Maintainable
Do you feel like you're hitting a wall with your existing software projects? Are you curious to hear how other people are navigating this? You're not alone. On the Maintainable Software Podcast, Robby speaks with seasoned practitioners who have overcome the technical and cultural problems often associated with software development. Our guests will share stories in each episode and outline tangible, real-world approaches to software challenges. In turn, you'll uncover new ways of thinking about how to improve your software project's maintainability.
Episodes
David Hayes: Boring Software, Clear Incentives, and Better Checklists
Drawing from his experience at PagerDuty, Sentry, and now FusionAuth, he joins Robby to explore what happens when software becomes trusted infrastructure. Their conversation touches on API design, naming things, product management, self-hosted software, and why customers rarely upgrade as quickly as we’d like them to.
They also discuss why “boring” software is often the most successful, how engine
Diana Pfeil: Building Confidence in Probabilistic Systems
Machine learning systems can degrade even when the underlying code has not changed. Diana Pfeil of Sunbeam Consulting joins Robby Russell on Maintainable to explain how changing data, model behavior, and non-deterministic outputs create a different kind of maintenance challenge.
Rather than asking whether a system is simply correct or incorrect, teams need reliable ways to measure confidence in it
Chris Coyier: The Long Game of Maintaining CodePen
What does it take to keep a product healthy after more than 15 years of continuous evolution?
In this episode, Robby Russell talks with Chris Coyier, co-founder of CodePen, about the long game of maintaining software. Chris shares how CodePen has evolved over time, the trade-offs involved in migrating parts of the platform from Rails to Go, and the challenges of balancing maintenance work with the
Sally Lait: Confidence Is the Real Metric
Sally Lait joins Robby Russell on Maintainable to explore software maintainability through a different lens… not just code quality, but how teams work together over time.
Sally is a fractional technology leader and advisor with more than two decades in the industry. You can follow her on LinkedIn or Mastodon.
They start with a familiar question: what makes software well maintained? Structure and s
Rein Henrichs: The Real Work of Maintenance Happens Before You Touch the Code
Software maintenance is often framed as a technical problem. Refactoring code, fixing bugs, or upgrading dependencies. In this conversation, Robby Russell talks with Rein Henrichs about a different lens, one centered on understanding.
Rein is a Principal Software Engineer at Procore, where he works within a large, long-lived system used across the construction industry. Rather than focusing on too
Russ Olsen: The Hidden Cost of Forgetting Why the Code Looks Like That
Software doesn’t become hard to maintain only because the code is messy. It often becomes hard to maintain because the reasoning behind it disappears.
In this episode of Maintainable, Robby Russell talks with Russ Olsen about trade-offs, legacy systems, and why maintainability depends on context more than dogma. Russ brings decades of experience across very different kinds of systems, each with it
Joel Oliveira: Predictability Is a Maintainability Feature
Long-lived software systems rarely stay tidy. Over time they accumulate decisions, workarounds, and layers of history that can make even simple changes feel risky. For engineers responsible for maintaining those systems, the challenge often becomes less about writing new code and more about understanding what already exists.
In this episode of Maintainable, Robby Russell speaks with Joel Oliveira,
Lucas Roesler: The Fast Feedback Loop Advantage
Maintaining software over time rarely fails because of one bad decision. It fails because teams stop getting clear signals… and start guessing.In this episode, Robby talks with Lucas Roesler, Managing Partner and CTO at Contiamo. Lucas joins from Berlin to unpack what maintainability looks like in practice when you are dealing with real constraints… limited context, missing documentation, and syst
Brittany Ellich: Using AI to Maintain Software, Not Rewrite It
Rewrites are seductive. Clean slates promise clarity, speed, and “doing it right this time.” In practice, they’re often late, over budget, and quietly demoralizing.In this episode of Maintainable, Robby sits down with Brittany Ellich, a Senior Software Engineer at GitHub, to talk about a different path. One rooted in stewardship, readability, and resisting the urge to start over.Brittany’s career
Kent L Beck: You’re Ignoring Optionality… and Paying for It
Kent Beck: You’re Ignoring Optionality… and Paying for ItIn this episode of Maintainable, Robby speaks with Kent Beck, a foundational voice in modern software development and author of Tidy First?. Kent joins from California to explore why optionality is a central, often underestimated dimension of maintainable software.Kent begins by describing the tension between features and future flexibility.
