CTO Series: Engineering Leadership, Automation, and Trust with Dan Hollinger

CTO Series: Engineering Leadership, Automation, and Trust with Dan Hollinger

CTO Series: Engineering Leadership, Automation, and Trust with Dan Hollinger

In this CTO Series episode, we sit down with Dan Hollinger, an accomplished engineering leader passionate about fostering empathy, transparency, and trust in tech teams. Dan shares pivotal lessons from his career, from building scalable automation systems to navigating complex leadership challenges. We cover key strategies for aligning tech initiatives with business goals, fostering collaboration, and ensuring long-term technical health.

Defining Leadership Through Automation and Empowerment

“Enable your humans to focus on the interesting work—automation should take care of the rest.”

Dan recounts his transformative experience at CCP Games, makers of EVE Online, where a robust test automation system changed his perspective on scaling technical processes. This role introduced him to the power of automation in freeing up engineers to focus on more exploratory and impactful tasks. He emphasizes how empowering self-directed teams with high-level vision statements enables creativity and innovation.

Building Self-Correcting Processes

“Always retro your processes—don’t let them run on autopilot.”

Dan explains the importance of self-correcting processes, using the SEV (Side Event) system as an example. He highlights how retrospectives can improve response times and prevent future crises. For Dan, consistent reviews are the key to maintaining agile, resilient systems that adapt to evolving needs.

Bridging the Gap Between Business and Tech

“There are no enemies—treat your colleagues like allies working toward a common goal.”

In cross-functional environments, Dan’s mantra is to focus on the project and maintain open communication. Drawing from his experience in gaming, where multiple departments collaborate on creative projects, he underscores the importance of empathy and curiosity. Asking questions and breaking down solutions into smaller, reviewable pieces can diffuse conflict and build trust.

Future-Proofing Through Strategic Roadmapping

“The lifespan of the solution dictates the scope of the work.”

Dan shares his approach to strategic roadmapping by considering the expected longevity of technical solutions. He gives an example of building a feature flag system for a game studio that needed to support a long-term vision while adapting to a new game engine. His advice: break large goals into smaller, adaptable increments that align with future changes.

Navigating Leadership Challenges During Organizational Change

“Trust is your greatest currency during periods of uncertainty.”

Dan reflects on a particularly challenging period when a leadership change caused a significant exodus of engineers at his company, leaving him with only one engineer. Despite the setback, Dan leaned into transparency and empathy, earning the trust of departing team members, which helped him transfer knowledge and rebuild the team.

Expanding the Scope of Leadership

“My role expanded from leading an engineering team to caring about the morale of the entire company.”

A surprising revelation for Dan was realizing the broader impact of his leadership on non-engineering teams. He discusses how this shift required him to listen to and support colleagues across all departments, emphasizing the value of empathy-driven leadership.

The Book That Shaped Dan’s Leadership Approach

“The DORA metrics help us measure what really matters for technical health.”

Dan highlights the book Accelerate by Nicole Forsgren et al., which introduced him to the DORA (DevOps Research and Assessment) metrics. These metrics help organizations measure software delivery performance and technical health, offering a data-driven approach to evaluate progress and identify improvement areas.

About Dan Hollinger

Dan Hollinger is a proven engineering leader who champions empowerment through support, empathy, and transparency. He fosters a culture of trust, prioritizing alignment over dictation. Technically adept, Dan advocates for automatable solutions and a blameless environment, ensuring his team thrives both personally and professionally in a collaborative space.


You can link with Dan Hollinger on LinkedIn.

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Why Your Process Changes Are Failing—The Stakeholder Alignment Problem | Deniz Ari

Why Your Process Changes Are Failing—The Stakeholder Alignment Problem | Deniz Ari

Deniz Ari: Why Your Process Changes Are Failing—The Stakeholder Alignment Problem 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. Deniz explores the challenges of implementing change in organizations, emphasizing that change is always a long and difficult process requiring patience and trust. Drawing on the Change Curve concept, Deniz shares a personal experience trying to improve project visibility by cleaning up backlogs in JIRA for 10 in-flight projects. Despite good intentions, Deniz found themselves as the only person using the tool, with team members and Product Owners using different systems that better suited their specific needs—POs wanting only high-level items while the development team needed to split items into smaller tasks. Through this experience, Deniz learned the crucial importance of having all stakeholders (Product Owners, development teams, and managers) aligned on using the same tool, and understanding the unique perspectives of each group before implementing process changes. In this episode, we refer to the Change Curve.  Self-reflection Question: What changes have you attempted to implement that failed because you didn't fully understand the different needs and perspectives of all stakeholders involved? [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

21 Maj 16min

Security Team Breakdown—The Devastating Impact of Poor Product Ownership | Deniz Ari

