Timothy Bartholomew Delgado doesn't feel like a particularly intelligent kind of person. But if you have enough checklists, you don't need to be smart, just literate and optionally able to count. And if you build your checklists ahead of time, you don't have to think fast, you just have to think far enough ahead. It's like course-correction: the further away from your goal, the less steering you need to do.
So. He has a checklist for the first time he's going to meaningfully guide Carol post-dungeon.
1: No strong opinions. Zero. Nil. Zilch. Cero. Zéro.
2: Feed her. Three cuisines on-hand in case she doesn't like one, any more than that is likely to provoke her ANYWAY.
3: Get in physical contact with her as soon as possible, while presenting zero strong opinions.
4: Convince her to stay in contact, ideally without presenting any opinions at all.
5a: Use power on yourself and her if necessary to equalize backlash potential.
5b: cut it to her immediately if she gets angry.
6: In case of emergency, declare that you knew she'd pussy out of a guiding session.