Behind the Deal Docs: What Really Happens When Lawyers Negotiate Your Business Sale

If you’ve ever been deep into a business acquisition and wondered, “Why is this taking forever?”—you’re not alone.

One minute, your attorney says, “Let me talk to the other side,” and the next, it feels like your deal has vanished into a legal black hole.

Spoiler: it hasn’t. It’s just trapped in the weird, messy, and surprisingly delicate world of transaction documents.

Welcome to the lawyer-to-lawyer negotiation zone. It’s less “Suits,” more “email ping-pong with occasional existential dread.”

But if you understand what’s actually happening in this phase—and why it matters—you’ll be miles ahead of most buyers and sellers.

Why Transaction Documents Take Time (and Brain Cells)

Let’s start with the basics. After the letter of intent (LOI) is signed and diligence is underway, the deal shifts into documentation mode. This is where lawyers earn their keep. And yes, it takes time—not because we’re slow, but because we’re trying to prevent your future lawsuit.

Here’s the typical process:

1. Buyer’s Counsel Drafts the Purchase Agreement

The buyer’s attorney usually kicks things off with the first draft of the purchase agreement. Ideally, they’ve reviewed the LOI thoroughly, incorporated all the agreed-upon terms, and flagged any ambiguities that need clarity.

Great counsel will also start drafting from a strong, balanced template—one that protects their client without blowing up the deal. But even the best draft is still just a starting point.

2. Seller Reviews and Marks It Up

Once the draft is ready, it goes to the seller. Most sellers (wisely) do a quick first pass to catch any glaring errors—wrong purchase price, incorrect payment structure, outdated deadlines.

Then it’s off to the seller’s attorney for the real work: redlining, revising, and negotiating. In our deals, we do a ‘tailoring call’ where we walk through the deal documents in real time with the Seller to answer questions and make sure it fits the deal as well as possible.

The Chaos of Markups: It’s Not Always Pretty

Now, let’s talk redlines. There are a few types of attorney feedback—and not all of them are created equal.

• Best case: You get a clean, track-changed Word doc that clearly shows every proposed revision. You might even get a short cover email summarizing the key issues. These are the MVPs of legal negotiations. We love them.

• Common case: You get a semi-structured bullet-point email demanding changes without context. Slightly annoying, but manageable.

• Nightmare fuel: You get a scanned PDF of a printed document with handwritten notes in the margins. Or worse, a “change summary” generated by outdated legal software that references sections that don’t exist anymore. It’s like trying to assemble IKEA furniture with pieces from three different sets and no instructions.

The buyer’s attorney then has to spend hours—sometimes days—decoding, cross-referencing, and figuring out what the seller is actually asking for.

Not Every Edit Is a Battle

Once the redlines are in, the buyer’s attorney goes to work again, evaluating:

• What can we live with?

• What do we need to push back on?

• What needs a real business discussion?

Here’s the secret sauce that most clients don’t realize: good deal attorneys don’t fight everything. In fact, we expect to accept 70 to 75 percent of the seller’s edits—especially in small to mid-sized deals where both sides are business owners with limited time and patience for prolonged legal warfare.

But the 25–30 percent we do push back on? Those are the points that matter. Think indemnification terms, liability caps, escrow structure, and restrictive covenants. You don’t want those negotiated on autopilot.

Why You Shouldn’t Jump Into Every Legal Discussion

When business owners see redlines, it’s tempting to want to jump into the mix. “Why are they changing this?” or “Tell them that’s ridiculous.”

And sure, sometimes your voice is helpful—particularly when the issues are commercial (e.g., how much working capital you need at closing, or who handles client announcements).

But not every redline needs a committee meeting.

Many proposed changes are legal structure issues—designed to allocate risk, tighten language, or reflect common practice. When you step into those discussions without context, it can actually slow the deal down and make negotiations more adversarial than they need to be.

Sometimes, the best thing you can do is let your attorney handle it. Good lawyers will come back with a summary: “Here are the edits we accepted, here are the ones we pushed, and here are a few we need to talk about.”

That’s where you come in.

The Art of Private Counsel Conversations

Here’s something you won’t see on the term sheet: the best legal negotiations happen when lawyers are left alone to talk shop.

Why?

Because without clients or brokers listening in, we can be candid. We can say, “Look, we can probably get there, but not with this language,” or, “My client’s flexible on this if yours is flexible on that.” It’s a quiet, behind-the-scenes dance where both sides try to get to “yes” without nearly as much posturing.

But when the whole group is on Zoom, and the lawyers are chest beating and performing for their clients, it’s hard to have those honest, practical conversations.

So when your lawyer says, “Let me circle back with opposing counsel”—let them.

What Slows Things Down (and What Speeds Them Up)

So, why does it feel like these docs take forever?

Here’s what tends to slow things down:

• Poor communication between attorneys (or attorneys who ghost each other)

• Lack of client alignment on key terms before redlines are sent

• Over-negotiating small stuff that doesn’t actually impact the deal

• Unclear or sloppy redlines that require multiple rounds of clarification

• Relitigating the same draft - you need to have ALL your proposed edits in the first returned draft, not be adding brand new changes with each turn of the documents. You’ve absolutely got to be whittling down.

On the flip side, here’s what speeds things up:

• Attorneys who collaborate and stay responsive

• Clients who trust their counsel and focus on the big picture

• Clear, clean redlines (bless those attorneys forever)

• Understanding that perfection is the enemy of done

No, We’re Not Arguing About Commas (Most of the Time)

Yes, some changes may seem silly or overly technical. But what looks like “just a wording change” can have real consequences in court, in tax treatment, or in post-close liability.

We’re not debating semantics for fun—we’re trying to write an agreement that stands up if things go sideways. And that requires precision.

Final Thought: This Is Where the Deal Lives or Dies

When your lawyer disappears into the redline cave and comes back saying, “Here’s what I think we should accept, and here’s where we push”—they’re not stalling.

They’re protecting the deal. They’re making the structure solid. They’re giving you the foundation you need to actually close and move forward.

Deals don’t die in the documents—they die when one party loses trust, momentum fizzles, or negotiations spiral.

If you want your deal to survive that stage, trust the process. And trust your attorney.

Need help navigating the redline phase like a pro? That’s what we do every day.

For resources, checklists, and behind-the-scenes strategy, check out Deal Academy.