Unpredictability Does Not Win Deals

The first time I saw this deal go sideways, it did not happen in a boardroom or over a redline. It happened in a moment that felt small.

We were midway through a process. The business was strong, the buyer was serious, and the management team had done the hard work to present a clean, consistent story. Everyone knew what the company was, what it was not, and why it mattered. Momentum was building.

Then the seller got spooked.

A call with the buyer had been a little cooler than usual. A question about churn landed awkwardly. The founder took it personally and decided, overnight, that the right move was to “take back control.” The next day, the tone changed. The messaging shifted. The posture hardened. Suddenly there were new conditions. The economics were “revisited.” Previously agreed points were reopened, not because the facts had changed, but because the mood had.

From the seller’s perspective, it was a power move. A way to show strength. A way to keep the buyer guessing.From the buyer’s perspective, it was the beginning of the end.

Because buyers do not fear tough negotiation. They expect it. What they cannot tolerate is unpredictability. In software M&A, the buyer is underwriting far more than revenue and retention. They are underwriting the credibility of the people sitting across the table. They are asking themselves, quietly: will this team behave rationally under pressure, or will we be dragged through chaos from here to close, and then after close?

When sellers become erratic, the buyer’s mental model flips. The asset stops looking like an opportunity and starts looking like a risk. And once that switch happens, everything slows down. Diligence deepens. Internal conversations get harder. The buyer begins protecting themselves, not just in the docs, but in their willingness to push for approval.

What makes this pattern frustrating is how common it is, and how avoidable it is.

The irony is that sellers get the edge they want through the opposite behaviour.Consistency is leverage. A disciplined narrative that does not change. A calm posture that does not wobble with every call. Transparency early, so nothing ugly appears late. And a structured process that creates real buyer tension, where competition does the heavy lifting and keeps everyone honest.If you want a deal to close on strong terms, do not try to be unpredictable. Be credible. Buyers stretch for sellers they trust. And trust is built the same way every time: clear messaging, steady process, and adults in the room from start to finish.