Preheat oven to 450°; cut off top ¼ of garlic + discard; place garlic in a small baking dish; drizzle exposed cloves with 1 tsp oil + a pinch of salt; cover with foil + bake 20-25 min until soft

Meanwhile, heat 1 tbsp oil in skillet over med-high; pat steak dry, season with salt/pep + sear 3-4 min per side for med-rare (for more well done add 1-2 min per side); for best results, use tongs to hold steak up on its edges for 1 min to render fat crispy; rest 5 min + slice into ½-inch slices

Mash olives with 2-4 cloves garlic in a bowl; spread on plates

Toast 2 pitas + slice in half; divide steak over garlic tapenade + serve with pita on side