For managers with large pipelines to review, asking three core questions can quickly get to the heart of a deal's health: Why do they need to buy? Why won't they buy? And why do they need to buy now?

During diligence, speak directly with the target's largest clients. You may uncover deal-breaking risks, such as a client who will leave post-acquisition because their internal rules prevent reliance on a single, monopolistic supplier, a fact you would otherwise miss.

Progress uses an "orange flag" system to identify diligence issues that, while not immediate deal-breakers, are serious enough to warrant a discussion with the CEO and CFO. This allows for an early decision to walk away before expending significant resources.

By the time a strategic acquirer enters due diligence, the desire to do the deal is already high. The process's primary purpose is not to hunt for deal-breakers but to confirm key assumptions and, more importantly, to gather the necessary data to build a robust and successful integration plan.

Trying to perfectly integrate everything before closing is an anti-pattern for serial acquirers as it kills deal flow. Instead, classify tasks into "must-do pre-close" (e.g., banking, payroll) and "can-do post-close" (e.g., vendor consolidation) to maintain speed and focus.

Instead of a linear process, treat M&A as a spiral. Constantly revisit and adjust deal structure, diligence findings, and integration plans. A discovery in one area (e.g., diligence) should trigger a reassessment of the others (e.g., deal structure), ensuring a cohesive and de-risked outcome.

Dealmakers often fear that bringing integration teams into diligence early will kill deals. The proper framing is that their job is to make the deal better by stress-testing assumptions and arming dealmakers with the right questions, leading to a better outcome.

Instead of a bloated checklist, Milliken focused its diligence for its largest acquisition on four critical questions tied directly to the investment thesis. This allowed a team of 100+ to prioritize efforts, "fail fast," and avoid analysis paralysis on the path to a go/no-go decision.

Instead of only relying on post-mortems, proactive M&A teams conduct "pre-mortems" before a deal closes. This involves bringing leaders together to brainstorm everything that could possibly go wrong, mentally preparing the team and identifying major risks and mitigation strategies early.