Some people (like me) have a problem asking for things. "Hesitation" is why Steve Blank suggests considering hiring a "sales closer" when you get to the customer validation stage (the stage where you are asking for the customer's money).
Regarding negotiation, low-balling and high-balling don't make sense in all situations. Especially if you are in a situation where the relationship between the negotiating opponents after the transaction is important.
You know, this is fascinating. I don't have a trouble closing - I have trouble cold calling and prospecting. In a negotiation, all you have to do is figure out the cost savings/additional revenue for your customer and find the highest acceptable price that's NPV positive for them. That's why healthcare sales people have all these fancy ROI models (built by third parties, wink wink) that they truck into sales meetings.
It's much easier mechanically and emotionally to deal with a negotiation; it's much harder to randomly call people and be cursed at/hung up on.
Regarding negotiation, low-balling and high-balling don't make sense in all situations. Especially if you are in a situation where the relationship between the negotiating opponents after the transaction is important.
I agree that there are circumstances where high/lowballing isn't appropriate: You don't go to a long-time customer and start negotiating for 10x the cost for the same service. But in the case of a new contract, that highballing will set the course for the following deals. You get more at the start, and the following deals will all follow a similar price-point.
Furthermore, by demanding high at the beginning, and then coming down, the person with whom you're negotiating will feel as though he/she "won" the negotiation, due to the huge concessions you made "He was asking a million dollars for a plan and we got him for $250k."
My point is you can highball and still have a solid post-negotiation business relationship.
I will definitely be checking out your book recommendations though.
Regarding negotiation, low-balling and high-balling don't make sense in all situations. Especially if you are in a situation where the relationship between the negotiating opponents after the transaction is important.
The best book for negotiation is "Bargaining for Advantage" http://bit.ly/HZwdW. "Getting to Yes" is also great: http://bit.ly/oHSCL.
Avoid any negotiation book with "Power" in the title. =)