Don MacKinnon: Why Simplicity Beats Cleverness in Software Design
Episode Highlights[00:00:48] What Makes Software MaintainableDon explains why unnecessary complexity is the biggest barrier to maintainability, drawing on themes from A Philosophy of Software Design.[00:03:14] The Cost of Clever AbstractionsA real story from a Node.js API shows how an unused abstraction layer around MongoDB made everything harder without delivering value.[00:04:00] Shaping Teams a
Chris Zetter: Building a Database to Better Understand Maintainability
Episode SummaryIn this conversation, Robby sits down with software engineer and author Chris Zetter to explore what building a relational database from scratch can teach us about maintainability, architectural thinking, and team culture. Chris shares why documentation often matters more than perfectly shaped code, why pairing accelerates learning and quality, and why “boring technology” is sometim
Denis Rechkunov: When Consistency Becomes a Culture
Maintaining consistency across a sprawling codebase is one of the hardest challenges in software engineering. Denis Rechkunov, a Principal Software Engineer at Elastic, joins Robby to share how his team turned consistency into a cultural practice rather than a technical checklist. From managing open source projects with hundreds of contributors to experimenting safely with new patterns, Denis beli
Nathan Ladd: Relentless Improvement and the Cost of Neglect
Episode NotesThe discussion moves into how standards evolve beyond tools, the trade-offs of monocultures vs. consensus-driven teams, and why ownership matters when the original authors move on. Nathan also unpacks the cost of neglect, describing defects as anything that slows developers down—not just issues that impact end users.Later in the conversation, Nathan recounts a migration from a React S
Taylor Otwell: What 14 Years of Laravel Taught Me About Maintainability
Taylor Otwell, creator of Laravel and CEO of Laravel LLC, joins Robby to reflect on his 14-year journey building and maintaining one of the most popular web frameworks in the world. From its PHP 5.3 origins to a full-time business with a 70-person team, Taylor shares what he's learned about code maintainability, developer experience, and what it means to evolve without overcomplicating things.He d
Sara Jackson: Why Resilience Is a Team Sport
Robby is joined by Sara Jackson, Senior Developer at thoughtbot, to explore the practical ways teams can foster resilience—not just in their infrastructure, but in their everyday habits. They talk about why documentation is more than a chore, how to build trust in test suites, and how Chaos Engineering at the application layer can help make the case for long-term investment in maintainability.Sara
Joel Chippindale: Why High-Quality Software Isn’t About Developer Skill Alone
CTO coach Joel Chippindale joins Robby to share what he's learned over two decades of building and leading software teams. Joel argues that maintainability has less to do with “clean code” and more to do with how teams communicate, prioritize, and make progress visible. Drawing on his time at Unmade and his current coaching practice, Joel outlines practical ways teams can build trust, navigate bri
Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage
Melanie Sumner: Why Continuous Accessibility Is a Strategic AdvantageMelanie Sumner, Product Accessibility Lead for Design Systems at HashiCorp, joins Robby to talk about what it takes to scale accessibility across legacy products—and how aligning design and engineering processes creates lasting change. Melanie shares her work making Ember.js more accessible, her team’s philosophy behind their des
Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner
In this episode of Maintainable, Robby speaks with Joe Masilotti, an independent consultant who helps Rails teams ship mobile apps using Hotwire Native.Joe shares his perspective on what makes software maintainable—especially for consultants who need to onboard quickly. He explains why setup scripts often add unnecessary complexity, and how he evaluates a project’s maintainability by how quickly h
Freedom Dumlao: What 70 Java Services Taught Me About Focus
Freedom Dumlao (CTO at Vestmark) joins Robby to explore what it means to maintain software at scale—and why teams sometimes need to unlearn the hype.With two decades of experience supporting financial systems, Freedom shares how his team manages a Java monolith that oversees $1.6 trillion in assets. But what’s most surprising? His story of how a team working on 70+ microservices rebuilt their plat
