How Not to Write a Business Letter

Let’s do an experiment. We are going to attempt to write the worst business letter ever. Why? Because you learn more from doing, from creating something from scratch based on the principles, rather than if you were just passively receiving a list of dos and don’ts.


Just like professional athletes who practice missing a goal on purpose, so they know in their muscle memory how to bounce back from a miss in a real game without losing too much rhythm. Just like high-level martial artists begin their careers learning how to take a hit, how to fall—and fall well—and get back up.

The Benefits of Doing It Wrong…at First

Learning to replicate the characteristics of what makes a bad business letter will help you see exactly what you should not be doing next time.

And if you’re following the instructions of writing a bad business letter, only to find yourself writing like you’ve always done, then congratulations. You’ve found a big problem.

And when a mistake is recognized as an error, it is no longer an error—it is now a learning opportunity. You’re already a step ahead of everyone who shares your mistake but is blind to it.


Perhaps the biggest reason why so many poorly written business letters are still being written (and why so many bad correspondence habits abound, despite the volumes on business etiquette written in turn to counter them) is simple.

You just don’t know what makes a bad business letter bad.

Often we don’t even know how to describe something as bad; it just leaps out at first glance and slaps us in the face.

Bad writing is like good art: you just know it when you see it. And like most people, you likely base snap judgments on this inexplicable quality. You can just tell something is off.

Many people find it’s next to impossible to explain why something just feels off. But that’s what we will try to do here.

Hopefully, you will get a sense of what others—coworkers, investors, supervisors, bosses, hiring managers—are looking at when they read your letter, whether it is through the mail, through email, or a template note left on their desk.

The Mindset of the Reader

Let’s take the email cover letter, for example.

Hiring managers will take one glance at your cover letter and instantly be able to judge your character, your personality, your teachability, your very potential to work with them.

You can have all the technical qualifications any company can ever ask for and have eye-watering impressive educational background and experience, but if you come across as egotistical, rude, arrogant, and delusional—guess what? Your certificates and awards won’t count for jack.

Don’t be surprised. You don’t have to sell yourself as great, period. You have to sell yourself as a great fit—for that particular company for that particular positionThis means stop setting off all your fireworks, and figure out what they want from you. See if you can give it to them.

Or don’t.

So what are the rules of a bad business letter? One way to know if you’re doing it wrong is to take the ground rules of good business writing, and then do the opposite.

Yes, it is that simple. It is also not. Because how do you know when you’re crossing the line? For example, are you being professionally concise, or are you omitting too much information that might be necessary?

There’s a saying making its way around the arena of the entrepreneurial and the innovative, this pragmatic mantra of: There is no right and wrong, there is only what works and what doesn’t.

So perhaps we can’t say these are “wrong” ways to write a business letter, just as there is no absolute “right” way to word your opening sentence, for example. There is only what works. In that sense, this checklist of writing don’ts will show you what works, what doesn’t, and why.

Let’s start writing.


12 Rules on How to Write a Successfully Bad Cover Letter

To start us off, let’s take the cover letter as our model.

This is a common type of business letter. A cover letter is what you send to the company’s hiring and recruitment personnel through the address provided in the job listing. This is the letter you’re writing to inquire and apply for a position at the company, and it will typically need to have your resume (note: not your CV) attached.

Let’s look at a few ways we can write it in the worst way we can, to get our chances of getting a second look as close to zero as possible. In the end, you will have quite a work of art that you can break down and decode to these principles—and hopefully help you avoid them in your actual writing.

The following are the red flags of a bad cover letter, which we will now embrace.

1. Get Very Conversational

Start with something along the lines of “Hey there, I know you probably get a lot of these letters, and God knows you must be bored, so let’s get right to the chase!” (And they don’t get to the chase, but start talking about how you didn’t actually feel qualified to write in for the job but, hey, everyone must start somewhere, and it’s better than nothing.)

Perhaps even use their first names, if you did your homework and found a name. Better yet, create a cutesy nickname for them. Talk about how you feel a little sick because of something you ate that morning, or mention in passing what a crazy weekend you had.

Come on, maybe we’re doing them a favor, rescuing some poor sample HR intern from their drab office-desk lives with our friendly—too friendly—cover letter. After all, we’re not trying to show how we’re perfect for the job, and doing so with a crisp collection of purposeful words. We’re just trying to make friends.


2. Forget the Point of the Letter

Remember the reason you were writing in the first place?

You wanted to inquire about an open position at that company. You’d seen an ad or a posting online, and you looked through the list of requirements and realized you had a healthy skill set that would be the perfect (or at least a valuable) match for what the company is looking for.

They are hiring in order to accomplish some company goal, not to do people a favor. You understand that goal, and you recognize what you have to contribute, and how you will be a valuable asset with an ROI that will pay back a hundredfold the costs of hiring and training you.



Yeah, forget all that. Let’s write about your childhood fascination with marching bands instead and how you always felt cut out for greatness.

3. Finally Get to the Point, and Then Leave It Hanging

“I am writing to ask for a job.”

End it there.

