Combine Shakeology, dates, almond flour, almond milk, and cinnamon in a food processor; cover. Pulse until fine crumbs form, scraping down sides as needed.
Shape mixture into six equal balls; insert a lollipop stick into the center of each, pressing the ball firmly around the stick. Set aside.
Add chocolate chips and oil to a small microwave-safe bowl; microwave on high for 30 seconds. Stir, then microwave 30 seconds more, if needed.
Dip each cake ball into chocolate mixture to coat. Place into a cake pop stand (see tips below) or arrange on a plate lined with parchment paper; refrigerate until chocolate hardens, about 15 minutes.
Refrigerate in an airtight container for up to 3 days, or freeze for up to 1 month.
Gluten-Free (GF), No Dairy (ND), Quick ’n’ Easy (QE), Vegan (V), Vegetarian (VG)
The Nutrition Facts box below provides estimated nutritional information for this recipe.*
* Total Sugar 12 g, Added Sugar 5 g