For the Observation Training, your worker seems to work X tasks in a row when you manually click them to assign a task, where X is their "Observation Training" level.
So that automates their work if you assign it to them manually.
The self-starter training seems to take effect when you've not manually assigned a task to them. They will search for a single task to complete X times in a row, with a slight delay between each task, where X is equal to their "Self-Starter Training" level.
When their tasks are started automatically via this skill, the "Observation training" seems to be ignored.
So that automates their work if you assign it to them manually.
The self-starter training seems to take effect when you've not manually assigned a task to them. They will search for a single task to complete X times in a row, with a slight delay between each task, where X is equal to their "Self-Starter Training" level.
When their tasks are started automatically via this skill, the "Observation training" seems to be ignored.