Unlearn

AI capabilities are advancing quickly, but changing how people work takes time. Leaders need to give teams the confidence to experiment while protecting sensitive information and keeping responsibility clear. How they manage that balance shapes whether AI leads to better business outcomes.

In this episode, Cassandra Pratt, CHRO at Progyny, and John Marcante, former Global CIO of Vanguard, join me to explore how governance can support that change. Cass shares lessons from Progyny’s internal HR tool, Lumi, and efforts to redesign workflows while building employee trust. John recalls how a Vanguard team improved website conversion by listening to clients and simplifying their choices. He connects that experience to governing AI through clear business outcomes, accountability, and oversight matched to risk.

This is the second podcast in The Adaptive Enterprise, our five-part article and podcast series on redesigning work, governance, and leadership for the age of AI.

• Start with a business outcome: Define the problem you want to solve before choosing how to use AI. John’s Vanguard example shows how customer research and simpler choices helped address a conversion problem that previous technology investment had not resolved.
• Design governance into the whole workflow: Bring the relevant business, risk, and technical partners together early. Cass explains why understanding the data and the full process makes it easier to establish appropriate controls.
• Build trust through visible action: Explain how information is handled and show what happens when work is automated. Cass describes employees moving into a new member services area after automation, giving them evidence that leadership would follow through on its commitments.
• Put recovered capacity toward what matters: At Progyny, reducing manual work can give people more time to listen to and support members. Judge progress against the business outcome and the experience you want to improve.
• Match oversight to the risk: John contrasts an internal productivity tool with autonomous trading to explain why different uses need different levels of oversight. Clear responsibility, human involvement, and monitoring remain important as AI becomes more autonomous.

• An initial tool can be a starting point: Cass describes Lumi evolving beyond its original HR use. At the time of recording, Lumi Landing, which would compile and present information across the company, was still being developed.
• Learning needs support across levels: Progyny’s champions program brings employees from different roles and seniority levels together, with engineers helping on more complex challenges.
• Leaders need firsthand experience: Cass’s executive team built skills and agents themselves. Experiencing the difficulties helped make the learning process more tangible and reinforced the importance of sharing mistakes.
• Human judgment remains a leadership responsibility: John describes AI’s value in gathering a fact base while emphasizing leaders’ responsibility to imagine the organization’s future and determine its direction.

00:00 – Episode Recap

Cass describes the gap between the speed of AI and organizational change, while John introduces his analogy of roadblocks, speed bumps, and guardrails.

02:39 – What Should Leaders Govern Now?

Barry introduces the conversation, and Cass explains why progress in HR has been slower than she expected.

04:37 – Start With the Outcome at Vanguard

John shares how a cross-functional team used customer feedback to identify confusing language and excessive choices affecting website conversion.

08:18 – Protecting the Human Experience

Cass describes how operational automation can free people to focus on member conversations and the human service Progyny values.

11:56 – Building Trust in an Internal HR Tool

Barry introduces the employee experience behind Lumi, and Cass explains how the team addressed concerns about information handling and anonymity.

14:06 – From an Initial Tool to Wider Learning

Cass discusses Lumi’s evolution, initiatives still in development, and the champions program supporting experimentation across the organization.

18:09 – Redesigning Work With Fresh Perspectives

Cass explains how colleagues from other disciplines help challenge familiar processes and design governance around the whole workflow.

21:17 – The Courage to Lead While Learning

John and Barry discuss vulnerability, visible experimentation, and leaders’ responsibility to keep attention on business outcomes.

24:15 – Giving Employees Evidence They Can Trust

Cass shares how employees moved into new work after automation and how hands-on executive learning supports confidence in change.

30:27 – Guardrails, Risk, and Accountability

John explains oversight matched to risk, enterprise-level coordination, and the governance questions raised by increasingly autonomous AI.

34:48 – Where to Start on Monday Morning

Cass recommends involving the right partners early, defining the problem, and understanding the data needed to redesign the workflow.

36:18 – Machine Intelligence and Human Ingenuity

John explains why leaders should use AI to inform strategy while retaining responsibility for imagining the future of the business.

• The Adaptive Enterprise: From Software Governance to Behavioral Governance
• Artificial Organizations Research Program: Measure AI Outcomes
• Artificial Organizations
• Cass Pratt’s previous Unlearn Podcast episode
• Cass Pratt on LinkedIn
• John Marcante on LinkedIn
• Progyny
• Vanguard

Making technology faster does not automatically make the business better.

John Marcante spent 28 years at Vanguard, including serving as Global CIO and leading its high-net-worth and advice business. As Deloitte’s U.S. CIO-in-Residence, he works with senior technology leaders navigating change.

In our conversation, John and I explore why AI investment needs to change how work gets done. John shares what happened when Vanguard’s cloud journey made IT faster than the business could absorb, and how shifting to cross-functional teams and shared outcomes helped address that gap. We also discuss human judgment, the anxiety people feel when familiar tasks are automated, and how leaders can direct freed-up time toward work that matters.

This is the first podcast in The Adaptive Enterprise, our five-part article and podcast series on redesigning work, governance, and leadership for the age of AI.

• Redesign work around new capabilities: Speeding up one step in a process can leave the overall business unchanged. Leaders need to bring people together to rethink the work from end to end.
• Align teams around a business outcome: At Vanguard, engineers and business colleagues needed a shared definition of success. Measuring each function separately made it harder to improve the result for clients.
• Decide how recovered capacity will be used: Time saved through automation creates an opportunity. Leaders are responsible for helping people use that time where judgment and expertise can improve outcomes.
• Help people redefine their value: As portfolio activities became automated, Vanguard advisors could spend more time helping families navigate important life decisions. John describes how client loyalty became the goal guiding that shift.
• Build a continuous cycle of adaptation: The Adaptive Enterprise Loop connects emerging capabilities, work redesign, outcome measurement and governance, and learning. Organizations need to repeat this cycle as new possibilities emerge.

• Technology foundations still matter: John cautions that organized data, modern platforms, and addressing technical debt remain important. Work redesign does not remove the need for those foundations.
• Technical capability and organizational influence are different: John describes a gap between technology leaders’ confidence in scaling AI and their confidence in changing how the business operates.
• Leaders need to model the change themselves: Barry shares how Progyny CEO Pete Anevski experimented with new ways of working and openly discussed what he was learning, helping others feel able to experiment.
• Humility helps reduce learning anxiety: John emphasizes honest communication and vulnerability when people are uncertain about their roles. Leaders do not need every answer before showing how they are learning.
• Stay close to the people doing the work: John moved his office onto the advisor floor to listen to client conversations, understand concerns, and help connect the change to what mattered for clients.

00:00 – Boards Are Asking Where the AI Value Is

John opens with the gap between AI adoption and business value, and the questions boards are asking about their investment.

01:41 – Introducing The Adaptive Enterprise Series

Barry introduces John and explains how their conversations grew into five articles and five companion podcasts.

02:54 – What Should Change Because of AI?

Barry frames the leadership challenge around what new capabilities make possible for work.

05:30 – When IT Gets Faster Than the Business

John recounts Vanguard’s cloud journey, the bottleneck that shifted into the business, and the move to cross-functional product teams.

07:50 – Business and Technology Need to Move Together

Barry shares a lesson from American Airlines about involving the wider business in transformation.

09:45 – Scaling AI Without Changing the Operating Model

John discusses why technical readiness does not necessarily give leaders the influence to change established ways of working.

