Table of Contents

1. Foreword

2. Preface

3. Prologue

4. PART I: Design Thinking Basics

   1. HOUR 1: Design Thinking Explained

      1. Thinking Slower to Deliver Faster

      2. A Process for Progress: Popular Design Thinking Models

      3. Our Design Thinking Model for Tech

      4. The Battle Between Perfection and Time

      5. The What: Techniques and Exercises

      6. The How: The Design Thinking Cycle for Progress

      7. The When: Ambiguity, Complexity, and Uncertainty

      8. The Why: Better Practices and Faster Outcomes

      9. The Who: Design Thinking by Technology Role

      10. Design Thinking in Action: Real-world Tech Examples

      11. What Not to Do: Lessons Learned the Hard Way

      12. Summary

      13. Workshop

   2. HOUR 2: A Design Thinking Model for Tech

      1. Human-Centered Thinking

      2. Design Thinking in Four Phases

      3. What Not to Do: Exclusively Left to Right

      4. Summary

      5. Workshop

   3. HOUR 3: Design Thinking for Small Audiences

      1. Design Thinking for Me

      2. Learning More Quickly

      3. Thinking and Problem Solving

      4. Coping with Ambiguity

      5. Prioritizing Next Best Steps for Uncertainty

      6. Executing More Effectively

      7. What Not to Do: This Isn’t for Me

      8. Summary

      9. Workshop

   4. HOUR 4: Resilient and Sustainable Teams

      1. Design Thinking for Tech Team Alignment

      2. Design Thinking for Sustainable Teams

      3. Responsibly Operating at Speed

      4. What Not to Do: The Archipelago Effect

      5. Summary

      6. Workshop

   5. HOUR 5: Visible and Visual Teamwork

      1. Making Teamwork Visible and Visual

      2. Tools for Visual Collaboration

      3. Executing a Design Thinking Exercise

      4. What Not to Do: Keeping It All Inside

      5. Summary

      6. Workbook

5. PART II: Understanding Broadly

   1. HOUR 6: Understanding the Lay of the Land

      1. Listening and Understanding

      2. Assessing the Broader Environment

      3. Understanding and Articulating Value

      4. What Not to Do: Ignore the Culture Fractals

      5. Summary

      6. Workshop

   2. HOUR 7: Connecting with the Right People

      1. A Framework for Finding and Prioritizing People

      2. Exercises for Stakeholder Mapping and Prioritization

      3. Exercises and Techniques for Engaging Stakeholders

      4. What Not to Do: Stick to the Happy Path

      5. Summary

      6. Workbook

   3. HOUR 8: Learning and Empathizing

      1. From Stakeholders to Personas

      2. Three Types of Empathy

      3. A 360-Degree Model for Empathizing

      4. A Recipe for Empathizing

      5. What Not to Do: Ignore the 20 Percent

      6. Summary

      7. Workshop

   4. HOUR 9: Identifying the Right Problem

      1. Identifying and Understanding a Problem

      2. Three Exercises for Problem Identification

      3. Techniques and Exercises for Problem Validation

      4. What Not to Do: Jump In! (to the Wrong Problem)

      5. Summary

      6. Workshop

6. PART III: Thinking Differently

   1. HOUR 10: Introduction to Thinking Differently

      1. Ideation and Thinking for Problem Solving

      2. Divergent and Convergent Thinking

      3. Warm-ups for Thinking Differently

      4. Techniques for Clearing the Mind

      5. What Not to Do: Stay Convergent!

      6. Summary

      7. Workshop

   2. HOUR 11: Guardrails for Thinking Creatively

      1. Constraints and Guardrails

      2. Simple Guardrails for Thinking Differently

      3. Exercises for Thinking Through Risks

      4. Crazy Techniques for Extreme Thinking

      5. What Not to Do: Avoid the Silly-Sounding Stuff

      6. Summary

      7. Workshop

   3. HOUR 12: Exercises for Increasing Creativity

      1. Creativity and Thinking

      2. Techniques and Exercises for Creative Thinking

      3. What Not to Do: Concluding Thinking Too Early

      4. Summary

      5. Workshop

