You can insert a series of conditional fields (noting the reference to MERGEFIELD
{IF { MERGEFIELD "Request_Staff_Person" } = "Minnie Mouse" "Mickey Mouse"}{IF { MERGEFIELD "Request_Staff_Person" } = "Donald Duck" "Another Mouse"}etc
Use CTRL+F9 for each bracket pair { } and no spaces between the items; but frankly it might be better if you modified the data source to include the appropriate bosses.

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Graham Mayor - MS MVP (Word) (2002-2019)
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Thank you so much, I'll give this a try. Unfortunately, the managers' names are not in our database, and I don't believe there are plans to add them, the best I could do was to modify the source by adding the available field for the secretaries.

One additional question, is there a limit to how many if statements I can run together?

This did no work for me.

There is no limit to the number of IF Fields you can have, so long as they are independent (not nested, one inside the other).