Born a Litigator: What I’ve Learned About Preventing Business Disputes

I started my career as a litigator. And have been in litigation for over fifteen years, representing businesses in court—contract disputes, partnership breakups, employment cases, shareholder battles. I sat through depositions where former business partners could barely look at each other. I argued motions in cases where family members were fighting over companies their parents built. I cross-examined witnesses about agreements they swore they understood but clearly didn't.

Somewhere a few years into practice, I had a realization that changed everything: almost every dispute I was litigating could have (and should have) been prevented. Not by better lawyers—by better planning. Better agreements. Better conversations when everyone still liked each other.

Most business attorneys draft agreements based on what they learned in law school or from templates they've used for years. I draft them based on what I've seen fail in court. I know which clauses look good on paper but crumble under pressure. I know which provisions everyone skims over that become the most fought-over paragraphs in litigation. I know what "fair market value" means when you're negotiating versus what it means when you're fighting.

That difference matters.

Being "born a litigator" isn't about being aggressive or contentious. It's about understanding what happens when business relationships go bad—and using that knowledge to keep them from going bad in the first place. It's about asking uncomfortable questions during the planning phase so you don't have to answer them in a courtroom later.

Let me share what I've learned.

What You Learn in the Courtroom

There's a moment in almost every business dispute where I see the exact provision that would have prevented the whole mess. It's usually something the parties skipped over when they were drafting their agreement because they were excited about the opportunity, trusted each other, or just wanted to get the deal done.

"We'll figure that out later if it becomes an issue," they said. And now, three years and hundreds of thousands of dollars in legal fees later, they're in front of a judge trying to "figure it out."

Here's what you learn when you litigate business disputes for almost two decades:

Contracts are tested when relationships fracture. When everyone's getting along, agreements don't matter much. But the moment trust breaks down—when someone wants out, when profits disappoint, when strategic visions diverge—suddenly every word in that operating agreement becomes critical. The provisions that matter most are the ones you hope never to use.

Ambiguity always favors the person you're fighting with. If your partnership agreement says shares will be bought out at "fair market value" but doesn't specify how to determine that value, guess what happens? Five expert appraisers will give you five different numbers, spanning millions of dollars. You'll spend $100,000 fighting about valuation methodology before you even get to a number.

Judges interpret documents literally. Your good intentions don't matter. What you "meant" to say doesn't matter. What you discussed over beers but didn't write down definitely doesn't matter. The judge will read the four corners of that document and apply the plain meaning of the words. And, even if the contract is not “integrated” (you can look beyond the four corners) or there are terms in the contract that are ambiguous, that does not mean that it will be interpreted how you (or the parties) intended it to be.

The most expensive three words in business are "we'll figure it out later." Every single time I see those words—or their variations—in a business agreement or email chain, I know litigation is coming. Because "later" arrives during a crisis, when emotions are high and trust is low, and "figuring it out" means it will be expensive and attorneys will be involved.

Five Disputes I've Litigated (And How to Try to Prevent Them)

Let me walk you through five actual disputes I've handled and show you how they could have been prevented. I've changed some details, but the patterns are real and remarkably common.

Dispute #1: The "Fair Market Value" Partnership Buyout

The scenario: Second generation family members inherited the shares of a business from their parents. After a number of years, disagreements arose, and some of the family members wanted other family members out of the business. Their operating agreement said the exiting partner's shares would be purchased at "fair market value." Seemed straightforward.

What went wrong: Family Member A hired an appraiser who valued the business at $X million. The Company hired an appraiser who valued it at $Y million. Both appraisals were professionally done and defensible—they just used different methodologies, different assumptions about future growth, and different market comparables.

The litigation cost: We spent years fighting about valuation methodology and other issues, including expert depositions, mediation, motions, and six figures of legal fees prior to a settlement—which neither party thought was fair.

How to prevent it: Specify exactly how "fair market value" will be determined. Name the methodology. Define what gets included and excluded. Pick the appraiser in advance or establish a process (like each side picks one, and if they're within 10%, you average them; if not, they jointly select a third). Make the valuation determination binding.

