I often talk to parents about their frustration and helplessness with their students' struggles to produce detailed, illustrated and analytical writing that most high schools and colleges currently demand.
Many public and private high schools over the last twenty years have developed comprehensive rhetorical and process based writing programs to help students have something specific and yet debatable to say. Still, parents can also play a role from the earliest grades on to help their students develop analytical and critical thinking and writing skills about culture, images and texts.
One of my more recent modes of engagement with young clients to get them involved in critical thinking and writing is this NYT online every Monday exercise called "What's Going On in This Picture?" Instead of the live conversation that follows, I turn this into a jump-off for spontaneous writing. This activity brings together a student's ability to observe, bring their understanding of multiple contexts to bear, and then write a 5-12 sentence paragraph, depending on their age. In that paragraph they first make an "interpretive claim" about the picture as their topic sentence, then provide evidence and examples to develop it. Try this with your kids at home. (In your spare time, right?) It might also spark all kinds of open-ended conversations about life and the world.