What Comes After… Outside General Counsel for Wisconsin Business Owners

The clients I’ve worked with longest didn’t hire me for a transaction.

They hired me for what their business was becoming. The transaction was just the door.

I think about one situation a lot, not a specific client, but a composite of something I’ve seen more than once. A family-owned manufacturer somewhere in Wisconsin. Third-generation. The grandfather started it, the father built it into something real, and now the son is running it, and trying to figure out what that actually requires. Not just operationally. Structurally. Legally. He called me about a contract, a supplier agreement that felt off to him. He was right, it did. We fixed it.

But we kept talking.

Because the supplier contract wasn’t really the question. The question was: what happens to this business when he’s ready to step back? His father was still involved. There was a sibling who had equity but wasn’t in operations. Nobody had looked at the operating agreement in years. The buy-sell provisions were written for a business that no longer existed.

That’s where it started.

How most legal relationships work

Most business owners hire an attorney for a specific thing. A formation document. A contract that needs review. A dispute that needs resolving. The engagement has a beginning and an end, and when the matter closes, so does the relationship, until the next thing comes up.

That’s not a criticism. That’s just how it works. Legal counsel has always been structured around problems rather than prevention.

The result is that most growing businesses accumulate attorneys the way they accumulate vendors. One for employment issues, one for real estate, one for whatever came up last year. Nobody has the whole picture. Nobody knows the business the way the owner does. When something new comes up, you start from the beginning, re-explaining the history, re-establishing the context, hoping the person you’ve called can understand the business quickly enough to give you useful advice.

The transactional model is efficient for isolated matters. For a growing business with compounding complexity, it has real costs. You pay them every time you have to bring someone up to speed. And you don’t always see them coming.

The moment something changes

What I’ve noticed is that the shift from transactional to something longer doesn’t usually happen because a client decides they want a different kind of relationship. It happens because a problem arrives that doesn’t fit neatly into a single matter, and the owner realizes they need someone who already understands the business well enough to anticipate the question they haven’t asked yet.

For the manufacturing family I described, that moment came about eight months after the supplier contract. The father was ready to start transitioning out. Not fully…  he wasn’t leaving tomorrow, but the conversation had started. There were tax implications, structural implications, family dynamics that had been carefully balanced for years. None of it had been documented in a way that would hold up if those dynamics shifted.

He called me. Not because I had done estate planning for them, I hadn’t. But because I was the attorney who already knew the business. I knew the operating agreement. I knew how the equity was structured. I knew who was in the room and what they each cared about.

That’s not something you can recreate in a first call with someone new. It accumulates.

What the relationship looks like across the arc

Over the next several years, here’s what that engagement actually covered, not in the sense of billing events, but in the sense of what it meant to have one attorney who was paying attention.

The operating agreement got rewritten when a key non-family executive came on and the ownership structure shifted. The employment agreements for the leadership team got updated when headcount crossed a threshold that changed what they needed to say. When the company looked at acquiring a smaller regional competitor, I was already carrying years of context on the business, I knew their risk tolerance, their financial position, and their family dynamics. The diligence was faster. The advice was sharper.

When the father eventually stepped back, the transition didn’t become a dispute. Not because transitions are simple, they’re not, but because the structure had been tended over years. The buy-sell provisions we rewrote actually reflected how the family thought about value. The governance documents said what they meant. When it mattered, they held.

The son called me after the papers were signed. He said something I’ve thought about since, that he didn’t realize until that moment how much of what went right had been invisible.

That’s the point.

What the litigation background adds to a long relationship

I’ve spent over fifteen years as a litigator. That doesn’t mean I’m waiting for something to go wrong.

It means that when I’m drafting or reviewing any agreement, operating agreement, buy-sell provision, supplier contract, employment structure, I already know what it looks like when that document fails. I’ve stood in a courtroom and defended the advice I gave. I’ve seen the gaps that seem unimportant until something forces a decision.

Over a long engagement, that perspective compounds. Every document I’ve touched across years of a client relationship has been written with one question in mind: what happens to this when things get complicated?

On a quiet Tuesday when nothing is wrong, the client doesn’t think about that. I do. That’s the job.

What most growing businesses are missing

Most Wisconsin business owners I know are building something real. A legacy, a life’s work, something they intend to hand off or sell on their own terms someday. They review their financials every month. They know their numbers.

The legal foundation of the business? Almost never, until something forces it.

That’s not unusual. Legal structures are invisible when they’re working and expensive when they’re not. The operating agreement sits in a folder somewhere. The buy-sell provision hasn’t been looked at since the attorney who drafted it moved firms. The employment agreements from five years ago still say what the business needed then.

An ongoing outside general counsel relationship, one attorney who knows the business, isn’t a luxury for businesses at a certain size. It’s the thing that makes that growth achievable without the detours.

The manufacturing family I described didn’t get lucky. They didn’t avoid problems by being careful. They avoided specific, costly problems because someone was paying attention to the legal foundation of the business across years, not just when a matter arrived that demanded it.

What “what comes after” actually looks like

I started this piece with the clients who’ve stayed longest. I want to end there too.

The businesses I know best aren’t the ones that hired me for the biggest matter. They’re the ones where the engagement never really ended, where one conversation led to another, where the relationship outlasted any single matter because it was useful in a way that isolated engagements couldn’t replicate.

The sale that went smoothly because the agreements were clean when it mattered. The transition that didn’t become a dispute because the structure had been tended. The owner who got to decide on their own terms because someone had been paying attention to the foundation while they focused on the growth.

That’s what “what comes after” looks like.

If you’re a Wisconsin business owner who has been operating without that kind of legal relationship, or with one that’s transactional and not quite working, I’d be glad to have that conversation. Reach out directly, I’d welcome the conversation.