iPhone 6s Plus calendar not properly syncing to Outlook 2007
Avoiding cloud in 2016 is strange, especially with Apple devices. However, you can set both devices to properly sync with Outlook 2007 using the software called Akruto. It works like Exchange server on your PC and allows syncing via Wi-Fi and over the Internet (without the cloud, through a 3-rd party DNS service).

Here's the link: http://www.akruto.com/sync-iphone-with-outlook/
What's good is that you don't have to install any apps on your boss' phone, everything will show up in the native calendar app.