The provision that works looks something like this: "Fair market value shall be determined by an independent appraiser selected by mutual agreement, or if the parties cannot agree within 30 days, by the President of the Wisconsin Institute of CPAs. Valuation shall be based on a multiple of trailing 12-month EBITDA, using the average multiple from three comparable transactions in the dental industry within the past 24 months. The appraiser's determination shall be final and binding."

Is that more complex than just writing "fair market value"? Yes. Does it guarantee there will not be litigation? No. But are both sides better protected and more aware of the outcome? Yes. 

Dispute #2: The Medical Expansion Gone Wrong

The scenario: A provider started a healthcare business with another provider as an investor who provided the majority of capital. After two years of success, they decided to open a second location. The investor wanted aggressive expansion; the provider wanted careful, managed growth. Neither had authority to break the tie.

What went wrong: Their operating agreement said major decisions required "mutual agreement" but didn't define what happened if they couldn't agree. It also wasn't clear who had day-to-day management authority versus who needed to approve major strategic decisions.

The cost: They spent months fighting through lawyers about whether the expansion was within the provider’s management authority or required mutual approval. The business nearly failed during the dispute because neither party could make decisions. By the time it resolved it, the opportunity for the second location was gone, and the relationship was destroyed.

How to prevent it: Separate day-to-day management from major strategic decisions. Specify exactly what requires unanimous approval (new locations, capital expenditures over $X, taking on debt, hiring key employees). Establish clear management authority for everything else. Most importantly, create a tiebreaker mechanism—whether that's giving one person casting vote authority, mandatory mediation, or a buy-sell trigger.

Consider provisions like: 

• The Operator shall have exclusive authority over all clinical decisions, staff hiring, marketing, and expenditures under $25,000.
• The following decisions require unanimous member approval:
  • opening additional locations
  • capital expenditures over $25,000
  • taking on debt over $50,000
  • selling the company or
  • materially changing service offerings.
• The following decisions require unanimous member approval: 

If the members cannot reach unanimous agreement on a major decision within 60 days, either member may trigger the buy-sell provision in Section X.

Dispute #3: The Key Employee Who Left With Everything

The scenario: A manufacturing company's top engineer had designed their primary product line over 10 years. When a competitor offered him more money, he left—and took all his knowledge, relationships, and processes to the competitor. Six months later, the competitor launched a nearly identical product line.

What went wrong: The company had a non-compete agreement, but it was so broadly written ("You can't work in manufacturing anywhere in the United States for five years") that it was unenforceable. They also never documented what constituted their trade secrets or had the engineer sign any agreement, employee handbook, or anything else about protecting confidential information.

The litigation cost: Without documented trade secrets and confidential information and without an unenforceable non-compete, the manufacturer had limited options. They spent money on legal despite being warned of their limited options and were disappointed with the outcome.

How to prevent it: Reasonable non-competes that courts will actually enforce (limited geographic scope, reasonable time period, specific to the employee's actual role). Document your trade secrets—literally create a list of what's confidential and what are trade secrets. Have clear protocols about returning information when employees leave. Include non-solicitation provisions that prevent them from taking customers and other employees.

Would that agreement have prevented the employee from taking the new job? Maybe. Maybe not. But it would have given the company leverage to restrict what the former employee could do for the competitor, protect the company's most valuable information, and have leverage over the change in circumstance.

Dispute #4: Family Business Shareholder Oppression

The scenario: Three siblings inherited equal shares in their father's successful company. Two siblings worked in the business; one didn't. After a few years, the working siblings started paying themselves large bonuses, refused to make distributions to the non-working sibling, and excluded her from all business decisions.

What went wrong: The father's succession planning had failed to address these exact issues. No buy-sell agreement. No provisions that expressly protected minority shareholders. No established distribution policy. No governance structure separating family dynamics from business decisions.

The litigation cost: The non-working sibling sued for shareholder oppression. The case went on for years. The business sustained instability during the dispute as employees worried about stability. Eventually, the parties settled on a buyout at a discount to fair value, and the family stopped speaking to each other.

How to prevent it: Buy-sell agreements that establish clear paths for exiting shareholders. Minority shareholder protections (guaranteed board representation, distribution requirements, information rights). Clear governance that prevents majority shareholders from freezing out minority owners. And honestly, proper succession planning that addresses whether non-working children should even own the business.