   4. HOUR 13: Exercises for Reducing Uncertainty

      1. Next-Step Thinking for Uncertain Situations

      2. Reducing Uncertainty and Ambiguity

      3. Working Through Uncertainty and What’s Next

      4. What Not to Do: The Brute-Force Path

      5. Summary

      6. Workshop

   5. HOUR 14: Thinking for Problem Solving

      1. From Ideas to Potential Solutions

      2. Visual Exercises for Problem Solving

      3. What Not to Do: Skimp on Brainstorming

      4. Summary

      5. Workshop

7. PART IV: Delivering Value

   1. HOUR 15: Cross-Teaming and Communicating for Outcomes

      1. Cross-Boundary Teaming for Collaboration

      2. Techniques for Working Across Teams

      3. Techniques for Communications Challenges

      4. What Not to Do: Using Words When a Picture Is Needed

      5. Summary

      6. Workshop

   2. HOUR 16: Prototyping and Solutioning by Doing

      1. The Prototyping and Solutioning Mindset

      2. Making Progress versus Solving the Entire Problem

      3. Techniques for Making Planned Progress

      4. What Not to Do: Ignoring the Inverse Power Law

      5. Summary

      6. Workshop

   3. HOUR 17: Solutioning Small and Fast

      1. The Progress Mindset: Showing Up and Starting Small

      2. Realizing Value Through Objectives and Key Results

      3. Starting Small and Delivering Fast

      4. Techniques for Delivering and Executing to Think

      5. For a Limited Time Only…

      6. What Not to Do: The Forever MVP

      7. Summary

      8. Workshop

   4. HOUR 18: Delivering Value at Velocity

      1. Delivery Techniques for Increasing Value Velocity

      2. Team Considerations for Velocity

      3. Change Control Considerations for Velocity

      4. What Not to Do: Shrink Sprints to Speed Up

      5. Summary

      6. Workshop

8. PART V: Iterating for Progress

   1. HOUR 19: Testing for Validation

      1. The Testing Mindset

      2. Traditional Types of Testing

      3. Testing Techniques for Learning and Validating

      4. Testing Tools for Feedback

      5. What Not to Do: Automate Everything

      6. Summary

      7. Workshop

   2. HOUR 20: Feedback for Continuous Improvement

      1. Simple Feedback Techniques

      2. Strategic Feedback and Reflection Techniques

      3. What Not to Do: Wait for Late Feedback

      4. Summary

      5. Workshop

   3. HOUR 21: Deploying for Progress

      1. Avoiding Perfection Traps

      2. Novel Techniques for Making Progress

      3. Edge Case Techniques for Deploying and Realizing Value

      4. What Not to Do: Deploying Too Soon

      5. Summary

      6. Workshop

   4. HOUR 22: Operating at Scale

      1. Techniques and Exercises for Effective Scaling

      2. Operational Resiliency Techniques

      3. Techniques for Sustaining Systems and Value

      4. What Not to Do: The Scale versus Features Mandate

      5. Summary

      6. Workshop

   5. HOUR 23: Making Change Sticky

      1. Change Management and Adoption

      2. The Four-Phase Change Process

      3. Methods for Creating Awareness

      4. Techniques for Providing Purpose

      5. Driving Readiness Through Design Thinking

      6. Four Techniques for Adopting Change

      7. Techniques for Timing Change

      8. What Not to Do: Change Management Can Wait

      9. Summary

      10. Workshop

   6. HOUR 24: Design Thinking for Project Velocity

      1. Project Management Velocity

      2. Leadership and Governance

      3. Stakeholders and Expectations

      4. Development Approach

      5. Risk Management

      6. Schedule Management

      7. Managing Scope

      8. Delivery and Quality

      9. Communications and Collaboration

      10. What Not to Do: No Courage, No Future

      11. Summary

      12. Workshop

9. Appendix A: Case Study Quiz Answers

10. Appendix B: Summary of Design Thinking Techniques and Exercises

11. Appendix C: Design Thinking in Action (by the Hour)

12. References

13. Index