Your M&A Attorney's Biggest Negotiation Was Their Last Car

TL;DR: The most common undergraduate major for U.S. law school applicants is Political Science. After three years of law school and fifteen years of practice, the typical M&A attorney is excellent at producing documents that protect the client from legal liability. None of that training was ever about negotiation. The seller who assumes the attorney's seat is the negotiation seat is making the same category error as the seller who assumes the banker's seat is the strategy seat.

The biggest deal the attorney had ever actually negotiated was the last car they bought.

Speaking as a recovering attorney myself, the truth most founders don't know about the lawyer they're about to hand the most important deal of their life to is this.

The most common undergraduate major for U.S. law school applicants is Political Science. By a wide margin.

English, History, and Psychology fill out most of the rest. Business majors are the minority.

What this means in practice is that the typical M&A attorney's pre-law training was the study of governments, term papers, and human behavior.

All worthwhile fields.

None of them is negotiation. None of them is operating a business. None of them is sitting across a table from a buyer who has done a hundred of these and is about to do another.

Then come three years of law school, which teaches case analysis, statutory interpretation, and how to draft documents that survive scrutiny.

Also worthwhile. Also not negotiation, and also not business.

Then comes practice. The first three to seven years are spent learning to draft cleanly, manage process, and not get sued.

By the time an attorney is senior enough to lead the documentation of a sell-side deal, they have spent roughly fifteen years getting very good at one thing.

Producing documents that protect the client from legal liability.

That is exactly the skill the deal needs from them. It is not the skill the deal needs at the negotiating table.

This is not the attorney's fault.

Nothing in their training was designed to produce a negotiator. Nothing in their career path required them to ever run a business, build a customer base, manage a P&L, or close a sale.

They are legal specialists, and they are good at being legal specialists.

The misunderstanding sits on the seller's side, the same way it does with the banker.

The seller assumed the attorney's seat was the negotiation seat.

It isn't.

The M&A attorney's job is to translate the deal terms into documents that hold up.

To draft the purchase agreement, the disclosure schedules, the ancillaries. To run the diligence response. To preserve the client's legal position against every conceivable post-close claim.

A good M&A attorney does this beautifully.

The documents are tight. The reps and warranties are bounded. The indemnity is structured. The carve-outs survive.

What the M&A attorney is not doing is managing the relationship between the two parties so that the deal actually closes at the price the seller wants.

Those are not the same skill.

A negotiator manages tone, pace, leverage, and what the other side can say yes to without losing face.

A negotiator knows when to concede a small point to anchor a large one, when to slow down because the other side is tired, when the right next move is silence.

A negotiator reads the room.

A legal specialist optimizes the document.

The document is what shows up at signing. The room is what gets you to signing.

What I see, repeatedly, is experienced M&A attorneys at competent firms making the most basic deal-management mistakes.

Not because they are bad lawyers. They are not. Most of them are excellent at what they were trained for.

They make the mistakes because nothing in their training, their education, or their career path ever required them to think like an operator, a salesperson, or a negotiator.

A recent example. The seller's M&A attorney, an experienced M&A attorney from a respected firm, drafted the seller's opening response to the buyer's term sheet.

Sixty-nine pages. Onerous in tone.

Aggressive across nearly every meaningful term, not because the deal called for it, but because the attorney drafted from a posture of maximum legal protection rather than maximum probability of close.

That document was about to be sent to the buyer.

If it had gone, the buyer's reaction would have been predictable.

The deal team on the other side would have read the first ten pages, concluded the seller was unreasonable or poorly advised, and recalibrated.

The reasonable buyer's response to a sixty-nine-page hostile redline is not to negotiate harder.

It is to walk, or to stay at the table while quietly downgrading the price, the structure, and the urgency.

The attorney had done their job. They had protected the client legally.

What they had not done was protect the deal.

We pulled the document back, reduced it to twenty-two pages, softened the opening, sequenced the harder asks for later in the process, and sent a version designed to keep the buyer engaged while still protecting the seller's actual leverage points.

The deal moved forward. Had the original gone, it would not have.

This is not a story about a bad attorney.

It is a story about an attorney doing exactly what their training told them to do, in a seat that needed a different skill set.

And in twenty-plus years of doing this work, I have seen the same dynamic play out hundreds of times.

Different deals. Different firms. Different attorneys. Same mistake.

The hammer drop on a relationship that needed a handshake.

The aggressive indemnity ask in week one that the seller would happily have given up in week six for something more valuable.

The diligence response written to defend rather than to advance.

The clause fight that wins the clause and loses the room.

