Channeling James Joyce, Or: The Email That Will Get You Fired

If a reader of average intelligence can't understand what you wrote, you failed. 

Suppose, hypothetically, that I’d sent this email:

“This draft of the brief is quite hard to follow.  Please use smaller words and shorter sentences in the next draft.  Think ‘Ernest Hemingway.'”

Suppose, hypothetically, I’d received this response:

“This is a very complex issue.  It’s hard to explain simply.  We actually think we’ve done a pretty good job of it.  Haven’t you ever heard of James Joyce?”

Yeah, I’ve heard of James Joyce.  Maybe you’re James Joyce, and maybe I’m wrong.  Send me the first draft of Ulysses, and I’ll let you know.  Maybe you’re Shakespeare.  Send me a few sonnets, and I’ll see if I’m convinced.  If I’m convinced, then you’re allowed to use fancy words and long sentences and to write stuff that I can’t understand.  Until you convince me, it’s Hemingway or bust. 

Compare this hypothetical exchange of emails: 

“I flipped through the first draft of the reply brief.  Can you please try again?  I think you can do better than this.” 

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This was the hypothetical response: 

“I’m terribly sorry, Mark.  [It’s funny how those hypothetical guys have my name.]  I was traveling when this brief went out, and I wanted to be sure we got this to you on time.  It was written by an associate, and I never reviewed it.  I’ve reviewed it now, and you’re right:  This draft isn’t any good, and I’m sorry we sent this to you.  Tomorrow, I’ll send you a revised draft.  I promise you:  This will never happen again.” 

I like to think this isn’t a matter of sucking up to in-house counsel.  

I’m a reasonably intelligent guy.  When outside counsel send me draft briefs, I really want to understand the points those briefs are communicating.  If I can’t understand the briefs, it’s probably not because I’m ignorant or choosing to be a pain in the neck.  It’s probably because a reader of average intelligence can’t figure out what you’re trying to say. 

So make things simpler. 

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(Remember:  Three years ago, I gave you a tool to check whether your briefs were simple.  Maybe you should use that tool and decide whether (1) your brief is too complex or (2) I’m gratuitously being a pain in the neck.)

I see the same thing on internal emails, although of course I have less control over what my colleagues write.  Consider hypothetically:

“I’m happy to pass on your email as you requested, but I’d like to send a cover note that explains precisely what we’d like the recipients of the email to do.  What exactly would we like people to do?”

(I’m trying to be nice; I really am.  The alternative was to write:  “I can’t understand what you wrote, so I can’t summarize it.  I could simply ‘forward’ your email, but that would embarrass you and leave readers confused.  What the hell were you trying to say?”) 

Again, I might get one of two responses.  Response one: 

“I think the people you send this to will understand what it means.  Just send it.”

Or:

“I’d like the recipients of the email to do these two things:  (1)  Thing one.  (2)  Thing two.”

Which is better?

As I get older, incomprehensible emails don’t simply offend my sense of aesthetics.

They make me worry about my mental well-being.

I read the sentence in your email or your brief.

I shake my head to clear the cobwebs out.

I read the sentence again, more slowly.

I still can’t understand your meaning.

I think to myself:  “Is this premature dementia?   I can’t fathom what this sentence means.   Maybe I’m losing my memory.  Is the dementia affecting other parts of my life?  I remember what I had for breakfast today and for dinner last night.  I remember my plans for the upcoming weekend.  I think I’m okay.  It’s gotta be the sentence.”

Please don’t do this to me.  (Sometimes, I look back on the days of Above the Law commenters with a hint of regret:  “Hey, Mark:  We’ve got some bad news for you.  It isn’t the sentence.”)

(I’m not making fun of the mentally disabled here.  I have really occasionally doubted myself when I read impenetrable sentences.  Perhaps a few of my 60-ish readers will let me know if I’m alone on that score.)

I’m begging you:  Just simplify stuff.

In particular, if a reader tells you that something is too complex, it is. 

When you write, your job is to communicate with a reader. 

If a reader of average intelligence can’t understand what you wrote, you failed. 

Simplify:  Short sentences.  Little words.  

Don’t try to convince me that you’re smart.  Convince me of the justice of your cause. 

And stay hired.


Mark Herrmann spent 17 years as a partner at a leading international law firm and is now responsible for litigation and employment matters at a large international company. He is the author of The Curmudgeon’s Guide to Practicing Law and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide (affiliate links). You can reach him by email at inhouse@abovethelaw.com.