Rethink Your Understanding: AI-Driven Insights on Digital Transformation & Software Delivery Welcome 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 strategies, lessons, and the impact of leadership in Agile, Lean, DevOps, Value Stream Management, and Flow Engineering. Occasionally, we explore software engineering. We present a fresh approach to my articles, delivering key concepts, practical advice, and insights from years in tech leadership. Join us on Rethink Your Understanding—where AI amplifies expert voices to deliver the insights you need to lead your organization’s digital journey. Connect with me on LinkedIn
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 experime...
This episode explores the complexities of merging two distinct engineering organizational models after an acquisition.
It highlights the friction that arises when one part of the organization uses small, self-managed, cross-functional teams with distributed leadership, while the other adheres to a traditional Engineering Manager (EM) model where a single manager oversees people, delivery, and agile practices.
The core challenge lie...
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 ma...
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 10 team health dimensions—from collaboration to delivery integrity—and how your team can use them as conversation starters, not scor...
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 ...
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 ro...
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, h...
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 come...
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 come...
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 responsib...
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 hidd...
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 h...
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 mi...
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 Solutions
In 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 ...
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 conti...
This episode picks up from the last episode, episode 27, Advocating for Refactoring: Prioritization in the Context of Business Goals
We 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-scal...
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 Prod...
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...
In this episode, I share my journey of implementing Value Stream Management (VSM) and a Product Operating Model (POM) within my organization, highlighting the challenges, insights, and results along the way.
It highlights the importance of not just implementing these frameworks, but also clearly articulating their value to foster alignment across teams and enhance operational efficiency.
The AI hosts delve into the striking performan...
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...
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