Try these directions on the Practice Area at the beginning of the Discussion Board first. 

1. With your Word document open, use Ctrl/Command A to select all of the text and Ctrl/Command C to copy the document.
   
   
2. In Learn@UW-Stout, click on Start a New Thread:
   
   
3. Click on the three dots on the right side of the toolbar to reveal more options:

4. Click and hold the pull down arrow in the second row, circled in red below:

5. Choose Paste from Word, as shown by the red arrow. A pop-up window will appear where you can paste the Word doc (Ctrl/Command V to paste). Then click Update.
   
   
6. Your post should appear in the document window.  Look over the formatting to see if it is exactly as you want it.  Make changes and then click Post -- .
   
   Open your post on the Discussion Board to double-check the document.  To make a change, click Edit, make the changes, and Save.