Prepare pumpkin dough first. Cream butter and brown sugar. Stir in pumpkin, egg and vanilla. Beat in pumpkin pie spice, baking soda and salt, making sure they are thoroughly mixed, then add flour and stir until it is absorbed. Place in refrigerator to chill while you make the chocolate dough.
To make the chocolate dough, cream butter and both sugars in a large mixing bowl. Add the egg and vanilla and beat until blended. Beat in the cocoa powder, then beat in the baking soda and salt. Add flour and stir until it is almost mixed in, then add chips and stir until chips are mixed and all flour is absorbed.
Chocolate dough should be fairly dry, but if it isn’t, chill it for about 30 minutes.
Form cookies. Scoop up chocolate dough and shape into golf ball size mounds. Working one mound at a time, break a chocolate dough mound in half and squish a large gumball size ball of pumpkin dough between (see photo at bottom). Place on parchment lined cookie sheets spacing 3 inches apart.
Bake cookies at 350 degrees for 13-15 minutes or until they appear set. Let cool on sheet for 5 minutes. Transfer to a wire rack to finish cooling.