There is no perfect language to prevent a lawsuit, but drafting intentional language that addresses current and future needs gives everyone a path forward and can prevent fighting that otherwise destroys families.

Dispute #5: The "Handshake Deal" 

The scenario: Two successful business owners decided to start a joint venture. They'd known each other for years, trusted each other completely, and agreed on the basic terms over dinner. They started operating their joint venture before getting around to "all the paperwork."

What went wrong: Everything. They couldn't agree on the business model, compensation splits, and the involvement of other family members in the business. They had conflicting memories about what they'd agreed to regarding staffing decisions. And they consistently butted heads and fought – with both sides feeling scorned for their contributions of capital, staff, and equipment. 

The litigation cost: Unwinding a partially formed joint venture can be a nightmare. The issue is not just unwinding the relationship, but the apportionment of risk, indemnification, and long-term exposure on the work performed while the joint venture existed. Both parties paid lawyers significant amounts and both left upset.  

How to prevent it: Never, ever operate under a handshake deal—even with people you trust. Get the agreement in writing before you commit time, money, and equipment. Detail exactly how the joint venture will operate: governance structure, compensation methodology, decision-making authority, expansion plans, exit provisions. 

The Questions a Litigator Asks That Other Attorneys Don't

When I review a business agreement or draft them, I'm asking questions that make people uncomfortable. That's intentional. Because these are the questions that will determine whether the agreement works when it's tested.

"What happens if this goes completely sideways?" Not just a little rocky—what if the relationship completely fractures? What if these business partners end up hating each other? What if one person wants out and the other refuses to let them leave? Your agreement needs to work in the worst-case scenario, not just the best case.

"How would an angry former partner weaponize this clause?" I read agreements looking for language that can be twisted or used against my client. If a provision could be interpreted multiple ways, you can be certain the person fighting with you will choose the interpretation that hurts you most.

"Can we prove this six years from now when everyone's memory is different?" If your agreement relies on oral understanding or assumed context, you're in trouble. Everything that matters needs to be documented. When I'm deposing witnesses six years after the fact, no one remembers what was "understood" in 2020.

"What assumptions are we making that might not hold true?" Maybe you assume the business will keep growing. Maybe you assume everyone will keep getting along. Maybe you assume technology won't disrupt your industry. Build your agreements to survive when those assumptions prove wrong.

"Who has leverage if this falls apart?" Understanding the leverage dynamics helps you build in protections for the weaker party. If one person controls all the customer relationships, the other partner needs contractual protections. If one person provides all the capital, they need control provisions.

"What's the worst-case interpretation of this language?" Courts often interpret ambiguous language against the party who drafted it. If there's any way to read a provision that hurts you, that's probably how a judge will read it in litigation.

"How would I attack this agreement if I represented the other side?" This might be the most important question. When I draft an agreement, I mentally switch sides and try to find every weakness, every gap, every ambiguous phrase. If I can find the problems, I can fix them before they matter.

These aren't pessimistic questions—they're realistic ones. I've seen too many business relationships fail to pretend they won't.

Red Flags in Your Existing Agreements

Pull out your operating agreement, your partnership documents, your key vendor contracts. Let me show you the phrases that could result in disputes:

"To be determined." This is just postponing the fight. If you can't agree on how to determine something now when you like each other, you definitely won't agree later when you're fighting.

"Fair market value" without methodology. As I showed you earlier, this phrase generates more litigation than almost any other. Define exactly how you'll determine value.

"Mutual agreement required" without a tiebreaker. What happens when you don't mutually agree? You're deadlocked, and deadlock destroys businesses.

"Reasonable" without definition. What's reasonable to you might be completely unreasonable to your partner. Define standards explicitly.

"Good faith" without specifics. Everyone thinks they're acting in good faith, even when they're screwing you over. Good faith doesn't mean anything without specific obligations.

Now look for what's missing entirely:

What triggers a buyout? Death and disability are obvious, but what about retirement? Divorce? Disability that isn't total? Moving out of state? Wanting to sell to an outside buyer?

