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Boil the diced potatoes in salted water until fork tender. Drain and add back to the pot. Mash and stir in heavy cream, sour cream, minced garlic, Parmesan, salt, and pepper until smooth and creamy.
Mix together chopped parsley, cilantro, white onion, garlic, salt, pepper, red pepper flakes, oregano, olive oil, and red wine vinegar for the chimichurri. Set aside.
Let the steaks rest for 20 minutes. Cube and season with Worcestershire sauce, olive oil, salt, pepper, and steak seasoning. Heat garlic butter in a cast iron on medium-high heat. Add the steak bites and flip after 2 minutes. Toss for 1 additional minute and remove.
Immediately add seasoned shrimp to the same pan. Flip after 1 minute and cook until pink and golden.
Heat a skillet with olive oil over medium heat. Add asparagus and season with lemon juice, Parmesan, salt, pepper, and garlic powder. Cook until bright green and tender.
Plate the Parmesan mashed potatoes and top with steak bites and shrimp. Serve with asparagus and top everything generously with chimichurri.