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Preheat a grill to medium high heat.
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Prepare chimichurri. Remove cilantro and parsley leaves from stems. Finely chop the herbs with sharp knife or in a food processor. Transfer to a medium bowl. Add the garlic, shallots, lemon juice, vinegar, salt, and pepper flakes. Stir well. Cover and set aside until ready to serve.
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Wash the cauliflower well. Trim away green leaves and the very bottom of the stem, but no more than 1/4". Keeping the stem intact will hold the steaks together. Place the cauliflower on cutting board, stem side down. Starting in the center, cut down through the center. Make cuts 1- to 1 1/2-inches out from the center to make the "steaks". Repeat with the other cauliflower. You should get between 4 to 6 good-sized steaks. This might vary if the florets fall away from the stem. (It's frustrating, so I always buy more cauliflower than I think I'll need just in case.)
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Rub or brush each cauliflower steak with a little olive oil and season with salt and pepper. Oil the grill grates using a wad of paper towels dipped in a little oil and held with tongs.
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Place the steaks on the grill and cook on each side for 3-4 minutes. When turning the steaks, do so very carefully so they don't fall apart. I find it's easier to firmly grasp the stem with the tongs and gently lift and turn it over.
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Transfer the steaks to plates and top with chimichurri. Serve warm.