Place the two naan on a cookie sheet lined with parchment paper. Combine olive oil and minced garlic in a large bowl and brush the mixture on the naan. Reserve the garlic oil for the arugula salad topping.
Bake the naan for 6 minutes to crisp them up a bit. Remove from oven and spread them with the hummus.
Layer the olives, Piquilllo peppers and dates evenly over the naan. Sprinkle the goat cheese in top and divide the prosciutto over the cheese.
Bake the naan for 8-10 minutes.
While the naan is baking, add the balsamic vinegar to the oil and garlic remaining in the large bowl and toss in the arugula.
Remove naan from oven and pile the arugula on them. Drizzle each one with balsamic glaze. Cut the flatbreads into 4 strips each and serve warm.