Writing a cover letter in which you are able to flaunt your awesome skill set, showcase your winning personality, and somehow not sound like a robot cheeseball narcissist can be a real challenge. But your cover letter is one of the first tools that will take you from where you are presently (a.k.a. the Island of Unemployment/Current Career Discontent) to the greener pastures of your dream job.
At Girlboss, we believe the cover letter is still one of the most underused opportunities in the job search. Most people treat it as an afterthought. The ones who get the interview do not. Make sure the boat that will carry you that distance is sleek, quick, and leak-proof by doing the following.
Don't Mess Up the Basics
Don't fuck up the basics. Obvious, right? You would think so. But cover letters that blunder badly right out of the gate are more common than you might think. Make sure the most basic elements of your letter, including the addressee, proper formatting, design, and the job title exactly as it appears in the listing, are pristine.
It is essential to convey attention to detail and seriousness about the prospective job. Super basic errors suggest you did not take the time to review your work before sending it off and that you could not be bothered to research simple information correctly. Not a great way to begin the conversation.
Print it out and read it, even if you are submitting it electronically. Make changes, print it out again, and then read it again. Ask a friend or family member to take a look at it. Then make changes, print it out again, and read it again (yes, again!) before you send it off. Your cover letter needs to be immaculate.
Don't Let AI Write It for You
This is the 2026 addition to every cover letter guide ever written, and it is the most important one. AI cover letter generators are everywhere; they are free, and hiring managers can spot them from the first sentence.
The fluency is uncanny, but the specificity is always missing: vague gestures toward "dynamic environments," generic passion for "the company's mission," and a polished emptiness where a real person should be.
The irony is that this article's original advice, "don't be a robot cheeseball," has never been more relevant. A cover letter written by ChatGPT is, by definition, a robot cheeseball. The whole point of a cover letter is to give a hiring manager a reason to believe there is a real person behind the application who has actually thought about this job. AI cannot do that for you because it does not know you.
Using AI as a starting point? Fine. Use it to get past a blank page, then rewrite everything in your own voice. The final letter should sound like you wrote it, because you did. If you are not sure whether it does, read it out loud. If it sounds like a LinkedIn post you would never actually write, start over.
For a deeper look at how to use AI tools in your job search without losing your competitive edge, this guide to AI job search tools is worth bookmarking.
Show, Don't Tell
Are you having flashbacks to your high school English class? Good. This is one of the oldest principles of compelling writing, and a cover letter is no exception. The person reading your cover letter has probably seen some variation of the following sentence approximately one million times: "I am an incredibly hard worker, extremely organized, and I think I would be a great fit for this company!"
Instead of resorting to something so generic and predictable that it holds almost no meaning, describe an occasion from a previous job or position that clearly illustrates the attributes you want to highlight. On the flip side of that coin: keep it efficient and as brief as possible.
The hiring manager has read "I am an incredibly hard worker" approximately one million times. Describe a moment that proves it instead.
If you want to see this principle in action, Ask a Manager's cover letter guide has some of the most specific, honest advice available on what a good cover letter actually looks like versus what most people write.
Answer the Ad
Most job listings hand you a literal map via the job description and required skills. Do not make this process any harder than it needs to be. Absorb the language used in the job listing and reflect it back when you are writing your letter.
A demonstrated understanding of what, specifically, the job entails and why your skill set and background are a good match goes a long way. This is not about keyword stuffing; it is about showing that you read the actual posting and understood it.
Do the Extra Homework
So you have adhered to all of the above. Now you have to separate yourself from the rest. Demonstrate that this is a company you know well. Read interviews given by the CEO. Check the company's LinkedIn activity, recent press, earnings calls, and any founder content that tells you where the company is headed.
Familiarize yourself with when, where, and why the company was founded. Mention recent developments or bits of news you find particularly exciting, whether that is a prestigious award, an impressive recent earnings report, advances in technology, or major press coverage, to show them you are passionate about the trajectory of the company. In other words, flattery goes a long way (but do not overdo it; no one likes a kiss-ass).
The cover letter is a short document with a disproportionate impact. Most people write a bad one because they rush it or outsource it. Treat yours like a first impression you actually care about, and avoid the mistakes that still kill applications in 2026. And once you get the interview, here is how to handle it even if it goes badly.
Career advice that does not waste your time. Get the Girlboss Daily for job search tips, salary intel, and the career coverage that actually moves you forward.