Don’t provide relevant information on your background, don’t attach a resume, forget to spell out your full address, and don’t leave a phone number anyone can reach you at easily. Or, leave a phone number, and say that you never answer your phone, so instruct them to leave a voicemail, and you will get back to them whenever is convenient for you.

God forbid they finally manage to reach you within a week or less and actually demand whether you have anything to offer. Make it as difficult and inconvenient as possible for them to get a hold of you.

The good news is, unless they are super desperate, they probably won’t bother.

4. Assume Right Away That the Reader Cares about Your Personal Problems

Say you’re applying for a job as a salesman, or as a writing intern at some big publishing firm, or as a software engineer.

You don’t have the necessary experience for this specialized role, but let’s talk about that blog you started in high school that had a few politely positive and encouraging feedback from friends and family members (or family members of friends).

Talk about how you quit writing or coding because of school obligations—why wait for the interview to divulge these things, if asked?—and how were you so frustrated with not being able to freely and creatively express your feelings and your anger about the world?

Look, if they’re going to hire you in future, you will want them to be involved in your personal issues, right? You think they’re hiring you for you as a person and the rapport you built up in your letter, not for what makes you the employee with the necessary skill set they need.

So don’t you think they should have the necessary knowledge of your personal life? It will help to back up your excuses of why you could not write on deadline or get the smallest tasks done on time.


Too bad they just don’t care.

No one cares (as you pointed out in that prescient poem you wrote in high school). Your future bosses are just not interested in picking up the pieces left over from your previous job.

5. Spice Things Up with Colorful Language

“Let’s cut the bullsh*t and get to the chase. I am f*@#%ing perfect for this job. You’d be a fool not to consider me for the job and hire me right away, seriously, man. I am everything you’ve been looking for.”

Honestly, though, this is a made-up example because literally no one dares to write like this to a hiring manager.

Business writing guides rarely have to point this out as a major no-no. It’s just that much of a no-brainer. Maybe it’s because no one has the guts. If you do it, that’ll help you stand out, won’t it? And if you never hear back from them, well, they’re f@$%ing idiots.

6. Turn Off the Spelling Checker, and Type with Your Eyes Closed, on Your iPhone

Your wriiting myt comeoff as something likethis.but. lmao Who cares right??

It’s the age of the smartphone. Mobile is eating the Web. If you’re all thumbs with your business writing, and it clearly says “Sent from my iPhone” at the bottom, then shouldn’t these business professionals understand the state of the world and forgive you for your lowercase i’s and lowercased everything, your emoticons, excessive punctuation, and wonky spacing?


Or maybe you won’t be forgiven, but that’s beside the point. You don’t have to prove to them you’re smarter than your smartphone. If they want to be a grammar Nazi-slash-Luddite about it, that’s their problem.

7. Come Across as Egotistical, Delusional, or Both

Tell them that you are destined for greatness. Don’t bother backing up your claims. You’re too important for that; it should be obvious to them.

Tell them you are a success at everything you do, that you have the Midas touch. Everything you apply your efforts to turns to gold. Tell them that their customers will love you, because everyone does.

Talk about how the competing applicants don’t have anything on you, because they don’t have the skills and that “aura” you have.

Dare them to get back to you if they actually want a blue blood professional on staff. Advise them not to be like the other companies in the past who gave you your impressive track record of declined applications.

(For bonus points: share an inside joke of how baffled you are that other companies would pass on a valuable asset such as you—because, after all, you can’t let the reader know you are even remotely aware what it is about you that is turning people off.)

8. Don’t Let Them Know You’re Talking to Them

The best chances for success is to create the most generic cover letter possible and machine-gun them to several companies at once, upping the odds that they’ll find something in your letter that will entice them.

To help you with that, find a good dictionary of all the inflated business jargon, the vague words and grand empty promises:

Tell them you are “highly motivated,” “goal-oriented” (better yet, SMART goal?oriented), “analytical” and “innovative,” that you “believe in excellence” and are ready to do what it takes to “successfully fulfill the company’s organizational objectives.”

That must be what all companies are looking for, since that’s what an overwhelming number of professionals are writing, isn’t it? Who wouldn’t want all those qualities?


Yes, these qualities may be a given, but if you start talking about what makes you specially suited for a particular job opening, you will need to get into concrete details that can be backed up and endorsed.

And that means you have to consider what a particular company is actually looking for, and showing them that what you have is a match.

You can’t do this for every letter, or your “flood of letters” strategy will be undermined. Being specific means you will be writing a targeted letter that shows them you are determined, that you have them and their goals specifically in mind. Who has the time for that? Certainly not you.

To further your reach in no time (and lessen the work from your end), don’t mention anything too specific. Don’t pin down your skills with anything concrete and endorsed. Don’t mention the company’s name or the position you are applying for (this way you can send the same letter to everyone with no editing necessary).

Say “the company,” and “the position,” and use every cliche in the book. There is probably a book.

9. Be Super Honest

We’re talking about inappropriate honesty, along the lines of TMI (too much information). For our purposes, ignore the bureaucratic politics and the restrictions of professional etiquette—especially when writing to a stranger about a job position.

Honesty is a virtue, after all.

