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AI For Sales

Building AI Workflows with Claude Cowork Skills

Brock Mesarich | AI for Non Techies

YouTube creator

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Duration
14 min

Claude Cowork's Skills feature lets you encode your entire workflow into a simple markdown file that Claude reads and executes consistently. This session walks through what Skills are, how they differ from slash commands, and how to combine them with plugins, connectors, and scheduled tasks to build automated AI workflows. Real examples include a client research brief, contract generation, and a LinkedIn repurposing pipeline, demonstrating how a single command can replace hours of manual work.

Learning objectives

  • Explain what a Claude Cowork Skill is and how it differs from a standard prompt or slash command
  • Create a basic Skill markdown file that defines a goal, steps, and required tools
  • Combine Skills with connectors and plugins to give Claude access to external apps and data
  • Set up scheduled tasks so Skills run automatically without manual triggering
  • Use the built-in Skill Creator to generate new Skills by describing a workflow in plain language

Key takeaways

  • A Skill is a plain-text markdown file that encodes your workflow once so Claude executes it consistently every time
  • Slash commands manually trigger a Skill, while auto-triggers fire it based on context or schedule
  • Plugins bundle Skills, commands, connectors, and sub-agents into a shareable, importable package
  • Connectors act as a live bridge between Claude and your external apps, enabling Claude to read and act on real data
  • Zapier MCP extends native connectors to over 8,000 apps, dramatically expanding automation scope
  • Scheduled tasks combined with Skills create fully autonomous workflows that run without any manual input
  • Skills are shareable files, making it easy to distribute proven workflows across a team or import community-built plugins

Free plan, no credit card. Watching opens this session in the Triple Session app.

How Triple Session works

One coaching loop, running every week

Coaching fails when it is an event. Triple Session turns it into a loop: measure the gap, train against it, and check whether the next call moved.

  1. 01

    Identify the gap

    Every call is recorded and scored against your own playbook, so the distance between what your team says and what the playbook asks for stops being a guess.

  2. 02

    Surface the insights

    Patterns roll up across reps, deals, and objections. You see which behavior is costing pipeline, not just which rep is behind.

  3. 03

    Train the people

    Training is assigned against that specific gap: short, expert-led sessions tied to the behavior you just measured.

  4. 04

    Deliver the feedback

    Managers coach from evidence instead of memory. A scorecard, the moment in the transcript, and the one thing to practice next.

Your team's next call is already on the calendar.

Start with the free plan and run the loop on your own playbook. No credit card, no procurement conversation.