In a large bowl, combine the cucumbers, tomatoes, red onion, and kalamata olives. Set aside.
Heat oven to broil. Place naan on a baking sheet, and brush with olive oil. Sprinkle with salt, then place in the oven for 2-3 minutes, or until the bubbles in the naan are dark brown and crispy. Remove from oven and cut into 1 inch squares, then add to the bowl with the vegetables.
In a large cast iron skillet, heat the canola oil to medium high. Combine the flour and a generous helping of salt and pepper in a shallow dish, then dredge the halloumi cubes in the mixture. Tap each cube gently to remove excess flour, then add to the skillet in a single layer and fry until light brown, around 5 minutes, flipping the cubes halfway through. Remove from pan to a paper towel to drain excess oil, then add to the bowl with the rest of the panzanella.
Drizzle the Greek dressing over the panzanella and toss lightly to coat, then gently turn out into a serving bowl and enjoy immediately!
*The amount of oil needed can vary, depending on the size of the pan used. I fried the cheese in a 12 inch cast iron skillet, for reference, and used enough oil to coat the entire bottom and bring it up the sides by about 1/8-1/4 inch.