If cutlets are thick, lay them between 2 sheets of wax paper and pound to 1/2-inch thickness using the flat side of a meat mallet or the bottom of a small, heavy skillet. Season with salt and pepper. Place 2 large sage leaves on top of each cutlet, then wrap 2 slices prosciutto crosswise around each cutlet, holding sage in place.

Heat 1 1/2 tablespoons olive oil in a large skillet over medium heat. Add 4 cutlets and cook until no longer pink in the center and the juices run clear, about 2 minutes per side. Transfer to a platter; tent with foil to keep warm. Repeat with remaining 1 1/2 tablespoons olive oil and remaining 4 cutlets.