About 20 minutes before grilling, remove the steaks from the refrigerator and let sit, covered, at room temperature. Heat your grill to high. Brush the steaks on both sides with oil and season liberally with salt and pepper.Place the steaks on the grill and cook until golden brown and slightly charred, 4 to 5 minutes.Turn the steaks over and continue to grill 3 to 5 minutes for medium-rare (an internal temperature of 135 degrees F), 5 to 7 minutes for medium (140 degrees F) or 8 to 10 minutes for medium-well (150 degrees F).hen I order a steak in a restaurant I ask for medium rare...closer to rare than medium and my steak always (or almost always) comes to me perfectly cooked. The key is to order the correct cut of steak for grilling and the correct cooking time. Otherwise you'll receive hot shoe leather.