Do so by opening the app shaped like a blue W. This wikiHow teaches you how to insert a check box in a Microsoft Word document. In the Home tab, click the small down-arrow next to the Bullets button. Step 1: In Word document, select the list that you want to insert a checkbox.If you know how to locate a check mark but the question is about putting it in a box, use a text box in Pages so that you can have text on top of text (or anything else).