Brush steaks with oil and season liberally with salt and pepper. Grill to desired doneness (160°F for medium). While steaks are grilling, sauté shallots, garlic, chile flakes, and anchovy in olive oil over medium heat until softened and aromatic. Add tomatoes and cook for 20 minutes over low heat. Spoon liberal amounts of the tomato confit over grilled steaks and serve immediately.