Cut prosciutto strips into two halves lengthways, ending up with 12 strips.
Place each prosciutto strip on a cutting board at a 45 degree angle. Place one of the sage leaves in the center then an asparagus spear on top of the meat, perpendicular to it. Wrap and roll the asparagus spear in a spiral like a candy cane stripe up to the top of the spear, allowing the tip to still show. Continue with the others and refrigerate for 10 minutes. I found this helps the prosciutto adhere and stay on.
Heat the olive oil in a large skillet and sauté wrapped asparagus spears for 1-2 minutes on each side until prosciutto is brown and crispy. Season with freshly ground black pepper and serve.
1. Wash asparagus and with one hand on the center of the spear and the other on the end, slightly bend until the tough end breaks. Discard the ends.