Three factors further complicate the upgrade process.


1. Upgrades are unforgiving when it comes to customization.
Enterprise software is the one-size-fits-all suit that you tailor to be a 38-short on one side for your manufacturing group and a 54-portly on the other side for your salespeople?along with some extra pockets from other vendors stitched onto the suit. Don’t expect the vendors to touch that suit with a 10-foot needle when it comes time to upgrade. It’s up to you to redo the customizations and connections with third-party software on the new version. Customizations that need to be carried over from one version of enterprise software to the next are the biggest technology headache and ROI killer that CIOs face in upgrades.


2. The move to Internet architecture changes everything for the IT staff and end users.
All the big vendors have moved their software from a client/server architecture, in which PC-based software accesses a central server through a company’s network, to an Internet architecture, in which a Web server joins the mix and the software is accessed through the public Internet and a Web browser. It’s new turf for both IT staffers and end users. Staffers suddenly must see the Internet as the platform for the company’s most important applications. End users must learn different ways to access programs and absorb all the business process changes that come when they can collaborate with people outside the company. These added capabilities are a good thing, of course. But the planning and change management that is required make them a migraine minefield. (For what one vendor is doing to respond to this problem, see "SAP’s Big Freeze," Page 56.)


3. The vendor’s "desupport date" frustrates a CIO’s best-laid plans.
The desupport date is the ticking time bomb of enterprise software upgrades. A vendor says, We won’t support version XYZ of our software after this date. Technology changes and customers?especially new ones?demand fresh functionality. Vendors can’t afford to support six different versions of their software simultaneously.

But CIOs object to what they call surprise desupport announcements that most major vendors have made in the past few years. They say they aren’t getting enough time to do one upgrade before a vendor announces a desupport date for an older version.

Nextel’s LeFave has been through this. "When the vendor comes to you and says the product is at the end of its life cycle, that’s code for saying, I’m going to be putting my maintenance and development resources on a new product, and you’re not going to get anything unless you pay for it yourself," he says. Even if the vendor continues to support old software versions, it will shift the bulk of its people and resources to new versions so that finding someone knowledgeable about your old version becomes like trying to find a department store salesperson on red-tag clearance day.