About:

Jason Diller is a software engineer turned engineering manager who writes about leading software teams, engineering management, and growing organizations, drawing on B2B startup experience.

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Specializations:

Interests:

Engineering management Growing organizations Software product development Leading software teams B2B startups
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The article critiques the concept of 'tech debt' as a metaphor that has lost its effectiveness in explaining technical issues to non-technical stakeholders. It emphasizes the importance of clearly articulating the specific types o...
The article draws an analogy between the roles of pilots in aviation and the relationship between Engineering Managers (EM) and Product Managers (PM) in organizations. It emphasizes the importance of shared goals and collaboration...
The post discusses the detrimental effects of scapegoating in modern work culture, particularly in software engineering. It emphasizes the importance of accountability over blame, arguing that organizations should focus on learnin...
The post discusses the misconception that AI tools will significantly enhance product development productivity by merely speeding up coding processes. It uses a metaphor of a morning routine optimized by an AI breakfast robot to i...
Effective leadership in a changing software industry requires acknowledging identity threats, providing reassurance, and relying on core values for decision-making.
Emphasizing flexibility and autonomy, the post introduces the 'API for Teams' concept to enhance communication and accountability while allowing teams to choose their own processes.
The article discusses the critical relationship between Autonomy, Accountability, and Alignment in creating high-performing teams, emphasizing that trust is the foundational element that supports this triangle. It explains how low...
The article discusses the contrasting approaches to job interviews, specifically the 'Gatekeeper' and 'Matchmaker' postures. The Gatekeeper approach focuses on disqualifying candidates through trivia questions and high-pressure co...
The blog post emphasizes the importance of calm leadership during incidents, particularly in high-stress situations like the recent AWS outage. It argues that panic from leaders can exacerbate problems, while a composed approach f...
The article discusses the importance of distinguishing between solving problems and merely coping with them in management. It critiques quick, attractive solutions that only address symptoms rather than root causes, using the '5 w...
The tech industry is experiencing a shift in mood due to factors like AI hype, return-to-office mandates, and widespread layoffs, leading to increased anxiety among workers. The article discusses how these changes have affected jo...
The post discusses the distinction between 'Agentic' and 'Systems' thinkers in the context of managing software teams. Agentic thinkers attribute outcomes to individual actions, while Systems thinkers consider broader factors infl...
The post discusses the pitfalls of creating 'Labs' teams or special project groups within organizations, often referred to as Skunkworks or Tiger Teams. It argues that while these teams are intended to foster innovation and speed,...
The post discusses the imbalance between creating and destroying work in development teams, emphasizing the ease of generating new ideas compared to the difficulty of executing them. It critiques common prioritization methods for ...
The author reflects on their journey in software engineering management, emphasizing the importance of adapting management styles as companies grow. They introduce the concept of 'Chaotic Good' management, advocating for a balance...
The author reflects on their first quarter of blogging, sharing insights on their posting frequency, audience engagement, and personal growth. They published 10 posts and 1 guest post, with the most successful being 'How to be a l...