Heat oven to 325 degrees F (165 degrees C). Line a small baking sheet with parchment paper or silpat lining.
In a small mixing bowl, beat butter, 3 tablespoons of sugar, and vanilla together with a hand mixer until creamy.
Add flour and beat until well mixed.
Knead mixture 3 to 4 times until dough forms a ball. Divide dough into 3 equally sized balls and place on baking sheet about 3-inches apart.
Using the palm of your hand or a large spoon, gently press down on the dough so that the dough flattens to about ¼-inch thickness.
Sprinkle ¼ teaspoon of sugar evenly over each of the cookies. Bake for 13-15 minutes.
Remove cookies from the oven and let cool on baking sheet for 5 minutes. Transfer cookies to a cooling rack and cool completely for 10 minutes.
While the cookies are cooling, microwave chocolate in microwaveable bowl on high for 30 seconds; stir. Microwave 10 seconds more; stir. Continue heating and stirring in 10-second increments until completely melted.
Dip spoon into melted chocolate. Drizzle chocolate over edges and tops of cookies.
Allow chocolate to harden before eating, about 20 minutes.