Chain of Learning: Leadership Strategies for Continuous Improvement and Transformational Change 69| Better Judgment, Not Better AI Tools: What Leaders Need to Learn and Unlearn [with Barry O'Reilly]
You're being told to use AI. But which tool you actually need to do your best work?
Leaders and change practitioners everywhere feel the same pressures right now — more meetings, more information, more mandates to adopt AI — with less time to think and less clarity about where to start. And most of the advice begins in the wrong place: with the tool.
In this episode of Chain of Learning, I talk with Barry O'Reilly, bestselling author of Unlearn and Lean Enterprise, and author of the new book Artificial Organizations, about why the real opportunity with AI isn't automation. It's better judgment.
Barry shares examples from his work with Fortune 500 executives who are successfully pairing human instinct with machine insight — not by adopting every new tool, but by understanding how they work, where judgment matters most, and what needs to be unlearned along the way.
It's about letting go of the belief that your expertise is your competitive advantage, and starting to see AI not as a replacement, but as a thinking partner that can sharpen your clarity, your presence, and your preparation.
In this episode, you'll learn:
- Why starting with the tool is the wrong place to start — and what to do instead
- How to identify your natural traits and highest-leverage tasks as the foundation for working with AI
- The unlearning required to shift from relying on instinct alone to combining human judgment with machine insight
- How successful leaders are using AI to pressure-test ideas and show up more prepared and present
- Why the skills that make you more effective with AI are the same skills that make you more influential with people
Where does judgment matter most in your role right now — and what might you need to unlearn to create space for a better way of working?
ABOUT MY GUEST: Barry O'Reilly is the bestselling author of Unlearn and co-author of Lean Enterprise. He hosts the Unlearn Podcast and is co-founder of Nobody Studios, an AI-driven venture studio. His newest book, Artificial Organizations, is a practical guide for leaders ready to combine human and machine intelligence to make better decisions faster.
Barry O’Reilly is also giving away a copy of Artificial Organizations to THREE lucky winners!
Artificial Organizations explores how leaders can combine human judgment with AI to make better decisions in an increasingly complex world. Instead of focusing on AI tools, the book shows how organizations must redesign how leaders think, work, and make decisions so technology enhances clarity rather than amplifies confusion. It presents a practical leadership system for using AI as a thinking partner to improve judgment, reduce decision overload, and lead more effectively.
Register now to enter the giveaway!
IMPORTANT LINKS:
- Full episode show notes with links to other podcast episodes and resources: ChainOfLearning.com/69
- Check out my website for resources and ways to work with me KBJAnderson.com
- Connect with Barry O’Reilly: linkedin.com/in/barryoreilly
- Follow me on LinkedIn: linkedin.com/in/kbjanderson
- Check out Barry O’Reilly’s book, Artificial Organizations: artificialorganizations.com
- Subscribe to my newsletter: kbjanderson.com/newsletter
- Learn more about my coaching, trusted advisor partnerships, and leadership learning experiences: organizations@kbjanderson.com
RELATED LINKS:
- Unlearn Podcast | Intentional Leadership with Katie Anderson
- Episode 59 | Get Better at Getting Better: Leveraging AI to Elevate Human Learning with Nathen Harvey
TIMESTAMPS FOR THIS EPISODE:
02:28 Where to start on adopting AI
05:04 Importance of understanding natural traits and strengths before looking into AI tools
07:12 Defining the problem first before looking for the tool to close the gap
08:17 Why some may see AI as a deflection tool
09:02 How to use AI for synthesizing data rather than rudimentary tasks
12:28 Why judgment is the leadership advantage and leveraging AI to make better judgment
12:38 Using decision velocity to improve decision making
13:35 Decision advantage in synthesizing data to make a decision
14:35 The difference between AI and human strengths in decision making
16:26 Unlearning how you work to make progress
19:32 Why human thinking plus machine equals a better outcome
20:28 Examples of how to use AI to be the best business and thinking partner
24:46 Importance of asking the right questions when brainstorming with AI
26:06 The limitations of AI and knowing how to use it to your advantage
30:18 How technology can help us be make a bigger impact
33:12 The loss of psychological safety when implementing AI and unlearning this fear
35:35 Better results when teams collaborate with AI vs. doing it independently
36:06 Shifting from control based learning mindset to influence based learning mindset for continuous improvement
37:54 Implementing AI to be the most effective in your organization
40:34 How to start building an AI stack knowing your natural traits, one or two tasks, and then experimenting with an AI tool
42:54 The skills that make us more effective with machines to increase influence
43:16 Questions for reflection on how to implement AI in your organization