Don’t Hire Your Cousin the Divorce Attorney to Sell Your Business (And Other Legal Advice That Shouldn’t Need Saying)

When it’s finally time to sell your business—the one you’ve poured your blood, sweat, and probably at least one stress-induced ulcer into—you want to do it right. You hire the best M&A advisor (hello, HartmannRhodes). You tidy up your financials. You mentally prepare to say goodbye to your “baby.”

And then… you call your cousin Steve.

Steve, the divorce attorney.

Because, hey, he’s a lawyer, right?

Wrong. So, so wrong.

Selling your business is not the time to phone a friend just because they passed the bar in 1987 and once helped you beat a parking ticket. You need a business transaction attorney—specifically, one who specializes in M&A (mergers and acquisitions) and has experience with deals in your size range. Anything less is like hiring your dentist to do brain surgery: technically possible but definitely not recommended.

Let’s talk about why choosing the right attorney is absolutely critical—and why choosing the wrong one could be the most expensive mistake you ever make.

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Just because they passed the bar doesn’t mean they belong at the negotiating table.

Not All Lawyers Are Created Equal

Here’s the thing: just because someone is a licensed attorney doesn’t mean they know a thing about selling a business.

Some lawyers are great at:

• Drafting wills

• Getting you out of a DUI

• Suing your neighbor for cutting down your favorite tree

• Filing a trademark

• Arguing passionately about who keeps the dog in the divorce

All of those are valuable skills—in their own contexts. But if you’re selling a $5 million business and your attorney thinks “due diligence” means reading the buyer’s LinkedIn profile, we’ve got a problem.

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The High Cost of "My Lawyer Can Figure It Out"

We see this all the time. A business owner is close to sealing the deal. The buyer’s serious. The LOI is signed. The champagne is on ice. And then—BAM!—the seller’s lawyer gets involved. And that’s when everything grinds to a screeching halt.

Here’s what “My lawyer can figure it out” often looks like:

1. Delay. Lots of it.

A generalist attorney isn’t used to the pace or structure of M&A deals. They may need to research every term in the purchase agreement. They might “re-draft” documents that already follow standard industry templates. Every week they spend figuring it out is a week the buyer gets cold feet.

2. Overlawyering the Deal

When someone doesn’t fully understand a deal, they get nervous. And when they get anxious, they start throwing in every legal safeguard they can find, no matter how unnecessary or counterproductive. This is how simple asset sales balloon into 100-page monster contracts that scare buyers away.

3. Missing the Big Stuff

Ironically, while they’re obsessing over petty wording choices, they often miss major red flags—like inadequate representations and warranties, poorly defined earn-outs, or lopsided indemnification clauses that could leave you liable for years.

4. Poking the Buyer Bear

An inexperienced attorney can offend or frustrate the buyer (or their attorney) with aggressive, unnecessary legal posturing. Deals are relationships. If the lawyers can’t play nice, the deal can fall apart before it hits the closing table.

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"But My Lawyer Is Smart!"

We’re sure they are. So is your orthodontist, but you wouldn’t ask her to perform open heart surgery.

Being a good lawyer doesn’t mean being good at every type of law. Business sales are a different beast—especially when millions of dollars, employees, legacy, and retirement are on the line. You want someone who’s lived and breathed dealmaking for years.

Someone who knows:

• What clauses are standard—and what’s totally off base

• How to negotiate without tanking trust

• How to navigate escrows, earn-outs, working capital targets, reps & warranties

• What your tax exposure will be (and how to reduce it)

• What buyers look for—and how they try to shift risk your way

This is not amateur hour.

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Even great deals can fall apart with the wrong attorney at the table.

Real Talk: Bad Lawyers Kill Good Deals

Let us tell you a quick story. Names changed to protect the well-meaning-but-deal-killing.

A client—we’ll call him Bob—was selling his HVAC company for $7.5 million. He had a great buyer lined up. They clicked. The buyer loved the team, the culture, the books checked out… it was all systems go.

Then Bob brought in his buddy from law school. Let’s call him Jeff. Jeff’s legal specialty? Workers’ comp litigation.

Jeff saw the asset purchase agreement and immediately went on high alert. “This whole thing is wrong,” he said. “We need to rewrite it.” So he did. All of it. Top to bottom.

He sent back a Frankenstein draft full of outdated language, redundant clauses, and demands that no sane buyer would ever agree to. The buyer’s attorney laughed, but the buyer himself didn’t. He walked.

The deal died. Bob called us six months later—after eventually hiring a proper M&A attorney. But by then, market conditions had shifted, and he sold for $6.9 million.

