Why M&A Deals Fall Apart: Timing Risks in Buy-Side and Sell-Side Advisory

In M&A, every tick of the clock matters. Time doesn’t just kill momentum—it breeds doubt, reshuffles priorities, and opens the door for deals to fall apart.

There’s no worse feeling than seeing a transaction unravel at the 11th hour. At INS Capital Group, we’ve advised on over 1,500 deals totaling more than $5 billion in value, and we’ve seen one thing hold true across the board: timing is everything.

Here’s how delays can derail deals—from both the sell-side and buy-side perspectives—and how experienced M&A advisors keep transactions moving forward.

Sell-Side Advisory: When Doubt Creeps In

Selling a business is emotional. For many owners, it's the biggest financial event of their lives, with implications for their families, employees, clients, and legacy.

Even small delays can chip away at a seller’s confidence. We’ve seen it firsthand: when timelines slip, questions start to pile up.

Common Seller Concerns During Delays:

• Is the buyer having financing issues?

• Did they find something concerning in diligence?

• Are they planning to renegotiate terms?

• Should I be talking to other buyers?

What begins as a schedule shift can quickly snowball into full-blown hesitation. Sellers start second-guessing the decision to sell—or worse, they walk away entirely.

That’s why our sell-side advisory team keeps the process structured and moving. We proactively manage expectations, head off unnecessary slowdowns, and protect the seller’s emotional momentum from start to finish.

Buy-Side Advisory: When Confidence Falters

Buyers face a different kind of pressure. Many are betting big—taking on debt, integrating teams, and banking on future performance.

But when sellers are slow to provide diligence materials or attorneys drag negotiations due to inexperience with insurance-specific nuances, doubt begins to fester.

Top Buyer Red Flags During Delays:

• Are the financials accurate?

• Are they hiding a client loss or retention issue?

• Will this culture fit with ours long-term?

• Is the deal still worth pursuing?

One buyer we worked with waited weeks for updated financials—by the time they arrived, the buyer had shifted focus to another opportunity. Deals can’t afford to stall.

That’s why we design buy-side advisory engagements to move quickly and efficiently. We gather the right data early, ask the tough questions up front, and keep everyone aligned from first call to close.

Why Timing Breaks Deals—and How We Prevent It

Sometimes deals fall apart, and that’s okay. But often, with the right advisory team, the outcome could have been different.

At INS Capital Group, we help both buyers and sellers design a transaction structure that works for everyone—and keep communication flowing every step of the way. From preparing diligence materials to managing legal negotiations, we focus on momentum, clarity, and deal certainty.

Because when timing kills deals, smart preparation and steady leadership can bring them back to life.

Let’s Keep Your Deal on Track

Whether you're buying or selling, INS Capital Group brings unmatched experience, industry-specific insight, and practical execution to every transaction. Our team has closed over 1,500 successful deals, helping insurance businesses navigate growth, succession, and exit strategies with confidence.

Reach out to us at info@inscapitalgroup.com to learn how we can help you move forward—without losing time.