I need to keep my contacts and calendar synced between my phone and Outlook. In order to do this, you need a third party software. The one I settled on is CompanionLink for Google.
Sync Palm Desktop, Microsoft Outlook, ACT!, Lotus Notes, GroupWise, and GoldMine with Google and your phone | CompanionLink
This syncs between your desktop Outlook and your Google contacts and calendar. Since your Droid syncs automatically with Google, everything ends up being in synch. The cost is $39.95 but it is worth it and does what it says it does.
CompanionLink also solved a problem I'd had since changing jobs to a company that uses Lotus Notes. I also bought a copy for the work computer and now also synch my Lotus Notes contacts and calendar with Google so I end up having both home computer, personal Droid, work computer and work blackberry all in sync. I just run CompanionLink on each computer a couple times a week or more often if I make a lot of changes anywhere.