.