To say that Larissa Weems was a workaholic was an understatement. The woman was always working. Always filling out paperwork, or teaching students, or making and managing public appearances and relationships with the normies in Jericho. Whatever it was, the Principal of Nevermore devoted her every waking moment to it - after all, that was the attention her position demanded. But that didn't mean it was easy on Larissa.
With her workaholic tendencies came her determination to not take a break. After all, the entirety of Nevermore relied on Larissa. What time did she have for a break? But after a while, the work begins to grind her down and burn her out. Not that she'll admit it. But you've noticed.
You're a teacher at Nevermore, and you're closer to Larissa than most others; you've known her for longer, and she trusts you like no other. So when the signs of her fatigue begin to show themselves, you're quick to act. It'll take some convincing, but you're the only one she'll listen to.
At the end of the school day, you make your way to Larissa; she had retreated to her office after teaching, of course, to continue her work. You place three gentle knocks on the door, then wait. A tired sounding, "Come in," rings out from within the office, signalling your permission to enter.