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How to Write a Scathing Email

Updated: Mar 12

There are a few essential skills that every leader must learn on the job. These are the things that no one will teach you in school. One of the most essential is how to write a truly scathing email. This article covers all of the necessary ingredients and competencies to compose a devastating digital missile.

Think of it like one of the Sith-arts of leadership. No, you can’t learn it from a Jedi. Here’s how to do it:

First, be self-righteous.

This is the foundational ingredient. In fact, I need to be so sure that I am right about my grievance, ideas, or position, that conversation is not required. Absolute certainty requires no further information. Invitation to discussion would only carry the odor of compromise and the stink of doubt. No compromise. No retreat.

Second, be convinced that this is actually good for the recipient.

My radioactive email will be like a purging fire. Sure, it’s harsh medicine. However, in the end my colleague will see that the email’s lack of charity and sensitivity was actually a kind of mercy. Whether they knew it or not, this was something they needed to hear… from me… right now… at 5am. This will show them just how important this topic is to me.

Third, include a long and exacting list of demands and solutions.

These can be framed as “suggestions” if I’m in a particularly touchy-feely setting or I’m dealing with a genuinely kind and sensitive person. However, I’ve found that with enough of the aforementioned self-righteousness baked into the text they are sure to get the point anyway. Do not be brief. This is the opportunity to say everything that I’ve been holding onto and haven’t shared over the last week… or year. Add multiple attachments if needed for extra evidence and clarity. An email like this is the perfect opportunity to clear the air, open those interpersonal windows, and let the sun shine in. Sure, the heat of that sun might be like being on Mercury at noon, but it’s all good. I’m doing this because I care.

Fourth, be convinced that this email will solve everything.

Everything amiss in this relationship could possibly be put right with this one definitive act of communication. Because my email will be so blunt, thorough, and entirely lacking in nuance and compassion, the recipient is sure to fully understand the issues and needed remedies. They might even be grateful that I have saved us both from wasting our time with potentially lengthy interpersonal learning and conversation.

If you haven’t picked up on the sarcasm yet, my lawyer told me that I must say explicitly:

Everything above is exactly what you should not do when you have a serious problem to discuss with a colleague, or friend, or… anyone.

When delivering difficult messages or sharing strong emotion, the medium can make all of the difference. In When to Drop the Big One at Work, I recommend four specific criteria to soberly consider before doing anything that will send massive shockwaves through a relationship or an organization.

And yet, this week there I was… Keyboard on lap, email composed, and about to hit send. Luckily, my best friend happened to ask me what I was doing. With a wild gleam in my eye, I said something that sounded like Tom Cruise at the end of the uber-80’s movie Taps.

To which my friend said, “Isn’t this everything you mentor people not to do?”

It’s dangerous to give people advice for a living. Someone might actually expect you to follow it.

There will be times when all of us are tempted by self-righteousness, arrogance, impatience, or generally thinking we have all the answers. No one is immune. Yours truly included.

If you even suspect that you might be falling prey to any of the above traps, fallacies, and temptations, learn to pause and get a second opinion. Find someone who knows you and has proven their ability to tell you that you are about to do the wrong thing.

This could be a friend or colleague, someone you supervise or a supervisor. Whoever it is, they need to be able to say, “No. Don’t do that.”

I have small group of such advisors. Their titles and positions have nothing in common. The one thing they all share in common is that they care about me, know me, and will give it to me straight – every time. Don’t ask for advice from an enabler or someone likely to tell you how right and brilliant you are as you boldly run off a cliff.

As providence would have it, one of my trusted advisors caught me that day and recommended that I re-read some of my own articles. Touché. Well-played. Mea culpa.

Email deleted. Face-to-face meeting upcoming. We are all still learning and practicing.

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