Preheat oven to 400 F. Lightly grease the foil-lined baking sheet with 1 tablespoon of olive oil.
Trim ends of Brussels sprouts and remove yellow leaves. Then, slice all Brussels sprouts in half.
In a medium bowl, combine halved Brussels sprouts, 2 tablespoons of olive oil, salt (to taste), and toss to combine.
Place onto a foil-lined baking sheet, cut side down, and roast in the oven at 400 F for about 20-25 minutes. During the last 5-10 minutes of roasting, turn them over for even browning.
In a medium bowl, combine cubed butternut squash, 1 tablespoon of olive oil, maple syrup, and cinnamon, and toss to mix.
Place butternut squash in a single layer on the baking sheet. Bake for 20-25 minutes, turning once half-way through baking, until softened.
Toast pecans in the preheated oven at 350 F for about 5 minutes until they get darker in color.
In a large bowl, combine roasted Brussels sprouts, roasted butternut squash, pecans, and cranberries, and mix to combine.
(OPTIONAL): For more sweetness, add 2 or 4 tablespoons of maple syrup, if desired, and toss with the salad ingredients to combine.
