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Place steak on a plate or platter. Drizzle olive oil on steak and rub to coat both sides. Allow steak to come to room temperature about 45 minutes.
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Heat grill to medium-high heat (about 450°F).
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Season steak with salt and pepper. Coat corn with olive oil and season with salt and pepper.
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Grill steak until desired doneness, about 4 minutes on each side for medium-rare.
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Grill corn until tender and turning occasionally, about 20 minutes. Cut kernels off cobb. Discard cobb.
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Allow steak to rest for 10 minutes after grilling. Thinly slice diagonally and across the grain.
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Place squash, bell pepper, asparagus, and green onions in a large casserole dish. Drizzle with olive oil and sprinkle with salt and pepper. Toss to coat vegetables with oil.
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Place vegetables on grill in a single layer (The steak should be resting and corn still grilling). Close lid and grill for about 3 to 5 minutes, until bottom side has grill marks.
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Turn vegetables over. Close lid and grill for another 3 to 5 minutes, until bottom side has grill marks and vegetables have softened. Cut asparagus and onions into bite-sized pieces.
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Brush cut side of romaine lettuce with olive oil. Place cut side down on the grill. Grill for about 2 minutes, until grill marks are on the lettuce. Cut or tear lettuce into 1-inch strips.
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Divide lettuce equally in 3 bowls or on plates. Top with equal amounts of vegetables, tomatoes, and steak. Serve with fresh herb dressing.