How to Write a Bad Email

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These are the faces you’re aiming for when sending a bad email. Fury and Seething Rage all round.

Today’s article topic comes courtesy of Jeff Castrovillari. Jeff has read his share of bad emails over the course of his career, and I’m sure most of us have too. Did you know if you google the phrase “email mistakes” you will get 379 MILLION results? Obviously we as a society are doing something wrong when we email. Not the least of which is emailing what should have been a phone call (you know who you are — stop stirring up drama and start picking up the phone).

While I would love to simply list out the email mistakes to avoid, I thought it would be more fun to write a terrible email as an example of what not to do. If your emails look anything like mine, slowly back away from the keyboard and don’t come back until you’ve thought about what you’ve done. No, don’t come back yet — go sit in email timeout for a while. We’ll tell you when it’s time to come back and try again.

A Template for Your Next Bad Email

To: Some poor chump who’s just trying to make it through the day & everyone else on the first email since you hit Reply All instead of Reply

CC: Co-worker with absolutely no context about the topic at hand

BCC: Your manager, your manager’s boss, your mama, your dog, your mama’s dog

Subject: Fw: Re: Re: Re: Re: Re: Re: Re: That one thing from before (not that thing the other thing)

Timestamp: 12:45 AM Sunday, September 6th

Importance: This email is the most important thing imaginable in the entire world and must be read in the next 60 seconds

Email body:

Per my previous email, I still don’t have what you were going to send me. I won’t describe what it is that I’m expecting, because you should have written it down when I meant to ask you for it before. I need it and I need it ten minutes ago. It’s very unprofessional to not send me things that I imagined asking you for before the arbitrary deadline that I may or may not have set.

I will now list out all the other times that you have disappointed me since the day we met (and maybe even before that). Item 1, item 2, item 3 — my car is still making a funny noise I’ll have you know, item 4, item 5, item 6, item 7. Oh, especially item 7…. Now that you have been thoroughly shamed, I still need that thing. And don’t do it like last time. I didn’t like certain elements which I didn’t tell you about. Don’t do those again.

I know you don’t report to me, nor do we work on the same team, so consider this email my version of “managing by influence”. That’s right, I’m not-at-all your manager so you have to do what I say. When I say jump, you need to hear it from wherever you are sitting and write me an email to ask how high.

I’ll expect the completed assignment in my inbox within the next hour. This is your top priority even though I don’t have a clear idea of what you do or what projects you might be working on. I’m going to be away from my desk to run an errand for the next 24 hours, but I still need it ASAP. I’ll reach out 10 minutes before the live presentation for any edits.

Let me know if you don’t receive this email.

Philip White, MBA, MS, BA, EIEIO, Bronze Swimming Certificate, Silver Swimming Certificate

MY COMPANY NAME IN ALL CAPS® | Overly inflated title to make myself feel more important | Street address like anyone is actually going to mail me a letter | accidentally misspelled email address@mycompny.com | C: only cool kids get my cell phone #

NOTICES: This message, including attachments, is confidential and may contain information protected by the attorney-client privilege or work product doctrine. If you are not the addressee, any disclosure, copying, distribution, or use of the contents of this message are prohibited. If you have received this email in error, please destroy it and notify me immediately. Any tax advice contained in this message is not intended or written to be used, and cannot be used, for the purpose of (1) avoiding penalties under the internal revenue code or (2) promoting, marketing, or recommending to others any tax-related matter(s) addressed here.

TO ENSURE COMPLIANCE WITH INTERNAL REVENUE SERVICE CIRCULAR 230, WE INFORM YOU THAT ANY U.S. FEDERAL TAX ADVICE CONTAINED IN THIS COMMUNICATION, INCLUDING ALL ATTACHMENTS, IS NOT INTENDED OR WRITTEN TO BE USED, AND CANNOT BE USED, FOR THE PURPOSE OF (1) AVOIDING PENALTIES UNDER THE INTERNAL REVENUE CODE OR (2) PROMOTING, MARKETING OR RECOMMENDING TO ANOTHER PARTY ANY TAX-RELATED MATTER(S) ADDRESSED HEREIN.

Confidentiality Note: This transmission may contain information which is privileged, confidential, and protected by the attorney-client or attorney work product privileges. If you are not the addressee, note that any disclosure, copying, distribution, or use of the contents of this message is prohibited. If you have received this transmission in error, please destroy it and notify me immediately at some place.

Ce courriel est confidentiel. Toute diffusion, utilisation ou copie de ce message ou des renseignements qu’il contient par une personne autre que les destinataires dsigns est interdite. Si vous recevez ce courriel par erreur, veuillez m’en aviser immdiatement, par retour de courriel ou par un autre moyen.

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Philip White (not that one, the other one)

Don't believe this photo, I'm way less handsome in person. And if you like my writing, let me know by sending me the word "plethora". It'll mean a lot to me.