1. Slice prosciutto in halves horizontally.
2. Trim bottoms of asparagus spears.
3. Working one at a time, wrap halved prosciutto slice on each asparagus spear at an angle, covering the entire length of the spear. Repeat with remaining prosciutto and asparagus.
4. Heat olive oil in a large skillet over medium-high heat. Add asparagus and cook until prosciutto is crisp and asparagus is tender, about 2-3 minutes.
5. Serve immediately.