Preheat oven to 425 degrees. Place sliced sourdough on a foil covered baking sheet and brush the bread with a small amount of olive oil. Bake 8-10 minutes until lightly toasted. Remove from oven and cool.
For the tapenade, place olives, capers, anchovies, garlic, herbs, 1/4 cup olive oil, lemon juice, lemon zest and chili flakes into a Cuisinart. Pulse until desired chunkiness, should be well blended. Taste as you may need to add more lemon juice.
Place Brie round on sheet pan lined with parchment paper. Bake under low broiler for 2-4 minutes until the top is golden. Serve with olive tapenade and crostini. Serves 6-8.