> I think one of my biggest challenges is learning how to progressively disclose the level of complexity about the task and not bombard them. But also providing them with clear measurable goals for them to work on.

I agree with this. It's not an easy problem to tackle. You could manage other people for years and still not have a good handle on it, but hopefully it gets easier to feel over time, as to what's too much for them. How well you know the other person is also a factor in this.