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A manager with eight reps has eight 1:1s a week and prepares for maybe three. The rest open with “so how’s it going,” which hands the agenda to the rep and turns the meeting into a status update the manager could have read. 1:1 prep gives the manager the read before they walk in: what moved in this rep’s deals, what is stuck, what was agreed at the last 1:1 and whether it happened, and the one or two places a manager can actually change an outcome.

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Data Sources

Starter (required only): the rep’s deals, what moved since the last 1:1, and what their calls say about the deals that are stuck. Full (required + recommended): the same, plus engagement patterns between calls, so a deal that looks fine in CRM but has had no customer reply in three weeks shows up as what it is. See the Context Graph for how each source feeds the prep.

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Choose your path

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Build in Clearskies

Build the workflow once and every manager gets a read on the right rep’s deals before each 1:1, without knowing the workflow exists.

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The Workflow

In the Clearskies app, open the workflow builder and describe what you want in plain language:
The app configures the trigger (the manager’s calendar, with an offset ahead of the meeting), the rep whose deals to pull, and the destination. Meeting workflows always start with a filter. Every calendar event counts as a meeting, so the filter is what narrows the run to actual 1:1s rather than every internal block on a manager’s calendar. A recurring 1:1 with a consistent title is the easiest thing to filter on, and getting that filter right is most of the work on this one. Test it against a real 1:1 before publishing. Test runs are always dry, so nothing sends while you are still refining.

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Deploy to Slack

Once published, each manager gets this before each 1:1:

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Customize the rollout

  • Set the timing anywhere from minutes to a day ahead of the 1:1
  • Choose what is in scope: the rep’s whole book, or only deals closing this quarter
  • Add the sections your 1:1s use and drop the ones they do not
  • Include a positive note by default, so the brief is not only a list of problems
  • Send a copy to the rep as well as the manager, so both walk in with the same read
  • Chain it with rep coaching so the deal read and the call-quality read arrive together

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Build in Claude or ChatGPT

For managers who prep in the ten minutes before a meeting, and for shaping the format before you automate it.

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The Prompt

Open Claude or ChatGPT with the Clearskies MCP connected and paste this (or modify to your needs). Replace the name and the window with your own.
The last line matters. This prep is about the deals and the behaviour on record, not a read on the person.

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Make it yours

  • Add Compare this to our last three 1:1s and tell me what keeps coming back to catch the pattern rather than the week.
  • Add What questions should I ask that the record cannot answer to build the agenda.
  • Add Which of his deals would I bet against, and why when the 1:1 is really a pipeline conversation.

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The Skill (Claude)

The clearskies:rep-coaching skill in the Clearskies plugin for Claude covers the conversation-quality half: it pulls a rep’s recent call transcripts, surfaces coaching moments with timestamps, identifies patterns across calls, and drafts specific feedback. Run it alongside a deal read when the 1:1 is about how the rep is selling rather than what is in their pipeline. clearskies:pipeline-review covers the deal half across a book, prioritized by urgency rather than close date.
Want this packaged for your team? Reach out and we’ll help you customize the skill to your workflow.

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The Plugin

Ready to make this part of your team’s workflow? We’ll set up the Clearskies plugin with you. Clearskies workflows, Claude skills, all tailored to how your team works. Book 15 minutes →

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Next steps

  1. Sign in to Clearskies
  2. Connect your data sources
  3. Get your Clearskies MCP server and try with Claude or ChatGPT