Here are the steps to check why your task list wasn't triggered as expected.
Navigate to Tasks > Task Lists Settings click on Manage on the task list in question.
1. Check “Applies to” and search for the employee in question on the list:

If an employee is not there, amend the task list conditions that will capture the missing employee and population (but won't capture other irrelevant employees).
There are cases where an employee used to meet conditions and the task list was triggered, but when the employee is no longer in the “Applies to” of the task list, scheduled tasks will be removed for the employee by Bob.
2. Check the task list owner, if owner is not an Admin, make sure that the task list owner has permissions to at least view the task list anchor event and permissions on “Applies to” condition fields.
If there are missing permissions, amend the owner’s permissions or change the owner.
3. Navigate to the employee’s profile to confirm that the anchor event date is not empty and when it was changed in Bob (use the employee’s audit).
If the anchor event was inserted with a delay of more than 7 days - task lists won’t be triggered, i.e if the termination date is 01/09, but the termination date was only added on 10/09, then the Offboarding/Termination task list won’t be triggered.
4. If the event date exists, go back to task list and search for the earliest triggering schedule. For example:
5. If earliest triggering is in the future, Bob will collect the task list to be triggered 24 hours before the first task needs to be launched out from Bob. The task list will be displayed in Manage Tasks and recorded in the Task list report only 24 hours before (not earlier than that).
6. If earliest triggering is today, please wait up to 6 hours when Bob goes and collect task list to be triggered (check also task list Timing time zone).

7. If all tasks on the task list are triggered in the past and the event date was typed in bob after the effective date (for instance, if the termination date was 06/03 but was changed in bob on 07/03 then the task list won't be triggered).
To avoid that, if you want to trigger the task list for past cases, then at least one of the tasks should be On event date (not before).