I’m pretty sure there are a few different ways to earn the achievements:
• Failing at a dialogue option.
• Going through all of the correct dialogue options.
• Clicking on everything in the main menu. (Spoon, Chair, text that puts prison bars on the screen)

Dialogue order to complete the game.
Option 2
Option 2
Option 1
Option 3
Option 2
Option 3
Option 3
Option 1
Option 3
Option 3
Option 1
Option 1
Option 2
Option 3
Option 3

Please let me know if you obtained achievements in any other way like closing the game or picking wrong answers! I’ll add them to this guide for others to see, thanks!