Mercedes Bernard: Friendly Code Welcomes Everyone In
Mercedes Bernard, Staff Software Engineer at Kit, joins Robby to talk about what it really means to write code that lasts—and who it should be written for.In this episode of Maintainable, Mercedes shares a thoughtful and practical perspective on working with legacy codebases, managing technical debt, and creating a team culture that values maintainability without fear or shame. Her guiding princip
Evan Phoenix: The Why of the One Line
Evan Phoenix (@evanphx), CEO of Miren, joins Robby to explore the subtle but powerful difference between writing code that works and writing code that explains itself. They discuss the role of clarity in maintainable systems, why splitting a monolith can backfire, and what developers can learn from artists and tradespeople alike.Episode Highlights[00:01:30] What Makes Software Maintainable?Evan de
Chris Salvato: Building Developer Paradise by Sitting in the Problem Space
Software isn’t always about rapid iteration. Sometimes, the real challenge lies in carefully assessing the existing environment. Chris Salvato, a Senior Staff Engineer at Shopify, believes that spending time in the “problem space” is vital for any long-lived application. Rather than diving immediately into controllers and tests, he begins by talking to everyone who interacts with the code—engineer
Heimir Thor Sverrisson: Architecture First, Tech Debt Second
Heimir Thor Sverrisson joins Robby to discuss the importance of software architecture in long-term maintainability. With over four decades in the industry, Heimir has witnessed firsthand how poor architectural decisions can set teams up for failure. He shares his experiences mentoring engineers, tackling technical debt, and solving large-scale performance problems—including one bank’s misguided at
Noémi Ványi: Only Fix Problems That Are Actually Problems
Not every messy piece of code needs a refactor. Noémi Ványi, Senior Software Engineer at Xata, joins Robby to discuss how to develop the intuition to know when refactoring is truly necessary and when it’s just unnecessary churn. She shares her approach to balancing pragmatism and maintainability, how product teams and developers can work better together, and why developer autonomy is key to sustai
Julia López: Code Tells a Story—Even the White Spaces
How much can legacy code tell us beyond just functionality? Julia López, Senior Software Engineer at Harvest, believes that even small details—such as white spaces, variable names, and formatting choices—can reveal a system’s history.In this episode, Julia and Robby discuss the importance of refactoring and how a strong engineering culture can make or break a team's ability to maintain and improve
Marty Haught: Rethinking Technical Debt—Is It Really Just Drift?
Episode OverviewMarty Haught joins Robby to discuss the sustainability of open-source projects, the challenges of maintaining RubyGems, and why the metaphor of technical debt may not fully capture how software ages. Instead, he suggests thinking of it as drift—the natural misalignment of software with its evolving purpose over time.They also dig into security challenges in package management, incl
Mike Bowers - From ISAM to JSON—Navigating 40+ Years of Database Evolution
Mike Bowers, Chief Architect at FairCom, has spent decades navigating the evolution of database technology. In this conversation, he and Robby explore the challenges of maintaining a 40+ year-old codebase, balancing legacy constraints with forward-thinking design, and the realities of technical debt.Mike shares how FairCom transitioned from ISAM-based databases to modern JSON-driven APIs, the trad
Lorna Mitchell: Writing Documentation Engineers Will Actually Read
Join Robby as he chats with Lorna Mitchell, open source advocate and technical writer, about the art of creating documentation that doesn’t gather dust. Lorna shares her experiences as a maintainer of the open source project RST2PDF, the value of API governance, and how documentation bridges gaps in developer experience.Highlights:What Makes Software Maintainable: Characteristics like great docume
Carola Lilienthal: Tackling Technical Debt with Patterns and Domain Knowledge
