Never Rewrite

Isaac and Jeffrey discuss the importance of effective bug bashing and how to prioritize bug fixes. They highlight the need for categorizing bugs, understanding customer impact, and installing analytics to make informed decisions. They also emphasize the importance of writing tests and having a team member close to the customer to provide context. They recommend starting with backlog grooming and prioritization before diving into bug fixing. Overall, the conversation provides valuable insights for managers and developers dealing with bug backlogs.

Isaac, Dustin, and Jeffrey discuss different profiles for de-risking releases. They explore the perspectives of software engineers, project managers, product owners, and executives in managing risk. They debate the benefits of incremental releases versus giant functionality releases and the importance of user feedback in de-risking product changes. They also discuss the trade-offs between time, size, and change in managing risk. The conversation touches on the challenges of balancing risk and reward, the importance of lean strategies in startups, and the need to be prepared for success as well as failure.

Isaac and Jeffrey discuss the importance of aligning oneself with a company's risk profile. They explore the concept of risk tolerance and how it varies depending on the company's stage of development and industry. They highlight the need for a balance between security and other business priorities, as well as the importance of having conversations about risk tolerance with managers and teams. They also touch on the potential misalignment between managers and companies, and the implicit cultural risk tolerance that can lead to security vulnerabilities. Overall, they emphasize the need for understanding and navigating risk in the context of software development.

Isaac shares a story about a project where a quick MVP was built to send text messages to users. As the project gained more partners and volume, it became clear that the system couldn't handle mass texting at scale. A small change in the architecture caused some batches of text messages to be reprocessed multiple times, resulting in some users seemingly receiving an excessive number of texts. However, through many strokes of luck, each area where duplicate texts could have been sent was saved by a downstream setting. The issue was resolved, and the team learned the importance of implementing proper safeguards and architecture.

Isaac and Jeffrey discuss the peculiar failure of correctly predicting problems. Jeffrey shares his experience of being able to accurately predict problems in projects but failing to gain traction and prevent them. They explore the importance of buy-in from leadership and the need for a collaborative engagement structure. They also discuss the role of consultants and the difference between being diagnostic and being collaborative. The conversation highlights the challenges of convincing leadership and the potential consequences of not being able to prevent problems.

Dustin Rea, CEO of Red Hook Agency, discusses the challenges and considerations of bringing new products into an existing platform and splitting products within the same platform. The conversation covers topics such as authentication and authorization, merging different products onto a platform, reorganizing teams, and converting internal tools to SaaS. The speakers also touch on the importance of onboarding experiences for new and existing customers.

Isaac and Jeffrey discuss the feeling of anyone being able to make small, simple changes in code and question the value of their own contributions. They share anecdotes of fixing issues that others could have easily addressed but didn't, highlighting the importance of being the one to take action. They emphasize the value of iterative changes and the knowledge work involved in understanding the system. They also encourage developers to listen to complaints and pain points in order to identify opportunities for impactful improvements.

Isaac and Jeffrey discuss the myth of the Boy Scout rule, which is the idea of leaving code better than you found it. Isaac shares his experience of encountering problems when trying to follow this rule in a codebase with no test coverage. He explains how fixing one issue led to unintended consequences and a cascade of errors. They emphasize the importance of being cautious when making changes in old and tightly coupled code and the need for thorough testing. They conclude that while refactoring is important, it should be done intentionally and not mixed with other changes.

Isaac and Jeffrey discuss situations where software development teams are pushed to have fewer, larger releases. They highlight the challenges of big release-driven development and the need for careful planning and more QA before each release. They also explore strategies to make the problem less severe, such as minimizing the final push, using an API-first strategy, and feature flagging.

We check in with Dustin Rea, head of Red Hook Agency, to discuss where White Label CRM is with their 'turnaround story' - how they're handling 'bug hell', scaling issues, and what their trajectory is now.