Reeling from Rewrites? with Richard Lawrence
04/17/25 • 41 min
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Next we examine user psychology, revealing why technical arguments for rewrites ("outdated technology," "unsupported platforms") fall flat with actual users.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
Follow us on LinkedIn:
https://www.linkedin.com/company/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
Follow us on LinkedIn:
https://www.linkedin.com/company/the-agile-within
Previous Episode
Can Anyone Be An Agile Coach? with Kamal Kalra
What separates a mediocre Agile coach from a truly exceptional one? The answer might surprise you. When Kamal Kalra posed the question "Can anyone be an Agile coach?" at an Agile open space, he challenged the conventional wisdom that knowledge alone qualifies someone for the role.
Kamal brings a refreshingly human-centered approach to Agile coaching. His journey began when a mentor recognized his natural tendency to prioritize understanding people over processes. Rather than immediately focusing on performance issues, Kamal's instinct was always to connect with the human first—a philosophy that would become the cornerstone of his coaching style.
The conversation takes a fascinating turn when Kamal shares his "apple-orange" analogy, illuminating how organizations often fundamentally misunderstand Agile from the beginning. When companies have been handed "apples" but told they're "oranges," they develop an entirely distorted understanding of what Agile truly means. This misalignment explains why so many organizations struggle to implement Agile effectively despite their best intentions.
Perhaps the most valuable takeaway is Kamal's personal "80-20 rule"—dedicating 80% of energy to addressing immediate problems while reserving 20% for examining and improving the underlying systems. This approach reflects the racing principle that "slow is accurate and accurate becomes fast," a counter-intuitive but powerful strategy for sustainable improvement.
What truly elevates this discussion is Kamal's assertion that Agile isn't just a methodology or even a professional skill—it's a way of life that extends into personal relationships, home environments, and every aspect of existence.
Connect with Kamal on LinkedIn:
linkedin.com/in/kamalkalra-agilist
Follow us on LinkedIn:
https://www.linkedin.com/company/the-agile-within
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Lessons from an Agile Journey with Max Dazer
In this episode of The Agile Within, I explore the fascinating Agile journey of Safety IO with Max Dazer, Agile Lead. Discover how Max navigated through frameworks like the Spotify model, Lean principles, and the Theory of Constraints to foster collaboration and break down organizational silos.
Gain insights into Safety IO’s innovative ecosystem planning and how the Theory of Constraints helped the team prioritize work, reduce wait times, and optimize delivery. Max also shares how embracing the Product Operating Model brought teams closer to business outcomes and bridged gaps across the organization.
Whether you're a Scrum Master, Agile enthusiast, or industry leader, this episode is packed with actionable lessons to elevate your approach to Agile transformation. Tune in now and take the next step on your own Agile journey!
Connect with Max on LinkedIn:
linkedin.com/in/maximilian-dazer-b43875199
Check out the Road 2 Mastery:
Follow us on LinkedIn:
https://www.linkedin.com/company/the-agile-within
The Agile Within - Reeling from Rewrites? with Richard Lawrence
Transcript
Welcome to the Agile Within . I am your host , Mark Metz .
Speaker 1My mission for this podcast is to provide Agile insights into human values and behaviors through genuine connections .
Speaker 1My guests and I will share real-life stories from our Agile journeys , triumphs , blunders and everything in between
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