Heat a grill to high (450° to 550°). Meanwhile, make olive salad: Combine beans, olives, celery, green onions, anchovy, garlic, parsley, capers, chile flakes, 1/4 tsp. each salt and pepper, the lemon juice, and 4 tbsp. oil in a medium bowl. Set aside until ready to serve.
Brush calamari all over with remaining 1 tbsp. oil and season with remaining 1 tsp. each salt and pepper. Grill over high heat (covered if using gas) until grill marks form, about 2 minutes. Flip and cook on other side until just cooked through, 2 to 3 minutes.
Serve steaks with olive and bean salad, with lemon wedges on the side.
Wine pairing: Zocker 2014 Paragon Vineyard Grüner Veltliner (Edna Valley; $20).