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Preheat your oven to 325°F (165°C).
Heat the olive oil in a large oven-safe pot or Dutch oven over medium-high heat. Season the beef chuck roast with salt and pepper and sear it on all sides until browned. Remove the roast from the pot and set it aside.
In the same pot, add the chopped onion and cook for 3-4 minutes until softened. Add the minced garlic and cook for an additional 1 minute.
Stir in the beef broth, tomato paste, Worcestershire sauce, dried thyme, dried rosemary, and bay leaves. Bring to a simmer.
Return the beef roast to the pot, cover with a lid, and transfer it to the preheated oven.
Roast for 3-4 hours, or until the beef is fork-tender, adding the carrots and potatoes halfway through the cooking time.
While the roast is cooking, place the cubed potatoes in a large pot and cover with water. Bring to a boil and cook for 15-20 minutes or until the potatoes are tender.
Drain the potatoes and return them to the pot. Add the butter and milk, then mash until smooth. Season with salt and pepper to taste.
Once the pot roast is done, remove the roast and vegetables from the pot. Slice the roast and place it on a serving platter, surrounded by the carrots and potatoes.
Spoon some of the sauce over the beef and vegetables, then serve alongside the mashed potatoes.