“Smart people solve problems, geniuses prevent them.”
— Albert Einstein*

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Quick: what’s the formula to calculate the volume of a cube? So how much dirt is in an empty hole that measures 2m x 2m x 2m?

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Did you catch yourself thinking “8” first? Such is the power of framing.

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Similarly, many modernization projects find themselves “framed” by traditional procurement practices, involving multi-page RFPs, a mad scramble to respond, resulting in a 92-slide presentation and a densely-spaced 41-page document. They suffer from:

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Confidence theater. RFPs often demand detailed timelines, budgets, and deliverables before any meaningful discovery has taken place. Vendors, in turn, are incentivized to "guesstimate" based on critically incomplete information: after all, legacy systems are often poorly documented, tightly coupled, and full of unknowns.

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Genericism. Vendors often recycle boilerplate materials. But organizations and their technology systems have grown together over time, and like fingerprints, no two are alike. At best, repurposing other proposals might be useful from a framework standpoint; at worst, it creates a misleading sense of omniscience and a profound underestimation of the degree of collaboration that will be required.

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False economies. The lowest bid on paper often turns out to be the most expensive path in practice. A vendor who lowballs to win the deal is either underestimating the real effort—or planning to make it up later through change orders, delays, or compromises on quality. Building a career on, “well, it was a cluster, but at least we didn’t spend that much money,” is pretty lame, tbh.

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Changing the frame means shifting the RFP’s focus from “what’s the final system and when will it be done?” to “how will we work together to modernize safely?” Here’s how:

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Explore collaboratively. Start with a short, structured engagement focused on exploration: include engineers, architects, and business stakeholders. The more complex the environment, the more experimentation needed. The goal is to learn together—map out dependencies, understand business logic, uncover unknowns, and assess risk.

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Tackle the biggest pain first. Find the system that incurs the most pain on the business. Is it that 80% of your budget is spent on maintenance and operations? Compliance issues looming? Anchor the effort around the business outcomes you care about most: speed of change, reduced maintenance costs, new product capabilities, ease of adapting to new regulations, etc.

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Agile procurement. It is a truth universally acknowledged that releasing software more frequently reduces risks: the risk of spending time building the wrong feature, of something not working, of missing opportunities in the market. Similarly, let go of waterfall procurement models. Refashion traditional ROI metrics around business outcomes, rather than feature checklists or burn-down charts.

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The best modernization efforts don’t happen through slide decks. They don’t blindly follow a set formula. Instead, they look hard at the right question to answer, and then they’re built through shared understanding, incremental delivery, and the humility to adapt as the system reveals itself.

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News and Views

The UK Treasury Committee found that nine major financial institutions experienced more than 33 days of technology outages in the past 2 years. That’s more days of holiday than I’ve taken in the same period.

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Few things reveal institutional strain like the tradeoffs the IRS is facing in its approach to modernization. First, the agency was flagged for using modernization funds to prop up legacy systems. Then, a pause altogether—to rethink its roadmap in light of AI. Two conflicting moves, one result: a system stuck between preservation and disruption rarely moves forward at all.

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AS400 to Oracle: what could go wrong? After four years and millions paid to consultants, the City of Syracuse delayed the rollout of its new payroll system, with city officials admitting the project has failed to deliver expected results even as costs ballooned. Add in a whistleblower and a convoluted procurement process, and I’ll be looking forward to the Netflix series.

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Emergence Capital General Partner Jake Saper held forth on AI-Enabled Services in a recent 20VC podcast, describing how we're starting to see a big shift from paying for software by the seat to only paying for outcomes.

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From the Orchard

Our head of pre-delivery, Nick Keune, knows a thing or two about mission-critical systems (like COVID-19 vaccines). Watch his presentation, “High Stakes, Low Risk Modernization,” from the Rise8 Prodacity conference.

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Earlier this month, we hosted the London book release party for Dr. Leda Glyptis, who recently published her second book, Beyond Resilience: Patterns of Success in Fintech and Digital Transformation. A fabulous evening with a who’s who of financial technology in the UK (and beyond!). Don’t miss our On a Limb episode with Leda, where she gives an unfiltered look at the challenges banks face—and what real progress requires.

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On our most recent episode of On A Limb, we talk with Logan Allin of Fin Capital about why America’s outdated banking tech is a looming crisis—and what banks keep getting wrong when they try to modernize. We dig into legacy risks, technical debt, and why moving fast (with the right incentives) matters more than ever.

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If you’re currently at Shoptalk, meet with us to hear how we helped a Fortune 500 retailer move 10M+ lines of COBOL to cloud-native infrastructure, faster than they thought possible.

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Applying AI to legacy systems at scale has always meant choosing between speed and certainty. We’ve come up with a way to deliver both—watch our live demo at Google Cloud Next ‘25. Alternatively, book time with our team here.

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Curious to learn more? Say hello@mechanical-orchard.com.

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Issue first published on March 26th, 2025.

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