Episode SummaryIn this episode of Maintainable, Robby sits down with Carola Lilienthal, Software Architect and Managing Director at WPS. Together, they explore the intersection of cognitive science and software architecture, strategies for tackling technical debt, and why simplicity, modularity, and domain knowledge are crucial for maintainability.Carola shares her approach to improving legacy sys
Joel Hawksley: The Hidden Costs of Frontend Complexity
Topics DiscussedThe importance of changeability as a core characteristic of well-maintained software.How GitHub has approached accessibility as a business and legal imperative.The evolution of GitHub’s frontend system, spanning over 2,000 pages, and the concept of "frontend vintages."Primer: GitHub’s design system and the paradox of its success—consistency vs. changeability.The disproportionate ma
Austin Story: Making Software Easier to Change, Remove, and Evolve
Austin Story, Senior Engineering Director at Doximity, joins Robby to explore the intricacies of building maintainable systems, fostering team accountability, and enabling faster iteration without sacrificing quality. Austin shares how his team approached migrating from a monolithic GraphQL architecture to a federated model, why simplicity matters for long-term success, and how guiding principles
Dan Moore: Building Developer-Friendly Authentication Solutions
Topics CoveredCharacteristics of Maintainable SoftwareDan emphasizes the importance of internal consistency in codebases, automated tests, and proper documentation to preserve decision-making context.[00:05:32] Internal consistency: Why it matters.[00:08:09] Lessons from maintaining legacy codebases.Working with Legacy SystemsDan shares stories of upgrading ORM frameworks, introducing caching syst
Tom Johnson: From Auto-Documentation to Better Collaboration
In this episode of Maintainable, Robby speaks with Tom Johnson, Co-Founder and CEO of Multiplayer. Tom shares his perspectives on the evolving landscape of distributed systems, the challenges of maintaining legacy software, and how innovative tools are transforming the way teams collaborate.Topics DiscussedCharacteristics of well-maintained software, from system-level documentation to effective wo
Gulcin Yildirim Jelinek: Maintaining Postgres for Modern Workloads
In this episode of Maintainable, Robby speaks with Gulcin Yildirim Jelinek, a Staff Database Engineer at Xata. Joining from Prague, Czech Republic, Gulcin discusses her experiences working with legacy databases, the evolution of Postgres, and her passion for building accessible tech communities.Gulcin shares practical insights into modern database management, including the rise of automation tools
Justine Gehring: Refactoring Software at Scale with AI
Robby sits down with Justine Gehring, an AI Research Engineer at Moderne, to explore how AI tools are transforming code maintenance and scalability. They dive into the unique ways AI can support refactoring for massive and legacy codebases, from retrieval-augmented generation (RAG) to lossless semantic trees, and discuss how developers can benefit from AI-assisted planning and refactoring.Justine
Katerina Skroumpelou: Bridging Engineering and Advocacy for Scalable Software
As a product advocate at Nx, Katerina Skroumpelou combines her engineering skills with a knack for connecting with clients. In this episode, she shares how clear documentation, scalable architectures, and a collaborative culture can transform software development for the better.Key Takeaways[00:01:25] Katerina’s Background: Robby and Katerina discuss her career journey, starting in engineering and
Moriel Schottlender: The Challenges of Modernizing MediaWiki's Monolith
Welcome to another engaging episode of the Maintainable Software Podcast! In this episode, Robby sits down with Moriel Schottlender, Principal Software Engineer at the Wikimedia Foundation, to explore the complex journey of modernizing MediaWiki, the software behind Wikipedia. Moriel shares her insights on what it takes to keep an enormous monolithic codebase maintainable while supporting an ever-
Kate Holterhoff: From Front-End Engineering to Developer Advocacy
Welcome to another engaging episode of Maintainable! Robby sits down with Kate Holterhoff, Ph.D., a Senior Analyst at RedMonk and former front-end engineer, to explore the intricate world of software maintenance, documentation, and the future of developer roles. Kate brings her unique perspective from her time as a practitioner at a digital marketing agency, her academic background, and her curren
Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing
Alan Ridlehoover: Building Robust Systems Through Behavior-Centric TestingIn this episode of Maintainable, Robby speaks with Alan Ridlehoover, Senior Engineering Manager at Cisco Meraki. Alan shares his perspective on building well-maintained software by focusing on behavior-centric testing, clear code ownership, and thoughtful technical decisions that stand the test of time.Alan discusses his exp
April Wensel: Navigating Legacy Code with Compassion
In this episode of Maintainable, Robby speaks with April Wensel, Founder and Owner of Compassionate Coding. April shares her journey in the software industry and how she came to embrace compassion as a core value in coding and team dynamics. She explains why empathy is critical when working with legacy code, mentoring junior developers, and addressing technical debt.Episode Highlights[00:05:32] In
Saron Yitbarek: The Balance Between Maintainable Code and Multiple Streams of Income
In this episode of the Maintainable Software Podcast, Robby sits down with Saron Yitbarek, founder and CEO of DiscoLink, to explore the challenges of maintaining early-stage software while balancing multiple streams of income. Saron shares her journey from being a solo developer to hiring her first teammate and the lessons learned along the way about code maintainability and business logic.Episode
Lutz Hühnken: Crafting Resilient Systems with Event-Driven Design
IntroductionIn this episode of Maintainable, Robby speaks with Lutz Hühnken, Head of Engineering Excellence at Upvest, about the transformative power of event-driven architecture in software development. Lutz brings his extensive experience to the table, discussing how breaking down complex systems into manageable modules and leveraging event-driven design can lead to more resilient and maintainab
Noel Rappin: Reviving the Pickaxe— A Journey through Ruby's Legacy
In this episode of the Maintainable Software Podcast, Robby is joined by Noel Rappin, Staff Engineer at Chime Financial, and the mind behind the latest edition of the classic Programming Ruby book, affectionately known as the "Pickaxe." Noel delves into the intricate process of modernizing a legacy technical book and the lessons learned along the way.Episode Highlights[00:05:32] A Legacy Revisited
Cassidy Williams: Navigating the Career Jungle Gym in Tech
In this episode of the Maintainable Software Podcast, Robby sits down with Cassidy Williams, Developer Advocate at GitHub, to explore the dynamic nature of a tech career, the delicate balance between clever code and maintainability, and the evolving trends in software development.Cassidy begins by discussing what makes software truly maintainable—starting with the ease of onboarding for new develo
Obie Fernandez: Pioneering AI in Ruby on Rails Development
In this episode of the Maintainable Software Podcast, Robby speaks with Obie Fernandez, Chief Scientist at Olympia, about the integration of AI into modern software development. Obie shares his unique perspective on leveraging AI to enhance the maintainability and functionality of software applications, particularly in the Ruby on Rails ecosystem.Episode Highlights[00:01:00] Characteristics of Wel
Tekin Süleyman: Balancing Complexity and Team Size
Topics DiscussedCharacteristics of Well-Maintained Software: Tekin emphasizes the importance of software that is easy to change and tailored to the team's needs.Balancing Complexity and Team Size: Tekin discusses how his small team manages complexity and features to maintain sustainable work practices without overburdening the developers.GovUK Project Insights: Tekin shares his experiences working
Ryosuke Iwanaga: The Benefits of Cell-Based Architecture
Ryosuke shares his insights on:Ownership in Software Maintenance: The role of single-threaded ownership and dedicated teams in maintaining software and shared libraries.Technical Debt: How his definition of technical debt has evolved over the years and strategies to manage it effectively.Monitoring and Alarming: The importance of comprehensive monitoring and alarming systems in handling legacy sof
Julia Ferraioli - Capturing Untold Open Source Stories
Welcome to the Maintainable Software Podcast! In this episode, Robby speaks with Julia Ferraioli, an Open Source AI/ML Strategist at AWS and co-founder of Open Source Stories. Julia joins us from Seattle, Washington, and shares her insights into the world of open source, AI, and software maintainability.Key Topics:Well-Maintained Software: Julia shares her thoughts on the characteristics of well-m
