Preheat the oven to 350˚F. Line baking sheet with parchment paper or a silpat mat.
Using a standing mixer, cream the butter and sugar together until fluffy, scraping the bowl as needed - about 5 minutes. Add the Grand Marnier and anise extract, and continue to mix until completely incorporated, about 3 minutes.
Whisk together the flour, baking powder, salt, and anise powder in a small bowl to evenly distribute the baking powder through the flour. Fold into the batter on the lowest speed just until barely mixed in.
Fold in the chocolate chips using a spatula.
Place the dough on the prepared baking sheet and form into a log about 2-3" in diameter and about 15" long.
Bake for 30 minutes, or until golden brown. Remove from the oven and let cool on a cooling rack for about 15 minutes - or until the chocolate chips begin to harden up a bit. Slice ¾" slices with a serrated knife, cleaning the knife after every slice to avoid smearing the chocolate chips.
Lay the slices back on the cookie sheet and slide back into the oven for a final baking. Bake for 10 minutes per side until lightly toasted.