Isaac Askew and Jeffrey Sherman
Never Rewrite: Software Engineering & AI Coding
‘Never Rewrite’ is a mantra of ours in the programming realm. Often times when software developers encounter nightmare codebases, the thought crosses their mind to work towards a rewrite, a port to a new language, or despair that their code is unfixable. It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.
Author
Isaac Askew and Jeffrey Sherman
Category
Podcast website
Latest episode
Jul 10, 2026
Where to listen?
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Episodes
Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge 24.01.2025 23:55
Erik Enge, COO of Ghost, discusses the principles of creating a culture of continuous improvement within organizations. He emphasizes the importance of applying the scientific method in business, setting measurable goals, and maintaining a learning loop to reflect on outcomes. The discussion also covers the significance of collaboration within teams, the risks associated with rewriting code, and t...
Episode 87: 2025 Update - State of AI Programming 17.01.2025 17:13
In this conversation, Isaac and Jeffrey discuss the advancements of AI in coding, reflecting on its potential to replace junior developers and the evolving role of developers in the tech industry. They explore the implications of AI tools on productivity, the necessity for developers to adapt their skills, and the future landscape of software development as AI continues to improve.
Episode 86: Annual Reminder - Prune Your Meetings 10.01.2025 8:27
Isaac and Jeffrey discuss the importance of reassessing the necessity of meetings, especially at the beginning of the year. They emphasize the need to cancel unnecessary meetings, optimize meeting structures, and empower team members to decline meetings that do not require their input. The conversation highlights the significance of effective communication and time management in the workplace.
Episode 85: 2024 Year In Review 03.01.2025 26:43
Isaac and Jeffrey reflect on their podcast journey throughout 2024, discussing their goals, achievements, and notable episodes. They share insights on their recording process, the impact of AI on their discussions, and the concept of 'musketeering' in problem-solving. The hosts also highlight their listener engagement and growth, expressing gratitude for their audience's support and outlining plan...
Episode 84: The Impact of AI on Interviewing 27.12.2024 19:37
Special guest Paul Giron discusses the transformative impact of AI on the interview experience, highlighting changes in candidate assessment, the shift towards remote interviews, and the evolving expectations of candidates. The discussion delves into the implications of AI in recruitment, including potential biases and the need for organizations to adapt their interview processes to attract top ta...
Episode 83: The Impact of AI on Recruiting 20.12.2024 33:32
Special guest Paul Giron discusses the transformative impact of AI on recruiting and interviewing processes. He highlights the challenges faced by recruiters in adapting to AI tools, emphasizing that while AI can streamline resume sorting, it does not necessarily improve the quality of hires. The discussion also touches on the importance of understanding high performers within organizations and ho...
Episode 82: Can You Like Tests And Also Believe You're Faster Without Them? 13.12.2024 21:45
Isaac and Jeffrey discuss the balance between unit testing and the need for speed in software development. The discussion delves into the contexts in which testing is most valuable, the challenges of rapid development, and real-world examples of testing practices. Ultimately, they emphasize the importance of adapting testing strategies based on the specific project and team dynamics.
Episode 81: The Pause 06.12.2024 11:22
'The Pause'—a critical juncture where development on the old system is halted in favor of completing a new system. Isaac and Jeffrey discuss the inherent risks of this approach, the implications for customer value, and the often misguided desire for dramatic reveals in software releases. The conversation emphasizes the importance of maintaining continuous value delivery and offers strategies to av...
Episode 80: What is "De-Risking"? 29.11.2024 12:27
Isaac and Jeffrey delve into the concept of de-risking in project management. They discuss the importance of iterative delivery over big bang releases, using gambling analogies to illustrate risk management strategies. The conversation emphasizes the value of decoupling projects to reduce risk and the significance of obtaining feedback early in the development process. The hosts highlight how thes...
Episode 79: The Toxicity of "Certainty" 22.11.2024 18:28
Isaac and Jeffrey explore the concept of certainty in software development and its potential toxicity. They discuss how certainty can lead to poor decision-making, the importance of experimentation, and the human behaviors that contribute to toxic environments. The dialogue emphasizes the need for a balance between certainty and uncertainty, particularly in leadership roles, and highlights the dan...
Episode 78: Is Frontend Modernization a Valid Reason for Rewriting? 15.11.2024 15:32
Isaac and Jeffrey discuss the validity of rewriting front-end systems for modernization. They argue against the notion that a dated front end necessitates a complete rewrite, emphasizing the importance of iterative updates and customer experience. The conversation explores the risks of big bang rewrites, the benefits of gradual improvements, and the need for design consistency while still deliveri...
