Artificial Organizations: Build Better Judgment, Speed, and Results with Human and Machine Intelligence

AI isn’t replacing leaders. It’s exposing them.

This book is the leadership operating system for the AI era—built to strengthen judgment, accelerate decision velocity, and deliver measurable outcomes at scale.

Senior executives are drowning in information, trapped in meetings, and making consequential decisions without the time or space to think. More tools haven’t solved the problem—they’ve amplified it. When decision-making falters, the cost isn’t inefficiency; it’s stalled initiatives, strategic misalignment, and capital deployed to low-return bets.

 

In Artificial Organizations, Barry O’Reilly shows how to redesign the way you sense, frame, decide, and act by combining human and machine intelligence. You begin by identifying the traits that make you most effective, followed by the tasks where you create disproportionate value. Only then do you apply AI tools—so they sharpen judgment instead of adding noise.

Using this system will help you:

  • Increase decision velocity without sacrificing rigor
  • Improve decision quality under sustained pressure
  • Turn meetings and conversations into compounding information assets
  • Build a personal AI operating system that reinforces executive presence
  • Move from scattered productivity gains to durable decision advantage

Grounded in more than a decade advising CEOs and executive teams—and informed by building and scaling Nobody Studios, a global Top 10 AI venture studio—O’Reilly distills this experience into practical judgment infrastructure for the age of intelligence.

 

Featuring real-world case studies from Amazon, American Airlines, Dotwork, HSBC, Progyny, Skyscanner, Slack, and more, Artificial Organizations shows how leading organizations have redesigned how decisions get made—not simply how work gets automated.

 

This isn’t about learning new tools. It’s about transforming how you lead—so clarity, conviction, and results strengthen as speed increases across your organization.

“The real shift wasn’t adopting new tools. It was changing how leaders made decisions. Speed came from clarity—not control.”

Pete Anevski
CEO
Progyny

“AI won’t transform your company by itself—leaders will. Artificial Organizations gives technology executives a practical blueprint to turn AI into sharper decisions, stronger teams, and real operating leverage at scale.”

Stephen Franchetti
CIO
Slack

“AI didn’t give me more time—it helped me turn intuition into better decisions. In Artificial Organizations, Barry O’Reilly guides leaders on how to achieve that in a way that’s both practical and deeply human.”

Misty Shafer Sterne
VP, Commercial Technology
American Airlines

“AI scales best when leaders start with themselves—using it to think better, not just work faster. Artificial Organizations shows how to do exactly that.”

Andrew Phillips
CTO
Skyscanner

Unlearn Let Go of Past Success to Achieve Extraordinary Results

Good leaders know they need to continuously learn. But great leaders know when to unlearn the past to succeed in the future. This book shows you the way.

Unlearn is a transformative system that shows leaders how to rethink their strategies, retool their capabilities, and revitalize their businesses for stronger, longer-lasting success. There’s a learning curve to running any successful business. But once you begin to rely on past achievements or get stuck in outdated thinking and practices that no longer work, you need to take a step back—and unlearn. This innovative and actionable framework from executive coach Barry O’Reilly shows you how to break the cycle of learned behaviors that were effective in the past but are no longer relevant, and limit or may even stand in the way of your success. With this simple but remarkably powerful three-step system, leaders can:

  1. Unlearn the behaviors and mindsets that keep them and their businesses from moving forward.
  2. Relearn new skills, strategies, and innovations that are transforming the world every day.
  3. Break through old habits and thinking by opening up to new ideas and perspectives while achieving extraordinary results.

“To succeed, it’s critical for executives to entrepreneurs to know how to let go of behavior and methods that have helped them achieve in the past but are now limiting. Unlearn explains how to continuously adapt in an every changing world”

Eric Ries
Co-Founder
The Lean Startup

“Surprisingly, many of the attributes that enabled companies to scale are the very things that impede their future prospects. Unlearn is an essential reminder that the ability to unlearn is an enduring competency of extraordinary individuals, and the organizations they lead”

John Macante
CIO
Vanguard

“Many executives and leaders hang on to thinking and methods that were once useful, but may limit their future success. Apply the lessons in Unlearn and unlock the full potential in yourself, your teams, and your organization”

Noelle Eder
Chief Information and Digital Officer
Hilton Group

“We work in a world of complexity, revolutionary technologies, and dynamic change. The only advantage is peopleengaged and rapidly learning and unlearning. This book shows you how to get there”

Dr Ed Hoffman
Former Chief Knowledge Officer
NASA

What is Unlearning?

Unlearning is the process of letting go, reframing, 
and moving away from once-useful mindsets and acquired behaviors 
that were effective in the past, but now limit our success.

Lean Enterprise How High Performance Organizations Innovate at Scale

Learn how to Lean and Agile principles to work as you transform your business into an effective, efficient and engaged organization.

How well does your organization respond to changing market conditions, customer needs, and emerging technologies when building software-based products? This practical guide presents Lean and Agile principles and patterns to help you move fast at scale—and demonstrates why and how to apply these methodologies throughout your organization, rather than with just one department or team. Through case studies, you’ll learn how successful enterprises have rethought everything from governance and financial management to systems architecture and organizational culture in the pursuit of radically improved performance. Adopting Lean will take time and commitment, but it’s vital for harnessing the cultural and technical forces that are accelerating the rate of innovation.

  • Discover how Lean focuses on people and teamwork at every level, in contrast to traditional management practices
  • Approach problem-solving experimentally, by exploring solutions, testing assumptions, and getting feedback from real users 
  • Lead and manage large-scale programs in a way that empowers employees, increases the speed and quality of delivery, and lowers costs.
  • Learn how to implement ideas from the DevOps and Lean Startup movements even in complex, regulated environments

“Required reading for every executive who understands that we’re all in the technology business now”

Stephen Foreshew-Cain
COO

GOV.UK

“Destined to be the classic, authoritative reference for how organizations plan, organize, implement, and measure work:

Gene Kim
Tripwire Founder, and former CTO, and coauthor of The Phoenix Project

“An essential guide to those that have come to the realization that they have to change to regain an innovative competitive advantage but are unsure where to start”

Jora Gill
Chief Digital Officer
The Economist

“This book integrates into a compelling narrative the best current thinking about how to create great software-intensive products and services”

Mary Poppendieck
Author
The Lean Mindset