Preheat your oven to 450°F to ensure it's hot enough for roasting the vegetables evenly and developing caramelized edges.

On a large sheet pan, toss the cubed butternut squash with 2 tablespoons of olive oil, 1/2 teaspoon kosher salt, and ground black pepper. On a separate large baking sheet, toss the trimmed and halved Brussels sprouts with another 2 tablespoons of olive oil, 1/2 teaspoon kosher salt, and ground black pepper. Make sure to place the Brussels sprouts cut side down for the best caramelization. If needed, use extra sheet pans to prevent overcrowding.

Roast the Brussels sprouts for 15-18 minutes and the butternut squash for 22-25 minutes. Try not to flip the Brussels sprouts during roasting so their flat sides get nicely browned. I find this method gives a beautiful deep flavor and texture.

Remove both sheet pans from the oven and drizzle about 2 tablespoons of maple syrup over each batch of roasted vegetables. Toss to coat and flip the veggies for even browning. Return them to the oven and roast for an additional 5 to 8 minutes, keeping a close watch to prevent the maple syrup from burning.

Let the roasted vegetables cool slightly for a few minutes. In a large serving bowl, toss together the maple-glazed butternut squash and Brussels sprouts, dried cranberries, and pumpkin seeds. Finish with an extra drizzle of maple syrup to taste. I like to toss everything while the veggies are still a little warm so the cranberries plump up a bit.