In a small bowl, whisk instant coffee with 2 teaspoon of heavy cream. Whisk until instant coffee is dissolved.

In a medium bowl, beat coffee-cream mixture with remaining cream and vanilla extract until soft peaks form. Add in powdered sugar and continue beating until stiff peaks form. Set aside.

To assemble, divide crumbled lady finger cookies into 8 miniature martini glasses or ramekins. Top with one heaping tablespoon of HERSEY chocolate pudding and 1 tablespoon of coffee whipped cream. Top with powdered sugar and drizzle with chocolate. Repeat with remaining ingredients.