Why is it that almost every time I travel, I can get a significantly better price than what’s offered on a hotel, rental car and, in some cases, airline Web site?

Just happened again today as I set hotel, air and car reservations for a San Diego and a San Francisco trip. I calculate that a little bit of social engineering on the phone saved me $400 in cumulative expenditures. Yes….$400!

This was done by bypassing the Web applications and going directly to the reservation agent. In one case I went directly to the hotel. I’ve been doing this for years and it works again and again and again.

So what’s clear to me as a voracious user of Web applications is that with a little bit of effort, I can always get a better price. The purveyors of these Web sites are teaching me (and my bride…who is a master at getting a better price) that a little bit of effort — and a direct human connection to an expensive customer service person — will save me money. (Note: it’s not just travel sites….I do the same thing with ecommerce sites in general and get stuff tossed in to the deal often).

Again….they’re teaching, instructing and rewarding me to cajole, ask, plead, tell sob stories, and call back again to "see if there is a better deal".  It makes me wonder if all these companies really know that they’re essentially helping me drive down their gross margins by increasing their costs and reducing their top-line revenue.

I suspect this is due to a reluctance on the part of these companies to expose too much in the way of their best deals online so that competitors could easily harvest their site and thus match or better them on price. But in the end, they’re ensuring their customers (and their best ones at that) learn to hammer on them to uncover those good deals. Gotta be a better way.