Start by cooking the pearl couscous according to package instructions until tender but slightly chewy. While the couscous cooks, cube your butternut squash and roast it in olive oil until golden and caramelized. This dual prep gives the salad its signature fall flavor.
In a small bowl or jar, whisk together olive oil, mustard, lemon juice, orange juice, honey, apple cider vinegar, garlic, salt, and pepper. Taste and adjust for sweetness or acidity. This zesty vinaigrette ties all the salad flavors together beautifully.
Massage the chopped kale with a spoonful of dressing to soften it. Combine the couscous, roasted squash, cranberries, pecans, and red onion in a large bowl. Drizzle with about a third of your dressing and toss gently. Adjust seasoning if needed and serve cold or at room temperature.