11:07 – Redesign the Whole Process

Barry explains how local productivity gains can leave end-to-end work unchanged, while John describes aligning teams around shared outcomes.

15:21 – When Automation Challenges People’s Roles

Barry explores the anxiety people feel when tasks that have defined their work begin to change.

17:13 – What Will You Do With the Time You Free Up?

John explains why efficiency alone is insufficient and why leaders need to direct capacity toward valuable work.

19:01 – Leaders Go First

Barry shares how Progyny’s CEO modeled experimentation, and John discusses humility and vulnerability in leadership.

22:46 – Helping Advisors Redefine Their Value

John describes moving the focus from portfolio mechanics and larger client books to client loyalty and important family decisions.

27:26 – The Adaptive Enterprise Loop

John explains the continuous cycle of capabilities, work redesign, outcomes, governance, and learning.

30:50 – Where Executive Teams Can Start

John offers practical starting points: rethink work, identify where judgment creates value, and align people around business outcomes.

• John Marcante on LinkedIn - https://www.linkedin.com/in/john-t-marcante/?isSelfProfile=false
• The Adaptive Enterprise Series: Article 1 - https://barryoreilly.com/explore/blog/how-ai-is-changing-work-and-leadership/
• Measure AI Outcomes survey - https://artificialorganizations.com/measure-ai-outcomes
• Artificial Organizations - https://geni.us/artificialorgs
• Vanguard on LinkedIn - https://www.linkedin.com/company/vanguard/
• Deloitte on LinkedIn - https://www.linkedin.com/company/deloitte/

When building gets easier, choosing what to build becomes even more important.

Ciaran Cosgrave is CEO of Nearform, a global AI-native engineering company for the enterprise. Before moving into entrepreneurship and technology, he spent the first decade of his career running refugee camps across Africa and Central America. Those experiences shaped how he thinks about resilience, problem-solving, and building teams.

In our conversation, we explore why Ciaran focuses on problems before technology, how AI software development is compressing months of prototyping into days and weeks, and why faster experimentation makes judgment even more important. We also get into the new challenge leaders face when teams can generate more ideas and prototypes than organizations can realistically absorb.

• Start with the problem, not the technology: Understanding the underlying problem and speaking with the people experiencing it creates a stronger foundation than chasing technology or quick financial returns.
• Knowing what to build remains difficult: AI can change how software gets built, but leaders still need judgment to determine which problems matter and what is worth creating.
• Faster prototypes can improve judgment: Moving from idea to prototype in days or weeks gives teams more opportunities to explore alternatives and test assumptions before committing to large investments.
• More experimentation requires better filtering: As testing ideas becomes faster and cheaper, leaders need mechanisms for deciding which prototypes deserve to move forward.
• Growth is becoming less dependent on headcount: AI is challenging the traditional services model where growing a business was closely tied to adding more people.

• Resilience can come from unexpected experiences: Ciaran credits his years working in refugee camps with teaching him perseverance and giving him perspective when facing rejection and uncertainty.
• Great teams still matter: Ciaran emphasizes finding good people, helping them work together, and building strong teams around difficult problems.
• Luck belongs in the entrepreneurship story: Timing, advice, unexpected opportunities, and good fortune can play an important role even when successful founders later describe a more deliberate strategy.
• Nearform was built around open source and small, senior teams: The company was built on a belief in open technology and in smaller groups of experienced people creating greater impact.
• The transformation experts are being disrupted too: After helping companies navigate mobile, cloud, and ecommerce, Nearform now finds its own services business directly affected by AI.

Episode Highlights

00:00 – Solve Problems Before Chasing Money

Ciaran explains why he has always been more interested in solving meaningful problems than pursuing technology or quick financial returns.

02:32 – Guest Introduction: Ciaran Cosgrave

Meet Ciaran Cosgrave, CEO of Nearform, whose unconventional career began with a decade spent running refugee camps before moving into entrepreneurship and technology.

03:52 – From Refugee Camps to Technology

Ciaran shares how he spent the first ten years of his career working in refugee camps before entering technology.

05:46 – Giving His Early Career to Others

A teenage encounter with a technology entrepreneur inspired Ciaran to spend the early years of his career serving others and tackling difficult problems.

08:18 – Becoming an Entrepreneur by Accident

After struggling to enter traditional corporate roles, Ciaran found an opportunity in financial services and started building technology businesses.

11:45 – Focus on Problems, People, and a Little Luck

Ciaran explains why understanding the problem, finding great people, and acknowledging luck have shaped how he builds businesses.

15:43 – What Drew Ciaran to Nearform

Ciaran describes Nearform’s origins and its early belief in open-source technology, small senior teams, and software as a force for good.

21:03 – When the Transformation Experts Get Disrupted

After years of helping companies navigate digital transformation, Nearform now finds its own industry being reshaped by AI.

25:45 – Knowing What to Build Is Still Hard

Ciaran argues that judgment about what to build remains one of the biggest challenges for organizations using AI.

29:38 – From Months of Prototyping to Days and Weeks

AI-assisted development allows teams to move from ideas to prototypes much faster and examine more alternatives before committing.

33:20 – Making More Bets With Greater Optionality

Barry explores how cheaper experimentation allows teams to test multiple possibilities instead of placing one large bet.

36:06 – When Innovation Becomes the Bottleneck

Ciaran explains why organizations need stronger filtering mechanisms as teams generate and prototype more ideas.

39:18 – Turning AI’s Potential Into Reality

Ciaran shares his optimism about putting AI into production and using it to build new services and tackle difficult problems.

• Ciaran Cosgrave on LinkedIn - https://www.linkedin.com/in/ciarancosgrave/
• Nearform Website - https://www.nearform.com/
• Nearform on LinkedIn - https://www.linkedin.com/company/nearform/
• Artificial Organizations – https://geni.us/artificialorgs
• Read Artificial Organizations? Leave a review on Amazon – https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328

LinkedIn: https://www.linkedin.com/in/barryoreilly

Website: https://barryoreilly.com

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Building AI startups can make past success a liability when it convinces you that the way you built before is the way you should build next.

Sam Kroonenburg knows what it feels like to build at scale. He co-founded A Cloud Guru, helped grow it into a business serving millions of learners, and eventually sold the company to Pluralsight. Now, as CEO and co-founder of Cuttable, he’s back at the beginning: finding customers, testing assumptions, shipping imperfect products, and learning how different company-building looks in the AI era.

In our conversation, we explore what Sam had to unlearn when he moved from running a 600-person company back into an early-stage startup. We get into why Cuttable walked away from nearly $1 million in annual recurring revenue, how enterprise customers can pull a young company away from the product it actually needs to build, and why AI is shifting product and engineering teams from owning parts of a system to owning measurable outcomes.

• Past success can distort your judgment: Starting Cuttable reminded Sam that reputation means little if the product does not solve a problem customers will pay for.
• Experience does not transfer automatically: Sam could trust his instincts when building for engineers, but entering advertising required him to test assumptions and learn from customers.
• Revenue can hide the wrong product: Cuttable reached nearly $1 million in ARR while engineers were still manually doing work the product was supposed to automate.
• Taking the long view can require a reset: Sam and his co-founders released every customer, returned to zero revenue, and rebuilt around end-to-end automation.
• AI shifts the focus from tasks to outcomes: Instead of teaching AI to copy a human process, teams should define the desired result and let AI determine how to achieve it.

