Trim the broccoli and cut it into bite-sized florets, including portions of the stem if tender. If any part of the stem appears tough or woody, remove and discard it to ensure even cooking.

Place a large cast-iron or heavy-bottomed skillet over medium-high heat. Add the olive oil and arrange the broccoli florets in a single layer, avoiding excessive overlap. It is not necessary to preheat the oil.

Allow the broccoli to cook undisturbed for approximately 5 minutes to encourage browning on the underside. Avoid stirring during this stage to develop color and texture.

Check one or two florets—if they appear golden brown, sprinkle the broccoli evenly with kosher salt and black pepper. Gently stir or flip to allow the remaining sides to brown lightly.

Evenly scatter the shredded cheddar cheese across the broccoli. Some cheese may fall onto the skillet surface, which is desirable for creating crisp edges. Continue cooking for an additional 5 minutes without stirring. The cheese on top will melt quickly, while the pieces that contact the skillet will become crisp and golden.

Once the cheese has melted and browned, remove from heat. If any cheese adheres to the skillet, carefully release it using a metal spatula. Serve immediately as a warm side dish to accompany main entrées such as chicken, steak, or pasta.