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We conceptualize this transition as a shift from Chatbot to Digital Colleague: from conversational answers to persistent work. We organize this transition along two tightly coupled dimensions. First, at the cognitive core level, LLMs are advancing from Chatbot-era \"fast thinking\" systems driven by next-token prediction toward Thinking LLMs that leverage inference-time computation, Chain-of-Thought reasoning, reflection, process supervision, and reinforcement learning to support more deliberate and reliable cognition. 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