Rewrite important or sensitive docs or emails the next day (and never send angry emails)

In other chapters, I’ve written about the importance of working very fast, even if that means you have to sacrifice perfection.

Today’s argument could be seen as a qualification of that, a specific situation in which the opposite is the case:

After writing any document that is important or sensitive, put it away for a day. Go back to it with a fresh mind, and rewrite it as much as necessary.

Perhaps this argument could be stated more concisely:

Never send an angry email. Never, never, never. And not even a passive-aggressive or subtly frustrated one.

So, you know that client who was a total asshole and you want to call out? Yeah—just don’t do that. It will feel good, you need to “let it out,” I understand, you’re human, and humans want to let it out! But it never achieves the desired effect. Let your emotions and frustrations out another way. Vent to your friends and family and loved ones. Go to the gym. Punch a punching bag. But after you do those, come back calmly and rationally plan out a response that is most likely to achieve your intended result.

A good rule of thumb to achieve that goal is that the more sensitive or emotional content is, the longer you should put it away before you go back, re-read it, edit it, and send it. With a minimum of 24 full hours. With more time, even just a day, your emotions calm down, and you can think and write in a clearer, more compelling, and less emotional way.

Note that sometimes you need to do major rewrites because you were far too emotional. For me, personally, I used to write very long and emotional emails to people and never send them; I’d write them knowing I would never send them. Just getting the thoughts down on paper helped me get over it. But sometimes, it’s just small words you need to change.

As an example, the partner of one of my clients once appeared out of nowhere and mandated pretty absurd stuff. (This man was known around the company as The Dictator, and that nickname says it all. Hi, if you’re reading this, I’m not talking about you, but the Other Guy with the same nickname!) He once appeared out of nowhere to intrude in my work and gave me some random, arbitrary commandments that would make achieving my goals quite hard. In an email I wrote to him, I referred to his requirement as, “Thy Commandments That I Shall Never Violate.” With that capitalization. But I put the email into my drafts folder, slept on it, and the next day, it was clear to me how passive aggressive my response sounded. Even if I’m right, I’m sounding like a petty asshole, not a problem solver. So, I rewrote the sentence into calmer wording—just saying, “the rules you made” instead—and voila, my email turned from sword fighting into problem-solving. But I still dream about sending him those words!

Even when we remove the emotional and sensitive angle, this rule is still important. In the above summary of the rule, think about the “important” qualification. If the issue is important, the same applies, even when there’s no emotionally-charged content. Coming back to anything important after one day always brings a clearer mind, clearer ways to say things, and even helps you spot typos you can’t spot on the same day.

But can it wait an extra day before you send it? As a rule of thumb, yes, always. There’s almost nothing that will have an adverse effect in any way if you send it a day later. And if it’s important, or sensitive, there’s a lot of benefits towards waiting that extra day. But of course, remember the trade-off with speed: if it’s not that important, or not that sensitive, much better to shoot it off very quickly, warts and all.

Learn With The Best

Morgan

Morgan has led digital for multiple presidential-level campaigns, has run 92+ person agencies in three continents, and has lots of experience managing challenging clients. He’s spent 11 years compiling the refining the list of his best managing-up practices that became the core of this course.