Best method, userform.
Here is another link: Create & Employ a Userform by Greg Maxey

Ask your questions in the UserForm. Checking a box can give you another page in a multi-page userform with more questions. Upon Clicking OK, use the responses to populate the document.

This is something that can be done, but you are stretching Word. A good vba coder can do it easily. However, it is not something that is intuitive for the ordinary user. Access is designed for doing things like this but has a steep learning curve.