Wash and prepare all your ingredients. Rinse the Brussels sprouts under cold water and trim the ends. Cut them in half. Peel the butternut squash and cut it into 1-inch cubes. Mince the garlic cloves and set aside.
Heat 1 tablespoon of olive oil in a large skillet over medium heat. Add the halved Brussels sprouts, season with salt and pepper, and sauté for about 8-10 minutes until golden brown and tender. Remove from skillet and set aside.
Preheat your oven to 400°F. Spread the diced butternut squash on a baking sheet, drizzle with 1 tablespoon of olive oil, season with salt and pepper, and roast for about 25-30 minutes until tender and slightly caramelized.
In the same skillet, add 2 tablespoons of butter over medium-high heat. Once melted, add the steak and cook for about 4-5 minutes on each side for medium-rare. Remove from skillet and let rest.
In the same skillet, lower the heat and add the minced garlic. Sauté for about 1 minute until fragrant, then add the remaining 2 tablespoons of butter and stir until melted.
Slice the steak against the grain into thin strips. In a large serving dish, combine the Brussels sprouts, roasted butternut squash, and sliced steak. Drizzle the garlic butter sauce over the top and toss gently to combine. Garnish with fresh herbs if desired.