Security Team Breakdown—The Devastating Impact of Poor Product Ownership | Deniz Ari

Deniz Ari: Security Team Breakdown—The Devastating Impact of Poor Product Ownership 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. Deniz shares the story of a security project with a team of eight experienced, senior engineers working on mission-critical systems. Despite initial motivation and clear architectural solutions, the team soon exhibited signs of negative behavior including complaints and criticism. The root cause traced back to frequent Product Owner changes—several within less than a year—and poor client management. Instead of shielding the team, the PO directly transferred stress from clients to the team, demanded overtime, and created unnecessary tension by bringing unfiltered conflicts to the team and requesting excessive details. Deniz emphasizes the importance of avoiding unnecessary tensions, being more political when necessary to protect the team, and being mindful of tone in written communications. Self-reflection Question: In what ways might you be failing to set proper boundaries in your role, and how could establishing clearer limits improve both your effectiveness and your team's performance? Featured Book of the Week: Boundaries by Henrik Cloud Deniz recommends "Boundaries" by Henrik Cloud, a book about human relationships and personal limitations. The book addresses crucial questions: Does your life feel out of control? Do you keep saying yes to everyone? Are you taking responsibility for others' feelings and problems? Have you forgotten your own limitations? Deniz explains how this book helped them learn to say "no" while still considering others' realities and feelings, and understanding why we often struggle with setting boundaries. Deniz highlights that being a Scrum Master involves much more than just processes and methods—it requires healthy personal boundaries. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

20 Maj 17min

How Intense Delivery Pressure Destroyed Team Trust, Culture, and Brought Burnout | Deniz Ari

How Intense Delivery Pressure Destroyed Team Trust, Culture, and Brought Burnout | Deniz Ari

Deniz Ari: How Intense Delivery Pressure Destroyed Team Trust, Culture, and Brought Burnout 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. Working in the public sector, Deniz faced a challenging situation during a particularly busy winter period when the client wanted to combine multiple major initiatives simultaneously: migration, new features, and security improvements. This led to an oversized team of 25 engineers, which ultimately caused significant problems. The pressure to continuously deliver became overwhelming, breaking team trust and leaving members feeling abandoned. Several team members left, the team culture disintegrated, and cases of burnout emerged. After this difficult experience, Deniz conducted a comprehensive retrospective to process what happened and provide feedback to management about the dangers of excessive pressure in Scrum environments. Self-reflection Question: How might you recognize the early warning signs of team burnout before it reaches a critical point, and what boundaries would you establish to protect your team? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

