Chain of Learning: Leadership Strategies for Continuous Improvement and Transformational Change

The messy middle is part of the learning process.

It’s the point where what worked before no longer fully fits—but what comes next is not yet clear.
Where your thinking is still forming, your ideas are evolving, and the answer has not fully emerged.
And while it can feel uncertain, this is often where the deepest continuous learning happens.

In this behind-the-scenes bonus episode on Chain of Learning, I share a live conversation with, Betsy Jordyn, my business coach and strategic thinking partner, recorded on the final day of a working retreat earlier this month. 
We pull back the curtains and invite you into our unscripted reflections from working through the messy middle of shaping my next book—and the leadership (and life) lessons that continue to emerge through the process.
Tune in to hear the real-time learning, reflection, and refinement happening as I shape the ideas behind my next book.

You’ll learn:
Why the messy middle is often a necessary part of continuous learning, growth, and effective change leadership
How to recognize when forcing clarity too early limits stronger thinking from emerging
What it looks like to let ideas evolve instead of defending what came before
How collaboration and outside perspective sharpen your judgment and deepen your thinking
Why modeling your own learning process creates stronger conditions for learning in others
How to stay engaged in uncertainty without rushing to jumping to answers too quickly
ABOUT MY GUEST:
Betsy Jordyn is the founder and CEO of Betsy Jordyn International, a strategic branding firm that helps transformational consultants and coaches refine their messaging, positioning, and offers to accelerate their success and amplify their impact. She is also the host of the Consulting Matters podcast and a sought-after speaker and trainer on brand strategy, executive influence, and the business of transformation.

Will you help me?
I have a quick favor to ask. I’m conducting research for my next book and would love to get your insights on people-centered, learning organizations and the leadership that creates them. The survey takes just 5 to 10 minutes and your responses will directly shape the book and a future Chain of Learning podcast episode.
-> Take the Survey here, open through May 22.
IMPORTANT LINKS:
Full episode show notes: ChainOfLearning.com/72
Connect with Betsy Jordyn: linkedin.com/in/betsy-jordyn
Listen to Betsy’s Podcast, Consulting Matters: betsyjordyn.com/podcasts/consulting-matters 
Check out my website for resources and working together: KBJAnderson.com
Follow me on LinkedIn: linkedin.com/in/kbjanderson 
Download my FREE KATALYST™ Change Leader Self-Assessment: KBJAnderson.com/katalyst
Subscribe to my newsletter: kbjanderson.com/newsletter 
Take the People-Centered Leadership Survey
TIMESTAMPS FOR THIS EPISODE:
01:16 The hidden reality of creativity and why books are written multiple times
02:39 What the messy middle feels like and why this stage matters more than we think
05:04 Re-centering leadership on what’s within your control in a world of constant change
06:00 Why influence isn’t about forcing change, but creating conditions for growth
08:12 Reframing resistance and what people actually need to move forward
10:06 How to keep evolving instead of staying stuck in old ways of thinking
12:26 The process of writing a book and getting clarity on the what the book is about
16:04 Why growth often requires releasing what once worked
17:09 Benefits of collaborating in person vs. using AI as a thinking partner
18:07 Why learning can’t be forced, but we need to allow space for insight
22:07 The concept of omotenashi and looking at a lens of caring from a human angle
24:14 The meaning of Intention = Heart + Direction to create the conditions for learning
29:15 What changes when you respect others’ agency instead of driving direction
32:19 How to have empathy and not push your agenda when leaders are not “bought in”
33:01 Why your expertise can become a barrier to connection and clarity
35:46 How different perspectives reveal whether your message actually lands
38:08 Moving beyond the lingo to prevent barriers
43:27 Why growth requires releasing identities, ideas, and ways of working

Participate in my Survey:
https://docs.google.com/forms/d/e/1FAIpQLScjlCi-Y3rfzihImMRahEfxMuPr4uqZ4TVqy7h5iRyEQ_uadQ/viewform?usp=dialog
Thank you

Caring becomes carrying.

It happens so naturally we rarely notice it. Someone brings us a problem. We care. We want to help. And somewhere in that desire to help, without meaning to, we take on the weight of solving it ourselves.
That shift is subtle. And costly.
Because the moment you take ownership of the thinking, you take away the very capability you're trying to build.

