Preheat oven to 400°F (200°C).
Using a sharp knife, cut a pocket into the thick side of each chicken breast, being careful not to cut all the way through.
Season the chicken breasts inside and out with salt, pepper, garlic powder, and paprika.
Stuff each pocket with one slice of cheese and 3-4 asparagus spears.
Secure the openings with 2-3 toothpicks to prevent cheese from leaking.
Heat olive oil in a large oven-safe skillet over medium-high heat.
Sear the chicken for 3-4 minutes per side until golden brown.
Transfer the skillet to the preheated oven and bake for 10-12 minutes or until the internal temperature reaches 165°F (74°C).
Let the chicken rest for 5 minutes before removing toothpicks and serving.