• Speed can be an advantage over scale: A Cloud Guru prepared courses before AWS certifications launched, then updated them using real exam feedback.
• Playfulness can strengthen a product: Short, entertaining lessons made cloud training easier to engage with and helped A Cloud Guru stand out.
• Paying customers provide stronger signals: Payment shows whether a problem matters enough to solve and makes the customer’s feedback more meaningful.
• AI is changing team ownership: Cuttable is moving from teams that own system components to teams accountable for measurable customer outcomes.
• Founder optimism needs a counterweight: Glitch Capital uses analysts and experienced operators to challenge assumptions and add rigor to investment decisions.

00:00 – Episode Recap

Sam reflects on starting again after a major exit and learning that customers care more about solving their problem than a founder’s reputation.

02:13 – Guest Introduction: Sam Kroonenburg

Meet Sam Kroonenburg, CEO and co-founder of Cuttable, co-founder of A Cloud Guru, and founder investor at Glitch Capital.

03:29 – The Moment Technology Clicked

Sam traces his entrepreneurial journey back to receiving his first computer and learning to code through an online pen pal.

09:11 – Winning Through Speed and Play

Sam explains how A Cloud Guru used informed bets, rapid updates, and playful learning experiences to move faster than larger organizations.

12:26 – Starting Again and Unlearning Founder Instinct

Moving from a 600-person company to an early-stage startup forced Sam to test his assumptions and relearn how to earn customer trust.

17:51 – Running a Startup Like a Large Company

Sam initially brought too much structure, reporting, and sales pressure into Cuttable before refocusing on product-market fit.

20:56 – Why Cuttable Went Back to Zero

After reaching nearly $1 million in ARR, Cuttable released every customer and rebuilt around end-to-end automation.

27:48 – Why Paying Customers Change the Signal

Sam explains why payment reveals whether a problem matters enough to solve and makes customer feedback more meaningful.

29:43 – Stop Teaching AI to Work Like a Human

Cuttable learned to give AI the available data and desired outcome instead of forcing it to follow a prescribed human process.

34:45 – Organizing Teams Around Outcomes

Sam explores why engineers focused on customer impact often embrace AI and how Cuttable is organizing teams around measurable outcomes.

38:41 – Why Founder Optimism Needs a Filter

Sam explains how Glitch Capital balances founder optimism with analysts and experienced operators who challenge assumptions.

42:03 – Smaller Teams and Bigger Impact

Sam shares his optimism that AI will help smaller teams create impact at a scale that once required much larger organizations.

Sam had to unlearn the confidence and operating habits that came with previous success. At Cuttable, he found that reputation could not replace customer value, evidence, or the search for product-market fit.

Enterprise demands were pulling Cuttable toward custom work and manual intervention. When engineers began generating and fixing campaigns themselves, the team released those customers and rebuilt around end-to-end automation.

Sam believes teams should spend less time telling AI how to perform a task and more time defining the desired outcome. AI can then use the available data to determine the best method.

Payment shows that a problem matters enough to solve. Free users can offer feedback without genuinely valuing the product, while paying customers provide a stronger signal.

Cuttable is organizing teams around measurable customer outcomes instead of software components. Teams can use AI and evaluation systems to improve those outcomes continuously.

• Cuttable — Sam Kroonenburg’s AI-powered creative production system for advertising.
• A Cloud Guru — The cloud computing education company co-founded by Sam and later acquired by Pluralsight.
• Glitch Capital — The Australia and New Zealand founders fund Sam started with fellow founders and operators.
• AWS re:Invent — Discussed in Sam’s story about how A Cloud Guru prepared training for new AWS certifications at launch speed.
• Square Peg — Cuttable’s investor, whose response to the company’s decision to reset revenue reinforced Sam’s understanding of seed-stage investing.
• Artificial Organizations — https://geni.us/artificialorgs
• Read Artificial Organizations? Leave a review on Amazon - https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328

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X: https://x.com/barryoreilly

Instagram: https://www.instagram.com/barryoreilly/

AI can accelerate a strong operating model, but when decision rights, incentives, or data are already unclear, it can make the mess spread faster.

In this episode, I sit down with Denise Tilles, a leading voice in product operations, to unpack how her career moved from editorial work at Condé Nast into product management, commercial leadership, and eventually product operations. Denise shares how learning to work with revenue data, product analysts, and operating models changed the way she thought about product leadership and led to her work helping enterprise organizations make faster, better-quality decisions.

We explore what product operations actually does, why an operating model needs to define how decisions get made, and where incentives can quietly undermine even a well-designed process. We also dig into what happens when AI makes producing documents, specifications, and analysis nearly effortless: generating more output doesn't remove the work of judgment. In many cases, it makes clarity about inputs, outputs, ownership, and what “good” looks like even more important.

• Product ops should improve decision-making: Denise defines it around business and data insights, customer and market insights, and the operating model.
• Commercial context changes product thinking: At Cision, learning P&L, ACV, and recognized revenue helped Denise connect product decisions directly to business outcomes.
• Good analysis reveals hidden opportunities: A product analyst uncovered an add-on opportunity that generated roughly $1 million within a year.
• Operating models need clear decision rights: Teams need to know what gets worked on, who decides, and how work actually gets done.
• AI amplifies the system already in place: If ownership, data, or processes are unclear, AI can make those weaknesses spread faster.

• Informal decisions can override formal processes: Denise learned that hallway conversations and executive requests often mattered more than the documented workflow.
• Proof does not create authority: Better analysis can earn credibility, but changing a system still requires ownership, sponsorship, and permission.
• Incentives shape behavior: Product and sales can both act rationally while optimizing toward conflicting measures of success.
• AI can shift work downstream: Faster artifact creation still leaves someone responsible for checking the reasoning, evidence, and assumptions.
• Operations may become more connected: Denise sees product ops, design ops, sales ops, and other functions moving toward a more unified “Omni Ops” model.

00:00 - Episode Recap

Denise explains why the starting point for operating-model and AI work should be the pain a company is actually experiencing, from PRD structure to data quality, rather than adopting AI simply because the technology is available.

02:01 - Guest Introduction: Denise Tilles

I introduce Denise Tilles and her work in product operations and operating models, setting up our discussion about data, decision-making, incentives, and how product organizations can operate more effectively.

03:13 - From Editor to Product Manager

Denise traces her move from media and content strategy at Condé Nast into product management, a role she initially had to define for herself because the discipline was still relatively young.

04:50 - Learning the Economics of Product

Moving to Cision gave Denise access to commercial data she had never had before, pushing her to learn from the CFO and understand product through revenue, P&L, ACV, and business outcomes.

08:41 - The Analyst Who Changed the Team

Denise explains how hiring a product analyst gave her team more objective insight into customer and product data, including an overlooked opportunity that generated roughly $1 million in its first year.

12:55 - Finding Revenue Hidden in Behavior

I share how an analyst at Lastminute.com identified a collapse in same-day booking conversion after 7 p.m., giving the team a specific customer behavior to investigate and improve through experiments.

15:14 - The Three Pillars of Product Ops

Denise defines product operations through business and data insights, customer and market insights, and the operating model, all designed to help product managers make faster and better-quality decisions.

17:01 - The Process You Don't See

Denise describes discovering that documented processes were often competing with informal conversations and executive requests, revealing why operating models need to account for how decisions really get made.

19:59 - Who Actually Gets to Decide?

