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Begin by seasoning the filet mignon steaks with salt and freshly ground black pepper on both sides.
Heat the olive oil in a skillet over medium-high heat. Once hot, add the steaks and cook for 4-5 minutes on each side for medium-rare, or until desired doneness is reached. Remove from the skillet and let rest.
While the steaks are cooking, place the quartered potatoes in a large pot of salted water. Bring to a boil and cook until tender, about 15-20 minutes.
Drain the potatoes and return them to the pot. Add the heavy cream, unsalted butter, and truffle oil. Mash the potatoes until smooth and creamy. Season with salt and pepper to taste.
Serve the filet mignon steaks with a generous helping of the truffle oil mashed potatoes. Garnish with chopped chives.