Heat oven to 425° F. Toss squash cubes in just enough olive oil to coat, and season with salt and pepper
Spread on a baking sheet (lined with parchment for easier cleanup), leaving space between the cubes. Roast in the oven until tender and caramelized, about 40 minutes, tossing with a spatula every 10-15 minutes.
Toast the almonds on a baking sheet in the same oven until they start to smell nutty, tossing once, about 10 minutes. Let cool.
n a large mixing bowl, toss the kale with the almonds, cheddar and squash. Season to taste with lemon juice and olive oil (approximately 1 tablespoon lemon juice and 2 tablespoons olive oil). Season to taste with salt and pepper.
Divide salad between two plates or shallow bowls. Garnish with shaved pecorino cheese, if desired, and serve.