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

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