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Managers listen to a handful of calls per rep per month, so coaching runs on a sample. The patterns that actually move a rep’s number, how they handle a pricing objection across ten deals, whether they talk past the close, what the top rep does that the others don’t, live across every call, not the three a manager had time for. Rep Coaching From Real Conversations surfaces coaching moments with timestamps from every call, identifies patterns across deals, and turns them into specific, evidence-based feedback.

Data Sources

Starter (required only): coaching moments pulled from a rep’s call transcripts with timestamps, plus the patterns that repeat across their deals. Full (required + recommended): the same, plus deal outcomes from CRM and follow-up behavior from email, so you can connect a habit on calls to whether deals advance or stall. Same workflow, significantly more depth. See the Context Graph for how each source feeds the analysis.

Choose your path

Build in Clearskies

For managers who want a coaching readout on every rep without remembering to run it. Build the workflow once and each manager gets a readout on each of their reps on a cadence you set.

The Workflow

In the Clearskies app, open the workflow builder and describe what you want in plain language:
The app configures the trigger (a schedule), the reps in scope, and the destination (a private DM, since coaching is sensitive). Scheduled workflows have no meeting context, so the reps come from a record lookup. Start with a manager’s direct reports and a weekly cadence. Test the workflow against last week’s calls before publishing. Test runs are always dry, so nothing sends while you are still refining.

Deploy to Slack

Once published, each manager gets a coaching DM per rep:

Customize the rollout

  • Keep readouts private to managers, or open a shared enablement channel for team-level patterns
  • Tailor what’s surfaced (discovery, objection handling, next-step discipline, talk ratio)
  • Set the comparison baseline: your top performers, a defined methodology, or a custom rubric
  • Adjust cadence: weekly per rep, monthly, or after every recorded call
  • Chain it with 1:1 prep so the coaching read and the deal read arrive together

Build in Claude or ChatGPT

For managers working in Claude or ChatGPT, or enablement testing the workflow before rolling it out. Output appears in your conversation.

The Prompt

Open Claude or ChatGPT with the Clearskies MCP connected and paste this (or modify to your needs). Replace the rep’s name with your own.
Claude or ChatGPT returns a readout structured like the Slack example above, generated from your data. Refine the prompt to fit how you coach.

Make it yours

  • Add Focus only on how he handles pricing objections to coach one skill at a time.
  • Add Draft this as feedback I can paste into our 1:1 doc to make it ready to deliver.

The Skill (Claude)

The clearskies:rep-coaching skill in the Clearskies plugin for Claude runs the same workflow on demand: it pulls a rep’s recent calls, surfaces coaching moments with timestamps, identifies behavior patterns, and drafts specific feedback, no manual listening required, all from your Context Graph.

Trigger phrases

  • “Coach [rep]”
  • “What should I work on with [rep]”
  • “Show me coaching moments from [rep]‘s calls”

Customize it for your team

  • Match the readout to the skills your team coaches on
  • Set the comparison baseline to your top performers or your methodology
  • Layer in 1:1-prep, ramp, or PIP framing depending on context
Want this packaged for your team? Reach out and we’ll help you customize the skill to your workflow.

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 →

Next steps

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