Perspectives
Lawyers Kill Deals Too: The Three Things That Actually End an Acquisition
Direct Answer
In my experience, deal fatigue, over-lawyering, and tire kicking kill more acquisitions than bad numbers ever do. All three trace back to the same root cause: poor qualification and poor process discipline at the front end, not malice, and not a deal that was doomed by its economics.
Deal Fatigue Is Not a Financing Problem
Most people assume a deal dies because the numbers stopped working: financing fell through, the multiple was wrong, or diligence surfaced something disqualifying. In my experience, a larger share of deals die from something quieter. The transaction drags for months. Legal spend keeps climbing. Progress stalls. Eventually someone on one side of the table does the math on sunk cost and simply walks, independent of whether the deal itself was ever a bad one.
"The longer a deal drags, the worse it gets. Deal fatigue is real. Even when both parties agreed to something early on, if dates slip and deadlines slip, human nature takes over. At some point one side goes back to the internal drawing board and decides they don't want to be part of it anymore."
Alex Lubyansky, The Truth About Buying a Business, Leo Landaverde M&A Podcast, 2026
I usually find deal fatigue to be symptomatic of a poor process on the front end, not malice and not fee-padding. Once poor alignment or poor qualification is the foundation a deal is built on, every missed date compounds. The fix is not more negotiation in the middle of a stalling deal. The fix is better qualification before the deal team is even hired.
The Working Capital Trigger: A Crisis of Truth
One specific and common trigger for deal fatigue deserves its own mention: sellers agreeing to a working capital target in the letter of intent without fully grasping what that number means in practice. Weeks or months later, when the real calculation lands, it can turn out to be a much larger holdback than the seller expected. I think of that moment as a crisis of truth. It is rarely a sign that anyone acted in bad faith. It is a sign that the number was not fully understood, or fully negotiated, when it was first agreed to.
That is precisely why the working capital mechanism belongs on the list of things worth getting right before the LOI is signed, not after. A dispute over a number both sides thought was settled is one of the more predictable ways a sound deal starts to drag.
Over-Lawyering: When Counsel Treats a Deal Like a Trial
The second killer sits closer to home for my own profession. Some attorneys jump in and fight every single provision on the front end, redline everything on principle, and then renege on points that were already agreed. The relationship sours so quickly that the deal ends before it ever had a real chance to develop.
"This is not litigation. This is transactional work. It's meant to be collaborative."
Alex Lubyansky, recorded voice memo, "Three Deal Killers," February 25, 2026
Litigation has a winner and a loser by design. M&A is meant to work differently. Both sides want to protect their own interests, and both sides want the deal to close. An attorney who cannot hold those two goals at once, and who instead approaches every provision as a fight to be won, is not protecting the client. They are burning the goodwill that a transaction needs to survive its own negotiation.
"A properly staged engagement can identify real issues early and resolve them without blowing up the relationship."
Alex Lubyansky, recorded voice memo, "Three Deal Killers," February 25, 2026
Tire Kicking: The Cost of Skipping Qualification
The third killer is the other side never having been serious in the first place. No real funding, no financing commitment, no genuine intent to close, just a process being used to extract free market information: customer lists, margins, proprietary processes, all disclosed in good faith by a seller who assumed the other side was qualified.
"I'm very slow to say yes. I'm very fast to say no. The discipline is qualify, qualify, qualify, qualify, qualify. Be patient. If after that process there's a good person on the other end, real desire, and what I think of as a calm EKG of the process, then it makes sense to keep going forward."
Alex Lubyansky, The Truth About Buying a Business, Leo Landaverde M&A Podcast, 2026
I tell clients I would rather decline a call than waste both sides' time. If there is no funding lined up, no defined target criteria, and no clear sense of what is actually being bought, it is too early to bring in a professional deal team at all. Qualifying aggressively before spending real money on due diligence protects everyone, including the buyer.
The Common Thread: Wrong People, Wrong Approach, Wrong Stage
All three killers share a root cause. Deal fatigue, over-lawyering, and tire kicking are not separate problems with separate fixes. They are what happens when the wrong people are in the deal, approaching it the wrong way, at the wrong stage of readiness. The best deals I have been part of share what I think of as disciplined momentum from start to finish. Not speed for its own sake. Momentum: steady, deliberate progress that does not stall long enough for fatigue to set in, does not invite unnecessary fights, and is never spent on a counterparty who was never going to close.
If You Are the Buyer
Qualify yourself before you qualify the seller. Have financing lined up, a defined target criteria, and a clear answer for why this business, before you ask a seller to open a data room. A buyer who cannot answer those questions in the first meeting is the buyer a disciplined seller will screen out, and rightly so.
If You Are the Seller
Screen for proof of funds, financing commitments, and track record before you disclose customer lists, margins, or proprietary processes. And understand the working capital target in the LOI before you agree to it. That single number is where a surprising number of otherwise sound deals start to unravel.
Where the Standard Guide Differs
Our guide to reasons business acquisitions fail walks through the legal and financial failure points: representations and warranties gaps, purchase price allocation, and diligence shortfalls. This page is a different lens on the same subject: my own read on the human and process causes that sit underneath many of those failures, drawn from years of watching deals stall and die before the paperwork ever became the problem.
Feeling the Drag on a Deal Right Now?
Alex Lubyansky leads every engagement, reviews every document, and leads negotiation and closing, with an associate supporting the work. If a transaction has stalled, or you are qualifying a counterparty before you engage, tell us where things stand.
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Frequently Asked Questions
Isn't it usually financing or diligence findings that kill a deal, not process?
Financing gaps and diligence findings do kill deals, but in my experience a larger share die from momentum loss: legal spend keeps climbing, dates slip, and eventually someone calculates the sunk cost and walks, independent of whether the underlying deal was sound.
How do I tell a serious buyer from a tire kicker early?
I ask about financing before I get on a call: is there a cash position, an SBA commitment, or a lender already engaged, and is there a defined target criteria. Sellers should ask the same questions before opening the data room, not after weeks of meetings.
What does over-lawyering actually look like in practice?
An attorney who fights every provision on the front end, redlines everything on principle, and reneges on points already agreed. M&A is transactional and collaborative work, not litigation, and treating it like litigation sours the relationship before the deal has a real chance.
Why does a working capital dispute cause deal fatigue specifically?
Sellers often agree to a working capital target in the LOI without fully grasping what the number means in practice. When the real calculation lands later and turns out to be a larger holdback than expected, it creates what I call a crisis of truth, and that moment is where a lot of otherwise sound deals start to drag.