Dear Insider,

In the high-stakes world of mergers and acquisitions, it’s not the flashy headlines or handshake moments that make or break a deal—it’s the missteps that happen before the proverbial ink dries on your Letter of Intent (LOI). If you’re looking to torpedo your own deal, here are five proven ways to do just that:

1. Rush to Sign a Pressured LOI Without Understanding What’s Inside It

The biggest trap sellers fall into? Resigning to a timeline set by a buyer. Many firm leaders rush to sign just because a buyer has set a deadline for them and they’re nervous to lose an interested buyer.

Signing too soon, under pressure or otherwise, without clarity on what’s negotiable and what’s not, can lead to months of friction and—worse—seller’s remorse. If the buyer reached out to you, and now they’re pushing you. Remember this: the LOI sets the tone for the entire deal. Make sure you know what is entailed in it and what you’re getting out of it.

An LOI isn't just a placeholder—it's a milestone that sets the key terms like price, deal structure, exclusivity, timelines, and even earnouts. Price and deal structure are identified as “non-binding” in the LOI. This means that they are subject to adjustment based on due diligence. If in due diligence both sides agree that profit as measured by adjusted EBITDA is lower than what was used to develop the LOI price, then a downward adjustment in price is a fair response. But looking to renegotiate the price and other key terms after the LOI is signed and absent a due diligence finding would be considered re-trading the deal and can lead to a broken deal. Consider the LOI the most important milestone on the path to a successful closing.

2. Save the Real Negotiations for After the LOI

Want to tank your own deal? Go ahead and “punt” the tough conversations until after the LOI is signed. Leave out the details around cultural fit, leadership transition, valuation mechanics, compensation structure, and post-close roles for your key people.

By deferring these critical issues, you’re not saving time—you’re setting a trap for future conflict. Once the LOI is signed, your leverage as a seller drops significantly, emotions run hotter, and the deal becomes that much more tenuous if you both don’t actually agree. Conflict delayed is conflict multiplied.

3. Go It Alone Against an Experienced Buyer

M&A might sound like any other business deal, but the sides are almost never balanced—buyers often come to the table with far more experience than first-time sellers.

If you think you can figure it out as you go, or rely on your general counsel to “figure it out” you’re already behind. You will miss out on getting the right structure, tax planning, payment terms, and more.

The worst part is, you won’t realize how much you’ve left on the table until the clock’s ticking and the legal bills are mounting, or worse yet, after the deal is done and you can’t go back.

4. Skip the Early Deep Dives—Deal With It During Due Diligence

Another classic blunder: assume that due diligence is when you’ll hash out the real deal. Wrong.

Due diligence should be confirmatory, any adjustments to the deal should reflect the same structure applied to updates in the business. If you’re still negotiating key deal terms during diligence—whether it’s around compensation structure, deal structure, or financial assumptions of your firm—you’ve set yourself up for a drawn-out process that drains energy, trust, and bank accounts.

Deals fall apart here more often than you think. You should never take the “Catch Me If You Can” approach. Get your major concerns out up front.

5. Assume the Deal Will Work Itself Out—Without a Trusted M&A Advisor

The “we’re both good people, this will work out” mindset is comforting—and completely wrong.

No one would start a major building project without reviewing the blueprints. Why would you approach an M&A deal—the largest financial event of your career—without an expert by your side? A seasoned M&A advisor helps you surface hidden issues, navigate technical complexities, and make sure your LOI and final agreement reflect what you actually want.

Bottom Line: If You Want Your Deal to Fail… Don’t Plan, Don’t Ask for Help, and Sign That LOI Blindly

The LOI isn’t just a formality—it’s the blueprint of your company’s future. If you rush it, ignore it, or walk in without expert guidance, you’re not just risking a bad deal—you’re risking your legacy.

At PSMJ, we’ve guided hundreds of architecture and engineering firm leaders through this exact minefield. The firms that win are the ones who pause, plan, and make the LOI the deal—not an afterthought.

Want to avoid these mistakes? Take your time, get smart advice, and remember: in M&A, what you don’t do can hurt you just as much as what you do.

Have you faced this kind of deadline from another party? Are you a buyer curious about how you can dial in your process to avoid these mistakes? Let us know with a comment below. All comments are reviewed by PSMJ's Growth and Transition Advisory Team, and are not shared publicly unless you request them to be.

This content is for informational purposes only, you should not construe any such information or other material as legal, tax, investment, or financial advice.