Tanmai Gopal: Unlocking the Potential of Unified APIs
In this episode of Maintainable, Robby Russell sits down with Tanmai Gopal, the CEO and co-founder of Hasura. Tanmai shares his insights into the characteristics of well-maintained software and the importance of a codebase that no team member fears. He emphasizes the need for accessibility and understandability in code, making it easier for developers to work with and iterate upon.Tanmai dives dee
James Socol: Building Social Capital in Engineering Teams
In this episode of the Maintainable Software Podcast, Robby Russell sits down with James Socol, a Staff Engineer at Fastly, to discuss the art of maintaining legacy code and the nuances of technical debt versus technical depreciation.Key Topics Discussed:Characteristics of Well-Maintained Code: James shares his insights on what defines well-maintained code, emphasizing the importance of continuous
Paola Ducolin: Building Trust and Communication in Engineering Teams
In this episode of Maintainable, Robby chats with Paola Ducolin, Staff Engineer at Datadog. Paola shares her insights on the characteristics of well-maintained software, the common struggles teams face, and effective strategies for working with stakeholders to prioritize refactoring.Key Topics Discussed:Characteristics of Maintainable Software: Paola explains the importance of well-documented code
Robin Heinze - React Native and the Art of Flexibility
In this episode, Robby welcomes Robin Heinze, Director of Engineering at Infinite Red, to discuss the intricacies of building and maintaining robust software systems. Key topics covered include:Characteristics of Maintainable Software: Robin shares insights from her team on what makes software maintainable, emphasizing the need for clear documentation, robust setup scripts, and ongoing code refine
Scott Hanselman - The Fear Factor in Maintainable Software
In this episode of Maintainable, Robby welcomes Scott Hanselman, VP of Developer Community at Microsoft and host of the Hanselminutes Podcast, to discuss the emotional side of maintainable software. Scott shares his thoughts on fear as a common thread in poorly maintained software, the importance of building a team culture of trust, and how finding a good work-life balance helps create better soft
Stig Brautaset: Understanding Alien Artifacts in Legacy Code
In this episode of Maintainable, Robby chats with Stig Brautaset, Staff Software Engineer at CircleCI. Stig shares his insights on maintaining well-documented but complex legacy code, the impact of team dynamics on software maintenance, and his experiences with the SBJSON library.Stig discusses the characteristics of well-maintained software, emphasizing the importance of team experience, domain k
Brit Myers - Decoding Product vs. Technical Risk
Join Robby as he welcomes Brit Myers to the podcast. Brit, currently thriving as the VP of Engineering at System Initiative, discusses the intricacies of maintaining software. She emphasizes the importance of navigable software, where the ease of tracing the code and understanding its structure is paramount. Brit highlights the significance of clear naming conventions and inline documentation, as
Andrea Guarino - Leveraging Static Analysis for Better Code
In this episode, Robby interviews Andrea Guarino, a Software Engineer at Sonar, about the importance of leveraging static analysis tools for maintaining clean and adaptable code. Andrea emphasizes that well-maintained software should be easy to change, consistent, intentional, and responsible. He explains that static analysis tools play a crucial role in identifying potential issues, ensuring code
Staffan Nöteberg - On the Power of Monotasking in Software Development
In this insightful episode, we dive deep into the essence of software maintainability with Agile Coach and author Staffan Nöteberg. Unpacking the layers of what it takes for software to be considered well-maintained, Staffan sheds light on the crucial roles of abstraction and modularity. These foundational elements not only make software easier to understand for newcomers but also ensure that it c
Martin Emde - Ruby Central and the Art of Being Tolerant to Change
