Preheat oven to 425F. Place the squash and Brussels sprouts on a large sheet pan. Drizzle with olive oil and then toss with the salt, garlic powder, onion powder and pepper until well coated.
Make sure the squash and Brussels sprouts are spread out on the pan. The Brussels sprouts should also be cut side down. Roast for 18-20 minutes, or until just fork tender.
While the squash and Brussels sprouts roast, cook the orzo al dente. Drain, rinse with cold water and drain again.
During this time, you can also make the vinaigrette. Just add all of the ingredients to a jar, seal and shake until combined.
Once roasted, remove the squash and Brussels sprouts from the oven and let cool slightly.
In a large bowl, add the orzo, butternut squash, Brussels sprouts, massaged kale, pumpkin seeds, dried cranberries and goat cheese. Toss to combine.
Pour the vinaigrette over the salad and toss again until everything is well coated. Let sit in the fridge for a few hours before serving.
Notes
I don't recommend using large Brussels sprouts. They take longer to roast and can sometimes taste bitter.
If the squash and Brussels sprouts are crowded on the sheet pan, they will steam instead of roast and could end up mushy. Make sure you use a large enough sheet pan so you can spread them out.
Chop the kale into small pieces and massage it before adding it to the salad. This will ensure it's tender and not tough in the salad.
Don't skimp on the vinaigrette. It might look like a lot, but the orzo absorbs most of it. If you're making this salad a day ahead, you can reserve a little vinaigrette to pour over the salad just before serving.