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Work chatbots fail when they cannot hold a project, cannot read a file, or reset personality every session. You want memory you control, file uploads, and an export path.
Memory and projects
ChatGPT Projects and Claude Projects are the reason to pay. A naked free chat that forgets the style guide is a toy. Notion AI is useful only if the work already lives in Notion.
File uploads
If your job is “summarize this deck,” test the 40-page PDF on day one. If the model refuses or hallucinates slide titles, you are not ready to put it on a client call.
When search is enough
Skip a chatbot if the question is a spec sheet number you can open on the manufacturer site in ten seconds. Models still round “up to” Wi-Fi speeds into facts.
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