this seems dumb. you should always be maximizing no matter what level you are at. I'm reading a book on negotiating right now. The author makes a point that if you can negotiate 2k lower price it doesnt matter if the contract is 10MM or 100k, its still a 2k bottom line cost savings for your company. Same logic applies to money at all levels IMO.
It really depends on the scale that you are operating at. Once you start getting to certain points a $2,000 savings on the bottom line can be a rounding error and the time required to get that savings might have been better invested elsewhere. Pragmatically you need to remember that you have two things to optimize: money and time. Let's put it this way, who would you prefer to hire: person A who spent a week in negotiations and saved the company $2,000 on a contract, or person B who overpaid by $2,000 but closed the deal the first day and closed a second deal worth $2M by the end of the week?