Preliminary note: This cookie dough requires at least 3 hours of chilling, but you can get by with freezing for 45 minutes. The colder the dough, the thicker the cookies.
Dry ingredients: Whisk the flour, cocoa powder, baking soda and salt together in a medium mixing bowl. Set aside.
Cream butter and sugar: In a stand mixer fitted with a paddle attachment, (may use a large bowl and hand-held mixer) cream the butter, granulated sugar and brown sugar together on medium-high speed until fluffy, about 2 minutes.
Add wet ingredients: Reduce speed to medium and beat in the egg, vanilla and milk just until combined, scraping the sides of the bowl as needed.
Add dry ingredients: With the mixer running on low speed, gradually mix in the dry ingredients until a few streaks of flour remain. Increase speed to medium and mix in the chocolate chips and ¾ cup chopped macadamia nuts just until combined (don’t overmix). The dough will be very thick and sticky.
Chill: Cover the dough tightly with plastic wrap clinging to the surface of the dough. Chill in the refrigerator for at least 3 hours up to 3 days or freeze for 45 minutes before rolling.
Preheat oven: When ready to bake, preheat the oven to 350°F. Remove cookie dough from the refrigerator and allow to sit at room temperature for 10 minutes. If the cookie dough chilled longer than 3 hours, let it sit at room temperature for about 20 minutes. Line baking sheets with parchment paper or silicone baking mats. Set aside.
Scoop: Using a 1 ½ tablespoon cookie scoop, scoop the cookie dough and roll into balls. The dough is sticky, so it can be helpful to wet your hands or spray hands with cooking spray. Place the balls on the baking sheet, leaving about 3 inches in between, 6 balls per half sheet. At this point, push the reserved ¼ cup chopped macadamia nuts onto the top of each ball, strictly for looks (this is optional). I also do the same with some extra chocolate chips.
Bake: Bake the cookies for 10-12 minutes or until the edges appear set and the centers still look soft (cooking times will vary based on how chilled your dough is). Tip I use every time: If they aren’t really spreading by minute 8, remove them from the oven and lightly bang the baking sheet on the counter 2-3x. This helps initiate that spread. Return to the oven to continue baking.
Cool: Cool cookies for 5 minutes on the baking sheet. During this time, sprinkle with flaky salt if desired. Transfer to cooling rack to cool completely.
