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PODCAST

Rethink Your Understanding

Rethink Your Understanding: AI-Driven Insights on Digital Transformation & Software DeliveryWelcome to Rethink Your Understanding, an AI-powered podcast where cutting-edge technology meets expert insights on digital transformation. We use AI to bring my articles and blog posts from rethinkyourunderstanding.com and Medium (https://medium.com/@rethinkyourunderstanding) to life, transforming written content into immersive audio episodes.Each AI-presented episode provides a "Deep Dive" into

technology

All Episodes

17:29

Why Value Stream Management and the Product Operating...

Rethink Your Understanding ·

2025/12/14

This episode explores why modern engineering organizations should move beyond activity metrics and project thinking and adopt a system built on measurable business outcomes. The AI hosts break down how Value Stream Management and the Product Operating Model work together to give teams long-lived ownership, product margin accountability, and the visibility needed to surface friction, align priorities, and understand where value is actually created.They also examine the leadership shift required to

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17:02

The Price of Alignment

Rethink Your Understanding ·

2025/10/26

In this episode, The Price of Alignment, we explore what happens when innovation meets bureaucracy. When a large, centralized organization acquires a smaller, agile one, the push for alignment and consistency can come at a steep cost.Drawing from the story of two companies, “LegacyTech” and “AgileWorks,” we examine how forcing uniform management models onto autonomous, microservice-based teams can unravel the very agility and speed that made them valuable in the first place.The conversation dives

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14:13

Beyond the Beyond Delivery: AI Across the Value Stream

Rethink Your Understanding ·

2025/10/24

Today's conversation is a short follow-up to season 2, episode 48. In this episode, Beyond the Beyond: AI Across the Value Stream, we explore how artificial intelligence is reshaping software delivery, not as a magic fix, but as a mirror reflecting the strength of your existing systems.Drawing insights from the 2025 DORA Report and emerging Software Engineering Intelligence trends, this episode unpacks why AI’s real potential lies in amplifying disciplined engineering practices and end-to-end

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19:38

What Happens When We Eliminate the Agile Leader?

Rethink Your Understanding ·

2025/10/12

When companies remove Agile Leaders, roles like Scrum Masters or Agile Delivery Managers, they often assume the system will self-regulate. But what really happens when no one is accountable for team health, continuous improvement, or flow?In this episode, the AI hosts unpack Phil's article about the quiet erosion of agility inside modern organizations, where well-intentioned efficiency moves end up dismantling the very disciplines that make agile work. Drawing from real-world transformations, he

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16:57

From Two Pizzas to One: How AI Reshapes Dev Teams

Rethink Your Understanding ·

2025/10/04

In this episode, the AI hosts explore how artificial intelligence might reshape the very design of software teams. The “two-pizza rule” once defined how agile, cross-functional teams operated, but AI is changing what small and effective really means.As AI and automation expand what individuals and small teams can achieve, leaders must rethink the scale, structure, and collaboration required. We unpack what this shift means for engineering management, decision-making speed, and value delivery, and

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17:04

Beyond Delivery: Realizing AI’s Potential Across the...

Rethink Your Understanding ·

2025/10/03

AI’s full potential in software delivery isn’t in writing code faster, it’s in transforming the entire value stream. In this episode, the AI hosts explore why most delays happen in ideation and release, not coding, and how AI applied narrowly to delivery can actually amplify dysfunction. Drawing on insights from Mik Kersten, Laura Tacho, John Cutler, Atlassian’s 2025 AI Collaboration Report, and the DORA 2025 findings, we discuss how leaders can use Value Stream Management and flow metrics to

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19:33

Smarter Pull Requests: Balancing AI, Automation, and...

Rethink Your Understanding ·

2025/09/28

In this episode, our AI hosts dive into Smarter Pull Requests: Balancing AI, Automation, and Human Review, a handbook redefining how teams approach code reviews in the age of AI. The framework shows how to integrate AI and automation responsibly, ensuring speed without sacrificing human judgment on quality, security, and design.We cover rules files, evidence-based PR templates, and AI gate checks with tools like GitHub Copilot and CodeRabbit, all reinforced by CI pipelines. These practices raise the

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18:33

So, What Does a VP of Software Engineering Do?

Rethink Your Understanding ·

2025/08/22

This episode takes you inside the evolving role of a VP of Engineering — far beyond a standard job description.The AI hosts discuss why the role is highly contextual, shaped by company size, leadership culture, and organizational maturity. I share the core accountabilities I’ve been held to: ensuring software quality and resilience, fostering people engagement, retaining and developing talent, and building the skills teams need to stay competitive.The conversation also explores the VP’s strategic

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15:16

AI in Software Delivery: Targeting the System, Not...

Rethink Your Understanding ·

2025/08/09

This episode advocates for a system-wide perspective when adopting AI in software development, extending beyond mere code generation to encompass the entire value stream.Recent studies show initial productivity dips and extra effort with AI tools, but this is just a transitional phase, not a failure of the technology. Robust delivery metrics, like those from SEI tools or Value Stream Management platforms, are key to pinpointing bottlenecks where AI can drive the greatest impact, avoiding

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16:59

AI Is Improving Software Engineering. But It's Only...

