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

Scrum Master Toolbox Podcast: Agile storytelling from the trenches

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.