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Pat the beef cubes dry with paper towels, then season all over with the salt and pepper. Toss the seasoned beef in the flour until each piece is lightly coated, shaking off any excess.
Heat the olive oil in a 12-inch skillet over medium-high heat until shimmering. Working in two batches to avoid crowding, sear the beef cubes undisturbed for 3–4 minutes per side until a deep brown crust forms, then transfer to the slow cooker insert. Do not clean the skillet.
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