Maintainable

Alan Ridlehoover: Building Robust Systems Through Behavior-Centric Testing

In 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 experience working in both startup environments and large-scale engineering teams, including how he navigates the unique challenges of each. He provides practical advice on managing conditional logic in code, scaling with third-party dependencies, and ensuring that testing strategies remain effective as systems grow in complexity.

Key Takeaways:

• The characteristics of well-maintained software: behavior-centric testing, solid code principles, and ownership boundaries.
• Balancing the needs of startups vs. large enterprises when it comes to software maintenance.
• Alan’s approach to handling conditional logic with a technique called "rehydration" to simplify complex code.
• Why focusing on behavior, not implementation, is critical for scalable, maintainable tests.
• The importance of interfaces and facades for managing third-party dependencies and future scalability.
• How to approach technical debt as a conscious trade-off, not an inevitable burden.
• Best practices for addressing flaky tests, including managing non-determinism, order dependencies, and race conditions.
• How to set up effective monitoring and alerting systems to maintain a healthy software environment.
• The role of team structure and product ownership in delivering sustainable, high-quality software.

Episode Highlights:

• [00:05:32] Introduction to the Guest's Background: Robby and Alan discuss Alan's work at Cisco Meraki and his approach to well-maintained software.
• [00:15:10] The Importance of Behavior-Centric Testing: Alan explains why focusing on behavior, not implementation, helps in both startups and large-scale environments.
• [00:24:30] Rehydration: A Strategy for Managing Conditional Logic in Code: Alan shares his method for simplifying code with many conditionals.
• [00:35:00] Navigating Technical Debt: Alan offers advice on how to strategically manage technical debt without slowing down business needs.
• [00:45:18] Monitoring and Alerting: Alan’s tips on keeping systems healthy and avoiding customer-facing issues through smart monitoring setups.

Resources Mentioned:

• Radical Candor by Kim Scott
• The Code Gardener

Connect with Alan Ridlehoover:

• LinkedIn
• The Code Gardener Blog

Thanks to Our Sponsor!

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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 knowledge, and risk appetite. He reflects on his own career journey, highlighting the transition from overconfidence to a balanced approach to risk-taking.

A significant portion of the conversation delves into Stig's concept of "Alien Artifacts," which describes highly resistant legacy code written by highly skilled engineers. He explains the challenges of modifying such code and shares examples from his own experiences.

Stig also talks about his work on the SBJSON library, addressing the complexities of handling multiple versions and dependency conflicts. He advocates for developers maintaining the software they ship and discusses the balance between shipping features quickly and maintaining long-term code quality.

Key Takeaways

• The influence of team dynamics on software maintenance
• Understanding the concept of "Alien Artifacts" in legacy code
• Strategies for handling multiple versions of a software library
• The importance of developers being on call for the software they ship
• Managing different types of technical debt

Book Recommendation:

• The Scout Mindset by Julia Galef
• Stig Brautaset on LinkedIn
• Alien Artifacts Blog Post
• SBJSON Library
• CircleCI
• The Confident Commit Podcast

Helpful Links:

• Stig Brautaset on LinkedIn
• Alien Artifacts Blog Post
• SBJSON Library
• CircleCI
• The Confident Commit Podcast

Want to share your thoughts on this episode? Reach out to Robby at [email protected].

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and soon, other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.

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 software over time. Julia shares her experience leading a multi-year overhaul of Harvest’s billing system, balancing stakeholder expectations while ensuring the rewrite delivered real value.

They explore how refactoring decisions evolve as teams grow, how to mentor newer developers to feel empowered to make changes, and why Julia doesn’t always trust her own estimations (for good reason). She also opens up about the complexities of transitioning a live billing system while supporting customers, finance teams, and engineering operations—all without disrupting payments.

Beyond technical decisions, they also dive into the challenges of communication in remote teams, the value of autonomy in software development, and how teams can make a case for technical debt reduction even when leadership isn’t prioritizing it. If you've ever struggled with refactoring legacy systems or advocating for improvements, this conversation is packed with practical lessons.

💡 Key Topics & Timestamps

• [00:00:22] Meet Julia López – Her background, role at Harvest, and passion for refactoring.
• [00:00:42] What Makes Software Maintainable? – A test suite you can trust and an engineering culture that values refactoring.
• [00:06:31] Leading Harvest’s Billing System Overhaul – Why a full rewrite made more sense than incremental improvements.
• [00:09:54] The Hidden Complexity of Billing Systems – Managing ACH, credit card, and invoice payments.
• [00:14:05] The Fear Factor in Large-Scale Refactoring – Why organizations hesitate and how to push forward.
• [00:18:47] Communication Challenges in Remote Teams – Why documentation and transparency matter beyond GitHub.
• [00:28:30] Finding and Enforcing Engineering Patterns – How teams can encourage consistency in a constantly evolving codebase.
• [00:35:45] Why Autonomy Matters for Developers – Learning through struggle and when to ask for help.
• [00:45:25] Advocating for Refactoring When Leadership Says No – Julia's approach: "Ask for forgiveness, not permission—but estimate higher."

🔗 Resources Mentioned

• Harvest – Julia's company
• Radical Candor by Kim Scott
• The Making of a Manager by Julie Zhuo
• Stripe – The payment processor used in Harvest’s billing system
• Git Blame – A tool for understanding code history

📢 Connect with Julia López

• Julia's Website
• LinkedIn
• GitHub
• BlueSky

🍇Thanks to Our Sponsor!

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Bonus for Maintai...

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 software.

The Role of Fear in Technical Debt

1. Scott believes that if you fear the software you work on, it's a tell-tale sign that it has maintainability issues.
2. Technical debt is rooted in fear--either fear of making a change that will break something or fear of being unable to change something when needed.
3. He encourages teams to talk openly about their fears and anxieties regarding the software and to consider what things give them confidence in the codebase.

Building a Team Culture of Confidence

1. Scott emphasizes the importance of empathy in overcoming technical debt and making software more maintainable.
2. Senior engineers and team leads have a responsibility to make junior developers feel safe enough to speak up and ask questions.
3. He advocates for providing new hires with small, achievable tasks to build their confidence and trust in the software.
4. Scott encourages teams to use "inner loop" and "outer loop" thinking.
5. Inner loop - The cycle of making a change, hitting f5, and seeing changes immediately.
6. Outer loop - Things like deploying the codebase, getting it tested, ensuring production stability.
7. Both experienced and junior engineers have their own inner and outer loops as individuals, and continuous improvement at all levels is key.

Overcoming Fear, Embracing Maintainability, and Finding Balance

1. Scott shares stories about Microsoft's journey with open-source software and how that process has shaped the company's culture around maintainable code.
2. He talks about the importance of striking a balance between source-opened and open-source software and finding the sweet spot for a project or organization.
3. Scott warns against the trap of striving for unattainable perfection. Aiming for good, solid repeatable work over perfection ultimately yields better results.
4. He uses his own projects, like the Hanselminutes podcast, as examples of focusing on consistent outputs and utilizing a simple workflow.
5. Scott advocates for using AI tools to transcribe coding sessions, freeing up developers from extensive note-taking.

Book Recommendation:

• The Daily Stoic By Ryan Holiday
• Scott Hanselman - Personal Website
• Hanselminutes Podcast
• .NET Open Source History: .NET Core | Microsoft Learn

Helpful Links:

• Scott Hanselman - Personal Website
• Hanselminutes Podcast
• .NET Open Source History: .NET Core | Microsoft Learn

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and soon, other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! Check them out!