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Bring a large saucepan of water to a boil, then remove from heat. Add cashews and let sit until tender, 30–60 minutes.
Drain cashews and transfer to a blender (preferably high-speed) or food processor. Add garlic, oil, salt, and ½ cup water and purée until smooth.
Cut broccoli into 1" florets. If your broccoli has a long stem, peel tough outer layer, then slice stem ¼" thick.
Heat oil in a large Dutch oven or other heavy pot over medium. Cook leek, stirring often and reducing heat if needed to avoid leek taking on any color, until softened slightly, about 2 minutes. Add garlic and fennel seeds and cook, stirring, until fragrant, about 1 minute. Add broccoli and broth and increase heat to medium-high. Cover pot with a lid, setting it slightly askew to allow steam to escape (this will help the broccoli maintain its vibrant green color). Bring to a boil and cook until broccoli is tender, 8–10 minutes.
Working in batches if needed, transfer broccoli mixture to a blender or food processor and add salt, ¼ cup dill, and ½ cup cashew cream. Blend until soup is smooth. (If the soup is no longer hot, you can return it to the pot and reheat gently before serving.)
Divide soup among bowls and drizzle with remaining cashew cream. Top with a few dill sprigs and season with pepper.