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1
Add the Parmesan to the bowl of a food processor. Pulse until the Parmesan is extremely finely ground (sort of like the pre-grated Parmesan you'd buy at the supermarket). Dump into a bowl, then transfer 2 tablespoons to a smaller bowl for later.
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2
Add the anchovies to the food processor (no need to wash it out first), then process until the anchovies are minced, scraping down the sides of the bowl as needed. Add the lemon juice, black pepper, and olive oil. Process until smooth. Add the larger bowl's worth of Parmesan. Process again until smooth. It should be creamy, almost like mayonnaise.
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3
Season the steak lightly with salt and pepper, then add to a plastic bag. Add 1/3 cup of the Caesar dressing to the bag and close, making it as airtight as possible. (The rest of the marinade will become our salad dressing.) Massage the bag for a minute, so the marinade gets all over the steak, then stick it in the fridge. (You can also add the steak and marinade to a baking dish or bowl, massage, then cover.) Marinate for at least 4 hours or up to 12.
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4
When you're ready to cook the steak, heat a grill pan (or cast-iron skillet) on the stove over medium-high heat. Remove the steak from the bag and use an offset spatula or the back of a butter knife to remove as much marinade as possible from the steak (if there's too much, it can burn in the pan and prevent the steak from properly browning). Throw away the marinade. Lightly season the steak with salt and pepper. Add the canola oil to the hot pan, then add the steak. Cook it for about 5 minutes per side for medium-rare (or in the 130u00b0 to 135u00b0F range on an instant-read thermometer).
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5
Let the steak rest for a few minutes while you toss the romaine and remaining dressing together in a big bowl. (I use all the dressing, but you do you.)
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6
Slice the steak as thinly as possible against the grain. Arrange it on top of the dressed salad. Serve with the lemon cheeks, remaining ground Parmesan, and more ground pepper.
