Rethink Your Understanding

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 ...

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 ...

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 engi...

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 h...

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 ...

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 ...

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 bot...

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...

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 e...

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...