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Drizzle 3 tablespoons of olive oil over both sides of the mushrooms. Sprinkle the mushrooms with salt and pepper. Drizzle olive oil on grill pan to prevent mushrooms from sticking. Grill until the mushrooms are heated through and tender, about 5 minutes per side.
Place 1 hot grilled mushroom gill side up on each of 4 plates. Sprinkle with more salt and pepper. Spoon the tomato salad atop the mushrooms, drizzle with extra-virgin olive oil to finish, about 1 tablespoon and serve.