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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Product Owner Patterns – The Great and the Bad | Ellen Grove

Product Owner Patterns – The Great and the Bad | Ellen Grove

Ellen Grove: The Messenger Anti-Pattern, When Product Owners Lack Authority Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: Building Shared Understanding, The Collaborative Product Owner Pattern Ellen describes an exemplary Product Owner (PO) who actively engaged with customers, often bringing the team along to meet users. This practice fostered a shared understanding of customer needs and amplified creativity within the team. A great PO promotes collaboration and ensures that the team is aligned with the product vision, enabling innovative solutions and meaningful outcomes. The Bad Product Owner: The Messenger Anti-Pattern, When Product Owners Lack Authority A poor PO, Ellen explains, is one who lacks decision-making authority. In one case, a PO served merely as a messenger for the CEO, repeatedly deferring to higher-ups for answers. This lack of empowerment hindered team progress and frustrated the development process. Ellen underscores that Scrum Masters play a crucial role in supporting POs to ensure they can fulfill their responsibilities effectively. Self-reflection Question: How can you support Product Owners to strengthen their ability to make informed decisions? [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

10 Tammi 16min

The Power of "Why", Modeling Coaching Behavior for Agile Teams | Ellen Grove

The Power of "Why", Modeling Coaching Behavior for Agile Teams | Ellen Grove

Ellen Grove: The Power of "Why", Modeling Coaching Behavior for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen defines success for Scrum Masters as the team developing a stronger sense of agency and self-sufficiency. When teams begin asking better questions and demonstrate ownership of their processes, it indicates growth and maturity. Scrum Masters must model this behavior by being thoughtful, curious, and consistently asking "why" to encourage a coaching mindset. This approach enables teams to think critically and solve problems collaboratively. Self-reflection Question: How can you model the behavior you want to see in your team during retrospectives and beyond? Featured Retrospective Format for the Week: Retromat Ellen recommends using Retromat, a versatile online tool that provides a variety of retrospective formats to match the specific needs of your team. Ellen values mixing up retrospective formats to keep sessions engaging and contextually relevant. She stresses the importance of paying attention to all steps of a retrospective process, ensuring teams reflect, ideate, and act effectively. [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

9 Tammi 16min

The Dual Work of Agile, Managing Projects and Change Simultaneously | Ellen Grove

The Dual Work of Agile, Managing Projects and Change Simultaneously | Ellen Grove

Ellen Grove: The Dual Work of Agile, Managing Projects and Change Simultaneously Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares her insights on managing organizational change effectively. She explains how Scrum and Lean Change Management offer tools to make the "change work" visible alongside project work. By putting infrastructure in place to support this dual focus, stakeholders and teams can gain transparency and clarity. Ellen emphasizes that lasting change requires collaboration and visibility, not isolation. Self-reflection Question: How can you make the "change work" more visible in 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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

8 Tammi 15min

Why Feedback Loops Are Essential for Agile Teams | Ellen Grove

Why Feedback Loops Are Essential for Agile Teams | Ellen Grove

Ellen Grove: Why Feedback Loops Are Essential for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares a story about coaching a team in a public sector enterprise working on a website project. Despite their commitment to Agile, the team’s disconnect from user feedback led them to build features that missed critical functionality. This stealthy anti-pattern—assuming "what should be done and why" without user input—resulted in wasted effort and budget. Ellen emphasizes the importance of direct feedback loops with real users, even for internal products. Self-reflection Question: How can you ensure your team receives continuous feedback from real users to avoid building the wrong product? Featured Book of the Week: Humble Inquiry by Edgar Schein Ellen highlights "Humble Inquiry," a transformative book that stresses the importance of relationships over tasks in solving problems. The book encourages leaders to build trust and respect through better questioning techniques. It challenges readers to rethink their interactions and adopt a stance of curiosity, fostering collaboration and understanding. [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

7 Tammi 14min

Managing Change in Complex Organizational Cultures | Ellen Grove

Managing Change in Complex Organizational Cultures | Ellen Grove

Ellen Grove: Managing Change in Complex Organizational Cultures Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen reflects on her early experiences as a Scrum Master, facing challenges in an environment that resisted the introduction of Scrum. She shares valuable lessons about handling external resistance, managing personal expectations, and avoiding emotional burnout when navigating organizational change. Ellen emphasizes the importance of focusing on what can be influenced and detaching from outcomes beyond one’s control. Self-reflection Question: How do you maintain focus and resilience when dealing with resistance to Scrum in 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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

6 Tammi 14min

Throwing Features Over the Fence, The Disconnected PO | Robert Finan

Throwing Features Over the Fence, The Disconnected PO | Robert Finan

Robert Finan: Throwing Features Over the Fence, The Disconnected PO Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: Fostering Quick Feedback Loops With Story Mapping Robert describes a great Product Owner as someone who immerses themselves in the team, fostering collaboration and ensuring quick market feedback.  By using tools like Story Mapping, these POs help teams focus on value while staying engaged and open to learning. The Bad Product Owner: Throwing Features Over the Fence, The Disconnected PO Bad Product Owners remain distant, throwing requirements “over the fence” without participating in the team’s efforts. This disconnect often leads to misalignment and poor outcomes.  For Scrum Masters and Agile Coaches, Robert suggests investigating the root cause of this distance and addressing it collaboratively. [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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

3 Tammi 14min

Promoting Agile Team Growth Through Experiments And Small Focused Changes | Robert Finan

Promoting Agile Team Growth Through Experiments And Small Focused Changes | Robert Finan

Robert Finan: Promoting Agile Team Growth Through Experiments And Small Focused Changes Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Robert defines Scrum Master success as driving impactful team improvements through small, focused changes.  By maintaining a backlog of improvement ideas and encouraging teams to experiment, Robert highlights the importance of measurable progress in both behavior and collaboration. Featured Retrospective Format for the Week: Sailboat Retrospective Robert recommends the Sailboat format, especially when working with new teams. By exploring current realities, future goals, and risks, this format provides rich insights and fosters alignment. The focus on improvement ensures actionable outcomes that resonate with team members. [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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

2 Tammi 14min

Flexible Change Processes, How To Adopt Agile With An Agile Approach | Robert Finan

Flexible Change Processes, How To Adopt Agile With An Agile Approach | Robert Finan

Robert Finan: Flexible Change Processes, How To Adopt Agile With An Agile Approach Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Robert discusses how top-down, project managed Agile transformations often fail to account for the complexity of change. By focusing on flexibility, inspect/adapt cycles, and bringing comfort to the change process, Scrum Masters can guide organizations away from one-size-fits-all solutions and toward the sustainable improvement that is the hallmark of Agile. Self-reflection Question: How can you bring comfort to the change process in 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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

1 Tammi 12min

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