At its core, Denise says an operating model defines what a company works on, who has the right to decide, and how the work gets done within the organization's real constraints.

24:41 - Operating Models Need Owners

Denise warns against treating an operating model as something you publish once and forget, because without clear ownership, maintenance, onboarding, and reinforcement, the system quickly falls out of use.

25:48 - Incentives Beat Better Process

A mismatch between how product and sales were measured taught Denise that people naturally optimize around their incentives, even when that produces conflicting outcomes for the wider business.

29:09 - AI Makes Drive-By Requests Harder to Reject

Denise explains how a senior leader's opinion can now arrive with an AI-generated specification, data, and outcomes attached, making an untested idea look more rigorous without necessarily improving the underlying thinking.

33:22 - Define What Good Looks Like

As AI increases the volume of work teams can produce, Denise argues that operating models need clearer standards for what should be created, what evidence belongs in it, and how colleagues are expected to consume it.

35:33 - Your Output Is Someone Else's Input

We explore the value of looking at work end to end, because one team's output often becomes another team's input and localized optimization can create problems elsewhere in the system.

38:56 - Use AI Where the Pain Justifies It

Denise is increasingly advising companies to use less AI than they initially expect, starting instead with the problem, the value AI might add, and the human judgment and context that still need to remain in the loop.

41:10 - From Product Ops to Omni Ops

Denise looks ahead to a more connected model where operational disciplines work across functional boundaries, allowing companies to design the engine of operations as one system rather than a collection of independent silos.

42:09 - Closing Reflections

I close by encouraging listeners to explore Denise and Melissa's Product Ops and to think of their own organizations as systems that can be deliberately redesigned and experimented on.

What is product operations?

Denise describes product operations as helping product managers make faster and better-quality decisions. Her model has three pillars: business and data insights, customer and market insights, and the operating model or ways of working that support product teams.

What is a product operating model?

At its simplest, Denise says an operating model determines what a company decides to work on, who gets to decide, and how the work gets done. Every organization has one in practice, but many have accumulated theirs informally rather than designing and communicating it intentionally.

How does AI affect product operations?

AI can accelerate activities across product operations, but Denise argues that judgment and context remain essential. When organizations apply AI to an unclear operating model, poor data, or unresolved decision rights, the technology can amplify those existing weaknesses rather than solve them.

Why do incentives matter when designing an operating model?

People tend to optimize around what they are measured on. Denise experienced this when product was focused on recognized revenue while sales celebrated closed contracts, creating different definitions of success even though both teams were acting rationally according to their incentives.

How should a company decide where to use AI in its operating model?

Denise starts with the pain points rather than the technology. She looks at issues such as PRD structure, data analysis, source quality, ownership, and decision-making first, then asks whether AI genuinely improves that part of the system and where human judgment still needs to remain.

• Product Operations — the book Denise co-authored with Melissa on building the systems and capabilities that help product managers make faster and better decisions.
• Escaping the Build Trap — Melissa's earlier book, referenced during Denise's story about how they came to write Product Ops together.
• Artificial Organizations — Barry O'Reilly's book on leadership, decision-making, and working with AI, referenced during the episode.
• Condé Nast — where Denise worked in media and moved from content strategy into product management.
• Cision — the B2B SaaS company where Denise developed her commercial product experience and built what she later recognized as a product operations capability.
• Produx Labs — the consultancy where Denise worked with Melissa and developed product ops as an area of expertise.
• Value stream mapping — referenced by Barry as a useful way to understand processes end to end, particularly as teams introduce AI and agentic workflows.

AI is forcing us to rethink a question most organizations have avoided for years: what is uniquely valuable about human work when intelligence itself is no longer scarce?

Tatyana Mamut, CEO of Wayfound and former CPO of Nextdoor, joins me to explore AI adoption through a lens that goes beyond software. Drawing on her background in anthropology, economics, organizational design, and product leadership, Tatyana explains why the real challenge is designing the rules, tools, norms, incentives, and relationships that shape how humans and AI agents work together.

We get practical about what this means at both an individual and organizational level. We explore the human capabilities that become more valuable as AI takes on more routine mental work, why fear leads companies into bad AI decisions, how poorly designed incentives can push agents toward unexpected behavior, and why the subject-matter experts closest to the work need to become responsible for managing the agents operating alongside them.

• Human comparative advantage is changing: As AI takes on more mental work, people need to rethink where their uniquely human value comes from.
• Develop taste, judgment, relationships, and performance: Tatyana sees these as practical areas where people can complement AI rather than compete with it.
• AI adoption is an organizational design problem: Success depends on redesigning rules, tools, norms, incentives, and accountability around the technology.
• Goals and guardrails can still produce the wrong behavior: An agent may follow its objective while still acting against the organization’s intent, as Tatyana’s refund example shows.
• Subject-matter experts need to become agent managers: The people closest to the work must be able to monitor, correct, and improve the agents operating in their domain.

• Organizational culture can be consciously designed: Tatyana frames culture as the interaction of rules, tools, and unwritten norms that shape behavior.
• Relationships become more valuable as outreach gets automated: When AI increases the volume of generic communication, trust and genuine relationships become more important.
• AI can generate options, but humans still decide what matters: Judgment becomes critical when the challenge shifts from what can be done to what is worth doing.
• Small failure rates compound across multi-agent systems: Edge cases that seem minor with one agent can become more significant as agents are connected into workflows.
• Building an agent and managing one are different jobs: Engineering can help create the agent, but functional owners must take responsibility for its ongoing performance.

00:00 - Episode Recap

Tatyana frames the AI shift as a deeper question about what it means to create value as a human when intelligent systems increasingly share responsibility for thinking and decision-making.

02:10 - Guest Introduction: Tatyana Mamut

I introduce Tatyana Mamut, CEO of Wayfound and former CPO of Nextdoor, whose experience across anthropology, organizational design, and product leadership shapes her approach to human and AI systems.

05:06 - From Economics to Anthropology

Tatyana explains how the failure of economic models to predict events such as Russia’s 1998 economic collapse pushed her toward studying the mental models and social institutions that shape human behavior.

08:07 - Designing Culture Through Rules, Tools, and Norms

Tatyana breaks organizational culture into practical components, showing how formal rules, available technologies, incentives, status, beliefs, and unwritten norms interact to shape behavior.

13:16 - The Multi-Sapiens Workplace

Tatyana argues that AI is forcing people to reconsider their comparative advantage as humans as intelligent systems begin participating in higher-level thinking and decision-making.

18:42 - Four Human Capabilities to Develop

Tatyana identifies taste, judgment, relationships, and performance as four areas people can strengthen as AI absorbs more routine mental work.

23:32 - Why Human Relationships Matter More

Barry and Tatyana discuss how automation can remove administrative work while making authentic relationships, lived experience, trust, and storytelling increasingly valuable.

27:21 - Fear Is the Enemy of Progress

Tatyana explains how fear can push organizations either to rush into AI using outdated assumptions or retreat when the technology does not behave like traditional software.

29:11 - AI Agents Need Different Supervision

Tatyana describes why AI agents require governance and oversight based on organizational context, including goals, rules, norms, and definitions of what good performance looks like.

31:32 - The Incentive Problem

The conversation turns to how model behavior and organizational goals interact, including Tatyana’s view that sycophantic behavior can create unexpected feedback loops in production agents.

