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Trick or Treat: 10 Lawyers’ Worst Nightmares About Contracts

Trick or Treat: 10 Lawyers’ Worst Nightmares About Contracts

Drafting and reviewing contracts is already scary enough. But how does it make you feel when you open a revised copy of a contract with no changes highlighted? Or when your hard drive fails, and you have no copies of a doc? Or, just imagine, you came to the courtroom leaving the briefcase with all the papers and agreements at home? 


​​With Halloween around the corner, we asked lawyers to share their scariest fears and real-life stories connected with contracts. 

CAUTION! The spooky stories you are to read may give you goose pimples.

Nightmare #1: Facing spine-chilling cyber threats and data breach

“A nightmare scenario for any attorney or law firm is one in which their clients’ documents and case data are either stolen or seen by unauthorized parties. The uptick in cybercrime, and particularly ransomware attacks, is very concerning in this new cloud storage environment.”

Christopher Aiello, attorney and managing partner at Aiello Harris

Nightmare #2: Losing important documents (and having no copies)

“Losing sensitive documents and/or ones that took a great many costly labors hours to draft is another nightmare situation for any lawyer. Hard drives can fail, data storage facilities can be affected by catastrophic weather and other unforeseen events.”

Christopher Aiello, attorney and managing partner at Aiello Harris

Nightmare #3: The other side uses outdated word processors

“As a former lawyer and now business owner, the #1 nightmare with legal documents is when the other side relies on desktop word processors. This software often has poor version control and is difficult to track changes in, making it very challenging to know what was changed and when. It is well known in the legal profession that even the specific placement of a comma can change the meaning of a contract term for better or worse, so having easy access to a changelog is critical.” 

Michael Alexis, former lawyer, CEO of TeamBuilding

Nightmare #4: Working with illegal documents

“The legal document is illegal. The worst thing that can happen to me as a lawyer is to work with illegal documents or face documents that are sometimes hard to spot and prove.”

Jacob J. Sapochnick, Immigration Attorney, Founder of Law Offices of Jacob J. Sapochnick

Nightmare #5: Сoming to the courtroom without necessary docs

“Standing empty in the courtroom. Every individual in any area of law practice has possibly had this abdomen fear, appearing to a meeting or a hearing entirely incompetent. Or worse, leaving the briefcase with all the papers and agreements at home.

This suspicion has resulted in various lawyers riding to the office in the middle of the night only to make sure all due agreements are prepared, the deadlines are not skipped, and the papers are precisely where they pertain.” 

Daniela Sawyer, legal adviser and Business Development Strategist of

Nightmare #6: The opposing side sends a doc in pdf format

“The worst thing about working with legal documents is when the opposing side sends a PDF. I have to convert it to make my comments, and it can really create problems with the formatting. That, in turn, affects the ability to run an electronic comparison between the previous version and the next one to show all of the changes that are made between versions. I’ve had programs used that didn’t show all of the changes between parties, and the final version STILL had errors, which involved phone calls and extra coordination to get completed, and further delays in moving the documents forward.”

Jenna Zebrowski, Commercial Real Estate Leasing and Franchise, Small Business Counsel at The Law Office of Jenna Zebrowski

Nightmare #7: Using outdated legal forms

“We cannot be in a position where we are using outdated legal forms. Using outdated forms is a nightmare because the bankruptcy court will require the use of the new form which means more work for our team and more stress for our clients, who worry we don’t know what we are doing when they see us using the wrong forms.”

Wesley W. Scott, Managing Partner of LifeBack Law Firm

Nightmare #8:  Getting a revised copy of the contract without changes highlighted

“One of my worst experiences working with a legal document was with an opposing counsel who couldn’t figure out how to use the track changes feature in Word. She kept sending me a lengthy document with revisions, but wouldn’t tell me what they were. I had to keep re-reading a 20+ page order with the predecessor version printed out next to it. (This was before Word had the feature allowing you to review and compare two versions of the same document.)

When I complained about and asked her to use track changes she said she didn’t know how to make it work and instead used the highlighter feature. I wasted several hours of time (and the client’s money) checking the same document over and over again. The slightest change to a document – including a misplaced comma – can alter the entire meaning of a document, so it’s critical to be detail-oriented.”

Sonja N. Aoun, attorney in Northern Virginia, attorney at Briglia Hundley P.C.

Sonja N. Aoun, attorney in Northern Virginia, attorney at Briglia Hundley P.C.

Nightmare #9: Dealing with boilerplate contracts 

“My worst nightmare concerning the legal documents I work with is dealing with standard form contracts or boilerplate contracts. For me, form contracts are like adhesion contracts, where there is no negotiation or mutual exchange between two parties. Of course, adhesion contracts have their place. Businesses that provide services and products on a mass consumer scale wouldn’t be able to do business without this kind of legal document.

However, there are lots of legal transactions that involve negotiated terms and specialized conditions. Generally, in those situations, a standard form contract will not be adequate. Lawyers can be rigid about using their legal contracts that contain their boilerplate language and preferred clauses. But, oftentimes, they don’t fit the party’s expectations or agreements.”

Lauren Blair, Owner at Lauren Blair Consulting, Legal & Insurance editor, and senior writer for 

Nightmare #10:  Drafting prenups (pre-nuptial agreements)

“By far, the scariest contracts are pre-nuptial agreements. The scariest one I litigated involved a billionaire. Every word in the contract was litigated to the end.” 

Paul Donovan, Attorney at Law, Founder of Donovan Legal PLLC

Perhaps you share some of these fears or have others of your own, don’t you? We wish you a silly and scary Halloween week, with lots of fun, but most importantly, safe and free of contract nightmares.

By the way, if you want to make contract drafting and review easier, you can always try Loio. And sleep tight.

Keep calm, trick or treat, and carry on!

Article by Yevheniia Savchenko

Yevheniia Savchenko is a Product Content Manager at Lawrina. Yevheniia creates user interface copies for Lawrina products, writes release notes, and helps customers get the best user experience from all Lawrina products. Also, Yevheniia is in charge of creating helpful content on legal template pages (Lawrina Templates) and up-to-date information on US law (Lawrina Guides). In her spare time, Yevheniia takes up swimming, travels, and goes for a walk in her home city.

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