This is a head scratcher. Until Word 2013, you could go into your Save options and select Prompt for Document Properties. If you have set up your Microsoft Office to connect to SharePoint, you may already have noticed that SharePoint may require you to add additional properties before allowing you to save. Unfortunately, Word 2013 doesn’t have the ability to force that prompting. You can [first activate under Options and then] select the Developer tab on the Ribbon and activate the Document Properties panel.
There appears to be some way to connect the Document Properties to a template based on SharePoint (under either your /Documents or /Documents/Forms folder) but it’s looking for an Infopath .xsn file, not the Template.dotx file that’s there. In order to enable less kludgy saving of data from the desktop to SharePoint, the metadata piece will need to be linked.
Update: If you go to your OneDrive, click the Library tab and choose Library Settings, you can then see your content types. Click on Document under Content Types and it will appear with a list of settings. Under Settings, click on Document Information Panel settings. You can choose the create a new document template option and it will open up a form editor that creates an .xsn file for the expanded document properties.
This creates an .xsn file that you can then save on SharePoint under /personal/your_username/documents/forms. Then you return to Word, PowerPoint, or Excel, click the Developer tab, click Document Panel (modify) and enter the address of your .xsn file. Mine is http://SharePoint_Site/personal/dwhelan/documents/forms/dw-documents.xsn. That will enable the dropdown menu below the URL to show “Custom Properties” and you can save that as part of the file.
Now to figure out how to link it together!
Update: Duh. You need to make the changes in your local or SharePoint template and save it. Once you do, it will automatically pull the .xsn panel from SharePoint and enable you to customize your file with the appropriate fields. When I load my template from SharePoint, it automatically pops up. This is what mine looks like in Microsoft Word – ugly, but functional.