Preheat oven to 400° Fahrenheit.
Place the cubed butternut squash on a large baking sheet and drizzle with olive oil, then season with salt and black pepper.
Toss squash to coat in oil then bake for 25-30 minutes, tossing halfway through.
While squash is roasting, make the maple Dijon dressing by adding all dressing ingredients to a small bowl and whisking to combine.
Once squash is tender, remove from the oven and set aside to cool slightly.
If making salad ahead of time, stack in large jar with the farro at the bottom and the chopped kale on top of the farro.
Pour maple Dijon dressing over the kale and farro, then stack in the roasted butternut squash, shallots, soft cheese (such as feta), apples, pumpkin seeds, and dried cranberries.
If preparing the salad to eat immediately, then simply add all ingredients to a large bowl and toss to combine.