32:34 - When an Agent Breaks the Intent of the Rule

Using a customer service example, Tatyana shows how an agent trying to maximize case closure and customer satisfaction can suggest a refund even when its guardrails tell it not to.

38:59 - Escaping Endless Pilot Mode

Barry explores why uncertainty can keep organizations trapped in experimentation rather than allowing AI systems to move into real operating environments.

40:10 - Who Owns the Agent After Deployment?

Tatyana argues that the functional experts closest to the work need direct responsibility and visibility once an AI agent is operating in production.

44:41 - Treat AI Agents Like New Employees

Tatyana compares engineering teams to recruiters who can help bring an agent into the organization, while the business owner remains responsible for coaching, compliance, and ongoing performance.

46:14 - Closing Reflections

Barry closes by reflecting on the emerging skills leaders and individuals will need as they learn to manage systems in which humans and AI agents increasingly work together.

Tatyana highlights four areas: taste, judgment, relationships, and performance. Her argument is that AI may generate options, perform routine mental work, and help with administration, but humans still create value by deciding what is good, what is worth doing, whom to trust, and how to motivate or persuade other people.

She uses the phrase to describe a workplace where humans are no longer the only entities carrying out higher-level thinking and decision-making. In that environment, organizations need new rules, tools, and norms for determining how humans and AI systems work together and where responsibility sits.

Because deploying an AI system changes more than the technology stack. Organizations also have to consider incentives, governance, supervision, communication, accountability, cultural norms, and who has the authority to evaluate and correct an agent’s behavior.

Tatyana explains that an agent can technically pursue its assigned goal while still behaving in a way the organization did not intend. Her customer service example shows an agent suggesting a refund because doing so could resolve the case and improve customer satisfaction, despite instructions designed to prevent refunds.

Tatyana argues that responsibility should move toward the subject-matter experts who understand the work the agent performs. Engineering or IT may build and deploy the system, but salespeople should oversee sales agents, finance teams should oversee finance agents, and other functional experts should have direct access to monitor, correct, and improve their agents.

• Tanyana Mamut on LinkedIn - https://www.linkedin.com/in/tmamut/
• Wayfound - https://www.wayfound.ai/
• Artificial Organizations - https://geni.us/artificialorgs
• Nextdoor - https://blog.nextdoor.com/
• Claude - https://claude.com/
• Salesforce - https://www.salesforce.com/
• Intercom Fin - https://www.intercom.com/fin
• Agentforce - https://www.salesforce.com/agentforce/
• IDEO - https://www.ideo.com/

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Before leaders can redesign their organizations with AI, they have to reconsider how they personally think, work, and make decisions.

In this special episode of Unlearn, Barry O’Reilly shares the opening chapter of the audiobook edition of Artificial Organizations, narrated in his own voice. After hearing from readers who wanted another way to experience the book, Barry spent four days in the studio bringing its ideas and stories to life. The process was rewarding, demanding, and personal. As someone who is dyslexic, reading every word aloud required a different kind of focus from delivering a keynote, teaching a workshop, or hosting a podcast conversation.

Barry then takes listeners into the central argument of the book: organizations often begin AI adoption with licenses, pilots, and tools while leaving leadership behavior and decision-making systems unchanged. Drawing from his own experiments, leadership research, and work with senior teams across North America, Europe, and Asia, he explains why meaningful AI transformation starts with human traits, high-value tasks, and the judgment leaders must preserve before selecting technology.

• AI should strengthen judgment, not simply increase output: Machines can process and synthesize information at a scale no individual can match, but leaders still have to decide what matters. The opportunity is to use AI to prepare, capture, and pressure-test thinking so human attention stays focused on consequential decisions.
• Start with traits, then tasks, then tools: Barry’s 3T model begins with how a leader naturally thinks, creates, communicates, and decides. Only after identifying the tasks where that judgment creates the most value should leaders choose tools to support the work.
• Decision velocity must be paired with decision advantage: Decision velocity is how quickly a leader moves from question to insight, decision, and action. Decision advantage is the quality and depth of context behind that choice; speed without insight creates chaos, while insight without timely action becomes irrelevant.
• Most leadership time is allocated away from leadership value: Barry describes an 80/20 mismatch in which meetings, updates, administration, and context reconstruction consume most of a leader’s time, while the greatest value comes from framing problems, evaluating tradeoffs, and making high-stakes decisions.
• Organizational AI adoption begins with personal behavior change: Broad mandates, task forces, and tool rollouts are often the wrong starting point. Leaders build more credible adoption when they experiment in their own workflows, share what they learn, and make new behaviors visible to their teams.

• Presence can be more valuable than productivity: Barry’s first AI experiment used a meeting assistant to capture and synthesize conversations. The practical gain was not only faster preparation and follow-up; it allowed him to stop carrying every detail in his head and remain fully present during critical discussions.
• Experience becomes a liability when it is not augmented: The instincts and institutional knowledge that helped leaders succeed can become limiting when they are treated as sufficient. Experience keeps compounding only when leaders combine it with broader recall, faster synthesis, and continuous testing.
• Senior leaders need psychological safety to learn: Barry’s executive study found that leaders preferred one-on-one coaching and small peer cohorts over large workshops or self-paced courses. Being a beginner is uncomfortable at senior levels, so smaller environments make experimentation and honest questions easier.
• New capacity should create thinking space, not more workload: In the Progeny case study, AI reduced the effort required to capture meetings, actions, owners, and deadlines. CEO Peter Nevsky framed the resulting capacity as time for strategic thought and better decisions rather than an invitation to place people on a faster operational treadmill.
• The unit of change is the judgment inside a role: AI may automate parts of a project manager’s, analyst’s, or executive’s work while increasing the importance of interpretation, challenge, and decision quality. The role may remain, but the judgment required within it changes.

00:00 – Episode Introduction & Why I Created the Audiobook

Barry introduces this special preview of the Artificial Organizations audiobook, shares why he chose to narrate it himself, and explains why leaders need a different approach to AI adoption through the 3T framework: Traits, Tasks, and Tools.

04:33 – A Quick Favor Before We Begin

Barry invites listeners to leave an Amazon review, recommend the audiobook to their network, and help more leaders discover its ideas.

05:16 – Preface: Why the Way We Work Is Broken

Barry introduces the central challenge facing modern organizations: leaders are overwhelmed by information, while better decisions remain harder than ever.

07:11 – Judgment Under Pressure

Barry explores why more data, more tools, and more technology haven't created better leadership, arguing that the real constraint is our ability to process information and make sound judgments.

10:07 – The First AI Leadership Experiment

A simple experiment with an AI meeting assistant transformed Barry's leadership by improving clarity, presence, and decision-making, leading to a new perspective on AI's role.

12:00 – AI as Judgment Infrastructure

Barry reframes AI as more than a productivity tool, explaining how it strengthens judgment, improves decisions, and helps leaders focus on what matters most.

16:07 – Part One: The Judgment Constraint

Barry introduces the first section of the book, explaining why AI creates little value unless it changes how leaders think, decide, and lead.

18:08 – Chapter One: Your Legacy Is Now Your Liability

Barry examines why experience alone is no longer enough and how decision velocity and continuous learning are becoming the defining advantages of modern leadership.

22:20 – The AI ROI Blind Spot

Barry challenges the common focus on efficiency and cost reduction, arguing that AI's greatest value lies in helping leaders make better and faster decisions.

28:16 – From Linear Leadership to Exponential Innovation

Barry explains why traditional leadership models struggle in the AI era and why organizations must adopt new ways of learning, experimenting, and making decisions.

