How to Write Emails Like a Real CEO

The sharp, swift handshakes. The booming but congratulatory voices of the board of directors bouncing off of the polished oak conference table. The slightly better grade of catering ordered to reflect the gravity of this affair. The whistles and shouts of glee from the mailroom boys and secretaries. You’ve made it! You’re the new CEO of your organization.

Yes, it’s a great daydream, but you’re not there yet. Not until you can prove you’ve got the chops to handle the job. You need to prove to everyone from the chairman of the board to the guy who “hired” you for that (unpaid) internship that you’re Steve Jobs, Lil Wayne, and the winning Super Bowl kicker all rolled into one.

So what do you do? Remember KISS—Keep It Simple, Stupid! You send emails everyday, or at least you should, because despite what some whiners say, email is indeed work. So take a winner’s shortcut and use those emails to show that you’re cut from CEO whole-cloth. How? Keep reading…boss!


Rule 1: Keep it as short as possible:

Nothing says “assistant manager’s personal assistant’s dishrag” like a long email. That type of behavior makes your reader wonder “Where did you get the time to write all four of those paragraphs, sport!?” If you can’t say it in six words, call a meeting and list everyone that your email may have involved as a “required” attendee. While at the meeting, identify someone you can swindle into writing the email for you (call it an “ideation lead opportunity” and you’ll have plenty of eager takers). The hidden benefit of this approach is the fact that your mark will be associated with the very un-CEO trait of writing long emails. Another potential career-challenger eliminated.


All caps is the universal was of saying “This message is important! Read it!” I was shocked to learn that some people do not even capitalize the first letters of their names. I’d tell you who they are, but they obviously aren’t important, so I can’t remember. Don’t make their mistake.

Rule 3: Use red text:

Red text is code for “read this”. People respect the fact that you have told them to read something, and are therefore guaranteed to read it. Remember that Jesus wrote in red, and his part was easily the best part of the Bible. So if you want to be anything like that, write in red.

Rule 4: Sign your emails with “regards”:

Business is no place for emotion. “Regards” is a great way of saying “Despite the fact that we’re communicating, my life would not change in any way whatsoever if you were to fall into a mile-deep ravine.”

Rule 5: Post-message quotes? Hell yes!:

The rest of your email may be business, but the quote at the end is your chance to show that you’re a real person just like the rest of the boys at the mill. Use a fun color like bright green, orange, or even purple to clearly demonstrate that even though you know you’re better than your soon-to-be-subordinates, it doesn’t mean you can’t kick back and page through a magazine while sipping a Blue Moon. Albert Einstein is a good, safe choice, since he pretty much just did math and science and didn’t really bother anybody regardless of their political leanings. Bob Dylan could mean that your soul is still bouncing around in there somewhere, but it could also mean that you enjoyed drug use as a young person. George Washington, Thomas Jefferson, and other founding fathers show you’re a patriot, and that there’s a good chance you’ll be interpreting whatever they said for the good of your industry. And should your detractors whine “But Thomas Jefferson couldn’t possibly have been talking about credit default swaps when he said ‘The price of freedom is eternal vigilance!’”, ask them why they’re not patriots and you’ll come out just fine.


So that’s all you need to know, future captain of industry! One more thing: use BCC, not CC. The last thing that your email recipients need is information on who else gets emails. An email address is a sacred thing, and sharing it freely with the world is like printing free money and handing it to children. Keep Karl Marx off the World Wide Web. He already ruined the typewriter.