In a small bowl, whisk together the balsamic vinegar, 2 tablespoons of extra-virgin olive oil, honey, Dijon mustard, minced garlic cloves, and a pinch of crushed red pepper flakes until the mixture is smooth and well-combined. Set the vinaigrette aside to let the flavors meld. I like to taste the vinaigrette and adjust the honey or mustard if I want it a bit sweeter or tangier.
Heat 2 tablespoons of extra-virgin olive oil in a large skillet over medium heat. Pat the chicken breast tenders dry and season both sides with kosher salt and freshly ground black pepper to taste. Once the pan is hot, add the chicken and sear until golden brown, about 3 minutes per side. When done, remove the cooked chicken from the skillet and set aside on a plate.
In the same skillet over medium heat, add the asparagus (with ends removed) and the cherry tomatoes (split in half). Season with additional kosher salt and freshly ground black pepper to taste. Sauté, stirring occasionally, until the asparagus becomes bright green and the cherry tomatoes are slightly wilted, about 5 minutes.
Move the sautéed asparagus and tomatoes to one side of the skillet. Return the seared chicken (from Step 2) to the pan. Pour the reserved balsamic vinaigrette (from Step 1) over the chicken and vegetables. Toss everything gently to coat. Continue to cook for about 5 minutes, or until the chicken is cooked through and the vinaigrette has thickened into a glossy glaze. For extra flavor, I like to spoon a bit of the thickened vinaigrette over everything just before serving.