1. Heat 1 tablespoon oil in a large skillet over medium-high heat. Season the steaks with 1/2 teaspoon each salt and pepper. Cook steaks for 4–6 minutes per side for medium-rare or to desired doneness. Let rest 5 minutes before slicing.
2. Wipe out skillet, and heat remaining 1 tablespoon oil over medium heat. Add the fennel and remaining 1/4 teaspoon each salt and pepper. Cook, stirring occasionally, 5–6 minutes or until slightly browned and just tender.
3. Stir in olives and jalapeño, and cook for 1 minute. Sprinkle with fennel fronds, and serve alongside the sliced steak.