Use Word 2010's Numbering feature in tables and make it automatically number multiple table columns vertically. This way, each cell in each column will be placed under the correct number.

How to Put Numbers Vertically in Word Documents. While it is more practical and convenient to use Microsoft Excel for documents with numbered fields, it is also possible in Word.

In Word you can number table rows just as you do paragraphs, and if you move a row then the numbering updates automatically. Word will automatically number the cells in the table.