*when I use the word correspondence in this article, I refer to all private and public statements made in printed or digital environments. This can be applied to public speaking as well.


Are your emails dreaded by your recipients? Do you even know if they are well-received or not? Most people will never tell you that you write horrible emails; but trust me, they want to. You can ensure your career is not shortened by careless or harsh words. Let me share some mistakes I may have made so you don’t have to, and a lesson or two.

In my career I have been a prolific emailer and letter writer. I strongly believe you should set time aside daily for correspondence with your family, friends, and colleagues. When you study great leaders, you will find they wrote a lot more than their less successful peers. But if you write a large volume of letters you are bound to have some correspondence disasters. I may or may not have turned poor phrasing and lack of discretion into an art form. Luckily, I had a few mentors and colleagues along the way that have told me when I misfired. Many people I know have probably been waiting for me to write about this; so here you go. Yes, I owe you all many drinks for my behavior.

Don’t write to be understood; write so that you cannot be misunderstood. -President Taft

My Hypothetical mistakes

Fire and Forget it

This is the easiest mistake. “If you don’t know where you are going, any road will take you there,” fully applies to correspondence. I have looked at many of my emails that folks replied to and thought, “how did they figure out my point.” Misspellings, sentences unfinished, auto-correct run amuck, poorly worded questions, wrong attachments…you name it; I have done it all.

My remedy learned the hard way: Know the purpose for your correspondence. Re-read what you wrote and if it is going to a very senior person, have a friend read it too. Double check the attachments to make sure it is the right topic and version. Blind carbon copy or carbon copy (Cc or Bcc) yourself if it includes tasks you need to follow up on, or to show the recipient it is something you are tracking. Turn off the auto-correct and turn on the spelling and grammar check, if you need to. Don’t send it at the end of the day as you run out the door, unless you have time to ensure it is a tight product.

Emailing angry

This one I have possibly made into a high art-form, even to 4-Star generals and their civilian equivalents. This one has gotten me in trouble a few times and maybe even cost a few friendships and professional relationships. Never write words down while you are ticked-off at the recipient. It is also not a good idea to write if you are frustrated with anyone else; it will spill over. Bottom line; if you must write while angry at least don’t hit send. Leave the words in your drafts and come back to them the next day. Deleting those emails or heavily editing them the next day is a sign of good correspondence skills. If you cannot stop writing while angry and launching them off, it may be a signal that it is time to retire or find a new job. Also, don’t reply in kind to angry emails you receive; instead be a Disney princess and “let it go.”

Burning bridges in every direction

This generally occurs to the angry email authors. If you send out your thoughts and think you are only going to possibly anger one person, you are probably wrong. The other people that are in on the correspondence or will be shown your words can be quite a long list. Some of those people might be your peers, some your bosses, and some people who look up to you. When they read your terse thoughts towards another person, even if you are in the right…they will take a new view of you. Never forget that even the most private of conversations in this era will be leaked or exposed at some point. It cannot hurt to write like your grandmother is being included in the conversation.

Auto-Forwarding Hell

A surefire way to put a colleague in hot water is to send them an email when you do not know who else is on the auto-forward of their email address. Quite often senior leaders like generals, ambassadors, cabinet members etc. will have an assistant set up their email to permanently auto-forward every email they get to a select group of assistants and deputies. They do this so that the staff can handle issues for them or draft replies for them to review. More junior members of an organization may also do this if they are seldom on email.

I may or may not have sent an email to the ambassador of the largest U.S. embassy in the world (at that time) to tell him his deputy ambassador just threw him under the bus in a small meeting I attended with our most senior host-nation leadership. I knew the ambassador well, and the fact that their deputy was undermining them often was an open secret. What I may have forgotten, having once set up that ambassador’s email system years earlier; is that he liked to use auto-forward. So, the 30-line rant I made about the low character and disgusting behavior of the deputy ambassador went straight to him too.