How to resolve deadlock? If partners can't agree on a major decision, what happens? Mediation? Casting vote? Buy-sell? Dissolution?

What happens if someone can't pay their share? If the business needs capital and one owner can't contribute, do the others cover it? Does the non-contributing owner's percentage get diluted? Can you force them out?

Who decides major business decisions? What constitutes "major"? Who has authority to commit the company to expenditures, contracts, hiring?

How the business continues if someone leaves? Does it dissolve? Do remaining owners buy them out? How is that funded?

If your agreements don't clearly answer these questions, you have problems waiting to happen.

Why This Matters More in 2026

Business relationships are more complex than they've ever been. Businesses have multi-state operations, remote workforces distributed across the country, intellectual property, technology, and cybersecurity considerations that didn't exist a decade ago, rapid growth and scaling that create strain, and private equity or outside investors with different expectations.

Courts are also less willing to "fix" bad agreements. Judges used to have more flexibility to do equity and craft solutions when agreements were unclear. Modern contract law is much more rigid—courts enforce what you wrote, not what you meant. That puts more pressure on getting it right the first time.

And litigation is obscenely expensive. A simple contract dispute that goes to trial will cost hundreds of thousands of dollars in legal fees – OR MORE. Complex shareholder battles often are in the seven figures. Even early resolution of these disputes through mediation and settlement usually costs six figures in legal fees. 

But more than the direct cost, business disruption from disputes is devastating. While you're fighting with your partner, no one's running the business. Customers worry. Employees leave. Opportunities pass by. I've seen thriving businesses lose value during a dispute, beyond just the legal fees.

Prevention is measured in thousands. Litigation is measured in hundreds of thousands. 

How to Apply Litigation Thinking to Your Business

Let me make this concrete for different types of businesses:

If you're a manufacturer: Your supply chain contracts need to address what happens with quality issues. Not just "they'll fix it," but specific remedies, cure periods, and rights to source elsewhere. What happens if they consistently deliver late? Can you terminate? What damages can you recover?

Your customer agreements should clearly establish payment terms, what constitutes default, and your remedies. What happens if a major customer stops paying? If they go bankrupt? You need security interests, guarantees, and clear breach provisions.

And your employment agreements, especially for engineers and key employees—what happens if they leave and take your processes? You need clear trade secret protections, reasonable non-competes, and documented confidential information.

Read More: Manufacturing in the Age of AI

If you own a medical spa: Look at your medical director agreement. What happens if they want to leave? Can they? Do you need to shut down? What happens if they're unhappy with your operations or think you're making clinical decisions inappropriately? Your agreement needs to address the tension between their medical authority and your business authority.

If you're planning multi-location expansion, think through what happens if a location fails. What happens if your location manager wants to leave and open their own med spa? Your employment and ownership structures need to prevent that nightmare scenario.

And your nurse injector or aesthetician contracts—what happens if your best employee opens a competing med spa across the street? You need enforceable non-competes that are actually reasonable enough for courts to uphold.

If you own a medical practice: Look at your partnership agreement. What happens if one of the doctor’s production drops significantly? What if clinical quality becomes an issue? What if you want to expand but your partner doesn't? These aren't hypothetical—they're the most common disputes I see in medical practices.

Your associate agreements need to address what happens if an associate isn't a cultural fit. What if they want equity earlier than you planned? What if they leave to open a competing practice? And most importantly, what specific patient and clinical standards are they required to meet?

If you're considering DSO conversion or joining a DSO, think through what happens if the relationship doesn't work out. Can you get your practice back? What are the exit terms? DSO agreements almost always favor the DSO—you need counsel who will negotiate for your interests.

The Preventive Legal Audit

Here's what I recommend to clients: Review your major agreements annually. Not just file them away and hope they're fine—actually read them and ask whether they still work.

Partnership and operating agreements: Do they reflect your current relationship? Have ownership percentages changed? Have roles evolved? Does the governance structure still make sense? Are the buyout provisions still fair?

Key customer and vendor contracts: Are the prices still accurate? Do the terms reflect current market conditions? Are there provisions you're not following? Are there gaps that have become apparent?