34:10 – What Makes an Artificial Organization

Barry defines artificial organizations and shares how leaders can replace memory-based management with shared judgment systems that accelerate decision-making and collaboration.

40:09 – The New Leadership Divide

Barry explores the widening gap between leaders who actively experiment with AI and those who continue relying on legacy ways of working, and why that difference will compound over time.

43:15 – Where to Start

Barry explains why successful AI transformation begins with personal experimentation, encouraging leaders to model new behaviors before scaling change across their organizations.

45:15 – Closing Reflections

Barry concludes the first chapter, thanks listeners for joining this special audiobook preview, and invites them to continue the journey with Artificial Organizations.

Yes. This special episode includes Barry O’Reilly’s recorded introduction followed by the opening chapter of the audiobook edition of Artificial Organizations, narrated by Barry himself. He explains why the audio edition was created, what recording the book required, and how its ideas connect to his work with executive leaders and teams.

An artificial organization is a company that deliberately combines human and machine intelligence to redesign how context is captured, information is synthesized, and decisions are made. Instead of adding AI to the edges of existing workflows, it builds judgment infrastructure into how the organization operates.

Leaders can use AI to capture conversations, summarize context, test assumptions, explore scenarios, prepare for meetings, and identify unresolved actions. This reduces the information leaders must carry mentally and gives them more capacity to focus on tradeoffs, consequences, and high-value judgment.

Decision velocity is the speed at which a leader moves from a question to insight, decision, and action. Decision advantage is the quality, accuracy, and depth of context behind that decision. Strong leadership requires both because speed without insight creates chaos, while insight without action loses relevance.

They often begin with tool purchases, pilots, and mandates without redesigning how work, context, and judgment flow through the organization. When leaders do not change their own workflows and behavior first, AI remains disconnected from the decisions and operating systems that produce results.

Barry recommends beginning with personal workflows rather than a company-wide transformation program. Leaders should understand how they naturally think and work, identify the tasks where their judgment creates the most value, and then experiment with tools that reduce low-leverage effort and improve decision quality.

• Artificial Organizations: Build Better Judgment, Speed, and Results with Human and Machine Intelligence by Barry O’Reilly
• Unlearn by Barry O’Reilly
• Continuous Delivery by Jez Humble and Dave Farley
• Barry O’Reilly on LinkedIn: https://www.linkedin.com/in/barryoreilly
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AI is making it easier than ever to build products, automate work, and scale ideas. The challenge is no longer access to technology. It's designing the systems, stories, and customer understanding that turn AI into real business outcomes.

In this episode of Unlearn, I'm joined by Eric Baxley, Chief Marketing Officer at Nobody Studios. Eric shares how a seventh-grade summer teaching himself to program on an Atari 800 sparked a 30-plus year career spanning software development, product management, marketing, sales, business development, and partnerships.

We explore what Eric has had to unlearn while building companies in the AI era—from challenging assumptions before execution and replacing corporate polish with authentic storytelling, to designing scalable systems instead of disconnected tools. Along the way, Eric explains why great marketing still starts with deeply understanding customers, and why AI works best when it amplifies human judgment rather than replacing it.

• Challenge the foundation before execution: Eric shared that in a previous large business, the team was “doing things right,” but not “doing the right things.” The segmentation was off, and correcting who they were really going after helped the team hit its goals for the next three years.
• Authentic stories build trust: Eric has had to unlearn the corporate habit of making everything polished before sharing it. He believes people respond when you show the journey, talk about the hardships, and ask for feedback along the way.
• Systems matter more than scattered tools: Eric warned against building a set of siloed point products. In a venture studio building multiple companies at once, he said you need systems that can scale, especially with the speed of AI.
• Use AI to strengthen your thinking, not replace it: Eric described writing and revising a LinkedIn post himself before turning to AI. The post performed well, and his takeaway was that people could sense it was naturally written and not simply generated.
• Real messaging starts with real customers: When Eric joined Nobody Studios, one of the first things he did was speak directly with patent attorneys for Evalify. That helped him understand their language, their concerns, and what message would actually resonate.

• Storytelling has to match the person and the moment: Eric explained that messaging should change based on persona, stage in the buyer journey, industry, and country. A CIO, CTO, or chief product officer may each need to hear the story differently.
• The right message needs different levels of depth: Eric talked about having a 30-second version, a 90-second version, and a longer version of the message ready. The point is to be prepared for the amount of attention and context the listener actually has.
• B2B messaging has to speak to head, heart, and wallet: Eric said that in larger enterprise deals, especially six- or seven-figure buying decisions, messaging needs to appeal to logic, emotion, and business economics.
• Consistency across channels is hard but necessary: Eric noted that messages can quickly become confusing when sales, TikTok, Instagram, LinkedIn, and other channels are all saying different things. The challenge is keeping the story consistent while still tailoring it to the audience.
• Automation still needs personalization: Eric uses some automated systems, but he emphasized that he still fine-tunes and personalizes messages based on someone’s background. Otherwise, outreach becomes the kind of generic message people ignore.

00:00 - Episode Recap

Eric Baxley explains why company building in the AI era requires scalable systems, curiosity, grit, and a willingness to dig into the details rather than staying at a high level.

01:53 - Guest Introduction: Eric Baxley

Barry introduces Eric Baxley, Chief Marketing Officer at Nobody Studios, and highlights his work across growth, marketing, partnerships, and company building.

03:13 - The Seventh-Grade Spark

Eric shares how teaching himself to program on an Atari 800 while growing up in Germany sparked his interest in technology and shaped the rest of his career.

05:10 - Unlearning Assumptions

Eric explains why he no longer assumes the base foundation of a business is solid, using a segmentation mistake from a large business as an example.

06:20 - Moving Past Corporate Polish

Eric talks about unlearning the need for everything to be buttoned up and why showing the real journey can make the work more relatable.

07:39 - Authentic Stories in a Noisy Market

Barry and Eric discuss why honest stories about what is working, what is difficult, and what is still being learned can stand out from exaggerated AI claims.

10:48 - Tailoring the Story

Eric breaks down how messaging needs to be adapted by persona, buyer journey stage, industry, and country.

13:24 - Learning From Patent Attorneys

Eric shares how he started shaping Evalify’s messaging by speaking directly with patent attorneys instead of creating sales and marketing materials in a vacuum.

18:08 - Head, Heart, and Wallet

Eric explains why enterprise messaging needs more than a clinical problem-and-solution structure; it also needs emotion, business value, and a clear story.

22:40 - Building Systems Backwards From the Customer

Eric talks about the explosion of marketing technology and why he starts with the persona, the outcome, and the channels where customers actually spend time.

27:37 - Writing Before AI

Eric describes how he wrote and revised a LinkedIn post himself before involving AI, and why he believes the human work helped it resonate.

31:48 - Human-in-the-Loop AI for Patent Attorneys

Eric explains how Evalify helps patent attorneys with work that can take 20 to 30 hours, while making clear that the product amplifies their work rather than replacing them.

33:49 - Building Companies Faster and More Frugally

Eric shares why he is excited that small teams can now use AI capabilities to build, fund, and scale companies differently than in the past.

35:36 - Closing Reflections

Barry thanks Eric for sharing lessons from his work at Nobody Studios and looks forward to continuing to build together.

Q1. Who is Eric Baxley?

