Your date list doesn't have a column for employee names. Does that mean the list of employees is static?
The Date List contains duplicate records. Should they be ignored or do you want a sheet for each record
Is the colour of the names in your output documents pertinent to what you want? If so, what does the colour mean?
It appears to me that the simplest solution for this is to use Microsoft Access. Is there a reason you are trying to do this with Word?
Finally, if staying in Word, I would suggest you work through the tutorial pinned at the top of this forum
https://www.msofficeforums.com/mail-...-tutorial.html as this looks like it aligns reasonably closely with what you are trying to do.