In this episode, I explore a critical shift in change leadership: how to hold the thinking process so others can solve their own problems — without taking on their work as your own.
Your value as a leader isn't in having the answer. It's in creating the conditions where others can think, test, and learn. When you want to create empowered problem-solving in your organization, stepping back is stepping up.
You'll Learn:
How to notice when you've shifted from supporting someone's thinking to carrying their problem
Why redirecting your focus from the problem to the person working through it changes everything about how you coach
How to use a simple problem solving structure (Target, Actual, Gap) to anchor your questions and keep ownership where it belongs
How to stay present to how someone is thinking instead of jumping ahead to solutions
How to choose intentionally when to step in with direction — and when to step back to build capability
IMPORTANT LINKS:
Full episode show notes with links to other podcast episodes and resources: ChainOfLearning.com/71 
Check out my website for resources and ways to work with me KBJAnderson.com
Follow me on LinkedIn: linkedin.com/in/kbjanderson
Download my free KATALYST™ Change Leader Self-Assessment: KBJAnderson.com/katalyst 
TIMESTAMPS FOR THIS EPISODE:

00:40 The subtle shift from caring to carrying problem solving
03:35 Realization of owning the process of solving the problem
04:39 What gets in the way of intentions to be helpful
05:27 Why problem solving and problem solving coaching are two different skills
05:50 How to stay focused on the thinking process and keep from sliding back into the problem itself
06:42 How to anchor questions around a structured problem solving flow
08:11 The mantra, “Target, Actual gap, Please explain,” to identify the real problem before jumping to solutions
09:13 Benefit of assigning a problem for a team member to solve
10:56 The identity shift from having all the answers to holding the process
12:28 One way to notice if you have a telling habit
14:41 Why you should avoid defaulting to giving the answer and ask questions to understand the problem first
16:59 The meaning of intention = heart + direction to coach with the right motives
17:21 Three steps to coach with intention:
17:25 [ONE] Take an intention pause
17:45 [TWO] Choose the behaviors that align with that impact
18:08 [THREE] Reflect and learn your way forward
19:15 Positive result from leading by asking questions that helped team gain confidence
21:41 Three reflection questions before you go into your next coaching conversation

Participate in my Survey:
https://docs.google.com/forms/d/e/1FAIpQLScjlCi-Y3rfzihImMRahEfxMuPr4uqZ4TVqy7h5iRyEQ_uadQ/viewform?usp=dialog
Thank you

What happens when leaders make decisions further and further away from the work itself?
In a world of AI, automated dashboards, and remote work, it’s easy to manage representations of work instead of understanding what’s actually happening for the people who do it.
Yet, when leaders rely on data rather than facts, they often end up solving the wrong problems, even with the best intentions.
In this episode of Chain of Learning, I'm joined by Nigel Thurlow, consultant, systems thinker, and Toyota's first-ever Chief of Agile, to explore how better decisions come from understanding how the system actually operates. And that understanding is built by engaging with the people doing the work.
When you stay connected, you don't just get better information. You see how work actually flows, where problems emerge, and what's getting in the way. You build trust, surface issues earlier, and make it easier for people to think and solve problems together.
In this episode, you’ll learn:
Why there's a critical difference between delegation and empowerment — and why one leaves people unable to act
How to distinguish between data and facts, and why going to see conditions firsthand changes the decisions you make
What "going to gemba" looks like in a digital or remote environment when there's no factory floor to walk
Why making work visible creates the conditions for people to surface problems,  before they compound
Why AI amplifies what's already there — and why fixing the underlying system comes first
ABOUT MY GUEST: Nigel Thurlow is CEO of The Flow Consortium and the creator of Scrum the Toyota Way. He spent over 20 years at Toyota, including serving as the first Chief of Agile at Toyota Connected. He is co-author of The Flow System and The Flow System Playbook, and his work focuses on improving decision-making in complex environments.

IMPORTANT LINKS:
Full episode show notes with links to other podcast episodes and resources: ChainOfLearning.com/70 
Check out my website for resources and ways to work with me KBJAnderson.com
Connect with Nigel Thurlow: linkedin.com/in/nigelthurlow
Follow me on LinkedIn: linkedin.com/in/kbjanderson
Download my free KATALYST™ Change Leader Self-Assessment: KBJAnderson.com/katalyst  
TIMESTAMPS FOR THIS EPISODE:
03:19 Effects of being detached from the work when working remotely
04:17 Difference between delegation and empowerment when assigning work to others
05:35 Fear of those who are delegated to of failing or making the wrong decision
07:15 What it means to empower someone and transfer the ownership of that decision to someone else
09:21 How to go to gemba and go where the work is done
10:07 The benefits of "presenteeism" and being present where the work is performed
11:46 Benefits of collaborating in person vs. a digital environment to make better decision
13:02 Nigel’s experience in working in a frozen food manufacturer and going out to the line to understand the pain workers experienced
15:42 Why you need to understand how work gets done to improve throughput and quality of work
16:39 Benefits of hiring an external or internal consultant to understand the problems that need solving
19:31 The effects of companies investing in tools and AI and realizing it doesn’t help with problem solving
21:30 How to avoid the leadership decision problem and get all the facts to avoid consequences
24:39 Technique known as “sense making” to understand the temperament and behaviors in the environment to reveal dark constraints
26:09 The difference between US and Toyota’s corporate culture in incentivizing leaders to be part of a system
29:10 How to help workers make changes that need to be made visible to senior leaders
35:04 Enabling others to communicate with leaders to improve decision making
37:14 Why badly designed systems and not the workforce are the cause of problems
38:25 Why you can’t implement AI with a broken system
40:31 The possible future of AI and how it can affect our decision making
43:37 Importance of embracing the human connection to better communicate and make better decisions
47:24 Reflect on where your decisions may be happening too far from the work

