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How would you design a "Pathfinder" tool for LinkedIn to help with career pivots?

Also asked as "Design a roadmap feature that gives users a step-by-step plan for a new goal."

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Interview question asked to Product Managers interviewing at Groover, Farfetch, Walt Disney and other companies. Original question asked: How would you design a "Pathfinder" tool for LinkedIn to help with career pivots?.