Why Do Deals Fail Before They Even Start?

Why Do Deals Fail Before They Even Start?

By Katya Fisher

It’s easy to assume that when deals fall apart, it’s because of market shifts, tough legal terms, or bad timing. But most deals start dying long before any of those factors come into play. The root causes are almost always human: misaligned expectations, personality clashes, ego, and poor communication.

Misaligned Expectations

Two parties come to the table thinking they’re aligned.

On the surface, everything looks fine—they like the deal, the numbers make sense, and the timeline feels reasonable. But dig a little deeper, and you’ll find they’re often operating on completely different assumptions. One side might be focused on speed and momentum, while the other is wired for caution and precision. One party expects to continue running their business independently post-close; the other is planning for full integration on day one. These differences aren’t inherently problematic—but when they go unspoken, they become landmines.

Everyone assumes things will “work themselves out.” They don’t.

Personality Clashes

Deals are negotiated and executed by people, not spreadsheets.

And people come with pride, fear, and the need to feel in control. When those dynamics aren’t managed, even a strategically sound deal can get derailed. This is especially true when egos start driving the conversation. If no one is willing to step back and say, “This isn’t about me—it’s about the outcome,” the deal starts to wobble.

Add in power plays, unspoken insecurities, or territorial behavior, and the whole thing can fall apart fast.

Ego Over Outcome

There’s a quiet but critical shift that happens in some negotiations: the goal moves from getting the deal done to winning the deal. That shift is fatal.

Suddenly, small asks turn into hills to die on. Concessions that should have been routine become personal. Every point becomes a referendum on respect or control. Progress slows. Trust erodes.

The deal—often a good one—bleeds out slowly while everyone digs in.

Communication Breakdowns

Finally, the most common deal-killer is the simplest: bad communication.

And not just what’s said, but what’s left unsaid. Unvoiced assumptions. Vague expectations. Unacknowledged timelines. These gaps often don’t feel urgent in the moment, but they create fault lines.

And when stress hits, those small cracks become unbridgeable divides.

So, What Do You Do About It?

This is the kind of risk we built Aracor to handle.

Not just the technical analysis of documents or flagging of missing terms—but the deeper, structural issues that derail deals before they’re even properly underway. Aracor helps dealmakers see the real dynamics early: where expectations are out of sync, where silence is hiding risk, and where momentum is starting to falter. It gives teams the tools to push for clarity before assumptions calcify into conflict.

Because great deals don’t just depend on terms or price.

They depend on clarity, trust, and early alignment—the things that rarely show up in the redlines, but always determine the outcome. Connect with Katya.

Ready to take dealmaking to the next level?

Built by dealmakers, for dealmakers. Whether you're closing your next transaction or reviewing hundreds of docs under pressure, Aracor gives you speed, accuracy, and confidence—at scale.

Sign up for a demo.

About Us

Aracor is the AI-powered deal intelligence platform built for the pace and pressure of modern transactions. From diligence, ti negotiation, closing to exit,  Aracor equips legal and deal teams with the tools to move faster, surface critical insights, and reduce risk—without sacrificing control.  

Founded by a chief legal officer, a Dealmaker of the Year, and a global tech investor and entrepreuner, Aracor combines deep legal expertise with cutting-edge AI to streamline the entire deal lifecycle and deliver the competitive edge today’s high-stakes transactions demand. Whether conducting preliminary evaluations, reviewing contracts, flagging obligations, managing due diligence, or tracking post-signing commitments, Aracor transforms deal friction into deal flow.  

Designed for family offices, in-house legal teams, venture capital and private equity firms, Aracor helps professionals identify risks earlier, accelerate review processes, and stay in control of even the most complex deals. Aracor empowers teams to close smarter, faster, and with greater confidence.  

With speed, security, and insight at its core, Aracor is redefining how deals get done.

On this page