Preheat your oven to 425°F and line a baking sheet with parchment or lightly oil it.

Spread the diced butternut squash in a single layer on the prepared sheet. Drizzle with olive oil, season with salt and pepper, and toss to coat evenly.

Roast for 25–30 minutes, stirring halfway through, until the squash is tender and lightly browned. Set aside.

Season the chicken thighs all over with ¾ teaspoon salt and ½ teaspoon pepper.

Melt the butter in a large Dutch oven over medium heat. Working in batches if needed, add the chicken in a single layer and cook until golden brown and cooked through (internal temp 165°F), about 4–5 minutes per side. Transfer to a plate and set aside.

Add the diced shallot to the pot and cook, stirring occasionally, until softened, about 2–3 minutes. Stir in the garlic, thyme, and sage and cook until fragrant, about 1 minute.

Whisk in the flour and cook, stirring constantly, until lightly browned, about 1 minute.

Pour in the chicken stock and Dijon mustard, scraping up any browned bits from the bottom. Stir in the orzo and season with a pinch of salt and pepper.

Bring the mixture to a boil, then reduce the heat to a simmer. Cook, stirring occasionally, until the orzo is tender, about 6 minutes.

Stir in the kale, Parmesan, and heavy cream. Continue cooking until the kale has wilted, about 3 minutes.

Gently fold in the roasted butternut squash. Taste and adjust seasoning with salt and pepper. Return the cooked chicken to the pot, nestling it into the orzo. Serve immediately.