Why Modern Chief Legal Offices Are Killing the Word “Shall”
Few words make my left eye twitch.
“Shall” is one of them.
After 25 years of litigation, contract disputes, investigations, and courtroom arguments, I have earned the right to say that.
My team knows it. If a draft lands on my desk with a buried “shall,” I usually spot it immediately. It is the lawyer’s version of hearing a smoke detector chirp from another room.
We stop. We fix it. And then we have the conversation.
Not because I am dramatic, but because I have spent too many hours arguing over what that one word was supposed to mean long after the drafter stopped thinking about it.
The Fight Is Never About What You Meant
Yesterday’s hearing was another round of Law & Order: Grammar Crimes Unit: six lawyers, five hours of briefing, and one hour in court.
But the dispute was not about whether “shall” generally means “must.” Legislative history and case law had settled that long ago.
The real issue was more common—and more dangerous. Years earlier, the drafter had never stopped to ask whether “shall” was the word they actually intended.
Law school does not teach that lesson clearly enough.
In contract disputes, the fight is rarely about what you meant. It is about what you wrote. Eventually, someone else decides what those words mean—usually while billing by the hour, and sometimes while wearing a robe.
The Conversation That Rewired My Drafting Brain
I learned that lesson early from one of the best lawyers I have ever known, Mike Wurst (Robin Minick).
Mike was big in every sense: presence, intellect, personality, opinions. He could shift from Ivy League precision to George Carlin in one sentence, and if you hid lazy thinking behind legal jargon, he would politely burn it down in front of you.
One afternoon, he asked me what sounded like a trick question.
“Why do lawyers draft contracts?”
I gave the textbook answer.
“So the parties understand the deal and know how to operate.”
He nodded.
“And what happens if they do not?”
“Then the court reads the contract and decides who is right.”
He clapped once.
“Exactly.”
Then came the question that permanently changed how I draft.
“If the point is for the parties—or eventually a court—to understand the contract, why use language no normal person uses and that often does not mean what you think it means?”
He was not trying to embarrass me. He was teaching something many lawyers never fully internalize.
Words are not decorative. They are operational.
Contracts are not academic exercises. They are operating systems for relationships, money, risk, expectations, and future conflict. Eventually, someone outside the room will interpret every word you chose.
The Real Problem With “Shall”
The problem with “shall” is not that courts usually struggle to interpret it.
The problem is that lawyers often use it without discipline.
Business teams frequently intend:
goals
expectations
targets
operational norms
future intentions
But “shall” quietly turns those ideas into mandatory legal obligations.
Once the contract is signed, opposing counsel reads every “shall” as if it were carved in stone.
That becomes a problem very quickly.
Most lawyers are not using “shall” to impose strict mandatory obligations every time. They use it as a drafting reflex—a vague mashup of must, may, will, probably, hopefully, and “this sounds lawyerly.”
That habit has consequences, especially years later when the relationship collapses and someone reads every sentence like a hostile forensic accountant.
The Unified CLO Drafting Rule
At Unified CLO, we take this seriously enough that everyone sets Word autocorrect to flag or replace “shall.”
Not because the word is always wrong. Because the pause matters.
It forces the drafter to decide what obligation is actually being created.
Do we mean:
must
may
will
Those are three different legal realities.
“Vendor must deliver the report by the 15th of each month.”
That is mandatory.
“Either party may terminate this Agreement upon 30 days’ written notice.”
That is discretionary.
“The parties will meet quarterly to review performance metrics.”
That describes an expected future event without necessarily creating a strict condition that later fuels litigation.
Each word shifts risk, allocates responsibility, and changes how a judge, arbitrator, regulator, or opposing counsel may interpret the agreement.
That is why drafting matters.
Not because lawyers enjoy arguing about grammar. Because contracts become evidence later.
Muscle Memory Is Not a Drafting Strategy
In 25 years, I have never seen a contract dispute improve because someone used “shall.”
But I have seen plenty where lazy drafting quietly expanded obligations beyond what the business thought it was agreeing to.
That is the real danger.
Muscle memory drafting.
Lawyers copy language they have seen a thousand times instead of stopping to ask:
“What obligation are we actually creating here?”
A modern Chief Legal Office cannot operate that way.
Good legal drafting is not about sounding impressive. It is about precision, operational clarity, and risk allocation. The goal is to ensure the business understands its commitments before anyone ends up explaining in litigation why “shall” did not mean what everyone now says it meant.
The Practical Takeaway for Your Team
If your organization uses standard templates, start there.
Audit every “shall” in the document and ask:
Do we actually mean:
must
may
will
Set up autocorrect rules that force a deliberate drafting pause.
Train junior lawyers and contract managers on the distinction early. It is a five-minute conversation that can save hundreds of hours later.
And if you end up litigating a “shall” clause someday, start with the case law in your jurisdiction before assuming everybody agrees what it means. Courts are not perfectly uniform, but most read it much more aggressively than the drafter probably intended.
Why My Eye Still Twitches
Yesterday’s hearing happened because someone used “shall” years ago without thinking through its later consequences. Not maliciously or recklessly. Automatically.
That is how drafting problems usually begin—not with a dramatic mistake, but with small moments of lazy thinking that go unnoticed because the deal must close, everyone is tired, and the language looks standard.
Then time passes. The relationship, the business, and the people change, and the contract resurfaces in a dispute, investigation, or lawsuit. Suddenly, every word matters far more than anyone appreciated when it was signed.
That is what younger lawyers often underestimate: contracts are time capsules. Later readers were not in the negotiation. They know only what made it onto the page.
Under pressure, people stop reading contracts generously. Opposing counsel reads aggressively, regulators literally, and judges carefully. A drafting reflex you barely noticed years earlier can become the center of an expensive dispute.
That is why “shall” makes my eye twitch—not because the word is evil or lawyers cannot debate its nuances, but because most people use it out of habit rather than deliberate choice.
And habit is dangerous in contracts.
A contract is not just a document. It is a roadmap for what happens if things go well and evidence if they do not. Once the words hit the page, they no longer belong to the drafter, but to the people who will enforce them.
