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Season chicken with ¾ teaspoon salt and ½ teaspoon pepper.
Melt butter in a Dutch oven over medium heat. Working in batches, add chicken to the Dutch oven in a single layer and cook until golden brown and cooked through, reaching an internal temperature of 165 degrees F, about 4-5 minutes per side; set aside.
Add shallot, and cook, stirring occasionally, until tender, about 2-3 minutes. Stir in garlic, thyme and sage until fragrant, about 1 minute.
Whisk in flour until lightly browned, about 1 minute.
Stir in chicken stock and Dijon, scraping any browned bits from the bottom of the Dutch oven. Stir in orzo; season with salt and pepper, to taste.
Bring to a boil; reduce heat and simmer, stirring occasionally, until pasta is cooked through, about 6 minutes. Stir in kale, Parmesan and heavy cream until the kale has wilted, about 3 minutes.
Stir in roasted butternut squash; season with salt and pepper, to taste. Return chicken to the Dutch oven.
Serve immediately.
Preheat oven to 425 degrees F. Lightly oil a baking sheet or coat with nonstick spray.
Place butternut squash in a single layer onto the prepared baking sheet. Stir in olive oil; season with salt and pepper, to taste. Gently toss to combine.
Place into oven and bake for 25-30 minutes, or until butternut squash is tender, stirring at halftime.