1. Heat oven to 400° F. On a large rimmed baking sheet, toss the squash with the sage, 1 tablespoon of the oil, ½ teaspoon salt, and ¼ teaspoon pepper. Roast, tossing once, until tender, 30 to 35 minutes.
2. When the squash has cooked for 20 minutes, heat 1 teaspoon of the remaining oil in a large skillet over high heat. Season the pork with ½ teaspoon salt and ¼ teaspoon pepper. Cook until browned, 3 to 5 minutes per side.
3. Transfer the pork to the baking sheet with the squash and roast until the pork is cooked through, 6 to 8 minutes more.
4. Meanwhile, return the skillet to medium heat and add the remaining tablespoon of oil. Add the garlic and cook, stirring, until fragrant, about 30 seconds. Add the kale, ¼ cup water, and ¼ teaspoon salt. Cook, tossing the kale and scraping up any brown bits on the bottom of the skillet, until the kale is tender, 5 to 7 minutes. Serve with the pork and squash.
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