BONUS Tom Gilb: Building True Engineering Culture and Delivering Value Through Evolutionary Methods

BONUS Tom Gilb: Building True Engineering Culture and Delivering Value Through Evolutionary Methods

BONUS: Tom Gilb on Building True Engineering Culture and Delivering Value Through Evolutionary Methods

In this BONUS episode, we dive deep into the world of true engineering discipline with Tom Gilb, a pioneer who was writing about Agile principles before Agile was even named. We explore his latest book "Success - Super Secrets & Strategies for Efficient Value Delivery in Projects and Programs, and Plans" and uncover the fundamental flaws in how organizations approach project delivery and stakeholder management.

The Genesis of Success-Focused Engineering

"People were failing at project deliveries - even when using Agile. I saw there was very little about setting clear goals and reaching them, it had nothing to do with being successful."

Tom's motivation for writing his latest book stems from a critical observation: despite the widespread adoption of Agile methodologies, project failure rates remain unacceptably high. The core issue isn't methodology but rather the fundamental lack of clarity around what success actually means. Tom emphasizes that true success is about achieving the improvements you want at a price you can afford, yet most organizations fail to define this clearly from the outset.

In this segment, we refer to the book How Big Things Get Done by Bent Flyvbjerg who published statistics on the poor performance of projects in general.

Beyond OKRs: The Power of Quantified Multi-Dimensional Objectives

"First you need to have a definition of what it means to succeed. And that needs to be multi-dimensional. And you need to clarify what they are."

While many organizations believe they're already quantifying objectives through frameworks like OKRs, Tom reveals significant weaknesses in these approaches. True value isn't just profit—it encompasses multiple dimensions including security, usability, and other stakeholder-specific benefits. The key insight is learning to quantify what needs to be achieved across all critical dimensions, as you simply cannot design for high-quality attributes like security without first quantifying and designing for them explicitly.

In this segment, we talk about Tom's paper on OKR's titled "OKR Objectives and Key Results: what's wrong and how to fix it".

The Missing Engineering Discipline

"Why is the failure rate of our projects so high?"

Tom identifies a paradoxical problem: engineering organizations often lack true engineering discipline. This fundamental gap explains why project success rates remain low despite technological advances. Real engineering requires systematic approaches to design, stakeholder analysis, and incremental value delivery—disciplines that are often overlooked in favor of rushed implementations.

Stakeholder Analysis: Beyond User Stories

"Stakeholders have a requirement - even if we don't know it. They might be people, but also law, contract, policies, etc. They all have requirements for us."

Traditional user-centered methods like user stories can lead to failure when critical stakeholders are overlooked. Tom advocates for comprehensive stakeholder analysis as the foundation of engineering discipline. Stakeholders aren't just people—they include laws, contracts, policies, and other constraints that have requirements for your system. The practical tip here is to use AI tools to help identify and list these stakeholders, then quantify their specific requirements using structured approaches like Planguage.

The Gilb Cycle: True Incremental Value Delivery

"Get things done every week, next week, until it's all done. We need to decompose any possible design into enough increments so that each increment delivers some value."

What distinguishes Tom's evolutionary approach from popular Agile frameworks is the focus on choosing the most efficient design and then systematically improving existing systems through measured increments. Each increment must deliver tangible value, and the decomposition process should be aided by AI tools to ensure optimal value delivery. This isn't just about iteration—it's about strategic improvement with measurable outcomes.

Building Engineering Culture: A Two-Leader Approach

"There are two leaders: the tech leaders and the management leaders. For management leaders: demand a value stream of results starting next week. To the tech leaders: learn the engineering process."

Creating a true engineering culture requires coordinated effort from both management and technical leadership. Management leaders should demand immediate value streams with weekly results, while technical leaders must master fundamental engineering processes including stakeholder analysis and requirement quantification. This dual approach ensures both accountability and capability development within the organization.

Further Resources

During this episode we refer to several of Tom's books and papers. You can see this list below

About Tom Gilb

Tom Gilb, born in the US, lived in London, and then moved to Norway in 1958. An independent teacher, consultant, and writer, he has worked in software engineering, corporate top management, and large-scale systems engineering. As the saying goes, Tom was writing about Agile, before Agile was named. In 1976, Tom introduced the term "evolutionary" in his book Software Metrics, advocating for development in small, measurable steps. Today, we talk about Evo, the name that Tom used to describe his approach.

You can link with Tom Gilb on LinkedIn.