In this episode of Maintainable, our host Robby Russell sits down with Martin Emde, a sage in the Ruby community and the current Director of Open Source at Ruby Central. Together, they weave through the intricacies of maintainable software, legacy code, and the unwavering power of the Ruby ecosystem. Martin, with his wealth of experience, shares tales from the trenches of open-source software deve
Esther Olatunde - AI's Role in Evolving Software Engineering Practices
In this captivating episode of the Maintainable Software Podcast, host Robby Russell delves deep with Esther Olatunde, Senior Product Engineer at Intercom, into the realms of software maintenance, technical debt, and the impact of AI on software development. The discussion kicks off with Esther's insights on what constitutes well-maintained software, emphasizing the importance of quality from both
Robbie Wagner - Whiskey, Front-End, and Whatnot
Starting off, Robbie Russell and Robbie Wagner bonding over the complexities of their names in the coffee queue.They dive into the essence of maintainable software, debating the importance of recent commits and the dangers of a single-contributor project.Tech debt, the ever-looming shadow over software development, gets a moment in the spotlight. They share a laugh over buying GitHub stars as a me
Irina Nazarova - Investing in Innovation: The Consultancy's Guide to Growth
In the latest episode of Maintainable, Robby Russell has a fascinating conversation with Irina Nazarova, the CEO of Evil Martians, a name that resonates with innovation and bold strides in the software development world. They dive deep into what it takes to maintain not just code, but also the delicate balance between rapid development and long-term sustainability in the ever-evolving startup land
Kyle Daigle - Scaling Up with AI: A New Era of Code Maintenance
Robby has a chat with Kyle Daigle, the Chief Operating Officer at GitHub. They dive into the evolution of software development from the perspective of maintaining and scaling software within large organizations like GitHub. Kyle talks about the importance of simplicity and readability in code over complexity, advocating for well-named variables and straightforward codebases to enhance maintainabil
Jon Moniaci - Can We Draw A Boundary?
Robby speaks to the Senior Software Engineer at Perchwell, Jon Moniaci. They discuss the delicate balance between innovation and stability in software development. Jon emphasizes the importance of fostering an environment where engineers can experiment without fear, advocating for a culture of defensive programming to mitigate the fear of breaking things in production. He shares insights from his
Chad Fowler - How Small Can We Make This Problem
Robby has a candid chat with Chad Fowler, the General Partner & CTO at BlueYard Capital. They delve into the nuances of software maintenance, the evolution and challenges of managing software projects, and insights from Chad's tenure as CTO of Wunderlist. They discuss the importance of building software in small, manageable pieces to facilitate easy updates or replacements, the counterintuitive pe
John Nunemaker - How Scary Is This Change?
Robby has a conversation with John Nunemaker, the Owner at "Box Out Sports" and "Fewer & Faster". They dive into the basics of maintaining software projects, highlighting the crucial importance of keeping dependencies and versions up to date. John shares his wealth of experience from his time at GitHub, shedding light on the delicate balance between exploring new architecture patterns and adhering
Jemma Issroff - Running the Parser in the Rain
Robby has a conversation with Jemma Issroff, a Senior Software Engineer, speaker and the author of the book, “Ruby Garbage Collection in Under Two Hours” They delve into the intricacies of well-maintained software, and Jemma brings her wealth of experience, particularly from her involvement in Prism, a notable rewrite of the Ruby parser. The duo explores the contrasting dynamics of maintaining sof
Jeanine Soterwood - Helping Clients Understand Maintenance Work
Robby has a chat with the Software Development Team Lead at Thoughtbot, Jeanine Soterwood. Unraveling the intricacies of Ruby on Rails, they explore the often overlooked importance of keeping apps up-to-date and maintaining a robust test suite. The conversation weaves through the delicate balance between enticing features and the long-term needs of software maintenance, shedding light on the aspec
Andrew Atkinson - Maintainable... Databases?
