Grind the black peppercorns on the coarsest setting of your pepper mill or crush them with a mortar and pestle. Alternatively, place them in a cheesecloth and smash them with a heavy skillet. Generously season the steak on both sides with kosher salt and crushed peppercorns, pressing down gently to help the mixture stick.
Heat 2 tablespoons of olive oil in a Dutch oven over medium-high heat until shimmering. Carefully place the steaks into the pot and sear for about 3 minutes on one side, pressing lightly to keep the pepper crust intact. Flip the steak, add thyme sprigs and 2 tablespoons of butter 🧈, and cook for another 2–3 minutes, frequently spooning the melted butter over the top. Remove the steak and set it aside to rest. Strain and reserve the fat left in the pot.
Wipe out any large chunks of pepper from the Dutch oven. Pour the reserved fat back in and sauté the finely chopped shallot over medium heat for 2 minutes until softened. Add the chopped garlic and thyme leaves, stirring until fragrant (about 1 minute). Sprinkle in the flour and whisk until combined, cooking for another 2 minutes until slightly golden.
Deglaze the pot with cognac, whisking until smooth. Slowly pour in the beef broth 🐄 while continuing to whisk. Add the baby potatoes and bring everything to a gentle simmer. Cook for 15 minutes, or until the potatoes are tender and the soup has thickened.
Lower the heat and stir in heavy cream and Worcestershire sauce, mixing until fully incorporated. Allow the soup to heat through for about 5 minutes.
While the soup simmers, heat ½ cup olive oil in a small saucepan over medium heat. Add the sliced shallots and cook, stirring occasionally, until golden brown (about 4–5 minutes). Remove using a slotted spoon and transfer to a paper towel-lined plate.
Cut the rested steak into cubes. Ladle the soup into bowls and top with steak cubes and fried shallots. Garnish with extra pepper, Parmesan, or lemon zest if desired.