How can you extol this virtue in your cover letter? The first step is to listen to your inner muse (or your inner insecurities and anxieties—same thing), and give that voice free rein.

  • Tell the recruiter you don’t think you are qualified for the position at all, but you thought you would give it a shot anyway.
  • Tell them the only reason you’re applying is because someone said to give it a try, and you don’t know what else to do with your life.
  • Tell them you don’t have most of the requirements they had listed on their job posting, but you don’t think it should matter because you have these other qualities that don’t actually suit what they’re looking for, but hey, you’re a fun snowflake.
  • Tell them you don’t think their company is all that great, based on their previous work and the reviews, but you think you can contribute to making it better.
  • Tell them you’ve never heard of them.

Every time you mention something that could count as a qualification, downplay it: “I wrote for the college paper, but it wasn’t anything special.”

Also be clear about your deliberate ignorance about the company: “I don’t actually read your publications, but I think I will be a good fit for your writing staff anyway since I studied Journalism.”


You are only trying to do part of their job for them, so it’s easier for both of you. Ever heard of the professional debater’s (or lawyer’s) tactic of addressing an opponent’s criticism before it’s provided? Look for all the recruiter’s possible criticisms and direct a searing spotlight on all the ways that you feel you’re not up to the task. Heaven forbid they look at a qualification objectively and see some potential in you. After all, you don’t want to disappoint them!

10. Make It Last at Least Five Pages

Not just five pages (or five complete screen changes, if you’re writing an e-mail), but make sure there are no paragraph breaks until you get to the fourteenth line, maybe.

Some ideas on how to do this: Include everything you can think of to make sure they understand you as a person, warts and all. Let them appreciate your uniqueness as an individual. Don’t stick with just the aspects of yourself that you think they would be most interested in, the aspects that would help them decide whether you can fulfill the job vacancy.

They need to know your hobbies (in depth and in detail), your charming whimsies, your informed opinion on the current president, a dissection of an editorial you read recently that irked you for whatever reason, the story of how you cleverly responded to someone’s criticism in the comment section of some blog post, or a comprehensive social critique of the state of humanity. (Don’t forget to add many parenthetical remarks laughing at your own wittiness.)

11. Make It One Line

Perhaps the previous point is just too much work. Haikus are profound in part thanks to their brevity, and what’s more brief than a one-liner? And you’ve often heard that conciseness is important in professional writing. All sorts of tools and apps are designed to help you with the readability of your prose, and one thing they flag are the too-long sentences. In this case, you’re safe, and the hiring manager should appreciate that.

So what if you’ve given them a lot more work figuring out exactly what you’re getting at and what you expect them to do next?

To help you make your too-short letter even shorter, lighten up the information load. Don’t provide any contact details, don’t weigh it down with your resume, neglect to even type in your full name or the job position you’re applying for.

Here are some ideas you can use:

“Hi, I would like a job.”

That’s it. That’s your full letter. Attach your resume—or better yet, don’t.

Or, here’s another option:

“Is this job position still open? Thanks.”

Yes, people have done this. Maybe it wasn’t meant to be a cover letter after all?

12. Get Long-Winded, Vague, Logically Scattered, and Incoherent

This is perhaps the most difficult rule to carry out successfully because almost no one can tell whether they are doing it.

Your best bet is to write free-flow. Don’t edit, don’t read back, don’t have someone else read what you came up with, and don’t refer back to the job posting for the requirements or even the job position.

Easy way in: see rule #10 and try for a full 10 pages. Also, see rule #9 and dive into a reminiscence of your past. Get personal and confidential. Leave nothing for the interview—if it ever comes.

Time to Defuse the Ticking Bomb of Bad Writing

Many of these rules may seem like an exaggeration—who in the real world writes this way?

Oh, but you’d be surprised. Most of the examples of the worst cover letters ever submitted are in fact genuine, earnest letters received by hiring managers—and each of them embody one or more of these “bad writing” rules exactly. In fact, all these rules for bad cover letter writing have been distilled from real-life cover letters.

It might be fun to laugh at these things—until you spot something that you do yourself, to some degree or another.

The sobering reality is that writing is difficult, period. It’s not the act of stringing words together that makes writing difficult. What’s difficult is the way you try to get your point across to the reader in the way you intend.

What’s difficult is having a point in the first place.

What’s difficult is being able to distance yourself enough to see how you might come across to the other person.

It’s about being able to consider things from your reader’s point of view—what are their needs, questions, fears, doubts—and being able to address those things clearly and reassuringly without being rude, condescending, flippant, or in a tizzy.

Anyone who knows how to write a compelling cover letter and email and avoids all these pitfalls demonstrates an overlooked quality that all companies want but few explicitly state in their list of requirements: professional empathy. In other words, being able to consider the situation outside of yourself.

The first step to defusing the ticking-bomb potential in all of us (the potential to write a terrible cover letter) is one that is unexpected for many people.

The solution is not to sign up for a writing course, or even to amass all the dos and don’ts out there. The solution is to develop empathy and consideration for the reader. Realize you are only one part of the picture—and not necessarily the most important part at that—and consider everything from within that framework.

If you get that right, you are already ahead of the curve and into the next level.

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