Begin by preheating your oven to 350°F (175°C).
In a large mixing bowl, combine 1 cup of shortening and 1 cup of packed light brown sugar. Using a whisk, cream them together until light and fluffy.
Add 5 large eggs to the mixture, one at a time, ensuring each is fully incorporated before adding the next. Stir in 1 teaspoon of vanilla extract and 1 teaspoon of maple extract.
In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, and 1/2 teaspoon of salt. Gradually add this dry mixture to the wet ingredients, stirring until just combined.
In a small saucepan, melt the two 1-ounce squares of semi-sweet chocolate along with 1 tablespoon of salted butter over low heat, stirring until smooth.
Pour the chocolate mixture into your cookie dough and mix until evenly distributed.
Drop rounded tablespoons of cookie dough onto a baking sheet lined with parchment paper. Bake for about 10-12 minutes, or until the edges are lightly golden.
While the cookies are baking, whisk together 1 cup of powdered sugar and 1/4 cup of milk until smooth for the drizzle.
Allow the cookies to cool on a wire rack for about 5 minutes, then drizzle the prepared icing over the top of each cookie.
