We’ve Seen Your Contracts From Both Sides. Here’s What We Know.

Between the two of us, we've spent decades on opposite ends of the same business agreements.

James builds them — corporate transactions, M&A deals, operating agreements, governance structures designed to give businesses a clean foundation and a clear path forward. Adam litigates them — sitting across a deposition table arguing over what a termination clause actually meant, or watching a "standard" indemnification provision become the centerpiece of a seven-figure dispute.

We don't always work on the same matters. But we've arrived at the same conclusion from very different directions:

Most businesses are carrying contract risk they don't know about. And in this economic environment, that risk is getting harder to ignore.

What We're Both Seeing Right Now

The disputes showing up in litigation aren't coming from new deals. They're coming from old ones — agreements that were drafted for a different business environment, a different relationship, and in many cases, a different economy.

On the transactional side, we see it in businesses that scaled quickly without updating their legal infrastructure to match. The operating agreement from year two doesn't reflect the business in year seven. The vendor contract that worked fine at $10M in revenue has real gaps at $50M. The partnership structure made sense when everyone was aligned — and creates serious exposure the moment they aren't.

On the litigation side, the pattern is just as consistent. When margins tighten and relationships strain, everyone suddenly reads the fine print. Termination rights that seemed straightforward become contested. Pricing adjustment clauses that both sides agreed to get interpreted very differently under pressure. Force majeure language that was boilerplate in one business environment becomes a liability in another.

The contracts aren't always bad. They're just built for a version of the business — and a version of the relationship — that no longer exists.

The Gap Between Signing and Surviving

Here's what the best corporate attorneys understand, and what the best litigators confirm: a contract that closes a deal and a contract that governs a relationship are not always the same document.

Speed is the enemy of good drafting. "We'll clean it up later" is the most expensive phrase in business. And the provisions that feel like formalities at signing — indemnification, termination rights, dispute resolution, pricing adjustments — are exactly the ones that matter most when something goes wrong.

We've both seen what happens when those provisions are vague, one-sided, or simply missing. The deal that felt clean at closing becomes a years-long dispute over what the parties actually agreed to. And by that point, the cost — in legal fees, management distraction, and the relationship itself — almost always exceeds whatever was saved by moving fast.

This isn't an argument for legal perfectionism. Businesses make decisions under time pressure, and not every agreement needs to be a 60-page masterpiece. But there's a meaningful difference between a contract that's intentionally streamlined and one that's just incomplete.

What "Outside General Counsel" Actually Means

One of the most consistent themes across both of our practices is the value of having a trusted legal advisor who knows your business before a problem develops — not just when one arrives.

When a business has that relationship in place, a few things change. Contracts get reviewed with someone who understands the business context, not just the legal language. Red flags get flagged before they become disputes. And when something does go wrong — because in any business, something eventually does — there's already an attorney in the room who knows the history, knows the documents, and knows how to move quickly.

The businesses that struggle most with contract disputes are often the ones that treat legal counsel as a cost to minimize rather than an investment in risk management. They bring in an attorney to close a deal, not to build a relationship. And when the deal later breaks down, they're starting from scratch with an attorney who has no context — and the other side has already gotten a head start.

The Questions Worth Asking

If you're a business owner or executive, these are worth sitting with:

When were your most critical contracts last reviewed? If the answer is "when we signed them," that's worth examining — especially if your business has grown, your industry has changed, or the relationship has evolved.

Does your legal infrastructure match your current business? An operating agreement, shareholder agreement, or partnership structure that worked three years ago may have real gaps today.

Do you have an attorney who knows your business — or one you call when something breaks? The difference in outcome, and in cost, is significant.

And if a dispute is already developing: how early are you addressing it? The gap between "this is getting tense" and "attorneys are involved on both sides with hardened positions" is where most of the options disappear.

We will leave you with this…

The through-line across both of our practices is the same: intentional businesses — the ones that treat legal structure and legal counsel as strategic investments — navigate these moments better than reactive ones.

That's not just a legal observation. It's a business one.

If any of this is landing close to home, we'd welcome a conversation. Whether you're building a deal, stress-testing your existing agreements, or dealing with something that's already in motion — between the two of us, we've seen most versions of this story. And we'd rather help you write a better one.

Adam Witkov is a business attorney and litigator at Michael Best, recognized in The Best Lawyers in America for Commercial Litigation. He serves as outside general counsel to businesses, healthcare practices, and family-owned companies throughout Wisconsin and nationally.

James Forrest is Managing Partner of Michael Best's North Carolina offices and leads the firm's Faith Based Practice. He has served as outside general counsel and M&A advisor to companies, executives, and organizations across the country for over two decades.