Participate in my Survey:
https://docs.google.com/forms/d/e/1FAIpQLScjlCi-Y3rfzihImMRahEfxMuPr4uqZ4TVqy7h5iRyEQ_uadQ/viewform?usp=dialog
Thank you

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: [email protected] 

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

Participate in my Survey:
https://docs.google.com/forms/d/e/1FAIpQLScjlCi-Y3rfzihImMRahEfxMuPr4uqZ4TVqy7h5iRyEQ_uadQ/viewform?usp=dialog
Thank you

Registration is now OPEN for the November 2026 cohort of my Japan Leadership Experience: https://kbjanderson.com/japantrip/

What changes when leaders stop learning alone—and start learning together?

Leadership development often focuses on individual insight: reading, listening, reflecting. But some of the most meaningful shifts in leadership don’t happen that way.

They happen when leadership teams go see, ask questions, and reflect together.

That shared experience becomes a catalyst—aligning leaders around a new way of seeing their organization, supporting one another in practicing new behaviors, and driving lasting transformation.

In this episode of Chain of Learning, you’ll learn why immersive experiences can transform how leadership teams align, learn, and develop—and why learning in context often leads to change that lasts.

Drawing on examples from my Japan Leadership Experience, we look at what happens when leadership teams step away from the day-to-day pressures of their roles and create space to learn and reflect in new ways.

Shared experiences give leadership teams something powerful: a common reference point for how they want to lead and improve—accelerating organizational transformation.

In this episode, we explore how to:
Shift from learning as an individual activity to learning as a leadership team practice
Create alignment by seeing and reflecting on the same things
Move from “What did I learn?” to “What are we seeing differently?”
Turn shared insights into new leadership behaviors back at work
Understand why immersion and context matter when developing people-centered leadership

IMPORTANT LINKS:
Full episode show notes with links to other podcast episodes and resources: ChainOfLearning.com/67 
Check out my website for resources and ways to work with me KBJAnderson.com
Follow me on LinkedIn: linkedin.com/in/kbjanderson
Download my free KATALYST™ Change Leader Self-Assessment: KBJAnderson.com/katalyst 
Learn more about my Japan Leadership Experience: kbjanderson.com/japantrip

RELATED EPISODES:
Episode 25 | Getting Results Through the Power of Serious Leadership with Kecia Kelly and Amy Chaumeton
Episode 20 | How to Coach Executives and Influence Change with Brad Toussaint
Episode 48 | Make Leadership Meaningful: From Tools to Purposeful Impact with Josef Procházka
Episode 67 | Why Lifelong Learning Is the Foundation of Influence (and Can Limit Your Impact)
Episode 4 | Leading for Impact: The Power of Being Over Doing
Episode 17 | Leading Change from the Middle with Pennie Saum

TIMESTAMPS FOR THIS EPISODE:
1:30 The gap between inspiration and the system you return to
2:46  Three conditions that most leadership development is missing.
4:13 The fundamental difference when others are learning beside you vs. learning alone
4:47 How Jim, Healthcare COO,  accelerated transformation by inviting his team on the Japan Leadership Experience
6:49 Transformations that past Japan Leadership Experience have experienced in accelerated learning and sustaining excellence in their organization
10:34 Unlocking shoshin - the beginner’s mind - through immersive experiences
12:04 The benefits of observing Japan employees and companies in person
14:22 The depth of connection that forms when you learn together
16:43 Why shared learning is important for leaders to make changes that sticks
18:55 The cultural impact of the Japan Leadership Experience
21:31 The deepest leadership changes that come from shared learning and shared leadership

Registration is now OPEN for the November 2026 cohort of my Japan Leadership Experience: https://kbjanderson.com/japantrip/