Preheat the oven to 400°F. Cut the top off the head of garlic, drizzle with 1 tablespoon olive oil, wrap in foil, and roast for 30 minutes until soft.
While the garlic roasts, combine the ground turkey, breadcrumbs, egg, Parmesan, Italian seasoning, red pepper flakes, salt, and black pepper in a bowl. Mix until just combined. Divide the mixture into four equal portions and shape into mini loaves. Place them on a baking sheet and bake for 25 minutes.
Peel and cube the potatoes. Boil them in salted water for 15 minutes until tender, then drain. Squeeze the roasted garlic cloves into the potatoes. Add the butter and milk, then mash until smooth. Season with salt and pepper to taste.
Spoon the mashed potatoes over the baked mini meatloaves. Return to the oven for 5 minutes to warm through. Sprinkle with chopped parsley before serving.