Heat the olive oil in a large pot over medium heat. Add the pork cubes and brown them on all sides for about 6 minutes.
Add the onion, carrots, and garlic to the pot. Cook for 4 minutes until the onion starts to soften.
Sprinkle the flour over the meat and vegetables. Stir well for 1 minute so the flour coats everything and begins to form a base for the gravy.
Slowly pour in the chicken broth while stirring to avoid lumps. Bring the mixture to a simmer.
Add the butternut squash, sage, salt, and pepper. Stir to combine.
Cover the pot and simmer on low heat for 45 minutes, stirring once or twice, until the pork is tender and the gravy has thickened.