In my latest contract, I negotiated in a kinda-piecemeal way. I was going to be hired by this big company, and got a fairly shitty contract: they never worked with contractors and got a contract from their parent company. It had unpassable clauses geared towards fucking me over, such as a clause that disabled you from handing over debts to collection agencies. The whole thing had in total about 20 problems I needed to address. I first negotiated the rate. Next, I wrote the CEO with the 16 least important problems. Once he parsed that and agreed to everything (because they weren't things important for him anyways) I wrote him with the outstanding big problems. He admitted to that all, after some argumentation. Finally, one issue was outstanding. I pressed on and he wrote the following to the middle manager: He beat me to a pulp, just agree to everything he wants. Finally, after the contract was signed, I made sure to remind the guys of some things that are implied by the local law that they would have to honor in the end. Doing things this way saved me a lot of trouble and won me a big fat wallet.