Ask the workflow consultant to enter deadline monitoring into the activity on which you need this check and put 3 days as the limit from the day the activity has been initiated. .
To identify the agent to whom the mail shoud go as him to use some rule to find the superior . I think you can use rule 168 to identify the superior.
Custom workflow seems to be the answer. We have done the same wherein the leave application has to go to the immediate superior and if not approved in 7 days the same has to go to the next superior and therein after 7 days to go to the hr administrator.
The Wofkflow consultant will have to create the same. You will have to let him know how to identify the Immediate superior and next superior.
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