Email Writing For The In-House Counsel Gladiator In All Of Us

Let’s face it, none of us like to lose. Full stop.

And while I adore the idea of compromise and collaboration in the abstract in much the same way I think about eating kale and quinoa, it still sticks in my craw when I have to give something important away because my counterparts skipped the “how not to telegraph your negotiation strategy in Hi-Def” lecture that day in B-school.

Yes, as in-house counsel, we rise and fall with the business, our successes and failures inextricably yoked to people who keep using “for all intensive purposes” like that’s a thing. That’s not a thing.

In our everyday interactions, we do an internal cost benefit analysis when a business partner refuses to see reason or throws us under the bus or makes life difficult through sheer ineptitude. We pick our battles, because we know it’s not personal. It’s just business.

But every once in a while, we must rise up and take our place in the pantheon of epic (yet instructive) beat downs because maybe, just maybe, the business might learn something from it. Even if that lesson is not to pick fights with Legal.

And because we’re lawyers, damn it. Have some pride.

There remains one arena where we are the reigning gladiators and woe to the unarmed idiot who steps into the blood-stained sand and starts slinging shade our way over email.

It’s a lopsided battle from the get go. For starters, most business people are email-illiterate, which doesn’t mean they can’t read (although, that may also be the case), it means they don’t know how email works. This is evident when they forward you a chain where they’re disparaging you or already letting their boss know it’s caught up in Legal. Before they ever asked you for it. Nor do they seem to understand the whole date to urgency ratio, i.e., if you indicate it’s an emergency (shameless plug: see my previous column on “emergencies”), but I read down the chain and see you’ve sat on the request for two weeks, then my sense of urgency diminishes considerably. As does my willingness to let you walk away with all your appendages intact.

For those of us who came from big firms, we’ve all had that experience of doing doc review or deal diligence, where we’re reading an email where somebody has lost it, written something so inadvisable, contradictory, or inflammatory that it can never be taken back. We wince in sympathy. And then we flag that sucker as responsive and offer it up for all to interpret and pass judgment. So, unlike the business, we know better than to lose our minds over email. Like ill-advised tattoos, emails are forever (or forever as determined by your document retention policy).

I’m sure you’re all pros at the fine art of emails by now, but on the off chance you’re new at the in-house game or you haven’t had the chance to roll your eyes today, here are a couple of real-life examples from my inbox:

Example 1: “Kay, I just left you a VM. Why the hell are you holding up my contract again? I am so sick of Legal screwing up what should be a simple process. Mike.”

Pro tip 1: Ignore Mike’s anger. Be the dispassionate observer with the company’s best interest in mind. Destroy him with policy.

Instead of responding: “Mike, you mouth-breathing troglodyte. Remember when I told you that if you ever changed the exclusivity language in the execution version after I sent it to you again, the feds wouldn’t be able to find enough of your remains to give you a proper burial? Run and hide, asshat. Run and hide. It’s judgment day.”

Consider: “Mike, I can appreciate your anger and understand why you feel the need to continually ignore our contract policy. As I’m sure you’re aware, this policy is not in place to hinder your ability to do business, but to protect our company from avoidable risk. Your repeated refusal to abide by this policy concerns me. Perhaps we should set up some time with you and [do it, insert Mike’s manager] to discuss how to better partner with you in the future.” And don’t forget to level up by copying Mike’s manager.

Example 2: “Hi Kay!!! Just checking in on Project Poppy Seed!!! I sent you the documents several weeks ago and we [as in, this business partner and every VP she can think to copy] are starting to get concerned this has fallen through the cracks. I think I mentioned that we need to get these signed up no later than Friday and it’s now Wednesday. If this is an issue, maybe we should loop in [insert’s Kay’s boss] to find someone else to work on these? Thanks! Amy.”

Pro tip: First, admire a worthy adversary. This would have been a thing of beauty if it were true. But since it’s not, crush her with the facts and set the story straight.

Instead of: “Nice try, princess. If you’d bother to pull your head out of your ass once in a while, you’d know I sent you that freaking contract weeks ago with the changes you requested and I never heard back from you, so don’t pin this on me.”

Consider: “Amy, I’m not sure where our lines of communication broke down, but I’m attaching the email I sent you on April 3^rd where I revised the draft agreements in accordance with your suggestions and noted in bold the three areas where I needed your commercial input prior to finalizing the draft. I’m also attaching the follow up email I sent on April 10^th where I indicated that I still needed you to weigh-in. Once I’ve got your thoughts on these open items, I’d be happy to send you an updated draft to help you achieve your timeline. Looping in [Kay’s boss] for visibility.”

Now, there’s just one last thing to do before you shut down these amateurs. Don’t forget to show your email to your burn buddy. Burn buddy? What’s a burn buddy, you ask? Your burn buddy is the only other person in Legal you show your email to. Note, I didn’t say send your email to, I said show your email to, as in, swivel your monitor around so that he or she can read it and make the decision you might be too close to make yourself. Send it or burn it. If your burn buddy votes it down, heed the advice and kill it.

Either way, don’t worry. Tomorrow is a new day and with it brings an opportunity to remind your business person who owns the final word over email. And maybe kick some sand in their face while you’re at it.

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Kay Thrace (not her real name) is a harried in-house counsel at a well-known company that everyone loves to hate. When not scuffing dirt on the sacrosanct line between business and the law, Kay enjoys pub trivia domination and eradicating incorrect usage of the Oxford comma. You can contact her by email at [email protected] or follow her on Twitter @KayThrace.