A board's duty to maximize shareholder value is an expected value calculation. A $100B offer with a 75% chance of closing is valued at $75B, making an $80B offer with 100% certainty more attractive. Boards weigh financing and regulatory risks heavily against the headline price.

In a large deal, Milliken discovered post-close that the seller's team had prioritized their diligence questions over other bidders. This preferential treatment, earned through a respectful and strategic approach, created a significant information advantage during the competitive process.

In a competitive M&A process where the target is reluctant, a marginal price increase may not work. A winning strategy can be to 'overpay' significantly. This makes the offer financially indefensible for the board to reject and immediately ends the bidding process, guaranteeing the acquisition.

To maintain momentum, Cisco makes critical integration decisions—like site strategy or system consolidation—during diligence, not after close. These decisions are embedded into the final deal commitment materials, preventing post-close paralysis and emotional debates, allowing teams to execute immediately.

Many M&A teams focus solely on closing the deal, a critical execution task. The best acquirers succeed by designing a parallel process where integration planning and value creation strategies are developed simultaneously with due diligence, ensuring post-close success.

Instead of focusing on transactional details, Milliken's M&A lead connects with founders on an emotional level. By understanding their ultimate vision, he frames the acquisition as the fastest path to achieving their dream, a question that has proven highly compelling and effective in closing deals.

To maintain pricing discipline, Fairfax has a strict M&A rule: it never participates in auctions or bidding wars. Once an offer is made, it's final. This strategy prevents them from overpaying and ensures they only acquire companies at prices that offer attractive future returns.

Instead of lowballing, Bending Spoons makes a very fair, near-final offer immediately. This tactic builds a reputation for seriousness, similar to Warren Buffett's approach. It avoids lengthy back-and-forth and signals that they are not a buyer that can be "pushed around," creating an efficient and powerful deal-making process.

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.