In a medium-sized bowl, prepare the guacamole. Shred or dice the chicken and shred the cheese.
Use a rubber spatula or fork to spread a thin layer of guacamole on the tortilla. Repeat for all 8 tortillas. The guacamole will act as the ‘glue’ to help the tortilla stick together.
Next, add some chicken to one side of the tortilla in a single layer.
Add a couple tablespoons of shredded cheese on top of the chicken, then fold the tortilla in half, tucking all of the ingredients inside. Repeat for remaining quesadillas.
Heat a skillet to medium heat. Add in oil and allow it to heat. Once it starts to sizzle, add the quesadillas and let them cook 3-4 minutes on each side.
Once they’re golden brown and the cheese is melted, flip them (you may need to add a bit more oil to prevent sticking or burning).
Serve warm with leftover guacamole, shredded lettuce, fresh pico, salsa or other desired toppings!