19 Maj 18min

BONUS The PRFAQ Framework With Marcelo Calbucci

BONUS The PRFAQ Framework With Marcelo Calbucci

BONUS: Marcelo Calbucci reveals Amazon's secret innovation framework that transforms product development! 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. In this BONUS episode, we explore "The PRFAQ Framework" (visit also the website) with author Marcelo Calbucci. He shares how Amazon's innovative approach to product development can be adapted by founders, product managers, and teams across industries. Learn how this powerful methodology creates alignment, clarifies vision, and ensures customer-centricity in product development. The Origins of PRFAQ "I learned the PR FAQ method at Amazon and realized this is a great tool that would be valuable for founders and product leaders." Marcelo Calbucci shares how his experience at Amazon introduced him to the PRFAQ framework—a structured approach to product ideation and development. He explains how this methodology transformed his thinking about innovation and why he felt compelled to share it with a wider audience through his book. The framework addresses a critical gap he observed in how teams approach product development, often lacking the clarity and customer focus needed for success. Understanding the PRFAQ Framework "PR FAQ stands for press release and frequently asked questions—it's a method to talk about and define a vision for the product." The PRFAQ framework is a six-page document with a highly prescriptive structure. Marcelo breaks down the components: Page 1: A press release announcing the product Page 2+: Customer FAQ addressing potential questions Page 3+: Internal FAQ covering implementation details This document serves as the foundation for product development, helping teams align on vision and strategy before diving into execution. Marcelo emphasizes that the framework forces teams to articulate the "why" behind their work, not just the "what" and "how." The Alignment Challenge "Challenge: pick a few people from your organization, ask each one 'why are we doing this?' Chances are you will get a different answer from different people." One of the most significant challenges in product development is the lack of alignment across teams. Marcelo highlights how common it is for team members to have different understandings of product goals and strategy. Without a shared vision, teams risk building features that don't solve the right problems or address customer needs effectively. The PRFAQ framework creates alignment by documenting and socializing product vision in a consistent format that encourages discussion and feedback. Practical Implementation Tips "Use the PRFAQ as a textual document, instead of a PowerPoint presentation—the discipline of writing helps clarify thinking." Marcelo offers several practical tips for implementing the PRFAQ approach effectively: Write things out in paragraphs rather than bullet points Consider writing the FAQs before the press release Use the document as a tool for discussion, not as a polished deliverable Conduct review sessions with peers, team members, and stakeholders Focus on substance over style—the goal is to discover feedback He emphasizes that the act of writing forces clearer thinking and exposes gaps in logic or understanding that might otherwise remain hidden. The Amazon Way "At Amazon, every product starts with a PRFAQ. It starts with someone having an idea. The first thing they do is to write the PRFAQ." Marcelo provides insight into how Amazon implements this framework across the organization. Every product initiative begins with a PRFAQ document that articulates the vision and strategy. Teams spend time discussing and refining this document before moving into execution. This methodical approach allows Amazon to get early feedback on ideas, helping to identify potential issues before significant resources are invested. The framework has been a cornerstone of Amazon's ability to innovate consistently across diverse product areas. Customer-Centricity in Practice "Here’s one lesson about product leadership: understand the problems better than even the customer understands them." The customer-centric nature of the PRFAQ framework is one of its greatest strengths. By forcing teams to anticipate customer questions and articulate benefits from their perspective, the framework ensures products are built to solve real problems. Marcelo explains that sometimes the "customer" might be internal, but the principle remains the same—deeply understanding the problems before proposing solutions. This approach has proven particularly effective at Amazon, where customer obsession is a core value. Learning from the Book Development Process "In interviewing teams using the method, I discovered that the problem was convincing the whole team about the PRFAQ method." Interestingly, Marcelo applied the PRFAQ framework to the development of his own book. Through this meta-application, he discovered that the biggest challenge wasn't explaining the method itself but convincing entire teams to adopt it. This insight shaped the book's approach—making product strategy discussions less academic and more practical. He focused on providing concrete examples and templates that teams could immediately apply to their work. Resources for Deeper Learning "Read examples first, pay attention to how you write the phrases in the document." For listeners wanting to explore the PRFAQ framework further, Marcelo recommends starting with examples to understand the tone and structure. His book website offers resources and templates to help teams implement the framework. He emphasizes that seeing the framework in action is often more valuable than theoretical discussions, which is why he includes numerous examples in his book and supplementary materials. About Marcelo Calbucci Marcelo Calbucci is a founder, product and engineering leader, and innovation expert passionate about solving customers' biggest challenges through software. With over two decades of experience, he has launched dozens of products across industries and mentored nearly a thousand founders and professionals, shaping the future of product development and innovation. Marcelo Calbucci is the author of "The PRFAQ Framework: Adapting Amazon's Innovation Framework to Work for You," which describes Amazon's PRFAQ method—a strategic approach designed to refine and present new product ideas by focusing on customer-centric narratives. You can link with Marcelo Calbucci on LinkedIn and connect with Marcelo Calbucci on Substack.

17 Maj 28min

Why the 'Why' Matters—Product Owner Communication Lessons | Simina Fodor

Why the 'Why' Matters—Product Owner Communication Lessons | Simina Fodor

Simina Fodor: Why the 'Why' Matters—Product Owner Communication Lessons 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: Transparency and Customer Focus This exemplary Product Owner shaped Simina's entire view of product management and even inspired her to consider a future transition to that role. Despite not having a traditional product background (coming instead from support), this PO demonstrated exceptional openness to both giving and receiving feedback. They consistently explained the logic behind decisions, sharing the "why" that motivated their priorities. What truly set them apart was bringing customer perspectives and use cases directly to the team, helping developers understand the features through the lens of personas and user scenarios. The PO's transparency extended to their own professional journey, openly sharing how they grew into the role, which created an atmosphere of continuous learning and development. The Bad Product Owner: The Ghost Commander This experienced Product Owner approached the role with a command-and-control mindset carried over from previous Project Management experience, believing that backlog grooming was "beneath them." Essentially a ghost to the team, they avoided retrospectives while issuing constantly shifting priorities with little explanation or logic. The PO would issue commands and demand immediate responses without considering consequences, creating a toxic environment that threatened to destroy team morale. Simina recommends coaching such Product Owners on agile mindset principles and seeking leadership support when necessary to prevent team deterioration. Self-reflection Question: How can you effectively bridge the gap between command-and-control Product Owners and teams seeking more transparency and collaboration? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Simina Fodor  Simina is a career rebel with a passion for bold moves. From HR to Agile delivery, she's ditched the rulebook to inspire others to build careers that ignite passion. No apologies, no detours—just fearless pivots and real talk about creating work that truly fires you up. You can link with Simina Fodor on LinkedIn.

