Hitting the Send Button When You SO KNOW You Shouldn’t.


You so know you have done it. You are on your email and you respond to or send an email that everything in your system is saying no and the red devil drinking a gin and tonic on your shoulder is rooting you on.  And it feels good.  The email that may hurt someone.  The email that is unprofessional.  The email that gushes out your feelings to the guy who just doesn’t love you anymore.  The email to the guy cursing his mom, sister, best friend and dog.  The email to your ex-best friend about how you can’t even believe you ever were friends and that she looked chunky in that dress last weekend.  Yes, it’s the email that when you hit the send button, everything in you is saying don’t send.  But.  You. Do.  Send.  Ouch.

Well, I am here to confess that this happened to me recently at work.  And it sucked.

It was a Friday afternoon after a long, stressful week and I was emotional.  And, I have been trying to work on not sending “emotional emails.” Trying.  And this imperfect leader of eleven sent the email, despite the smart part of my brain saying not to send.  My system was saying “stop it you jack, don’t send the email.”  The drunk devil was high-fiving me saying “yes, send it!” and I decided to team up with him.

The content of the email wasn’t inherently wrong or bad.  It was the tone that was wrong and bad. The emotion.  And the receiver, my colleague, felt it. And the response I received went something like, “I do understand where you are coming from but I’d like to talk vs. do this over email.”

Eh.  I received that response at around 6 p.m. on Friday and knew this person was right, mature and professional.  I logged off and grabbed a glass of wine.

I thought about my behavior the whole weekend.  I prayed about it.  But, my pride was getting in the way.  My heart knew the right thing to do, but my head and lack of good leadership skills – at the moment – didn’t.  And then I shared my emotional, “don’t hit send” email with a mentor of mine.  This person’s response was “you shouldn’t have sent an email like that and you should talk to [him/her] next week. This is your fault and you shouldn’t send emotional emails.”  Frick.  I knew my mentor was right.  And so I flung that obnoxious drunk devil off my shoulder and prayed more and tried to get my head – and heart – straight.  I knew I owed this person an apology.

Monday morning came and I asked this person to come into my office.  I apologized for my email with no excuses or “I’m sorry but…” language.  It was simple. I was wrong.  I also commended this person’s professionalism and said thank you for teaching me the better way to do it.  (Talk like mature adults vs. email like an emotional jack.)

What is the lesson here?  Email is great for so many reasons.  It’s not great to replace physical meetings.  Or to send your emotions into cyber space like a coward.  Or to break up with your boyfriend.  Or tell your friend she’s fat.  It’s a platform to communicate in a professional way.  It’s not a platform to say things you wouldn’t otherwise say in person.  And for me, as I continue to work on this, the big lesson is don’t send the email.  Sleep on it for at least a day.  And every single time I have done it that way, I have never sent the email.

The other lesson here is about grace.  We have all been on the other side of the jack-of-a-person who sends an emotional, unprofessional email.  And we have two choices on how to respond: like a jack, fighting fire with fire or with grace, knowing it’s the better way and we are all humans and we all make mistakes.

Have you ever done this?  What was the outcome?  A good lesson learned?  Haven’t said sorry yet?  Well, you still can 🙂


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