Prepare the Steak Medallions: Pat the steak medallions dry with paper towels on all sides. In a small bowl, mix the salt, coarse black pepper, and garlic powder. Season the medallions generously on all sides and let them rest at room temperature for 20–30 minutes.
Start the Mashed Potatoes: Place the peeled, chunked potatoes in a pot and cover with cold water. Add 1.5 tsp kosher salt. Bring to a boil over medium-high heat, then cook for 12–18 minutes until very tender.
Sear the Steak Medallions: Heat a large skillet over medium-high heat. Add the olive oil and 2 tbsp unsalted butter. Sear the medallions for 3–4 minutes on each side, adding garlic and herbs midway through cooking.
Baste and Rest the Steak: Baste the tops of the medallions with the butter and juices during the last minute of cooking. Transfer and let rest for 8–10 minutes.
Make the Garlic Pepper Pan Sauce: Deglaze the pan with red wine, then add beef broth and let it reduce by half. Whisk in cold butter until the sauce is silky.
Finish the Buttery Mashed Potatoes: Drain the potatoes, mash them with butter and warm milk, and season to taste.
Plate the Dish: Place mashed potatoes on each plate, add steak medallions, and drizzle with pan sauce. Garnish before serving.
Serve immediately with any remaining sauce on the side.
Notes
Allow the steak to rest after cooking for more tenderness. Use room temperature ingredients for fluffy mashed potatoes.