Every one of them, made by attorneys who are excellent at law and were never asked to be excellent at deals.

When the negotiation seat is filled by a legal specialist, three things happen.

The deal terms get sharper than the relationship can bear.

Buyers walk away from deals not because the price was wrong but because the process became hostile.

And the seller, watching from one step back, thinks the lawyer is fighting hard for them when the lawyer is actually killing the deal.

The pace gets wrong.

Lawyers are trained to be thorough, which on a deal often translates to being slow at exactly the moments when speed is the seller's leverage.

The buyer's enthusiasm is a perishable asset.

Most lawyers are not trained to feel the difference between a buyer who is engaged and a buyer who is cooling.

And the wrong battles get fought.

The clauses that make the document elegant are not always the clauses that determine the seller's net proceeds.

A negotiator picks four to win and lets forty go.

A legal specialist tends to push on all forty-four, because all forty-four affect the document, and the document is what they are trained to optimize.

None of this is malpractice.

The attorney is delivering exactly what they were hired for, they're just killing the deal in the process.

The seller is the one who didn't know they needed something else, and it cost them everything.

But hey. They'll have some really great agreements.

The negotiation seat on a sell-side deal is not a single discipline.

It is the integration of about a dozen of them, held by one person, applied in real time, while the deal is moving.

It requires legal fluency, enough to read the documents the attorney is drafting and know which terms are actually movable.

Operational experience, enough to understand what the buyer will find when they look under the hood and what story the seller can credibly tell about it.

Negotiation chops, the kind built across hundreds of deals, not theorized in a textbook.

Tax knowledge, deep enough to see how the structure being proposed today will land on the seller's net wire after close.

Deal structuring, the kind that knows when to offer a rollover, an earnout, a CVR, a stock swap, a hybrid.

Psychology, because deals are made and broken on what the other side can say yes to.

Comparable transaction data, real ones from real deals, not what an associate pulled off a database.

Financial and accounting depth, because the numbers in the model are the numbers that get fought over.

Buy-side experience, because you cannot negotiate against a buyer effectively if you have never been one.

And working knowledge of how PE firms, family offices, and institutional buyers actually think, because each one wants something different and signals it differently.

That set, in one person, is rare.

Most of the people who can do one or two of these well do not also do the others.

Most of the people who specialize in any one of these have built their entire career inside that one specialty, which is exactly why they are good at it and exactly why they cannot fill the seat.

The seat needs someone who has built across all of them.

That person is an M&A advisor with the operating background to sit in the room, the legal background to read the documents, and the deal volume to know what the buyer is going to do before the buyer does it.

If your deal team does not have someone like that, the deal can still close. Sometimes.

The number on the wire just isn't going to be what it could have been, and a meaningful percentage of the time, the deal won't close at all.

This is not a complaint about the legal profession. I came up in it.

Most M&A attorneys are excellent at the work they were trained to do, and most sell-side deals would be worse off without them.

The documentation is the floor. Without it, every concession the seller made at the table can be re-litigated by the buyer for years after close.

The point is structural, the same point as the banker piece.

The attorney's seat is the documentation seat. It is not the negotiation seat. It is not the strategy seat.

And no amount of seniority or pedigree at the firm changes which seat they are sitting in.

The training that produced the attorney did not include the skills that fill the other two seats.

That is not the attorney's failure. It is the seller's blind spot.

The seller who assumes "I hired a top firm, I'm covered" is making the same category error as the seller who assumes "I hired a top banker, I'm covered."

Both hires are necessary. Neither is sufficient.

The seat that protects the relationship, manages the negotiation cadence, holds the dozen disciplines the deal actually requires, and tells the attorney when to soften the sixty-nine-page redline is filled separately.

By someone built for it or it is not filled at all…most of the time, it is not filled at all.

Those are the skills and perspectives I bring into the deals I work.

So when you are building the team to sell your business, ask yourself one question.

Is the poli-sci major the right person to negotiate this, or do I need an exit advisor to handle that part of it for me?

— Roland

P.S. Coming soon: a closer look at the six things that get done in that seat before the LOIs land. None of them tactical. All of them worth significantly more than the fee.

Equity without control sounds amazing… until you understand the trade-offs.

A lot of people focus on upside when structuring deals. Very few think carefully about what they’re giving up in exchange.

Sometimes the right move is maximizing control. Sometimes it’s maximizing flexibility and cash flow.

Neither is automatically better. They’re just different bets.

The key is understanding the trade-offs before you structure the deal, not after.

Want to see the hidden trade-offs inside deal structures? Watch the video below.