Preheat oven to 400 degrees F. Line two medium baking sheets with parchment paper or silicon baking mats.
Whisk together all of the ingredients for the lemon poppyseed dressing and set aside.
Cut off the stem of each Brussel sprout and peel off as many of the leaves as you can. Place them in a medium bowl along with the remaining part of the Brussel sprouts. Drizzle 1 Tbsp olive oil with a ½ tsp of salt and ½ tsp of pepper on the Brussels, stir to coat, and place in an even layer on the baking sheet.
Put the butternut squash on the second baking sheet, using a drizzle of olive oil to coat with ½ tsp of salt and pepper, along with ½ tsp of cinnamon. Mix well to combine. Place both baking sheets in the oven on the center racks and bake for 35-40 minutes, or until the Brussel chips get nice and crispy. Some of them will charr, but that adds another dimension of flavor to this salad.
Once everything is done baking, let it cool to room temperature.
Finely chop the kale and place in a large bowl. Squeeze the juice of half a lemon and about 1 tsp of olive oil on the kale, season with salt and pepper, and massage the kale until it begins to soften.
Add all the other ingredients and toss with the dressing. Enjoy!