Set a wire rack in a rimmed baking sheet.
Pre-heat the grill pan over medium-high heat for 5 minutes before beginning to grill.
Lightly oil the grill pan using tongs and paper towels dipped in canola oil.
Place the first piece of steak on the grill pan and cook, covered, until the steak is brown on the first side, about 2 minutes.
Flip the steak over and continue to cook, covered, flipping the steak every 2 minutes, until the steak registers 125° (for medium-rare) or 130° (for medium), 2 to 6 minutes longer.
Remove the steak to the prepared rack and tent with foil.
Repeat with the remaining pieces of flank steak.
Let the last piece of steak rest for 10 minutes before serving.