Isaac Askew and Jeffrey Sherman discuss the social and emotional ramifications of failed rewrites in project management. They explore the loss of patience from leadership, the burnout experienced by teams, and the importance of taking responsibility for project outcomes. The discussion emphasizes the need for teams to salvage lessons from failures and to approach leadership with solutions rather than just problems. The conversation concludes with strategies for ensuring future success and maintaining trust within teams.

Chapters

00:00 The Impact of Failed Rewrites

03:03 Team Dynamics and Leadership Pressure

06:01 Salvaging Lessons from Failure

09:00 Taking Responsibility for Project Outcomes

12:02 Strategies for Future Success

Isaac Askew, Dustin Rea, and Jeffrey Sherman delve into the complexities of developing Minimum Viable Products (MVPs) and the challenges of balancing simplicity with the need for future scalability. They discuss the Goldilocks problem in software development, emphasizing the importance of finding the right balance between over-engineering and under-engineering. The discussion highlights the distinction between maintainability and optionality, the significance of timing in product development, and the lessons learned from past experiences. The trio also explores the concept of gaming out scenarios to prepare for potential challenges and the importance of aligning teams to ensure a cohesive approach to development.

Today we discuss the relationship between Conway's Law and software quality, exploring how a company's structure and culture can impact code quality. We delve into the signs of a toxic culture, the consequences of a 'yes culture', and strategies for identifying and changing company culture. The conversation emphasizes the importance of communication patterns and the long-term nature of cultural transformation in organizations.

We debate the merits of consolidating technology stacks versus diversifying them. Today we explore the implications of each approach on business value, engineering efficiency, and organizational dynamics. Key points include the importance of evaluating the business value of consolidation, the impact on developer fungibility, and the balance between engineering optimization and business leverage.

Jeffrey and Isaac dive into a comment made by Allen Holub to 'rebuild' instead of 'rewriting' legacy software and dive into the terminology.

Show Notes:‪

Allen Holub's thread mentioned: https://bsky.app/profile/allenholub.bsky.social/post/3lmcyvi3kag2f

Isaac and Jeffrey explore how to halt a rewrite, the importance of learning from the process, and how to effectively communicate changes in direction to a team. The conversation emphasizes the value of reframing discussions around rewrites to focus on new insights and solutions rather than perceived failures.

Guest Nick Gerace discusses the rewrite of the core engine at System Initiatives, detailing the challenges faced, the technical decisions made, and the importance of aligning development with business goals. The conversation covers the transition from the old engine to the new, the role of user feedback, and the iterative process that led to a more efficient and user-friendly product.

Show Notes:

Domain-Driven Design book: https://www.oreilly.com/library/view/domain-driven-design-tackling/0321125215/

Nick's LinkedIn: https://www.linkedin.com/in/nickgerace/

Guest Paul Stack shares his experiences in transforming a massive logging infrastructure from a monolithic architecture to a microservices-based system. He discusses the challenges faced during the transition, the implementation of Kafka for log management, and the importance of data retention and cost management. The conversation highlights the evolution of logging practices and the empowerment of teams through decentralization, ultimately leading to a more efficient and effective infrastructure.

Show Notes:

Paul's LinkedIn: https://www.linkedin.com/in/stack72/

Paul's Github: https://github.com/stack72