While the tomatoes and shallots are cooking, take the steaks out of the fridge to bring them up to room temperature. Place the potatoes in a large pot and add enough cold water to cover by two inches. Place the potatoes over high heat and bring them to a boil, add some salt, and cook for 10-12 minutes, until tender -- you should be able to pierce them easily with a knife. Drain the potatoes and let them cool enough so that you can handle them. Once cool, cut the potatoes into half-inch slices and set aside.
Once the potatoes are cooking, start the steaks: Preheat a stainless steel sauté pan or cast iron skillet over medium-high heat until it is screaming hot. While the skillet is heating, pour about a tablespoon of EVOO over each steak and season on both sides with salt. Press a generous amount of coarsely ground black pepper into one side of the steaks. Arrange the steaks, pepper side down, in the screaming hot skillet and do not move them. Cook for 2-3 minutes per side for medium-rare or until desired doneness. Transfer the steaks to a plate and cover loosely with aluminum foil to rest for about 5 minutes.
For the Au Poivre dressing, combine the Dijon mustard, Worcestershire sauce, sherry vinegar, salt and pepper in a bowl. Whisk remaining 1/4 cup of EVOO in a slow, steady stream. Place a few sliced potatoes on the plate along with the steaks and a handful of watercress and pour the Au Poivre dressing over everything.