Pat the steak dry and, if not already thin-sliced, freeze slightly (10–15 minutes) to make thin slicing easier; then cut across the grain into very thin strips.
Heat 1 tablespoon olive oil in a large skillet over medium-high heat. Add the sliced onion and peppers, season with a pinch of salt and pepper, and sauté, stirring often, until softened and beginning to caramelize, about 6–8 minutes. Remove vegetables to a bowl and set aside.
Wipe the skillet with a paper towel if needed, add the remaining 1 tablespoon olive oil, and bring the pan back to high heat. Spread the steak strips in an even layer and let them sear undisturbed for 1 minute to develop color, then stir and continue cooking until just browned, about 2–3 more minutes total.
Push the beef to one side of the skillet. Add the mushrooms and garlic to the empty side and cook until the mushrooms release their juices and begin to brown, about 3 minutes. Stir everything together.
Pour in the beef broth and Worcestershire sauce to deglaze the pan, scraping up any browned bits. Return the cooked peppers and onions to the skillet and toss to combine. Taste and adjust seasoning with the remaining salt and pepper.
Reduce heat to low, arrange the provolone slices evenly over the meat and vegetables, then cover the skillet for 1–2 minutes to allow the cheese to melt gently.
Once the cheese is melty, remove the skillet from the heat and let the pan rest for 2–3 minutes before serving — this helps the juices settle and makes it easier to scoop.
Serve the cheesesteak skillet family-style (with whole-grain rolls on the side if desired) or spoon onto plates for a lower-carb option.