Legal Horror Stories: The Mistakes that Haunt Us

The legal industry breeds perfectionism. This expectation of perfection often makes any type of mistake, big or small, jarring and haunting.

Some mistakes are so ridiculous that they are terrifying or hilarious, depending on whether or not you are the one who made the blunder.

We asked our former colleagues, current clients, and other legal professional friends about the mistakes that haunt them.

Let’s just say, it was more entertaining than we could have imagined.

Big Bologna Guy

“A partner at my old firm dictated a memo regarding our client’s operation of a below knee amputation. His assistant drafted the entire memo referring to it as a bologna amputation. Unfortunately, we were in a rush to get it to the client, so it did go out with the typo throughout the memo. I have never laughed and panicked harder when reading an attachment sent to a client.”

It’s Always the Signature Pages …

“This is a tedious “mistake” but I’ve done signature pages where they filled in both the “name” and the “title” section with the first and last name of the signatory. So it read (fake name used here) signed by John Smith in his capacity as John Smith.”

“I was once closing a real estate transaction while my boss and the rest of the commercial real estate world was at a conference in San Diego — including the signatory from the Borrower side. Realized I forgot a page and the only way to take care of it was to make the managing partner of my office go find this guy (who turned out to be drinking wine on a yacht) so that he could sign a page and we could close.”

“We were super understaffed on a huge deal, and due to sensitivities of everything we kept amending the NDA. I hadn’t slept more than 4 hours a night in weeks and missed the last amendment to the NDA in the signing set. The deal had to be signed that day and no one on our side ever even saw that NDA amendment. Finally, someone asked where that page was, but that was after I had confirmed probably 5 different times that I had all signature pages ready to go. It was a panicked shit show for the next few hours, but we figured it out.”

“I was closing a big transaction and had to get the signatures of all of the beneficiaries of a trust. Really thought I had everything and timed it perfectly. The day before closing I realized I had missed a beneficiary, and this beneficiary was out of pocket because she had gone to Burning Man. She was in the middle of the desert, with no phone, no computer, no FedEx, and an … altered state of mind for the next few days, and the other party wouldn’t close over the missing signature. Not good.”

Email Fails

“Colleague of mine in her first few weeks on the job was a part of a big case that was just about to go to court. He was instructed to update the client on strategy and send a detailed memo to them. Instead he sent it to our opposition!”

“Me sending an internal draft out to opposing counsel was pretty lit.”

“I sent a client’s marriage settlement agreement to the wrong client, with my boss cc’d. Luckily, she was kind about it.”

“Accidental reply-all on an email I thought I was sending to my work BFF bad-talking another associate.”

“I accidentally sent draft discovery responses to opposing counsel who has a very similar email address as co-counsel. Two months into being an associate at a very large firm, I realized my error relatively quickly, consulted with the partner to solve the issue. Six years later, I’m on partner track. Raise your mistakes immediately, own them, and fix them.”

Dude, Who’s Our Client?

“Attorney I used to work for was confused about who we represented and even argued with opposing counsel about it, said she was going to reach out to ‘our client’ in numerous emails. I was monitoring her email while she was out of town and saw all these emails and had to tell her she was mixed up and to stop contacting the person who was most certainly not our client … “

“Partner left firm A and took client Y. Meeting with client Y and client Z. Attorney from firm A who was supposed to represent Z argued for Y at an in-person meeting until client Z intervened and told him that they believed that he represented them. He disputed that until the meeting told him client Z got it right. Lots of draining color from faces.”

The One Time You Don’t Double Check.

“Co-counsel filed a version of the summary judgment brief we wrote together that still had track changes and my comments to him in it. Yeah, that was mortifying.”

“I didn’t run my own redlines on final execution versions of legal documents. I trusted opposing counsel’s redlines. Unfortunately, we later found out from the client that changes had been made and not told to us that made the executed versions.”

Client Service 101

“I saw a Partner make his own witness cry. Not once, but multiple times. Not even for any jury sympathy, just in prep. I judged him, noted never to do that, and I judged him.”

“Never trust a client’s work without questioning it. I drafted a declaration for a witness based on his direct statement to me not expressly asking him to review it before he signed it and I submitted it. He reviewed the declaration on the eve of trial and called me that night to communicate angrily that he did not agree with the statements in the declaration. Luckily, the partner I was working for was very experienced and somehow cleaned up my mess before trial.”

“I do a lot of divorce work. When I first started, I forgot to make a claim for alimony or child support in the original complaint. Trial was delayed and we amended our complaint because the partner and judge took pity. I nearly threw up in the courtroom when opposing counsel called me out on it.”

Terrified of making mistakes? Looking for ways to reduce those pesky errors that just happen. Don’t worry, we got you.

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