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1
Preheat the oven to 400 degrees F.
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2
Rub the cut sides of the squash with butter and place cut-side down on a baking sheet lined with foil. Bake until very tender, 1 to 1 1/4 hours.
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3
Remove the squash from the oven and let cool slightly.
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4
While the squash cools, heat a nonstick skillet over medium-low heat and add the olive oil. Add the ginger and saute 1 minute, until softened.
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5
Scrape the pulp of the squash into the skillet and add 1 tablespoon of butter and the milk. Season with salt and pepper. Use a potato masher or fork to combine the ingredients, mashing the squash to a creamy consistency.
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6
Combine the garlic, ginger, chile paste, soy sauce, and 1 tablespoon of olive oil in a medium bowl. Add the beef tips and toss to combine. Cover with plastic wrap and refrigerate 1 hour. (Let sit at room temperature 30 minutes before cooking.)
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7
Place the fennel slices in a medium bowl and drizzle with olive oil. Season with salt and pepper and toss to combine. Set aside.
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8
Heat a cast-iron griddle over medium-high heat on the stovetop. Brush with olive oil and add the beef tips (discard the marinade) on one end and the fennel slices on the other.
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9
Grill, turning two or three times, until the beef is medium rare and the fennel is crisp-tender, 5-6 minutes.
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10
To serve, toss or stir the beef and fennel together and divide among 4 plates. Divide the squash puree alongside.