Eric Baxley is the Chief Marketing Officer at Nobody Studios. In the episode, he describes a career that began in software development and later moved into product management, marketing, sales, business development, and partnerships.

Q2. What does Eric Baxley say leaders need to unlearn?

Eric says he has had to unlearn assuming the foundation is already right, relying too much on corporate polish, and building around siloed tools instead of scalable systems.

Q3. Why does Eric Baxley focus so much on customer segmentation?

Eric believes many teams jump straight to execution without checking whether they are going after the right customers. He shared an example where fixing segmentation helped a business focus on the right audience and hit its goals.

Q4. How does Eric Baxley approach messaging for AI products?

Eric starts by talking to the people the product is meant to serve. With Evalify, he spoke with patent attorneys, used their language, tested the message, and worked with an advisory board to see whether the story resonated.

Q5. What role should AI play in marketing, according to this episode?

AI can help with speed, systems, and efficiency, but Eric and Barry emphasize that human judgment still matters. Eric’s examples show that personalization, customer understanding, and careful writing are still needed for the message to land.

• Eric Baxley on LinkedIn - https://www.linkedin.com/in/ericbaxley/
• Nobody Studios on LinkedIn - https://www.linkedin.com/company/nobodycrowd/
• Nobody Studios
• Evalify
• The Challenger Sale
• Artificial Organizations - https://artificialorganizations.com/

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AI is changing how leaders think, decide, and work with their teams. But as John Cutler points out in this conversation, the real shift is not simply about faster answers or more productivity. It is about becoming more aware of the judgment systems we already use, often without noticing.

In this episode of the Unlearn Podcast, I’m joined again by John Cutler, product thinker, systems explorer, and Head of Product at Dotwork. We explore how AI can help leaders expose their thinking, pressure test decisions, and build stronger team judgment, while also making it easier to accelerate poor habits, shallow work, and false confidence.

John shares practical examples from product prioritization, survey design, objection handling, and team collaboration to show where AI can genuinely improve decision quality. We also get into the tradeoffs: why AI can make work feel like “hard mode,” why downtime still matters, and why intentionality is becoming one of the most important leadership skills in this moment.

AI exposes how leaders make decisions: AI tends to amplify the decision system already there. When a leader’s thinking is clear, AI can help make it visible and reusable; when it is vague, AI can make that vagueness move faster.

Judgment is built differently depending on the situation: John explains that some judgment comes from repetition and tacit pattern recognition, while other judgment develops through coaching, discussion, and working alongside people with more experience.

AI can help turn intuition into something teams can use: John’s example of documenting his product prioritization heuristic shows how AI can help make internal judgment concrete. The value comes from helping others understand why certain decisions matter, not just what the decision is.

Better AI use starts with knowing what you know: John contrasts product prioritization, where he has deep experience, with survey design, where he knows there is established expertise to draw from. The skill is recognizing whether AI should extend your own judgment or help you borrow from a domain expert.

Teams using AI well can raise decision quality: Barry shares how AI can help teams pressure test assumptions, run scenarios, and ask disconfirming questions without losing momentum. The real advantage comes when AI strengthens collaboration rather than replacing it.

AI can also accelerate bad instincts: John warns that AI can make poor thinking look polished. A team can paste AI onto an existing process and call it transformation without changing how decisions are actually made.

Intentionality matters more than productivity: AI can reduce friction, but it can also remove the pauses where judgment forms. Leaders need to design space for reflection, not just optimize for more output.

Individual metacognition: This is understanding how you think and make decisions. John’s examples show that leaders get more value from AI when they can first make their own judgment system visible.

Social metacognition: This is understanding that other people think, perceive, and engage differently. AI becomes more useful when it supports the conversation between people instead of flattening everyone into the same process.

Computational metacognition: This is understanding what LLMs are good at, where they fail, and how to work with them responsibly. John argues that leaders need this skill so they know when to trust AI, when to challenge it, and when to bring in human expertise.

Objection handling as a repeatable system: John’s team did not ask AI to create a generic sales guide. They role-played real objections, captured the discussion, compared their responses against best practices, and turned that into a system that could review future calls.

The deeper lesson: AI becomes more useful when it is connected to real work, real context, and a team’s actual judgment. Without that grounding, it risks creating more output without improving the quality of decisions.

00:00 – Episode Recap

John Cutler opens with a story about how judgment often comes from repetition and tacit signals, not neat frameworks. The episode explores what happens when AI starts making those hidden decision systems visible.

02:02 – Guest Introduction: John Cutler

Barry welcomes back John Cutler, product thinker, systems explorer, and Head of Product at Dotwork, for a conversation about judgment, decision making, and collaboration in the age of AI.

04:59 – How Judgment Gets Built

John explains that judgment develops differently depending on the context: through individual practice, repeated exposure, mentorship, team discussion, and comparison against examples of quality.

08:58 – Making Prioritization Thinking Visible

John shares how he used AI to document his own scoring heuristic for product prioritization, giving a teammate deeper insight into why certain ideas mattered more than others.

12:11 – Knowing When to Borrow Expertise

Using survey design as an example, John explains how AI can help access existing expert knowledge when you are not the expert yourself. The key is being honest about the limits of your own judgment.

13:56 – From Answers to Better Questions

Barry reflects on the shift from using AI to get answers toward using it to challenge thinking, improve decisions, and bring stronger questions to colleagues.

18:04 – Why Better Surveys Lead to Better Decisions

John explains how improving a survey from average to strong can materially change the quality of insight a team gets back, which then affects the quality of product decisions.

23:04 – Teams, AI, and Decision Advantage

Barry shares how AI can help teams maintain momentum during ideation by quickly pressure testing scenarios, asking disconfirming questions, and bringing outside information into the room.

27:48 – Turning Objection Handling into a System

John describes how his team recorded a live objection-handling exercise, analyzed it against best practices, and turned the team’s collective knowledge into a reusable system.

31:32 – The Three Forms of Metacognition

John introduces individual, social, and computational metacognition as three skills leaders need to work effectively with AI and with each other.

35:19 – AI Exposes Leadership Systems

Barry and John discuss why AI can feel uncomfortable for leaders: it reveals whether there is a real decision-making system underneath the confidence.

37:34 – When AI Makes Every Decision Feel Hard

John raises an important limitation: AI can remove small pauses in the workday, leaving people constantly operating at high cognitive load.

41:58 – Productivity Fatigue and Agent Overload

Barry and John discuss the temptation to run too many AI-assisted tasks at once, and why that can create more noise rather than better outcomes.

44:23 – Designing Time to Think

Barry shares how he intentionally creates time for walking, exercise, and reflection to avoid over-optimizing for fast, reactive decisions.

46:38 – Intentionality Over Process Theater

John explains why intentionality is different from rigid process. The opportunity is to design better systems without flattening the richness of how teams actually work.

50:11 – Closing Reflections

Barry wraps the conversation by reflecting on the opportunity for leaders to use AI not just to move faster, but to become more aware of how they think, decide, and scale judgment across teams.

• Dotwork – John Cutler’s work focuses on helping teams and organizations better understand how work, decisions, and systems connect.
• Artificial Organizations – Barry references the book and the CSTA loop as part of his work on AI, decision making, and organizational performance.
• Daniel Kahneman’s System 1 and System 2 Thinking – Referenced in the discussion on snap decisions, deeper thinking, and productivity fatigue.
• Pugh Analysis – John mentions this as an example of a prioritization approach originally intended to help experts independently rate options and then discuss differences in judgment.

