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Uploading a file to Assets does not automatically make the employee send it — you tell it when through a guideline, typically under Conversation flow & objectives.

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Tag the asset in a guideline

Type @ in the guideline editor and select Assets to reference a configured file directly in a sentence:
Guideline prompt with an asset inserted through the @ mentions menu
Use this asset when the contact asks about sizing.
No extra automation is needed — the employee sends the file automatically when it judges the moment fits, the same way it decides when to answer from Content.

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Examples in practice

In each case, the pattern is the same: the file itself lives in Assets, while the judgment call — when is the right moment to use it — is defined here, in the guideline. The two work as a pair: Assets supplies the material, the guideline supplies the timing and reasoning.

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Be specific about when

A vague instruction to send assets “when helpful” leaves the employee guessing about which file and when. Reference each asset exactly where it is relevant to a specific step in the conversation.
Pair asset rules with Boundaries so the employee does not over-share files or send the wrong document to the wrong contact.