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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

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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29:57

Mindsets That Shape Team Models

Rethink Your Understanding ·

2025/03/30

This episode dives into various team models within technology organizations, focusing on a comparison between the traditional Engineering Manager (EM) model—where a single manager handles both technical direction and people management—and autonomous cross-functional teams, inspired by frameworks like Team Topologies. I make the case for the latter, highlighting the intentional separation of people management from delivery responsibilities. This approach promotes greater autonomy, distributed

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18:37

Why Cutting Agile Leadership Hurts Teams More Than It...

Rethink Your Understanding ·

2025/03/23

In this episode, we examine the growing trend of cutting Agile leadership roles like Scrum Masters. While often viewed as a cost-saving move, I argue this approach harms team effectiveness and productivity.The AI host shares my experience evolving the role into an Agile Delivery Manager focused on flow metrics and value stream management, contrasting it with a parent company's decision to distribute these tasks. We discuss the hidden costs of removing such roles, including added burden on managers,

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17:33

Responsible Engineering: Beyond the Code, Owning the...

Rethink Your Understanding ·

2025/03/20

In this episode, we shift focus from software delivery to engineering and explore the topic of responsible engineering. The AI hosts discuss a conversation that broadened the definition of responsible engineering, emphasizing the importance of considering the consequences beyond just functionality.Leadership is key to creating a culture of responsibility by setting clear expectations and encouraging accountability. The discussion highlights the need for engineers to approach their work with care and

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17:40

Avoiding Flow Metric Confusion: Aligning Agile Work...

Rethink Your Understanding ·

2025/03/18

This episode addresses confusion surrounding Flow Metrics in Agile environments by emphasizing the importance of understanding Value Stream Management, Flow Items, and the Agile Work Hierarchy. It clarifies how to align Agile work items, such as initiatives or themes, epics, features, user stories, and tasks, with Flow Items, which represent units of value like features, defects, risks, and debts. The AI hosts discuss the common misunderstandings, such as incorrectly mapping Jira issue types or

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23:03

Decoding the Metrics Maze: How Platform Marketing...

Rethink Your Understanding ·

2025/02/16

The episode is a follow-up to my August 2024 article and Podcast Episode 18 from Season 1: Navigating the Digital Product Workflow Metrics Landscape: From DORA to Comprehensive Value Stream Management Platform SolutionsIn this episode, the AI hosts share my perspective on the increasing confusion between Software Engineering Intelligence (SEI) and Value Stream Management (VSM) platforms caused by overlapping features and marketing messages.The discussion highlights the importance of choosing

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14:23

Beyond outcome-focused metrics: Connecting Work to...

Rethink Your Understanding ·

2025/02/09

In this episode, we delve into the article "Beyond Outcome-Focused Metrics: Connecting Work to Outcomes," which emphasizes the importance of aligning software development efforts with tangible business value. We discuss how adopting value stream thinking can transform software teams from perceived cost centers into strategic enablers. By focusing on customer value streams, organizations can enhance strategic alignment, foster continuous improvement, and ensure that every initiative contributes

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14:30

Managing Technical Debt: Interest Rates, Impact, and...

Rethink Your Understanding ·

2025/02/08

This episode picks up from the last episode, episode 27, Advocating for Refactoring: Prioritization in the Context of Business GoalsWe continue the conversion advocating for a proactive approach to managing technical debt, suggesting that teams treat it like a financial loan. I support making continuous "minimum payments" by regularly refactoring code, similar to making minimum payments on a loan, rather than waiting for large-scale cleanups. We also discuss prioritizing technical debt based on its

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19:18

Advocating for Refactoring: Prioritization in the...

Rethink Your Understanding ·

2025/01/20

In this episode, the AI hosts dive into my article, which makes the case for viewing refactoring in software development not as a routine technical chore, but as a strategic business investment. The discussion examines the common drivers behind the need for refactoring—tight deadlines, shifting requirements—and outlines practical strategies for embedding it into established frameworks like Value Stream Management (VSM) and the Product Operating Model (POM). A key focus is on quantifying the business

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16:00

Dependencies Are Here to Stay: From Challenges to...

