calendar syncing between Outlook and iCloud

I have an iPhone 3GS, iCloud / Lion on my Desktop, and Outlook at work. There are various weird issues going on:

1) If I enter something into the calendar in Outlook, it shows up on my phone, but not on my desktop (or via icloud.com). I can obviously get round this by changing what calendar it is saved under on my phone, ie. changing it to iCloud, but this is a pain.

2) If I add something to my phone or desktop, or via icloud.com, it doesn't show up in Outlook.

Any ideas how I can get all of these things to sync properly?