Heat the grill: Preheat a gas grill to medium-high or prepare a hot charcoal fire. If using a grill pan, heat it over medium-high until very hot.
Prep the squash: Trim the ends.
Slice lengthwise into planks about 1/3 inch thick. This thickness helps prevent sogginess and slipping through the grates.
Make the marinade: In a large bowl, whisk olive oil, lemon juice, garlic, salt, pepper, oregano, and red pepper flakes.
Toss to coat: Add sliced zucchini and squash to the bowl. Gently toss until every piece is lightly coated.
Let sit 10 minutes while the grill heats.
Oil the grates: Dip a folded paper towel in oil and, using tongs, carefully wipe the grill grates to reduce sticking.
Grill the squash: Lay slices across the grates. Cook 3–4 minutes per side, until grill marks appear and the squash is tender but not mushy.
Finish and season: Transfer to a platter. Taste and sprinkle with a pinch more salt, a squeeze of lemon, and the fresh herbs.
Serve: Enjoy right away, or let cool slightly and serve at room temperature.