Pat dry the chuck roast. Season with salt and pepper on all sides.
In a large bowl, whisk together the olive oil, Worcestershire sauce, and Italian seasoning.
Place the seasoned raw chuck roast in the olive oil mixture and coat all sides.
Preheat a grill to medium-high heat. Alternatively, place a grill pan over medium-high heat.
Grill the chuck roast, turning it every five minutes, for twenty minutes. Continue cooking until the chuck roast reaches an internal temperature of 120°F for rare, 125°F for medium-rare, 135°F for medium. My 3-pound chuck roast took exactly 40 minutes to cook.
Transfer the chuck roast to a cutting board and let the meat rest for five minutes. Thinly slice it against the grain and serve.
Notes
Marinate the meat: If time allows, let the beef sit in the Worcestershire mixture for 20 minutes or up to overnight. If you go this route, I suggest adding a splash of balsamic vinegar, since the acid will help break down the roast.
Add some sweetness: Mix in 1 tablespoon of brown sugar with the sauce or baste the roast in BBQ sauce about 6-8 minutes before serving.
Seasoning ideas: Add 1-2 teaspoons of paprika or onion powder for extra flavor.
Storage: Let the leftover chuck roast cool, then keep it in an airtight container in the refrigerator for 3-4 days.