Season and cook the chicken. Pat the chicken dry and rub with 1 tablespoon olive oil, salt, and pepper.
Grill over medium-high heat for 5–6 minutes per side, or pan-sear in a skillet until golden and cooked through (internal temp 165°F/74°C). Let it rest for 5 minutes, then slice.
Make the croutons. In a large skillet, heat 1 tablespoon olive oil and 1 tablespoon butter over medium heat. Add bread cubes and a small pinch of salt.
Toss until the edges begin to brown, 5–7 minutes. In the last minute, add 1 minced garlic clove and toss just until fragrant. Transfer to a plate to cool.
Whisk the dressing base. In a bowl, combine minced garlic, anchovy (if using), Dijon, Worcestershire, and lemon juice.
Whisk until smooth. Add mayonnaise and Greek yogurt (if using), then whisk in 2 tablespoons olive oil. Stir in finely grated Parmesan.
Season with salt and pepper. Adjust lemon to taste.
Prep the romaine. Wash, spin dry, and chop into bite-size pieces. The leaves should be very dry so the dressing clings.
Keep chilled until assembly.
Toss the salad. In a large bowl, add romaine and enough dressing to lightly coat. Toss gently with tongs, then add more dressing if needed. Fold in half the croutons and a handful of shaved Parmesan.
Top and finish. Add sliced chicken on top, scatter remaining croutons, and finish with extra shaved Parmesan.
Serve with lemon wedges and cracked black pepper.