Calculate the materiality of each point. Much of the time sink of negotiations is unfortunately spent on elements that don’t really matter — things that will not materialize, or if they do won’t have a major impact. Legal and tax counsel is always critical and highly valuable, but can sometimes also be the tail that wags the dog. Once I was leading an important negotiation where we debated at length with legal and tax experts over “edge scenarios” that might negatively impact us. This went on for two days until I took a step back to actually calculate what our largest dollar exposure could be. It turned out to be less than the cost of of preparing a structure to avoid it and likely less than the professional and legal fees we had already accumulated thinking about it! Do the math and calculate how material a point is — then determine if it is really worth fighting for in the bigger picture.