That’s a $600,000 mistake.

Thanks, Jeff.

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What a Great M&A Attorney Actually Does

Okay, enough doom and gloom. Let’s talk about what the right attorney does.

A seasoned M&A attorney:

• Works seamlessly with your advisor to protect your interests without blowing up the deal

• Knows when to push and when to concede

• Uses plain English whenever possible

• Streamlines the process instead of overcomplicating it

• Spots risky clauses and negotiates better terms

• Helps you structure the deal to minimize your post-sale liability

• Keeps the closing timeline on track

They are your deal’s legal bodyguard, therapist, translator, and fixer—all rolled into one.

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This is what it looks like when you surround yourself with the right team.

How to Find the Right Attorney

Wondering where to find this magical unicorn of legal competence? Here’s what to look for:

✅ M&A Experience (Specifically Sell-Side)

Ask how many deals they’ve closed in the last year. Look for someone who routinely works on business sales in your deal size range. If they say, “Well, I’ve done a couple,” run.

✅ Deal Size Match

Attorneys who typically work on $100 million private equity transactions may not be the best fit for your $3 million sale. Find someone who understands deals in the $1M–$25M range (hey, that’s our sweet spot too).

✅ Collaborative Style

Your attorney should work well with your other advisors—not try to take over the deal. Avoid lawyers who believe they alone are the final word on everything.

✅ Business Mindset

Great deal attorneys are legally sharp and commercially savvy. They understand that selling a business is about more than risk mitigation—it’s also about getting you across the finish line with your goals intact.

✅ Clear Communicator

You want someone who explains things clearly, doesn’t talk down to you, and returns your calls before you retire to Florida.

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Questions to Ask a Potential M&A Attorney

Before you hire someone, ask these:

1. How many business sales have you handled in the last year?

2. What’s the typical deal size you work on?

3. Have you worked with business owners like me before?

4. What’s your approach to balancing legal protection and deal momentum?

5. Can you provide references from past clients who’ve sold businesses?

And yes, feel free to casually ask, “Do you also handle divorces?” just to be sure.

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A Quick Word on Legal Fees

Good M&A attorneys aren’t cheap. But neither is a failed deal. Think of it like buying a helmet: the cheaper it is, the less you want to test it in a crash.

Most M&A attorneys bill hourly, though some may offer flat fees for portions of the work. Don’t be afraid to ask for an estimate and get clarity on what’s included. Remember: efficiency comes from expertise. A seasoned attorney will do in 5 hours what a generalist might spend 20 on.

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So...Who Should You Hire?

We’re not going to name names here (although we’re happy to recommend a few top-tier M&A attorneys if you call us), but know this: Your cousin Steve is not it.

Unless he is an M&A attorney. In which case, call him and tell him we said hi.

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Final Thought: Protect the Exit You've Earned

You’ve spent years—maybe decades—building your business. This is your moment to cash out, move on, or finally take that trip to Italy without worrying about payroll.

Don’t let the wrong attorney derail it.

Surround yourself with the right team: your M&A advisor, your CPA, and yes—your attorney—the right one.

Because at the end of the day, your goal isn’t just to sell your business. It’s to sell your business successfully. On your terms. For top dollar. Without unnecessary headaches, lawsuits, or buyer freakouts. And if that means gently telling your cousin Steve, “I love you, but no,” then so be it.

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Need help finding the right legal partner for your exit?

At HartmannRhodes, we’ve seen it all and work with some of the best attorneys in the business. Call us before you call Steve.

Blog: Don’t Hire Your Cousin the Divorce Attorney to Sell Your Business (And Other Legal Advice That Shouldn’t Need Saying)

Mark Hartmann is a former business owner turned M&A advisor who knows firsthand what it takes to build, grow, and sell a successful company. A three-time Inc. 5000 CEO, Mark did just that before navigating its eight-figure sale—giving him a rare perspective that sets him apart from most brokers. Today, he helps owners of companies valued between $1M and $25M plan and execute smooth, profitable exits.

Mark understands that selling a business isn’t just a financial decision—it’s personal. That’s why he works closely with owners to protect their legacy, maximize value, and make the transition on their terms. He holds an MBA from Eastern University, a Master’s Degree in Organizational Change Management from St. Elizabeth University, and a Graduate Certificate in Executive Coaching from Columbia University. Some of his professional credentials include Certified Mergers & Acquisitions Professional (CM&AP), Certified Business Intermediary (CBI), Certified Exit Planning Advisor (CEPA), and Certified Value Builder (CVB).

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