By: Jordan Gerheim, CEO – Outside Chief Legal LLC
Why OCL Still Takes Cases to Court (and Why That Makes Us Better at Everything Else)
Most outside general counsel services are staffed by lawyers who stopped litigating years ago. They review contracts, advise on compliance, and handle the day-to-day legal questions that growing businesses generate. That work matters. But something changes in the quality of legal advice when the person giving it has not stood in a courtroom recently and does not expect to again.
At OCL, we still take cases to court. That is a deliberate choice, and it shapes everything else we do for Gulf Coast businesses. This post explains why – and what it actually means for a business owner working with us.
What Active Litigation Experience Actually Changes
When a lawyer has not been in a courtroom in years, their contract review looks different. Not wrong, exactly, but focused on the wrong things. They look for clarity. They look for completeness. What they do not always see as clearly is what happens to that contract when it gets handed to a judge or argued in front of an arbitrator.
A lawyer who is actively litigating sees contracts differently. They know which clauses actually get enforced in Alabama courts and which ones look strong on paper but collapse in practice. They know what judges in Mobile and Baldwin County respond to and what language creates confusion at trial. They know where the real exposure is because they have watched it play out, not just read about it in a treatise.
That knowledge does not stay in the courtroom. It comes into every contract review, every vendor agreement, and every employment dispute conversation we have with a subscription client. When we tell a Gulf Coast business owner that a particular indemnification clause creates real risk, we are not reading from a checklist. We are telling them what we have seen that clause do when it gets tested.
A concrete example: a Gulf Coast manufacturing company came to OCL after signing a supply agreement that included a broad consequential damages waiver. Their outside counsel at the time had reviewed the contract and flagged it as standard. When a supplier failed to deliver and the company lost a major client contract as a result, the waiver they had agreed to prevented them from recovering the most significant portion of their losses. A lawyer who had recently handled a commercial contract dispute would have recognized that clause as a live issue, not a formality. The cost of that unrecognized clause was far greater than any contract review would have been.
How Litigation Makes Preventive Work Sharper
The goal of outside general counsel work is to keep businesses out of litigation. That is not in tension with actively litigating. It is the direct result of it.
Every case we handle in court gives us a clearer picture of where businesses get exposed, what documentation actually matters when a dispute surfaces, and what the difference is between a contract that holds up and one that does not. That picture makes our preventive work more targeted and more useful.
Take employment matters as an example. A business that has never faced an employment claim may not fully appreciate why an offer letter matters, why careful documentation of performance issues is essential before a termination, or why a poorly written non-compete is worse than no non-compete at all. A lawyer who has litigated employment disputes in Alabama knows exactly what a plaintiff’s attorney will look for in discovery, what a judge will ask about at summary judgment, and what documentation changes the outcome. That knowledge makes the employment advice we give to subscription clients significantly more concrete.
The same applies to vendor contracts, lease agreements, and partnership disputes. When we help a Gulf Coast business owner negotiate contract terms or structure a business relationship, we are drawing on what we have seen those same types of agreements do when they end up in front of a court. The advice is sharper because the stakes are real to us, not theoretical.
A Gulf Coast construction company that works with OCL on an ongoing basis told us the most valuable thing about the relationship is not just that we review their contracts. It is that when we tell them something matters, they know it is coming from experience. That credibility changes how they approach their agreements and how their vendors respond when OCL is on the other side of a negotiation.
What This Looks Like Across the Most Common Business Situations
Contract review is the most obvious place litigation experience shows up. But the practical difference extends into other situations Gulf Coast businesses face regularly.
In vendor negotiations, knowing how Alabama courts have interpreted exclusivity clauses, payment terms, and force majeure provisions changes the conversation. We are not negotiating in the abstract. We are negotiating with a clear picture of what those terms mean when the relationship breaks down.
In lease reviews, understanding how landlord-tenant disputes have played out in Mobile and Baldwin County helps us identify the provisions that create real exposure versus the ones that sound serious but rarely matter in practice. A commercial lease for a Gulf Coast restaurant group looks different when reviewed by a lawyer who has handled a commercial tenancy dispute than when reviewed by one who has not.
In employment matters, litigation experience shapes the advice at every stage. Hiring documentation, offer letters, handbook provisions, performance management processes, and termination procedures all look different when the person advising on them has seen what happens when each one gets scrutinized in a legal proceeding.
For businesses involved in licensed or regulated industries along the Gulf Coast, regulatory compliance advice is similarly sharpened by courtroom experience. We have seen how regulators and courts treat certain compliance gaps differently, and that shapes the risk assessments we give clients in those industries.
Why This Matters for Your Business
The businesses that manage legal risk well are not just the ones with good contracts. They are the ones whose legal team has enough experience with what goes wrong to know where to look before anything does.
Outside general counsel who are actively litigating bring that experience into every conversation. A subscription client who calls OCL about a vendor dispute is not just getting a contract review. They are getting a read from lawyers who have handled similar disputes in Alabama courts, who know what the other side will argue, and who can tell them with real confidence whether a situation is worth fighting or worth settling.
That combination is not common in the outside general counsel space. Firms that focus primarily on transactional work tend to lose their litigation sharpness over time. Firms that focus primarily on litigation tend not to build the ongoing business relationships that make preventive work effective. OCL does both deliberately because each makes the other better.
The ongoing nature of the subscription relationship also means that we carry context about your business, your contracts, and your risk profile from one conversation to the next. When a dispute situation comes up, we are not learning your business for the first time. We already know which vendors have been difficult, which contracts have weak terms, and where the gaps in your documentation are. That context, combined with active litigation experience, produces a very different quality of advice than what you get from a general practitioner who only hears from you when something has already gone wrong.
If you are working with outside counsel who cannot tell you what your contract looks like from the other side of a dispute, that is a gap worth thinking about. A Risk-Free Strategy Session with OCL is a good place to start that conversation.
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.
Our Corporate/Business Counsel Services
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.
