Preheat oven to 350 degrees F. Prepare 3 baking sheets with parchment paper.
Prepare the delicata squash by slicing it in half lengthwise, scooping out and discarding the seeds (or save them to roast as a snack!), and slicing each half into half moons. Toss the squash in 1 tablespoon olive oil, salt, and pepper. Transfer to 1 of the lined baking sheets and roast for ~30 minutes or until tender, flipping halfway through.
Toss the dry kale leaves (make sure they are completely dry) with 2 tablespoon olive oil, salt and pepper. Transfer to the last 2 lined baking sheets. Make sure the kale pieces do not overlap, to prevent steaming the kale instead of roasting it. You may need more than 2 baking sheets, or you may need to roast the kale in batches. Roast for 10-15 minutes or until crispy (check at 10 minutes to be careful not to burn it). You can do this at the same time that the squash is roasting.
While the veggies are roasting, whisk together the tahini, garlic, and lemon juice in a small bowl. Gradually whisk in water until it gets to your desired consistency.
When the squash and kale are finished, remove from oven and transfer to a serving dish. Top with pomegranate arils, and drizzle with dressing. Enjoy!