If you are in a situation where you have a Custom Field on the Worker Object that has to be updated depending on clear parameters, like if they participate in Employee Stock Purchase Plans (ESPP), then a Studio Boomerang can help solve the problem of automating this.
Using a custom report that shows the current value and the proposed value as a data source the Studio Integration can run on a set schedule to update this info in the tenant automatically.
The key is to have a clear definition of when it should be updated.