Start by preheating your oven to 375°F. Pat the chicken breasts dry and rub them with olive oil. Mix salt, pepper, onion powder, garlic powder, and paprika, then coat the chicken evenly with the seasoning.
In a bowl, combine chopped broccoli, cream cheese, cheddar, minced garlic, salt, and pepper. Stir until the mixture is creamy and well combined. I always taste a tiny bit to adjust the seasoning—it makes a big difference.
Cut a pocket into each chicken breast, being careful not to slice all the way through. Stuff each breast generously with the broccoli cheese mixture. Use toothpicks if necessary to hold the filling inside.
Heat a cast iron skillet over medium heat with a bit of olive oil. Sear the chicken breasts for 2–3 minutes on each side until lightly browned. This step locks in flavor and keeps the chicken juicy.
Transfer the skillet with seared chicken to the preheated oven. Bake for 20–25 minutes, or until the internal temperature reaches 165°F. The cheese should be melted and bubbly. Let the chicken rest for a few minutes before serving.