This one ended okay, because the deputy ambassador took the hint that he should stop being a backstabber. But it put my old friend the ambassador in a tough spot with his number two. So, when in doubt, assume there is more than one recipient. This turned out differently in a recent email to an embassy mass-email box. I was trying to reach a fellow I had just met at a conference and the person who answered me back was a different person who had been following my blog for a few years and was happy to send on my message.

Jokes and Sarcasm

Humor does not translate well in written word. If you use it on social media, you know that sarcasm is seldom understood. It is now the trend in our society to feign massive and even crippling offense when faced with humor or sarcasm, so your best bet is to simply avoid it. I still use it with my close friends but it doesn’t take long for those words to reach someone who doesn’t know me and accuses me of the most heinous of crimes. I will keep trying to add levity to the world, but remember your efforts will fail the majority of the time.

No more than one task per email

I learned this lesson very late in my life, and maybe people just have different reading comprehension skills today. If you need someone to carry out a specific task or answer a specific question, then don’t send more than one. I used to number the tasks and people would reply in the original text and highlight their answers in a different font color, but that seems to be too hard for recipients today. If you get a reply at all, often you will just get one partial answer to the easiest question you asked.

Don’t bother the boss when their staff will do

The boss of every organization is too busy to effectively manage their correspondence on multiple platforms. The last thing they need is to be bombarded with copy messages or direct emails that pertain to mundane work their staff can deal with easily. I learned this one very early on, when I was a lieutenant working for a 2-star…because I broke it daily. Your boss won’t be impressed that you let them know everything that you are doing. A senior person in your organization won’t be impressed that you looped them in on a conversation they don’t care about, so that you can show them you are a problem-solver. Only email the boss if it is something they have asked to be included in, or you are replying to an email they sent out and they expect to remain included in until the issues are resolved.

Cc and Bcc skills

These took me a while to figure out, but once I did, my work became easier. Although you do need to feel out your new bosses to see how they use these email functions. I came from one unit recently that used cc and bcc relentlessly, and the teams really did a good job of jumping on various parts of a task and resolving it quickly. They even had alternate group chats going on about the tasks at the same time. Then I may have gotten a new boss that angrily told me to stop ccing anyone else and to run all email replies through her so she could decide who to include in our conversations. Her system backfired within a week when she failed to send my confirmation to speak at a large event to the vice-president of our organization. The night before the event the VP emailed me angrily that he had to ask the president to step in and speak for lowly little me, because I hadn’t confirmed my attendance. I sent him the copy of the email I sent my boss weeks ago, that she failed to send to the VP. Somehow that response managed to make everyone madder at me. So, sometimes you will get this right, and sometimes you won’t. Never stop learning how your organization communicates and help them to improve.

Parting Shot

These rules work for social media as well. In fact, social media, with its restrictions on word-count and the inability to edit or retract, make these lessons even more important. I already noted sarcasm and humor seldom translate on social media, although on social media you will often get instant feedback from someone who misunderstands you. That bravery borne of anonymity is missing from correspondence with people you know well.

So, determine if you should write at all, then draft your thoughts, then edit the words to ensure the message is clear, and then publish or hit send. If you are ever unsure (and this is something I do a bit more often now that I can drink cold beverages at lunch) ask a trusted person to review your email or social media post before you send it out into the world.

Don’t send out ideas that could be misconstrued by the recipient (or the public when they are released by a hacker or a FOIA). When you screw up, and you will; just own that mess, learn from it, and move on. They are only words. I have sent so many stray words off into the world, I have thought about putting a photo of a “No Regerts” tattoo in my signature block. You can do better than I did, I am sure of it.

Related News

Jason spent 23 years in USG service conducting defense, diplomacy, intelligence, and education missions globally. Now he teaches, writes, podcasts, and speaks publicly about Islam, foreign affairs, and national security. He is a member of the Military Writers Guild, works with numerous non-profits and aids conflict resolution in Afghanistan.