Episode 77: Who Gets To Define 'Shit' Code? 08.11.2024 15:19
Isaac and Jeffrey explore the subjective nature of coding standards and what constitutes 'shit code.' They discuss the lack of industry-wide standards, the importance of intention in coding, and the balance between flexibility and adaptability in code quality. The conversation also touches on the fluidity of language and how it parallels coding practices, emphasizing that coding standards should e...
Episode 76: Aligning Your Company Standards to its Lifecycle Phase 01.11.2024 24:31
Guest Dustin Rea joins us to discuss the importance of aligning a company's standards and processes with its lifecycle stages. The discussion covers five key phases: the MVP phase, where the foundation is built; the Product User Fit phase, focusing on understanding customer needs; the Product Market Fit phase, solidifying the offering; the Scaling Up phase, managing growth; and finally, the Multi-...
Episode 75: Rewriting is Gambling - A Lesson in Risk 25.10.2024 16:52
Jeffrey and Isaac discuss the inherent risks associated with software rewrites, emphasizing how rewrites push risk to the end of the development cycle. The discussion highlights the need for iterative development and the significance of delivering independent components to ensure project success, particularly within the SaaS model, which thrives on continuous improvement and customer satisfaction.
Episode 74: Musketeering 18.10.2024 11:14
Jeffrey and Isaac explore the concept of 'musketeering' in software development, emphasizing the importance of collaboration in solving complex problems. They discuss the challenges of legacy code, the necessity of testing, and the strategy of 'divide and conquer' to tackle intertwined issues effectively.
Episode 73: The Politics of Delivering Trivial Changes 11.10.2024 12:05
Isaac and Jeffrey discuss the philosophy of continuous iteration in software development, emphasizing the importance of making small, incremental changes rather than large, risky updates. They explore the challenges of communicating the value of these trivial changes to non-technical stakeholders and the benefits of refactoring code for future development. The discussion also highlights the signif...
Episode 72: Perfectionism in Programming 04.10.2024 26:50
Isaac and Dustin Rea discuss the impact of perfectionism in programming, particularly how it can hinder project success. They explore the importance of launching minimum viable products (MVPs) to validate ideas in the market, the challenges of managing change in production software, and the balance between perfectionism and practicality. The discussion also highlights the significance of team dyna...
Episode 71: Are Ignorable Errors Still "Errors"? 27.09.2024 12:51
Isaac and Jeffrey explore the complexities of error management in software development, particularly focusing on the significance of logs, the philosophical implications of ignoring errors, and the importance of proactive log management. They discuss how to differentiate between true errors and warnings, the role of telemetry in alerting, and the necessity of maintaining clean logs to enhance syst...
Episode 70: Resource Engineering 20.09.2024 22:33
Isaac and Jeffrey delve into the concept of resource engineering, emphasizing the importance of understanding cost implications in engineering decisions. They discuss how engineers often overlook financial aspects while focusing on technical solutions, leading to potential inefficiencies. The dialogue highlights the need for engineers to have greater visibility into costs, particularly in cloud se...
Episode 69: Anxiety When Fixing a System You Didn't Create 13.09.2024 17:08
Isaac and Jeffrey delve into the anxiety developers face when dealing with legacy systems they did not create. They explore the reasons behind the fear of fixing such systems, the challenges of refactoring, and the skills required to navigate these situations. The discussion emphasizes the importance of understanding legacy code, learning from it, and developing strategies to reduce anxiety when a...
Episode 68: The Fallacy of Rewriting Software to Save Money 06.09.2024 17:09
Jeffrey and Isaac discuss the fallacy of rewriting software to save money. They highlight that organizations end up running multiple systems simultaneously, resulting in increased costs. The conversation also touches on the challenges of maintaining multiple versions of a software system and the importance of continuous delivery and iteration. It concludes by emphasizing the need to prove the abil...
Episode 67: Revisiting "The Joel Test: 12 Steps to Better Code" 30.08.2024 38:50
Jeffrey revisits The Joel Test, a 12-question test to determine if a software development team is set up for success. Jeffrey and Isaac discuss the relevance of each question in today's context and how the industry has evolved over the years. The topics covered include source control, building and deployment processes, bug tracking, bug fixing, project scheduling, specifications, working condition...
Episode 66: Squashing the Right Bugs 23.08.2024 23:02
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 p...
Episode 65: Exploring Different Perspectives on Risk with Dustin Rea 09.08.2024 19:22
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, si...
Episode 64: Aligning Yourself With the Company's Risk Profile 02.08.2024 16:10
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. The...
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