To experience what new users encounter, ask the instructor who teachers the Introduction to Computers class if you can sit with students during a lab session. It is optimal to watch them while they learn to surf the Web, but watching any laboratory activity is useful for this exercise.

From an unobtrusive distance, watch one of the class members for 20 minutes. Maintain a neutral disposition at all times during your observation. List the top three problems that the user encountered and how they reacted to them.

This is an empathy-building exercise. Without empathy for the user, none of the techniques presented in this book is very effective.
The answers to this question will vary, depending on the lesson. More important than the actual problem is the manner of tone your student uses to record the incident. Words like “dumb” are warning signs that the student will have trouble with embracing user-centered methodology.
If there aren’t a lot of introductory sections being offered at your college (or if the instructor pales at the thought of having a large group of observers in the room), there are lots of alternative opportunities for observation at places like community centers or youth groups that offer computer classes.