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Selecting the Appropriate Agile Values for Organizational Impact | Pascal Papathemelis

Selecting the Appropriate Agile Values for Organizational Impact | Pascal Papathemelis

Pascal Papathemelis: Selecting the Appropriate Agile Values for Organizational Impact Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Pascal defines success for Scrum Masters through his recent mantra of "effectiveness over efficiency," "outcome over output," and "create value for the customer." Working with a client introducing a new digital platform, he focuses on understanding the value for both the organization and end customers while minimizing confusion in the process. Pascal emphasizes the importance of ensuring work sustainability over time by focusing on Agile values and principles and their deep understanding. He customizes the Agile Manifesto's values and principles for each organization, such as focusing on customer value, collaboration, and constant learning. Pascal strategically highlights the principles and values that address the biggest challenges facing the organization at any given time, making Agile concepts relevant and actionable for the specific context. Featured Retrospective Format for the Week: Sailboat Pascal recommends the sailboat retrospective as his preferred format, though he emphasizes that the choice depends on context and team focus. He values this metaphor-based retrospective because it helps teams discuss critical aspects of their work through different perspectives. The sailboat format allows teams to explore what propels them forward (wind), what holds them back (anchors), what they need to watch out for (rocks), and their destination (island). Pascal also uses timeline retrospectives and stresses the importance of varying retrospective formats to prevent teams from falling into routine patterns that might limit their ability to bring fresh insights to their work. He believes that good data and effective visualization are essential components of any successful retrospective format. Self-reflection Question: How effectively are you customizing Agile principles to address your organization's specific challenges and context? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Pascal Papathemelis Pascal is an Agile & Professional Coach that wants to make a positive impact to the people working with. Coaching in Finnish, German and English language. Focus areas are human factors, outcomes, effectiveness, flow, decision making, clarity and constant improvement. You can link with Pascal Papathemelis on LinkedIn.

10 Juli 15min

From Waterfall to Agile—A Multi-Level Change Strategy | Pascal Papathemelis

From Waterfall to Agile—A Multi-Level Change Strategy | Pascal Papathemelis

Pascal Papathemelis: From Waterfall to Agile—A Multi-Level Change Strategy Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Pascal describes a successful agile transformation where he collaborated with a fellow coach in the IT department of a large organization with a waterfall history and heavy documentation-driven processes. The two coaches worked together effectively, sharing information and scouting for opportunities to take action. They began with an assessment and discussions across IT, business, and management levels to understand the current state. Using the Cynefin framework to understand complexity, they conducted a two-day workshop to introduce Agile vocabulary, covering concepts like Push/Pull and process waste. The coaches operated at multiple levels simultaneously - working strategically with leadership who typically pushed excessive work to the organization, while also helping teams visualize their processes and clarify priorities. At the team level, they acted as Scrum Masters to demonstrate the role while mentoring the actual Scrum Master through one-on-one sessions. They also supported the Product Owner in understanding their role and used story maps to help visualize and organize work effectively. Self-reflection Question: How might collaborating with another coach or change agent amplify your effectiveness in leading organizational transformation? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Pascal Papathemelis Pascal is an Agile & Professional Coach that wants to make a positive impact to the people working with. Coaching in Finnish, German and English language. Focus areas are human factors, outcomes, effectiveness, flow, decision making, clarity and constant improvement. You can link with Pascal Papathemelis on LinkedIn.

9 Juli 15min

The Hidden Cost of Removing Scrum Masters from High-Performing Teams | Pascal Papathemelis

The Hidden Cost of Removing Scrum Masters from High-Performing Teams | Pascal Papathemelis

Pascal Papathemelis: The Hidden Cost of Removing Scrum Masters from High-Performing Teams Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Pascal shares a cautionary experience with mature Scrum teams that appeared to function flawlessly. These teams demonstrated excellent Scrum practices with minimal impediments, leading management to conclude that Scrum Masters were unnecessary. When management removed all Scrum Masters from the department, the previously high-performing teams began to struggle significantly. Team members had to absorb the responsibilities previously handled by their Scrum Masters, causing them to lose focus on their core value-creating work. Different teams adopted various approaches to fill the Scrum Master void, but none proved effective. Pascal reflects that the Scrum Masters could have made their value more visible by supporting Product Owners more actively and becoming more involved in team tasks. This experience taught him the importance of demonstrating the ongoing value that Scrum Masters provide, even when teams appear to be self-sufficient. Featured Book of the Week: Learning Out Loud—Community Learning and Networking Pascal draws his greatest inspiration not from a single book, but from active participation in the Agile community. He finds tremendous value in discussions within local communities, networking events, and sparring sessions with colleagues. Pascal particularly benefits from Agile Coaching circles in Helsinki, which provide practical knowledge and insights. He also gains inspiration from Agile conferences, but credits Agile Coaching Camps as having the biggest impact - these 2.5-day open space format events are intense and packed with valuable insights. Pascal recommends that Scrum Masters actively engage with their local Agile communities and attend coaching camps to accelerate their professional development and gain diverse perspectives. Self-reflection Question: How visible is the value you provide as a Scrum Master, and what steps could you take to make your contributions more apparent to your organization? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Pascal Papathemelis Pascal is an Agile & Professional Coach that wants to make a positive impact to the people working with. Coaching in Finnish, German and English language. Focus areas are human factors, outcomes, effectiveness, flow, decision making, clarity and constant improvement. You can link with Pascal Papathemelis on LinkedIn.

