Cook the chicken breast in a skillet over medium-high heat until no pink remains inside — about 8 to 10 minutes total. I season it with just salt and pepper so the seasoning doesn't compete with the dressing later, which is the mistake most people make when they overcomplicate this step.
Boil your short pasta in salted water until just under al dente, about 2 minutes shorter than the package suggests. This seems aggressive, but the pasta continues softening as it cools and absorbs dressing, so catching it earlier prevents mushiness in your cold chicken pasta salad family summer.
Drain the pasta and toss immediately with the olive oil, lemon juice, and mustard while it's still warm and steaming. This is the crucial move that most recipes skip — the warm pasta absorbs the dressing instead of it just coating the surface, which is why this version tastes so much more intentional than basic versions.
Let the dressed pasta cool for about 5 minutes on the counter, then transfer it to your serving bowl. I confess I used to refrigerate it immediately, but cooling slightly first prevents condensation from making the dressing separate later.
Once the pasta reaches room temperature, add your diced chicken and all the vegetables — tomatoes, cucumber, onion, and bell pepper — and fold everything together gently. The reason you add vegetables after cooling is that their moisture won't steam off into the pasta if everything's already cold.
Stir in the cheddar cheese cubes and Kalamata olives, then taste and adjust salt and pepper because you need to own the seasoning rather than guessing. This cold chicken pasta salad family summer is only as good as your willingness to taste and adjust before plating.