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Generative AI and Claude Cowork for Leaders and Managers

Published by O'Reilly Media, Inc.

Intermediate content levelIntermediate

Use Claude and Claude Cowork to help you set goals, delegate, coach, and give feedback

Course outcomes

  • Discover how generative AI can enhance your effectiveness across core leadership functions
  • Develop practical skills in using AI tools to tackle real leadership challenges
  • Experience how AI can work across your existing tools and workflows, not just in a chat window
  • See AI behave agentically; executing multi-step workflows, reading across real files, and running automatically on a schedule
  • Create a comprehensive action plan tailored to your own leadership context

Course description

Harness the power of generative AI to expand your leadership toolkit. In this innovative course, leadership coach Dave McKeown shows you how to leverage Claude and Claude Cowork to develop solutions and insights for the leadership challenges you face every day.

This isn't a course about AI in the abstract. Working through realistic leadership scenarios, you'll see how Claude can help you think through problems in conversation and how Claude Cowork can take those insights and turn them into polished, professional outputs that live in your real workflow. By the end, you'll have seen AI in action the way it actually works: connected to real information, producing real documents, and building on itself across a series of leadership tasks.

Through practical demos, you'll learn how AI can help you set clear, actionable goals grounded in real data, navigate complex and shifting priorities, delegate tasks with confidence, support team members through coaching, deliver constructive feedback, and hold people accountable, all while building toward a comprehensive 30-day leadership action plan.

What you’ll learn and how you can apply it

  • Use Claude to define clear, actionable SMART goals grounded in real team performance data
  • Leverage AI to rebalance priorities and communicate clearly when the goalposts shift
  • Identify what to delegate, to whom, and how; with AI analysing your team's capacity and strengths and executing the brief in one step
  • Develop personalised coaching plans that help team members take ownership of their challenges
  • Prepare for difficult feedback conversations using the SBI model with AI surfacing patterns across your notes, transcripts, and performance data simultaneously
  • Build team accountability frameworks that set clear expectations without micromanaging
  • See how AI outputs from each leadership task chain together into a single, comprehensive 30-day action plan
  • Discover how to turn a recurring leadership workflow into an automated scheduled task that runs itself every week

This live event is for you because...

  • You're a manager, team leader, or aspiring leader who wants to see how AI can genuinely elevate your leadership, not just save you time on admin
  • You work with teams and are responsible for setting goals, delegating, coaching, and driving results
  • You want to move beyond the chat window and see how tools like Claude and Claude Cowork can work with your real documents, your real data, and your real workflow, including taking over your screen to complete tasks autonomously

Prerequisites

  • Sign up for a Claude account (optional, if you’d like to follow along with the hands-on portion of the course)

Recommended preparation:

Recommended follow-up:

Schedule

The time frames are only estimates and may vary according to how the class is progressing.

Introduction and setting personal context (5 minutes)

  • Presentation: The current AI landscape for leaders: tools, prompting best practices, risks, and limitations
  • Meet Alexa Rivera: the leadership scenario we'll follow throughout the session
  • Preparing for your weekly team meeting (10 minutes)
  • Presentation: Why grounding AI in real data matters
  • Demo: Using Claude and your team's performance data to prepare a clear, motivating team update
  • Setting goals for the next month (15 minutes)
  • Presentation: The importance of goal setting; the role of clear goals in leadership; the SMART framework
  • Hands-on demo: Transforming raw meeting data and team metrics into three measurable monthly goals, complete with weekly milestones
  • Q&A

Handling conflicting priorities (15 minutes)

  • Presentation: Managing conflicting priorities; techniques for prioritization and adaptability in leadership
  • Hands-on demo: When a new company-wide directive lands mid-week, see AI read the announcement alongside your existing goals and produce a clear reprioritisation plan and team communication simultaneously
  • Q&A

Delegating tasks effectively (15 minutes)

  • Presentation: The art of delegation; criteria, process, and common pitfalls
  • Hands-on demo: AI analyses your team's capacity and strengths and recommends who should own the task, then a single instruction produces the delegation email and books a calendar check-in at the same time
  • Q&A
  • Break (5 mins)

Coaching a team member (15 minutes)

  • Presentation: Coaching for development; powerful questions and the coaching mindset
  • Demo: When a team member says they're overwhelmed, see AI read their message alongside private 1:1 notes to produce a personalised coaching agenda with questions tailored to the full picture
  • Q&A

Delivering constructive feedback (15 minutes)

  • Presentation: Techniques for effective feedback; delivering feedback with the SBI (Situation, Behavior, Impact) model
  • Hands-on demo: AI reads conversation notes, a previous 1:1 transcript, and performance data simultaneously, surfacing the complete pattern and producing a structured feedback script
  • Q&A

Holding team members accountable (10 minutes)

  • Presentation: Establishing accountability; the importance of accountability and how to foster it
  • Hands-on demo: AI reads everything produced in the session and builds a team accountability framework ready to share with your people
  • Q&A

Creating a comprehensive action plan (10 minutes)

  • Presentation: Integrating leadership actions
  • Hands-on demo: Using Claude Cowork to synthesise everything from the session into a single 30-day leadership action plan

Wrap-up and Q&A (5 minutes)

Your Instructor

  • Dave McKeown

    Dave McKeown is the CEO of Outfield Leadership, a leadership consultant, and the author of The Self-Evolved Leader: Elevate Your Focus and Develop Your People in a World That Refuses to Slow Down. He has a wealth of experience in connecting individual and team performance to improved business results, with a particular focus on fast-growing, complex organizations. Dave speaks, coaches, and trains on moving from execution to excellence. His goal is to help organizations build a culture of real, authentic, and ultimately results-driven leadership. He’s shared his leadership strategies at the Inc. 500 and GrowCo Conferences, for Bank of America, the British Government, Entrepreneur's Organization, and Bamboo HR, and with countless others. He’s the host of the podcast Lead Like You Give a Damn and writes a regular leadership column for Inc.com.

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Skill covered

Generative AI