Reeling from Rewrites? with Richard Lawrence

The Agile Within

Software rewrites promise exciting technological advancements but frequently become risky, budget-draining quagmires. Why do these projects fail so consistently, and what can we do differently?

Richard Lawrence, founder of Humanizing Work, joins us to unpack the hidden complexities and psychological pitfalls lurking beneath seemingly straightforward rewrites.
We explore why the common directive to "just do what the old system does" is a dangerous trap, overlooking crucial hidden requirements, workarounds, and integrations that have developed over years. Richard introduces the "strangler approach"—a method that uses existing systems as scaffolding while gradually building new capabilities, allowing teams to deliver immediate value rather than delaying benefits until a complete replacement.
Next we examine user psychology, revealing why technical arguments for rewrites ("outdated technology," "unsupported platforms") fall flat with actual users. "That's your problem, not mine," reflects the realistic user perspective Richard articulates. Instead, we explore human-centered strategies that recognize users care about job performance, not technical implementation details.
Perhaps most valuably, Richard shares his "complexity-aware planning" framework, combining strategic exploration, active experimentation, and analytical planning to manage rewrite risks. We also tackle the difficult question of what to do when legacy customers no longer fit your product direction, offering alternatives to the blunt instrument of "firing customers" that build goodwill while still allowing strategic evolution.
Ready to transform how you approach your next system rewrite? This episode provides practical wisdom that could save your team months of frustration and your company millions in wasted effort.
Book a FREE 30 minute call with Richard:
https://www.humanizingwork.com/contact/
Connect with Richard on LinkedIn:
linkedin.com/in/richardslawrence

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Chapters

1. Introduction to The Agile Within (00:00:00)

2. Understanding Software Rewrites (00:01:42)

3. The Strangler Approach to Rewrites (00:06:54)

4. Complexity Aware Planning (00:10:40)

5. Data Migration Strategies (00:17:29)

6. Human-Centered Business Decisions (00:28:37)

7. Psychology Behind Rewriting Software (00:35:17)