I think that there is a better way for you to configure this to work smoothly for you.
The pre-smartphone method of getting calendar data onto a phone (or the Palm Pilot's of the past) was to "sync" the device with a computer using a physical cable. In this setup, the computer was the central repository of information. The reason for this was simply that old Palm devices simply didn't have an Internet connection of their own like modern smartphones do. Put simply, modern smartphones should rarely be "synched" with a computer any more to exchange data.
Instead, your iPhone is as capable as your computer to connect directly to your work server to exchange calendar data. You iPhone is also capable of having multiple email/server accounts (i.e a connection to iCloud, another to your work server, and possibly another to a Gmail or Yahoo mail account).
Therefore, the solution to your configuration problem is simple. Set up your iPhone in Mail/Calendar/Contacts settings to connect to your iCloud account, and then set up a second account to connect with your work's server (Exchange)? Your iPhone will then get calendar data right from the two source servers over the Internet (no more sync cables needed). The iPhone will then overlay the calendar data from both accounts. It will also allow you to show or hide each calendar separately, or simply see them both in the same calendar. When you create a calendar event from the iPhone, you can even choose which calendar it belongs to.
On your computer, you should do the same. Set up Outlook to get email/calendars/contacts directly from the iCloud server, and also from your work server.
Once you have your computer and your iPhone connecting directly with the servers then calendars, email, and contacts will always be current and "in sync" thereafter.