What should we focus on when storyboarding? Application interaction or user goals?

I'd like to know in what context do we build "Jobs-To-Be-Done" stories. We are going to build a portal/system for teachers to report certain incidents (currently they are not using any).

For example, I'm using the method of "When..., I want to..., So I can...".

The more I create the stories, the most confused I get. Do I write the stories in the point of view when they are interacting with the portal/system, or do I write the stories in the point of view on their normal day-to-day basis.

Stories interacting with the portal: When I login to the system, I want to be able to see ..., so that I can ...

OR

Stories on a normal day to day basis: When I want to monitor a situation, I want to be able to ..., so that I can...

or are both of them the same things?

===EDIT=== I'm also in a dilemma because currently, teachers are not monitoring any situation. But due to a change in school processes, they are now required to monitor the situation. So it's not like I can say "When I want to monitor a situation, I want to see who are the parties involved, so that I can keep track", because, it's not something that they "want to do", but it's a "rule" that is required of them. Not sure if I'm thinking too deep into this.

How then, do I go about writing JTBD?