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Sales Rep Onboarding Plan

Gets a first close from a small winnable deal rather than the biggest in the patch, because early confidence compounds.

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CategorySalesForSales Teams, Operators, FoundersTested onClaudeChatGPT

Running it, start to finish

  1. Define checkable capabilities by week rather than knowledge goals.
  2. Hand them a small winnable opportunity early.
  3. Capture what the onboarding revealed as undocumented.

What you get back

The output this produces, every time.

  • Engineers an early small close rather than assigning the largest opportunity.
  • Prioritises customer exposure over product training, which is usually the wrong way round.
  • Uses the new person to find what is undocumented, which is only visible in their first month.

Getting better results

Where this usually goes wrong, and how to avoid it.

  • Do not give them the biggest deal. A large first opportunity takes months, teaches slowly and produces anxiety rather than competence.
  • Send them to support tickets. A rep who has read fifty tickets sounds different on a discovery call than one who has read the product deck twice.
  • Do the reverse-shadowing. Watching is comfortable and teaches little. Being watched while running the call is where it lands, and it is what gets skipped.

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Written for The AI University. Every prompt in this library is original work — authored, tested and revised here, not collected from elsewhere. 365 of them, free with an account.