Rethink Your Understanding ·

2025/08/01

AI is transforming software engineering, but it addresses only one part of a much larger system. Speeding up code creation doesn’t solve deeper issues like unclear requirements, poor architecture, or slow feedback loops, and in some cases, it can amplify dysfunction when the system itself is flawed. Engineers remain fully responsible for what they ship, regardless of how the code is written. The real opportunity is to increase team capacity and deliver value faster, not to reduce cost or inflate

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17:51

Leading Through AI Hype in R&D

Rethink Your Understanding ·

2025/07/28

In this episode, the AI hosts unpack the growing tension between AI hype and real-world adoption in software delivery.While AI is advancing rapidly, many leaders focus on bold claims, like replacing entire teams, without grounding them in metrics that matter. Leaders find it challenging to determine the right metrics to measure the impact of AI, as well as the success of AI adoption and investments. I challenge this narrative and explore how frameworks like Flow Metrics and developer sentiment can

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19:29

Bets, Budgets, and Reframing Software Delivery as...

Rethink Your Understanding ·

2025/06/12

In this episode, our AI hosts dive into an article advocating for a radical reevaluation of software delivery commitments, shifting away from rigid, project-based models and “precise” estimates toward a probabilistic, continuous-discovery mindset. Drawing on Vasco Duarte’s insights and the Three Ways outlined in The DevOps Handbook, they explore treating development as a series of adaptive bets, budgeting for change, using experiments as real-time status reports, and empowering end-to-end team

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25:07

When Team Structure Collides with Role Alignment

Rethink Your Understanding ·

2025/06/01

This episode the AI hosts discuss the challenges of integrating different engineering team structures following a company merger. It examines two primary models: an Engineering Manager (EM)-led structure where a single manager holds multiple responsibilities, and a self-managed, cross-functional team model where accountability is distributed.My article that they cover argues that simply standardizing job titles without considering the context, responsibilities, and underlying architectural alignment

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18:06

We Have Metrics, Now What?

Rethink Your Understanding ·

2025/05/23

This episode addresses a common pitfall in software delivery management: using system-level metrics, such as Flow Metrics, to evaluate individual performance. The AI hosts cover how this practice, while logical to some leaders, can damage trust, produce misleading data, and hinder real improvement. The conversation covers using metrics as a tool to help teams improve, focusing on context, collaboration, and actionable steps. The main takeaway is clear: metrics should promote overall improvement, not

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14:10

A Self-Guided Performance Assessment for Agile...

Rethink Your Understanding ·

2025/05/03

In this episode, The AI hosts explore why teams—unlike individuals—rarely get a performance review, and why that needs to change. Based on my latest article, you'll hear a practical framework designed for Agile and DevOps teams to reflect on how they work, not just what they deliver. We’ll walk through twelve team health dimensions—from collaboration to delivery integrity—and how your team can use them as conversation starters, not scorecards. If you're ready to look beyond metrics like DORA, Flow,

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13:03

How Value Stream Management and Product Operating...

Rethink Your Understanding ·

2025/04/30

In this episode, the AI hosts explore my latest article on evolving our approach to Value Stream Management (VSM) — which we originally adopted to bring greater visibility to our Agile, Lean, and DevOps efforts. But while preparing for a conversation with an industry leader about the Product Operating Model (POM), I had a realization: we weren’t just managing flow — we were also structuring teams around outcomes.This episode dives into how VSM and POM, often seen as separate frameworks, are actually

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15:31

From Scrum Master to Agile Delivery Manager:...

Rethink Your Understanding ·

2025/04/16

This episode covers a recent shift from the title of Scrum Master to Agile Delivery Manager (ADM). The AI hosts discuss how a change for the role of Scrum Master to Agile Delivery Manager represents a natural progression driven by an expanded need for delivery leadership, the adoption of Flow Metrics and Value Stream Management, and a move towards alternative practices from Scrum to Kanban or other custom Agile practices.The ADM role goes beyond a traditional Scrum Master, covering delivery metrics,

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14:47

Beyond Frameworks: The Real Weight of Leading...

Rethink Your Understanding ·

2025/04/15

This episode, "Beyond Frameworks," reflects on the challenges of leading large-scale Agile and DevOps transformations, even within successful organizations. It argues that despite adopting new structures and frameworks, persistent friction arises from diverging leadership philosophies and a superficial sense of alignment, leading to transformation fatigue.The AI hosts share my personal experiences and insights from over a decade, highlighting that real transformation takes ongoing effort, fresh

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17:35

From Feature Factory to Purpose-Driven Development

Rethink Your Understanding ·

2025/04/12

In today’s episode, we explore the idea of documenting anticipated outcomes and introduce Purpose-Driven Development (PDD), which focuses on defining expected outcomes for every software project. This approach helps ensure alignment with business goals and moves away from a "feature factory" mindset that prioritizes output over value.The AI hosts discuss my recent story about resistance to this idea, pointing out that it often comes from a lack of understanding or alignment. To track progress, they

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17:35

From Feature Factory to Purpose-Driven Development:...

Rethink Your Understanding ·

2025/04/12

In today’s episode, we explore the idea of documenting anticipated outcomes and introduce Purpose-Driven Development (PDD), which focuses on defining expected outcomes for every software project. This approach helps ensure alignment with business goals and moves away from a "feature factory" mindset that prioritizes output over value.The AI hosts discuss my recent story about resistance to this idea, pointing out that it often comes from a lack of understanding or alignment. To track progress, they

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