"Every time someone in my Outlook contacts list changes jobs or gets a new phone number I have to make changes to my contacts. In some cases, I lose track of contacts because they didn't let me know they changed career paths. Is there any tool to I can use to update my contacts automatically?"
Unless you're telepathic, you'll have a hard time keeping up with anyone who doesn't tell you when their contact information changes. Those people who drop off your radar can be hard to track down later, although occasionally you can find them via sites like LinkedIn, Facebook, and MySpace. While it won't cover 100% of your contacts, Plaxo is the free solution I use to keep up with the changes in my own contacts list. Plaxo has an add-on for Outlook, Outlook Express, Thunderbird, and Mac Address Book, making it a viable solution for almost any personal information manager.
For each contact you have who also maintains a free Plaxo account, you get automatic updates anytime they change their address, job title, email or phone numbers. Of the hundreds of people in my own contacts list, about 30% of them use Plaxo. These also seem to be the most active members of my contacts list, so maybe there's a connection between frequent change and the use of Plaxo.
To automate your contact updates, first go get a free Plaxo account. You may be surprised how many of your contacts are also using Plaxo. Once you've signed up, you can optionally contact those contacts in your address book who aren't currently using Plaxo and attempt to convince them to sign up. Keep in mind that many people won't accept - as I've mentioned in the past, it took me years to sign up for Plaxo. Now I'm a convert.