8 Juli 19min

From Mechanics to Human Factors—How Scrum Masters Grow | Pascal Papathemelis

From Mechanics to Human Factors—How Scrum Masters Grow | Pascal Papathemelis

Pascal Papathemelis: From Mechanics to Human Factors—How Scrum Masters Grow Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Pascal shares his evolution as a Scrum Master, moving from focusing purely on the mechanics of Scrum to understanding the critical importance of human factors. Early in his career, Pascal worked with teams that struggled to achieve sprint goals, with stories floating from one sprint to another. Through retrospectives and continuous improvement, he learned essential tips like not taking too much into sprints and making stories smaller. However, Pascal's biggest transformation came when he shifted focus to human elements - involving everyone in the team, improving collaboration during refinement, and developing people's skills and attitudes. He emphasizes that every person is an individual with the intention to be their best, and a good Scrum Master must sense when something is wrong and create safe environments for open conversations. Pascal highlights the importance of corridor conversations and coffee machine breakthroughs, especially before COVID, and stresses the need to invest effort in how teams start, using models like Tuckman's team growth model and Diana Larsen's Team Liftoff approach. In this segment, we also refer to the episode with Arne Roock, about the importance of team design and setup in the success of teams. Self-reflection Question: How might shifting your focus from Scrum mechanics to human factors transform the way you support your team's growth and collaboration? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Pascal Papathemelis Pascal is an Agile & Professional Coach that wants to make a positive impact to the people working with. Coaching in Finnish, German and English language. Focus areas are human factors, outcomes, effectiveness, flow, decision making, clarity and constant improvement. You can link with Pascal Papathemelis on LinkedIn.

7 Juli 15min

Millions of Users, Multiple Stakeholders—The Art of Product Owner Navigation | Bernard Agrest

Millions of Users, Multiple Stakeholders—The Art of Product Owner Navigation | Bernard Agrest

Bernard Agrest: Millions of Users, Multiple Stakeholders—The Art of Product Owner Navigation Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: The Stakeholder Navigator Bernard describes an exceptional Product Owner who managed a product impacting millions of people while navigating constantly evolving requirements from multiple stakeholders. This Product Owner excelled at understanding each stakeholder's unique needs and communicating effectively with all of them. What made this person truly great was their ability to come to the development team with a clear understanding of both the business case and user needs, having done the hard work of stakeholder management upfront. This Product Owner understood that their role was to be the bridge between complex stakeholder requirements and clear team direction. The Bad Product Owner: The Collaborative Hoarder Bernard identifies a dangerous anti-pattern: the Product Owner who adds everything to the backlog under the guise of being "collaborative." While this behavior appears inclusive and team-friendly on the surface, it actually demonstrates that the Product Owner isn't following through on delivering real value. These Product Owners become almost exclusively focused on authority rather than outcomes, making them particularly difficult to coach since they resist guidance. Bernard recommends using Cost of Delay as both a prioritization technique and a tool to help Product Owners understand why certain items shouldn't be added to the backlog at all. Self-reflection Question: Is your Product Owner truly collaborating by providing clear direction, or are they avoiding difficult prioritization decisions by adding everything to the backlog? In this segment we refer to the Coach Your Product Owner e-course that we created for everyone who needs to help their Product Owners succeed! [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Bernard Agrest Bernard currently leads a major software implementation at University of Wisconsin—Madison Medical School, serving over 10,000 employees. Previously, he built a PMO and led Data and Learning at Teach For America. His journey began redesigning operations for a Veteran Service Organization, where he co-led national initiatives and launched a new alumni program. You can link with Bernard Agrest on LinkedIn.

