How could we have learned a better way of doing things, if we had never made mistakes?” 

― Lailah Gifty Akita

Oh, the sins I’ve committed, the misery I’ve perpetrated, the havoc I’ve wreaked, during my long and illustrious career as a professional business writer and communicator. My tormentor? The dreaded email correspondence.

I’ve made every mistake in the book, especially in the early days of my career when I was eager (okay—desperate) to make a name for myself. Email was new. It was wonderfully convenient. It meant never having to walk to the next cubicle again. It’s as if I’d discovered a new way to destroy myself.

Your readers are the best teachers, albeit the cruelest. There are times I would have preferred to have been smacked in the head with a two-by-four rather than have endured the ridicule or harsh criticism of an offended reader, or worse yet, my boss. Even worse, his/her boss; triple worse: the bread-and-butter client.

Despite the occasional tragic mistake, however, my communications skills have improved significantly, and at this stage of my career, I commit myself to sharing my numerous humiliations with you so that I can help you avoid some of the horrors of my hard knock education. True wisdom is learning from other people’s mistakes.

1. Don’t write an email if  you’re emotional.

Someone’s actions or email has infuriated or embarrassed you. It’s time to hit them back with a scathing email while your anger is fresh and you’re at your brilliant best, right? NO! No matter how much steam is blowing out of your ears, step away from the keyboard before someone gets hurt—you. Instead, breathe. Take a walk. Vent to a friend or two. Sleep on it. If you must communicate or confront, do it in person or over the phone, when you’ve remembered it’s best not to vent your emotional un-intelligent-ness in writing. Moral of the story: Always take the high road.

2. Don’t use humor in your email if you don’t know your recipient well.

I crack myself up. I really do. I am a “creative” type who loves to laugh and have fun, especially in the workplace. These days, I am able to be “appropriately professional” in most situations, but when I was younger, I could barely contain myself. In the years since, I’ve taken many personality assessments, such as Myers-Briggs, all of which taught me that there are several distinctive types of personalities other than mine. Introverted people. “Save the World” people. “Nothing makes me laugh” people.  I’d always wondered why certain people looked at me as though I’d just beamed down from looney town. It was an epiphany to me to learn how to author my communications accordingly. Don’t try to be funny in your professional email correspondence unless everyone on your distribution list (the members of your crazy marketing team, for example) have accepted lively banter as the order of the day. Otherwise, just stick to the facts, ma’am. It’s simply sensible. Many see humor as unprofessional in the business context.

3. Spellcheck isn’t always write.

The above sentence makes my point.

4. Beware of the, “Who wrote this?” question.

This piece of advice is mostly for those of you who are in subordinate writing positions. One time, the meanest boss I’ve ever had blasted over the office intercom (in a very belligerent tone of voice, as was her style), “Tell me who wrote the Biltmore proposal NOW!” Sheepishly, I stopped by her office and said, looking at the floor, “I did.” She said, “This is the most fantastic proposal I’ve ever seen. Give me a hug!” A few years later, a male boss waved some paper in my face and said, “Who wrote this?” I said proudly, “I did,” and waited for his praise. He replied, “I meant to ask, who’s the idiot who wrote this?” Luckily, I was able to walk him through the copy and get him to recognize that what I’d written was pretty darned awesome, but it taught me a lesson. From now on, when someone asks, “Who wrote this,” ask, “Why do you want to know?” If the person thinks it stinks, smile. claim it was only a draft, and say, “Jeepers, I really appreciate your feedback.”

5. Short sentences rule.

I knew an IT manager once who wrote emails comprised of hundreds of words in one, long, run-on sentence. This was a nice guy, and a brilliant technology expert. It was his responsibility to explain highly complex new developments to the staff: New procedures, new technology equipment, new developments in fraud protection for our customers, etc. Unfortunately, his emails were baffling. No one but the most motivated reader understood the critical take-aways. I encouraged him to keep  his sentences short, and use bullet points.

6. Don’t hit “reply all” by mistake.

There is no deodorant or sedative in the world strong enough to cure the sweat and panic caused by this terrible faux pas. It cannot be undone. There’s no lie or excuse sufficient enough to remove the stain on your sterling reputation. The toothpaste has left the tube. Once, a woman in the compliance department wrote an email to me, with a copy to my assistant, complaining about our failure to provide sufficient lead time to approve the advertising copy we needed by 12 noon. I wrote the following note to my assistant: “Don’t worry—she clearly doesn’t understand what we do,” and hit “reply to all.” Then, I screamed. Then, I tried to recall the message, which doesn’t work, by the way. Was I able to save the situation? Not really. I apologized to the woman (a very nice woman, I might add), but the damage was done. Word of my foolish mistake spread through the C-Suite like red wine on expensive white carpet. Naturally, it’s best not to write anything acerbic in an office email. If all your emails are professional and reasonable and you mistakenly hit the “reply all” button, you’ll never have to fear being shunned by the villagers.


I THOUGHT EVERYONE KNEW THIS BY NOW. THEY DON’T. STOP IT! YES, I’M YELLING! (There are also many folks out there who object to the use of exclamation points, too. What’s your opinion?)

8. Be able to defend your grammar choices.

As the newly promoted vice president of marketing for a huge regional bank, I was assigned the task of explaining the advantages of a recent merger in a letter to our customers. Each paragraph highlighted one of the advantages of the merge. “Most important,” said the fourth paragraph, “you’ll enjoy the same, friendly service which is our hallmark.” (Or something like that.) Marci, a highly influential, albeit argumentative, member of the C-Suite, stomped into my office and insisted that the correct phrase was, “Most importantly.” In a workplace populated by grammar sticklers (e.g., your CEO was an English major), be sure to look up any words or phrases with which you’re not 100 percent comfortable. For example, is it “I feel bad,” or, “I feel badly?” My family still argues over that one. “Between you and me?” Or, “Between you and I?” In the Marci situation, I was able to flip open my handy dandy grammar book and show her the correct usage. Two points for me.

9. A phone call or face-to-face conversation trumps an email every time.

In this age of electronic communication, people are avoiding human interaction in favor of email and text messages. A recent YouTube video illustrates this growing trend. Have you ever emailed a coworker who’s sitting in the cubicle next door? Have you ever texted a family member who’s in the same house? Emails are so easily misinterpreted. I wrote a totally innocuous email once to someone once who wrote back that she didn’t appreciate my “tone.” Emails are cold, and can build a distance between people. Don’t assume in an email that everyone will derive the same meaning from it. When in doubt, pick up the phone.

Are these the only mistakes I’ve made? Of course not. I’m sure we could all write books on the subject. Please share! I’d enjoy hearing about some of your blunders, and what you’ve learned as a result.


Wishing you fame and prosperity.