Employment agreements and policies: Are your non-competes still reasonable? Do your trade secret protections cover new processes? Are your handbooks current with new employment laws?

Buy-sell agreements and valuations: Has your business value changed significantly? Is the funding mechanism (life insurance, etc.) still adequate? Does the formula still work?

Non-compete and confidentiality agreements: Are they written to comply with current state law? Do they cover new employees and new roles? Are they actually enforceable?

For each agreement, ask yourself:

Does this still reflect our business relationship? Agreements written five years ago often don't match current reality. Update them before disputes arise.

Are the financial terms current? Valuations, prices, compensation—if the numbers are significantly outdated, renegotiate now while everyone's reasonable.

Would this hold up if tested? Read the agreement imagining you're in litigation. Are there gaps? Ambiguities? Provisions that favor the other party?

Are there issues we've now identified through experience? Maybe you've had problems you didn't anticipate. Add provisions to address them prospectively.

My Approach

When I review a contract or draft an agreement, I'm thinking about three things simultaneously:

First, does this serve my client's business objectives? I'm not drafting to create the most legally bulletproof document—I'm drafting to support what you're trying to accomplish in your business. If an agreement is legally perfect but impractical, it's worthless. I need to understand your business goals first, then craft legal structures that enable them.

Second, what would happen if this completely falls apart? This is the litigation lens. I read every provision imagining we're in a dispute three years from now. Does this agreement give my client protection and leverage? Does it close off attacks? Does it provide clear remedies?

Third, can we prove our position if needed? Litigation is about evidence and documentation. An agreement is only as good as your ability to prove what was intended and what was performed. I structure agreements to create documentation, establish clear standards, and make proof straightforward.

I've stepped into the courtroom to defend advice I've given. That keeps me honest about the advice I provide. I'm not going to tell you a provision will work if I'm not willing to stand up in court and argue for it.

The goal isn't to create bulletproof documents that anticipate every conceivable scenario. That's impossible and impractical. The goal is to create clear, fair agreements that reduce the likelihood of disputes and provide a roadmap if disputes occur. Good agreements make litigation unnecessary. Great agreements make litigation unwinnable for the other side, so they settle quickly on reasonable terms.

What You Should Do Now

Let me give you some immediate action items:

Pull out your three most important business agreements and read them with fresh eyes. Imagine you're in a fight with the other party. Where are the gaps? What phrases are vague? What major issues aren't addressed? Make a list.

Ask the litigation questions about any new agreement you're considering. What happens if this goes wrong? How would this be weaponized against me? Can I prove this? What assumptions am I making?

Think about your key business relationships and risks. What's your biggest vulnerability? A partner who could leave? A key employee with critical relationships? A major customer who could stop paying? A supplier you're dependent on? Make sure you have contractual protection.

If you're entering a major transaction —bringing on a partner, selling your business, merging with another practice, raising outside capital—get counsel before you commit. The time to negotiate protections is before you sign, not after things go wrong.

Schedule time with an attorney who thinks like a litigator. This doesn't have to be me, but it should be someone who's actually tried cases and seen agreements tested under fire. Have them review your most critical agreements and tell you what they see.

The real cost of "we'll deal with it later" isn't the legal fees—though those are substantial. It's the business value destroyed, the relationships ruined, the opportunities lost, and the years of your life consumed by disputes that could have been prevented.

Here’s the thing…

I didn't stop being a litigator when I became a business attorney—I brought that perspective with me. Every agreement I draft, every deal I structure, every partnership I help establish, I'm thinking about what I've seen fail in court and how to prevent it.

The best business advice I can give isn't about how to win in court. It's about how to never need to be there in the first place.

Understanding what happens when business relationships fail makes me better at helping them succeed. That's the advantage of being born a litigator.

If you're looking at a major business agreement—whether it's bringing on a partner, expanding your medical spa or dental practice, navigating family business succession, or structuring a complex transaction—I'd be happy to talk. No pressure, no hard sell. Just a conversation about what you're trying to accomplish and how to think through the risks.

Because the questions that make you uncomfortable now are the ones that keep you out of court later. And that's exactly where you want to be—building your business, not defending it in litigation.