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It's just a bug with the UI, you have to complete the computer game to then talk to the boss and open the elevator. For some reason the UI changes when you interact with the boss even if he doesn't talk to you.

Hi everyone! This is Daniel, one of the devs for this game. Due to the time limit for turning in the project. Some sneaky little bugs got into our game (oh no!). These include:

1. Losing on the 4th day makes it so you can't play the meeting game again
2. Losing on the final day makes you get softlocked
3. On Day 1, talking to the boss before the computer task messes with the UI and elevator, preventing progess

Encountering these bugs sadly means that you'll have to restart the game from the pause menu

We'll fix these problems if we are allowed to, but for now practice the hidden art of not losing.