One of the texts I've been teaching for a number of years in my classes is Anselm of Canterbury's On Freedom of Choice. It's a short dialogue between a teacher and a student, with the teacher clearly as a stand-in for Anselm. On Freedom of Choice is the second dialogue in a trilogy of works, intended originally to aid the monks under his charge with their study of Scripture.
The other two works in that trilogy are also dialogues, the first one being On Truth, and the third, the significantly longer On The Fall of the Devil. If you're interested, you can get all three in a single affordable volume, ably translated by Thomas Williams and published by Hackett.
Anselm summarizes what On Freedom Of Choice is about in the preface to the three dialogues:
[W]hat freedom of choice is, whether a person always has it, and how many distinctions of freedom there are with respect to having or not having uprightnessof-will. . . In this treatise I show only the natural strength of the will for keeping the uprightness which it has received; I do not show how in order to keep uprightness the will needs the accompaniment of grace.This summer, knowing I'd be teaching the text again, I decided it was about time to create some core concept videos as aids for my students. Here are those seven videos:
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