Rinse the barley and bring to boil in a medium saucepan with 1 cup salted water. Turn down heat and let simmer for about 45 minutes or until barley is fluffy, tender and chewy. Add more water while cooking if the barley starts to dry out.
Meanwhile, peel and chop the squash into small chunks. Drizzle with 1 tablespoon olive oil and sprinkle with salt and pepper. Roast at 400 degrees F for 30-45 minutes, or until tender.
Once the barley and squash are done, let cool while you wash the kale and lettuce and tear into bite-sized pieces. Add the remaining ingredients to the bed of greens.
Make the dressing
Whisk all ingredients together and season with salt and pepper to taste!