A lot of it just takes experience and practice. There are a few good books available. "The Knack" by Norm Brodsky is very good, and the source of the "You don't

A lot of it just takes experience and practice. There are a few good books available. "The Knack" by Norm Brodsky is very good, and the source of the "You don't ask, you don't get quote". The chapter on negotiation is small, but the rest of the book contains tons of invaluable insight. Many books stress formulating a "win-win" situation, and "expanding the pie" so that "everybody wins". This is good in theory, but rare in practice. In almost every negotiation someone will have the upper hand. I think the best approach is to listen carefully and try to understand the other party's need. This may not necessarily be more money. Maybe they want to build a long term relationship. Maybe they are willing to lower the price if you pay upfront, or provide a larger deposit, because they prefer the cashflow now. Maybe business is slow. You never know. You also need to know your best alternative. If you have options, it is easy to walk away from the deal. If you are informed, you will know the true market price. You can't be afraid to walk away. I think it just takes time and practice to develop this mentality, and the opposing side can typically sense if you're serious about it or not. A strategy that has worked well for me is to just say something like "I really like your product/service, and would love to start using it, but the price is a bit out of my range. Is there any way you can give me a discount?". It doesn't work for everything, but I've been surprised how often it does work. The worst thing that happens is that they say no. Remember, you have to ask!