16 Maj 18min

The Courage to Question—Signs of a Healthy Agile Team| Simina Fodor

The Courage to Question—Signs of a Healthy Agile Team| Simina Fodor

Simina Fodor: The Courage to Question—Signs of a Healthy Agile Team 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. For Simina, Scrum Master success goes far beyond facilitation skills – it's about what happens when you're not in the room. True success means creating a self-sustaining team that maintains healthy practices even in your absence. Simina looks for indicators like: Do team members feel safe raising concerns regularly? Can they push back with the Product Owner and offer suggestions? Do they proactively ask for the "why" behind requests instead of blindly following directions? She emphasizes that successful teams raise dependencies early in the sprint, have the courage to plan work with other teams, and handle integrations independently. The ultimate test of Scrum Master effectiveness is whether the team continues to thrive even when you step away for a few days. Self-reflection Question: What specific behaviors would indicate that your team has reached a level of self-sustainability that would allow you to step back? Featured Retrospective Format for the Week: Start/Stop/Continue Simina advocates for the simplicity of the Start/Stop/Continue retrospective format. After experimenting with numerous complex approaches, she found that sometimes the most straightforward formats yield the best results. This classic structure cuts through noise and focuses teams on what truly matters: what new practices they should begin, what isn't working and should stop, and what's effective and should continue. Simina appreciates how this format's simplicity makes it accessible and easy to follow, allowing teams to concentrate on meaningful conversation rather than getting lost in complicated retrospective mechanics. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Simina Fodor  Simina is a career rebel with a passion for bold moves. From HR to Agile delivery, she's ditched the rulebook to inspire others to build careers that ignite passion. No apologies, no detours—just fearless pivots and real talk about creating work that truly fires you up. You can link with Simina Fodor on LinkedIn.

15 Maj 15min

Building Bridges—How Cross-Department Champions Drive Agile Adoption| Simina Fodor

Building Bridges—How Cross-Department Champions Drive Agile Adoption| Simina Fodor

Simina Fodor: Building Bridges—How Cross-Department Champions Drive Agile Adoption 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. Simina shares her experience leading an enterprise Agile transformation from her position in Project Management. Rather than pushing for immediate, wholesale change, she started small - seeking out interested colleagues, sharing case studies from other companies, and gradually building internal support. This patient approach took years before the organization officially embraced Agile and Scrum, but created a strong foundation of champions across departments. When business needs finally demanded faster releases and better responsiveness to change, Simina had already established a community of practice ready to support the transition. She began with a single pilot team implementing just daily standups, which then expanded into a full Agile program that ultimately facilitated her transition from Project Manager to Scrum Master. Self-reflection Question: How might building informal networks and starting with small changes create a more sustainable foundation for organizational transformation than top-down mandates? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Simina Fodor  Simina is a career rebel with a passion for bold moves. From HR to Agile delivery, she's ditched the rulebook to inspire others to build careers that ignite passion. No apologies, no detours—just fearless pivots and real talk about creating work that truly fires you up. You can link with Simina Fodor on LinkedIn.

14 Maj 14min

How Leadership Communication Can Destroy Team Morale | Simina Fodor

How Leadership Communication Can Destroy Team Morale | Simina Fodor

Simina Fodor: How Leadership Communication Can Destroy Team Morale 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. Simina recounts working with a diverse, remote team on a high-visibility project to retire legacy systems under strict deadlines. The team made sacrifices, working overtime and through vacations to meet the challenging timeline. When Simina recommended team bonuses to recognize their extraordinary efforts, leadership not only rejected the request but publicly announced that overtime was simply "expected" as part of the job. This single communication destroyed the team's trust, leading to disengagement, dropped velocity, missed deadlines, and team members skipping Scrum events. Simina highlights how quickly team dynamics can collapse when leadership dismisses extra effort and fails to acknowledge team contributions. Self-reflection Question: How might you advocate for proper recognition of your team's extraordinary efforts when leadership views such work as simply expected? Featured Book of the Week: The Making of a Manager by Julie Zhuo Simina recommends "The Making of a Manager" by Julie Zhuo, a book she initially dismissed because she wasn't in a management role. However, upon reading it, she discovered numerous parallels between effective management and Scrum Mastery. The book's message that managers don't need to know all the answers resonated deeply with her, reinforcing the importance of understanding humans first before implementing processes. Despite not being an Agile-specific book, Simina found its people-focused approach incredibly valuable for her Scrum Master practice. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Simina Fodor  Simina is a career rebel with a passion for bold moves. From HR to Agile delivery, she's ditched the rulebook to inspire others to build careers that ignite passion. No apologies, no detours—just fearless pivots and real talk about creating work that truly fires you up. You can link with Simina Fodor on LinkedIn.

13 Maj 19min

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