Garlic / Broccoli - If prepping right before cooking, get oven heating before continuing with prep. Prep as directed and combine. (Can be done up to 4 days ahead)
Make chimichurri sauce - In a blender or a food processor, combine cilantro, garlic, shallot, capers, red wine vinegar, lime juice, salt and cooking oil (the first portion for steak). Add more some more oil if it’s too thick. Season to taste with salt or more lime juice. (Can be done up to 4 days ahead)
Steak - Season generously with salt and pepper. Tenderize with a fork. (Can be done up to 1 day ahead) Take steak out of fridge 30 minutes before cooking.
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Toss garlic and broccoli with cooking oil (the portion for the broccoli), chili powder and cumin. Season with some salt and pepper. Place on a sheet pan and roast in oven until tender, 18 to 22 minutes, stirring halfway through cooking.
Heat grill pan or skillet over medium-high heat. Brush with cooking oil (the second portion for the steak). Place steak onto hot pan. Sear steak for ~4 minutes on each side. Lower heat to medium, cover with foil, and cook for another 2 to 3 minutes for medium-rare; another 4 to 7 minutes for medium; 8 to 10 minutes for well-done.
Remove steak from heat, cover in foil and let rest for at least 10 minutes before slicing across the grain (i.e. perpendicular to the fibers).
Toss roasted broccoli with lemon juice.
Serve chimichurri over steak and broccoli on the side. Enjoy!