Robby engages with independent consultant and author, Andrew Atkinson, delving into the intricate world of software development and database maintenance. The duo kicks off with a profound exploration of the importance of swift and intuitive change management in software, unraveling the key traits that transform a database into a well-maintained powerhouse. From securing data to cleaning up legacy
Jimmy Koppel - Aspects of Good Code
Robby engages in a captivating conversation with the CEO at Mirdin and UpToSpeed, Jimmy Koppel. They delve into the transformative power of evolvable code, shedding light on its myriad benefits and how it contributes to an enriching coding experience. Drawing inspiration from Jimmy's insightful blog post, "The 11 Aspects of Good Code," the discussion unfolds to explore the external qualities of co
Hila Fish - Maintainable Infrastructure Code, Culture, and Documentation
Robby has a chat with Senior DevOps Engineer, Hila Fish. They start off by discussing the key characteristics of maintainable infrastructure code. Hila shared insights on providing software engineering teams with the necessary space for exploration while maintaining essential guardrails to ensure the stability of production environments. The conversation also touched upon the significance of offer
Jacob Aronoff - At Least One Person Who Cares To See It Through
Robby has a chat with Staff Software Engineer at Lightstep from ServiceNow, Jacob Aronoff. Their conversation delves into the vital signs of a thriving open source software project. They unpack the characteristics of well-maintained open source endeavors, emphasizing the importance of a passionate community behind the project, rather than misleading indicators like GitHub stars. They discuss the n
Oliver Drotbohm - Modulithic Applications
Robby has a chat with Oliver Drotbohm, a Staff 2 Engineer at VMware. They explore the essence of maintainable software, pinpointing understandability and modifiability as its foundational pillars. Drawing from Dr. Carola Lilienthal's "Sustainable Software Architecture: Analyze and Reduce Technical Debt," Robby and Oliver dissect the metaphor of technical debt, discussing its historical context and
Colin Campbell - The Daily Habits of Effective Engineers
Robby has a chat with Colin Campbell, the Director of Engineering at Tucows. Colin delves into the professional ethos of software development, emphasizing that the caliber of an engineer’s work is a reflection of their daily habits. He stressed the importance of humility for software engineers, arguing that it is crucial for continuous improvement and effective teamwork. He also talked about the s
Dave Bryant Copeland - Quantifying the Carrying Cost
Robby has a chat with the Author of Sustainable Web Development with Ruby on Rails, Dave Bryant Copeland (he/him/his). Dave is a Senior Software Engineer and speaker. Reflecting on his experience, Dave believes that well-maintained software is software that people understand what it does, how it works, and that it can be changed. He starts off by highlighting the challenges that developers face wh
Cameron Jacoby - Am I Learning From This?
Robby has a chat with Cameron Jacoby (she/her/hers), a Senior Full-Stack Engineer at BetterUp, a platform that uses world-class coaching and science-backed solutions that help people grow personally and professionally. The one thing that Cameron says should stand out about code being maintainable is that it should be easy to read and understand. She explains why procedural code can often be easier
Adriana Villela - On Being a Serial Refactorer
Robby has a chat with Adriana Villela, a Senior Developer Advocate at Lightstep. Adriana highlights that well-maintained software should be software that one can understand when they go into the code even if they’re not super familiar with it. She shares why she values being a serial refactorer and describes what beautiful code should look like. Adriana views debuggers as her best friends because
Ahmed Wasfy - Thriving as an Engineering Manager
Robby has a chat with Ahmed Wasfy (he/him/his), the Senior Development Manager at Amazon. On the topic of the common characteristics of well maintained software, Ahmed feels that one critical thing is that software should serve a purpose in terms of what values it adds and the trackable business goal it fulfills. He shares some valuable insights about legacy code based on his vast experience and d
Naomi Ceder - People-Centric Community Building
Robby has a chat with Independent Python Instructor and Consultant, Naomi Ceder (she/her/hers). Naomi values clear organization, separation of concern and capsulation, visibility instrumentation, and tests when it comes to creating a legacy piece of code that will be continuously useful. She will talk about the importance of weighing up the costs of using 3rd party tools vs rolling your own soluti
Nadia Odunayo - Don't Try to Solve a Pain Point For a Problem You Aren't Experiencing
Robby has a chat with Nadia Odunayo (she/her/hers), the Founder and CEO at The StoryGraph. Nadia starts off by highlighting solid test coverage, up-to-date gem language platform versions, all security patches, and proper documentation as some of the few common characteristics of maintainable software. She talks about when it makes sense to document debugging processes for your future self, the tra
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