Rethink Your Understanding ·

2025/01/18

In today's episode, the AI hosts discuss my article, which expands on a recent piece by John Cutler about managing cross-team dependencies. It explores three common approaches to handling dependencies: minimizing them, institutionalizing them, and actively addressing them.I build upon Culter's concepts by introducing a prioritization framework that emphasizes prioritizing work based on anticipated outcomes and available capacity. I advocate for a dynamic approach to reprioritization as circumstances

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13:24

Why VSM and the Product Operating Model Matter

Rethink Your Understanding ·

2025/01/07

This episode explores how Value Stream Management (VSM) and a Product Operating Model can improve organizational efficiency. The AI hosts discuss how these approaches focus on outcomes, align teams around products, and streamline workflows to deliver value. They also promote sustainable delivery, reducing wasted effort while boosting morale and retention. While not a universal fix, Phil suggests these practices as effective solutions to challenges like limited capacity and conflicting

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17:10

From Good to Great: Shifting to Outcomes in 2025

Rethink Your Understanding ·

2025/01/04

In today’s episode, the AI hosts discuss my vision for our team in 2025 as we move into the next phase of our 10-year transformation. Our aim is to address capacity pressures by shifting from an output-focused approach to an outcome-driven mindset. We’re also reinforcing our commitment to a product operating model and value stream management. The episode emphasizes how feedback and collaboration can improve team alignment, increase engagement, and amplify impact.

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15:56

Breaking Free from the Build Trap: Delivering...

Rethink Your Understanding ·

2025/01/03

In this episode, the AI hosts discuss that engineering teams should prioritize meaningful outcomes over simply delivering outputs—a concept known as the "build trap." It advocates for a product operating model using Value Stream Management (VSM) and Objectives and Key Results (OKRs) to ensure every effort delivers measurable business value.The discussion emphasizes the importance of defining anticipated outcomes for epics, fostering accountability through clear ownership of key results, and

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13:51

Transforming Engineering: From Cost Center to...

Rethink Your Understanding ·

2025/01/02

This is the second episode in a three-part series exploring Profitable Engineering and how Phil as a technology leader is transforming the engineering department from a cost center into a strategic business partner. The AI hosts dive into Phil's response to peer feedback recommending him to prioritize focusing on business results, highlighting how it prompted a transformation in his leadership approach.Link to the article: Transforming Engineering: From Cost Center to Strategic Partner, originally

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11:00

Engineering’s Business Value: From Black Box to Clarity

Rethink Your Understanding ·

2025/01/01

This episode is the first in a three-part series exploring the often-misunderstood role of software engineering, frequently dismissed as just a cost center. The AI hosts dive into my argument for adopting a product operating model and Value Stream Management to redefine engineering's value. By leveraging OKRs, teams can align their efforts with measurable business outcomes and customer impact. This shift requires intentional team design, emphasizing the movement of work to teams rather than

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8:55

Profitable Engineering: Linking Software Engineering...

Rethink Your Understanding ·

2025/01/01

Happy New Year! We're excited to kick off season two of the podcast. In this opening episode, the AI hosts introduce a three-part series on Profitable Engineering, exploring how to connect technology investments to meaningful business results.This three-part series dives into reimagining software engineering as a strategic business partner rather than merely a cost center. Tailored for technology leaders, product managers, and anyone seeking to align engineering efforts with customer value and

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14:20

Crossroads 2024: Reflections on Leadership, Legacy,...

Rethink Your Understanding ·

2024/12/03

This episode marks the end of Season 1 of the AI-generated podcast experiment and the culmination of my initial efforts to share insights from my three-year article-writing journey. At the same time, I reached a key point in my career where there's no turning back time, and I take a moment to reflect on my experience in software engineering and leadership. It's been a journey through two distinct eras of software delivery, which have shaped my growth and perspective.The AI hosts interpret my

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16:58

Navigating the Digital Product Workflow Metrics...

Rethink Your Understanding ·

2024/11/25

In this episode, the discussion by the AI hosts is based on my article, "Navigating the Digital Product Workflow Metrics Landscape: From DORA to Comprehensive Value Stream Management Platform Solutions." It acts as a guide for senior leaders in choosing the best software delivery metrics platform for their needs. It evaluates four types of platforms: DORA metrics, which focus on deployment; DX Core 4, which emphasizes speed, effectiveness, quality, and business impact; Software Engineering

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