Turn on the oven's broiler and place an oven rack 6 to 8 inches below the broiler element. Put the cast iron skillet on the rack to heat up with the oven.
Pat dry the steaks with paper towels. Sprinkle both sides of each steak with the salt and pepper.
Turn on the stove burner to high heat.
After the oven has preheated, reduce the oven temperature to 400 degrees F. Very carefully remove the hot cast iron skillet from the oven, using your thickest oven mitts or pads. Place the skillet on the stovetop burner.
Add the canola oil to the pan, it will sizzle.
Using long kitchen tongs, place the steaks on the hot pan.
Cook the steaks for 30 seconds on each side, then flip each steak over. Cook the steaks for an additional 30 seconds on the other side.
Using your oven mitts, carefully transfer the skillet with the steaks back in the oven. Turn off stove burner.
Roast the steaks in the oven for an additional 4 minutes. Carefully turn the steaks over and roast for another 4 minutes for medium-rare steak. If you prefer your steak closer to medium, add 2 minutes to the oven time.
Carefully remove the skillet from the oven. Place the steaks on a plate and cover with foil. Add the vegetables to the skillet and sprinkle with a pinch of salt and a pinch of black pepper and an additional tablespoon of oil. Place skillet back into the oven to cook the vegetables for 5 minutes.
Slice the steak diagonally into thin slices and arrange on a tortilla. Top with roasted vegetables and cilantro.