4 Juli 12min

Creating Conditions for Healthy Conflict and Continuous Improvement in Agile Teams | Bernard Agrest

Creating Conditions for Healthy Conflict and Continuous Improvement in Agile Teams | Bernard Agrest

Bernard Agrest: Creating Conditions for Healthy Conflict and Continuous Improvement in Agile Teams Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Bernard believes successful Scrum Masters focus on creating conditions where tension and healthy conflict can emerge naturally, rather than maintaining artificial harmony. Too many organizations remain stuck in fear-based cultures where people avoid raising important issues. For Bernard, success means ensuring people regularly surface problems and engage meaningfully with each other—it's not enough to simply monitor green dashboards. He emphasizes that real leadership involves focusing on creating conditions for teams to discuss what truly matters, moving beyond surface-level metrics to foster genuine dialogue and continuous improvement. Self-reflection Question: Are the people on your teams regularly raising issues, or are you relying too heavily on dashboard metrics to gauge team health? Featured Retrospective Format for the Week: 4L's The 4L's retrospective format is simple yet powerful, examining what the team Liked, Learned, Lacked, and Longed for. Bernard particularly values the "Longed for" category because it asks people to connect the dots between how they felt and how they performed. In one memorable session, using 4L's helped his team understand what they were missing in their regular sync work, leading them to change how they conducted meetings to better support upcoming deliveries. This retrospective format had long-term organizational impact, helping teams realize gaps in their collaborative processes and make meaningful improvements to their working relationships. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Bernard Agrest Bernard currently leads a major software implementation at University of Wisconsin—Madison Medical School, serving over 10,000 employees. Previously, he built a PMO and led Data and Learning at Teach For America. His journey began redesigning operations for a Veteran Service Organization, where he co-led national initiatives and launched a new alumni program. You can link with Bernard Agrest on LinkedIn.

3 Juli 12min

One-on-One Insights—Building Change Strategy Through Individual Conversations | Bernard Agrest

One-on-One Insights—Building Change Strategy Through Individual Conversations | Bernard Agrest

Bernard Agrest: One-on-One Insights—Building Change Strategy Through Individual Conversations Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. When faced with a tool that needed complete rebuilding rather than more "duct-tape" features, Bernard knew that disruption was inevitable—but where to start? Through extensive one-on-one conversations with employees and stakeholders, he discovered that teams didn't understand their work was cyclical, and more importantly, that the onboarding team was central to the entire process. By starting the transformation with this pivotal team and focusing on training and user adoption, the new tool provided immediate organizational impact with data-driven decision making. Bernard's approach demonstrates that successful change management starts with understanding the true workflow and identifying the critical connection points that can drive the most significant positive impact. Self-reflection Question: In your current change initiatives, have you identified which team or process serves as the central hub that could accelerate transformation across the entire organization? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Bernard Agrest Bernard currently leads a major software implementation at University of Wisconsin—Madison Medical School, serving over 10,000 employees. Previously, he built a PMO and led Data and Learning at Teach For America. His journey began redesigning operations for a Veteran Service Organization, where he co-led national initiatives and launched a new alumni program. You can link with Bernard Agrest on LinkedIn.

2 Juli 13min

Avoiding Hard Conversations—When High-Performing Agile Teams Self-Destruct | Bernard Agrest

Avoiding Hard Conversations—When High-Performing Agile Teams Self-Destruct | Bernard Agrest

Bernard Agrest: Avoiding Hard Conversations—When High-Performing Agile Teams Self-Destruct Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Bernard describes how a high-performing, fun-loving team began to unravel when a new member joined who wasn't delivering on their commitments. Instead of addressing the performance issue directly, team members started picking up the slack, avoiding the difficult conversation that needed to happen. As morale dropped and people checked out, Bernard realized the team was paralyzed by fear of confrontation and assumptions that raising the issue would be ignored. This experience taught him that individual performance problems quickly become whole-team problems when left unaddressed, and that strong relationships require the courage to have honest, supportive conversations. Self-reflection Question: What difficult conversation are you avoiding on your team, and what assumptions might be preventing you from addressing it? Featured Book of the Week: The 6 Types of Working Genius by Patrick Lencioni Bernard recommends The 6 Types of Working Genius by Patrick Lencioni because it helps leaders understand that everyone has specific "genius" areas in different phases of work. When people work outside their natural genius zones, they feel unfulfilled and frustrated. This framework has been invaluable for Bernard in understanding team dynamics—why some teams click naturally while others struggle. By recognizing each person's working genius, leaders can better position team members for success and create more effective, satisfied teams. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥 Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people. 🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Bernard Agrest Bernard currently leads a major software implementation at University of Wisconsin—Madison Medical School, serving over 10,000 employees. Previously, he built a PMO and led Data and Learning at Teach For America. His journey began redesigning operations for a Veteran Service Organization, where he co-led national initiatives and launched a new alumni program. You can link with Bernard Agrest on LinkedIn.

1 Juli 14min

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