Preheat your oven to 375°F (190°C).
Prepare the stuffing by mixing cream cheese, Parmesan, garlic powder, onion powder, salt, and pepper in a bowl.
Add the trimmed asparagus to the cheese mixture and gently fold it in until combined.
Using a sharp knife, create a pocket in each chicken breast by slicing horizontally but not all the way through.
Stuff each chicken breast with the asparagus and cheese mixture, ensuring they are well-filled without overflowing.
Secure the pocket with toothpicks or kitchen twine to keep the filling inside while baking.
Heat olive oil in a large ovenproof skillet over medium-high heat, then sear the chicken breasts for 3-4 minutes on each side until golden brown.
Transfer the skillet to the preheated oven and bake for 25-30 minutes or until the internal temperature reaches 165°F (75°C).
Let the chicken rest for 5 minutes before serving. Garnish with parsley if desired.