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Jim Highsmith has been thinking about decision-making for a long time. When he wrote Agile Project Management in 2004, he went looking for practical guidance on decision-making in the project management literature and found very little. That gap matters even more now.

In this episode, Jim and I talk about why AI raises the stakes for executive judgment. AI can remove friction, speed up work, and take on repeatable tasks, but it can also make it easier for leaders to stop practicing the very capabilities they are paid to use. Jim brings this to life through John Boyd’s OODA loop, the risk of judgment atrophy, mountaineering decisions, Rob Hall’s Everest threshold, Phil Knight’s pattern recognition at Nike, and a personal story from Jim’s own time leading a collaborative project team at Nike.

This conversation is really about how leaders build judgment deliberately: by making consequence-bearing decisions, setting thresholds before pressure arrives, creating space for slow thinking, and reflecting honestly on how decisions were made.

• AI can weaken judgment when leaders stop practicing it: Jim compares the risk to driving an autonomous car: the more the system takes over, the less sharp the driver becomes. AI can remove low-value effort, but leaders still need to practice making consequence-bearing decisions.
• The OODA loop is mostly about orientation: Jim explains that John Boyd’s edge was not just speed, but his ability to update his mental model quickly. For leaders, the real work is noticing when old assumptions no longer fit the situation.
• Capability is knowledge plus experience plus judgment: AI can make knowledge easier to access, but it cannot replace the experience of carrying consequences. Judgment develops when people make real decisions, reflect on the outcome, and adjust how they think.
• Thresholds only work when enforced under pressure: Jim uses Rob Hall’s Everest story to show why decision thresholds matter before emotion, ambition, or sunk cost take over. In business, those thresholds might be cost, risk, customer impact, or reversibility.
• Leaders need to separate fast decisions from slow judgment: Some repeatable, data-heavy decisions can be automated with guardrails. Higher-context decisions still need human orientation, pattern matching, and time to think.
• Reflection turns experience into better pattern matching: Barry shares his practice of documenting decisions, what was known at the time, and why the call was made. That kind of review helps leaders improve the decision process, not just judge the outcome.

• Role modeling beats mandates: Jim describes how Boyd taught by showing the mechanics of his performance. Barry connects this to AI adoption: leaders create more movement by sharing how they are using the tools in real work.
• Productivity fatigue is a real AI-era risk: Barry reflects on how AI can increase output while shrinking the space to think. That matters because senior leadership work often depends on judgment, not just throughput.
• AI transformation is still a people problem: Jim returns to Jerry Weinberg’s reminder that “no matter what they tell you, it’s a people problem.” Tools help, but organizations still need to redesign the work, behaviors, and decisions around them.
• Pattern matching is different from gut feel: Jim uses Phil Knight’s Nike decisions to show how instinct can come from years of context. What looks intuitive on the surface is often pattern recognition built through experience.

00:00 – Episode Recap – Jim Highsmith frames the core tension of the episode: AI can accelerate work, but it can also expose whether leaders have a real decision-making system or are quietly handing judgment to the machine.

01:45 – Guest Introduction – Barry introduces Jim Highsmith, a pioneer of adaptive leadership and original Agile Manifesto signatory whose work has shaped how organizations navigate uncertainty and make high-stakes decisions. (Jim Highsmith)

04:27 – Decision-Making Was Missing from the Playbook – Jim explains that when he wrote his first Agile Project Management book in 2004, he found surprisingly little practical guidance on decision-making in standard project management sources.

05:47 – The Real Power of the OODA Loop – Jim revisits John Boyd’s observe, orient, decide, act model and argues that orientation, the ability to update mental models under pressure, is the part leaders often underdevelop.

07:19 – From Process-Centric to Judgment-Centric Management – Jim makes the case that if AI takes over more process improvement work, organizations need decision-making capacity distributed through the system, not concentrated at the top.

09:14 – The Judgment Muscle Can Atrophy – Barry and Jim use the autonomous car example to show how useful automation can quietly weaken a capability when people stop practicing it.

12:33 – Role Modeling Beats Mandates – Jim explains how Boyd taught fighter pilots by showing the mechanics of superior performance, which Barry connects to leaders demonstrating their own AI experiments instead of simply telling others what to do.

15:50 – Capability Is More Than Knowledge – Jim defines capability as knowledge plus experience plus judgment, pointing out that LLMs can provide knowledge but not the consequence-bearing experience that shapes better calls.

18:56 – Thresholds Keep Decisions Honest – Jim shares the Rob Hall Everest story to show why thresholds only matter if leaders are willing to honor them when pressure, ambition, or sunk cost pushes the other way.

20:58 – Automate the Right Decisions – Jim distinguishes fast, data-dependent System One decisions from slower System Two judgments, giving leaders a practical way to decide what to automate and what to protect.

24:31 – From Search Engine to Human-Agent Teams – Jim describes his own progression from using AI as a search engine to working daily with multiple humans and agents, showing that the practice evolves through use.

27:06 – Productivity Fatigue and Constant Execution – Barry reflects on how AI can create more throughput while leaving less space for slow thinking, especially for leaders whose real value is making judgment calls.

31:05 – Relearning the People Problem – Jim returns to Jerry Weinberg’s reminder that “no matter what they tell you, it’s a people problem,” and Barry connects that to companies buying AI tools without redesigning how people work.

33:21 – Pattern Matching Is Not Gut Feel – Jim uses Phil Knight’s early Nike decisions to explain why seasoned executives often seem intuitive because they have built patterns from industry knowledge, relationships, and lived context.

36:09 – Decision Journaling Builds Better Judgment – Barry describes documenting decisions, the information available, and the rationale at the time as a way to learn from both strong and weak outcomes.

37:22 – A Nike Lesson in Collaborative Judgment – Jim recalls a project decision at Nike where the team agreed with the outcome but challenged the process, giving him a lasting lesson about when people need to be part of the call.

38:51 – Closing Reflections – Barry thanks Jim and points listeners toward his writing as these long-standing ideas about judgment, adaptability, and decision-making become even more relevant in the AI era.

• Jim Highsmith’s website – Jim’s home base for his bio, books, articles, podcasts, and current work. (Jim Highsmith)
• The Adaptive EDGE – Jim’s Substack on leadership, adaptability, and AI. (jimhighsmith.substack.com)
• The Agile Manifesto – The original manifesto and signatories list, including Jim Highsmith. (Agile Manifesto)
• Adaptive Leadership: Accelerating Enterprise Agility by Jim Highsmith – The book Jim references when discussing his earlier work on adaptive leadership and decision-making. (Google Books)
• Robot-Proof: When Machines Have All the Answers, Build Better People by Vivienne Ming – The book Jim mentions as influencing his thinking about creative human capability in the AI era. (Google Books)
• Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram – A deeper look at John Boyd, the OODA loop, and the “40-second Boyd” story discussed in the episode. (robertcoram.com)
• Thinking, Fast and Slow by Daniel Kahneman – The source behind the System One and System Two framing referenced in the conversation. (PenguinRandomhouse.com)
• Shoe Dog by Phil Knight – The memoir Jim uses to discuss pattern recognition, risk, and judgment in Nike’s early years. (Simon & Schuster)
• Artificial Organizations by Barry O’Reilly – Barry’s book on building better judgment, speed, and results with human and machine intelligence. (Artificial Organizations)

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