I just posted these resources in response to another thread, and thought they might be helpful here as well:
The books of Elizabeth Wissner Gross. Two for parents, one for kids but you may want to read it first
What High Schools Don't Tell You and Other Parents Don't Want You to Know,
What Colleges Don't Tell You, and Other Parents Don't Want You to Know,
Write Your College Essay in Less Than a Day.

These books help parents and kids see that there are many activities helpful to kids when looking forward to college, and many approaches to essay about them.

In addition to being an author, Elizabeth Wissner Gross is an educational strategist coaching for college admissions.