Summary
Second post in the litigation series. Explains three specific ways trial experience changes contract drafting: knowing which clauses actually get fought over, understanding how a judge reads disputed language, and recognizing where overlooked boilerplate provisions cause the most damage. Each point includes a real-world consequence. Closes with a call to book a Risk-Free Strategy Session.
By: Jordan Gerheim, CEO – Outside Chief Legal LLC
The lawyer who drafts your contract and the lawyer who would argue it in front of a judge are often not the same person. That gap can sound abstract until you realize what it actually means: the person writing your agreement may never have seen language like it tested, challenged, or picked apart by someone looking for a way out of it.
This is the second post in our series on why litigation experience matters, even to clients who never end up in a courtroom. This time, the focus is contract drafting and what changes when the person writing your agreement has actually watched contract language tested in a real dispute.
Most business owners assume a contract is well drafted because it reads clearly and covers the obvious points. That is a reasonable assumption, and it is also incomplete. A contract can read clearly and still fail at the exact moment it is needed most, because the person who wrote it never had to defend it in front of someone actively looking for its weak points.
You Learn Which Clauses Actually Get Fought Over
Most contract language never gets challenged. It sits in a signed agreement, unread again until a renewal date or a dispute forces someone to look closely. A lawyer who only drafts contracts, without ever litigating a dispute over one, has limited direct insight into which specific clauses actually become the battleground when something goes wrong.
Litigation experience closes that gap directly. When you have argued a case over a termination clause, a liability cap, or an indemnification provision, you know which words in that clause carried the argument and which ones turned out not to matter. That knowledge changes how the next contract gets written.
A Baldwin County service business had a termination clause reviewed by two different lawyers before signing a new vendor agreement. The first lawyer, working purely from a drafting and review practice, called the clause standard and did not flag it. The second lawyer, who had litigated a nearly identical dispute the year before, immediately flagged the notice period as too short to give the business a realistic opportunity to find a replacement vendor before service was cut off. That specific gap had been the deciding issue in the case he had tried. The business renegotiated the clause before signing.
You Learn How a Judge Actually Reads What You Wrote
Contract language that sounds airtight in a conference room does not always hold up the same way in front of a judge. Legal drafting has its own internal logic, but a judge or arbitrator interpreting a disputed clause is reading it cold, without the context the parties had when they negotiated it, and is often looking for ambiguity that either side can exploit.
Trial experience teaches you to write for that audience, not just for the client reviewing the document before signing. It means anticipating how a clause would be read if it were pulled out of context and argued over by two lawyers with opposite interests. A lawyer who has never made that argument in front of a judge is drafting from theory. A lawyer who has made it and watched a judge rule on it is drafting from direct experience.
This shows up most clearly in ambiguous terms: what counts as a material breach, what triggers a cure period, what “reasonable efforts” actually requires. These phrases feel fine on a first read and become the entire dispute once a disagreement happens.
A lawyer without that direct experience tends to treat these phrases as settled, because on paper they look like standard contract language used across the industry. A lawyer who has argued over exactly this kind of phrase knows it is only settled until someone with an incentive to interpret it differently gets involved, at which point vague language becomes the entire fight instead of a footnote to it.
You Learn Where Businesses Actually Lose
It is rarely the big, obvious risks in a contract that cause the most damage. Everyone reviews the payment terms and the termination rights closely. The damage tends to come from the smaller provisions that get treated as boilerplate: notice requirements, cure periods, the specific definition of a triggering event, and dispute resolution mechanics.
Litigation experience shows you exactly where those overlooked provisions have mattered in real disputes, because you have been the one arguing over them. That perspective does not come from reading case law summaries or attending a seminar. It comes from sitting across from opposing counsel and a judge, watching which arguments land and which ones do not.
A Gulf Coast contractor’s standard subcontractor agreement had gone unchanged for years, reviewed periodically but never by a lawyer who had actually litigated a subcontractor dispute. When a project went wrong and the business needed to enforce an indemnification clause, the clause’s language turned out to be too narrow to cover the actual damages at issue. A lawyer with litigation experience in exactly this type of dispute would likely have caught the gap during a routine review, because it is the kind of gap that shows up repeatedly in this type of case.
What This Means for the Contracts You Sign
None of this means every contract needs to be drafted as if litigation is inevitable. Most agreements never end up in a dispute, and over‑lawyering a routine contract creates its own costs and friction in a business relationship. What it means is that the person reviewing your agreements should know, from direct experience, which provisions are worth spending real time on and which ones genuinely are standard.
That judgment is hard to fake. A lawyer can read about contract disputes, but reading about an argument and having made one in front of a judge produce a different level of instinct for where the real risk sits in a document.
This is also why a periodic review of standing contracts matters, not just review at the time of signing. A template that was fine when it was written can accumulate risk as the business grows, as the relationships it governs change, or as the law around a particular type of clause develops. A lawyer with litigation experience reviewing an existing agreement is looking at it with the same eye they would bring to a document already at issue in a dispute, which tends to surface gaps a first‑pass review would miss.
If you want your contracts reviewed by a team that knows firsthand which clauses actually get tested, not just which ones look standard, a Risk‑Free Strategy Session with OCL is a good place to start.
No representation is made that the quality of the legal services to be performed is greater than the quality of legal services performed by other lawyers.
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Outside Chief Legal LLC is a modern, forward-thinking law firm serving as fractional chief legal officers and outside general counsel for businesses and their owners. With over 200 years of combined litigation, in-house, general counsel, and administrative legal experience, the firm delivers approachable, comprehensive counsel that blends legal expertise with practical business insight to help clients navigate ownership complexities with confidence. OCL is a trusted partner for founders, business owners, and leadership teams nationwide. Learn more about our firm, meet our team, or schedule a Risk-Free Strategy Session to talk with an attorney about how we can help your company.
