POUR milk into large bowl. Add dry pudding mix and flavored instant coffee. Beat with wire whisk 2 minutes. Gently stir in whipped topping.
SPLIT each ladyfinger segment horizontally in half. Place bottom half of 1 of the ladyfinger segments, cut side up, on each of 8 dessert plates; top evenly with the pudding mixture. Cover with tops of ladyfinger segments, cut sides down.
DRIZZLE with chocolate syrup just before serving.