What might you do in a typical first session with a student?

On the first day, I like to get a feel for the student's interests, areas in which they are confident, and those in which they feel they could use improvement. I generally ask that if students are working in a specific subject, that they bring examples of their work, and even teacher feedback on areas they need improvement. We work together to come up with a plan for the course of study, including types of assignments, amounts of homework, and time management.

How would you help a student get excited/engaged with a subject that they are struggling in?

I try to determine what actually does get a particular student engaged, and relate the assignments and exercises to those areas. This is particularly helpful in writing and reading, but in history and social studies as well. There is always material related to any interest, and this can be used to motivate and entertain as they make progress.