Preheat your oven to 375°F and line a baking sheet with parchment paper.
In a small saucepan, brown 8 tablespoons of butter over medium-low heat. Stir occasionally until the butter develops golden-brown flecks and a nutty aroma. Remove from heat, pour into a bowl, and set aside to cool slightly.
In a stand mixer, combine the remaining 8 tablespoons of butter with the browned butter. Add the brown sugar and white sugar, and cream on medium speed for 3-4 minutes until light and fluffy.
Mash the ripe banana with cinnamon until smooth, then mix it into the butter mixture alongside the vanilla extract. Beat until fully incorporated, about 2-3 minutes.
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, blending until a smooth dough forms.
Fold in the chocolate chips until evenly distributed.
Use a scale to measure out nine 4-ounce dough balls and place them on the prepared baking sheet with plenty of spacing. If making smaller cookies, divide into 16-18 balls (approximately 2 ounces each).
Bake for 13-14 minutes until the edges are set, but the centers appear slightly underdone.
Immediately after removing from the oven, gently smack the baking sheet on your counter to flatten the cookies. Use a bowl to swirl around their edges for a perfectly round shape and sprinkle with flaky salt.
Let the cookies cool for 15 minutes before enjoying.