The method I would use to do this is:
1. First add the Sort... button to your Quick Access Toolbar. You will find it in the list of All Commands when you 'Customize the Quick Access Toolbar'

2. Modify two styles to set the Outline levels by modifying the Paragraph Outline level attributes for the style.
Tit needs an Outline level of Level 1
num needs an Outline level of Level 2

3. Change the View to Outline View (on the View ribbon tab).
4. On the Outlining ribbon tab, set Show Level to Level 2
5. Select the block of headings you want to sort (these are all second level entries under the Very Short Answer Questions heading) and the click on the Sort button you added in step 1. This opens a dialog and you can tell it to sort on Descending order

6. Repeat step 5 for the second level headings under the Descriptive Answer Questions heading.

Then change back to the Print Layout view and check what has happened to your file.

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Andrew Lockton
Chrysalis Design, Melbourne Australia