Technical Debt: Design, risk and beyond

Maxim Silaev & Nikita Golovko
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  • TECHNOLOGY

We talk to experienced architects and technology leaders about the architectural choices they’ve made — the good, the bad, and the costly. From scaling systems to integrating legacy platforms, from misaligned domains to governance gaps, we discuss how architecture impacts technical debt.You’ll hear honest stories of architectural missteps, what teams learned from them, and how they built systems designed not just to work, but to last.

  1. 2D AGO

    From decision debt to system fragility: a CEO’s view on technical debt with David Cruz

    In this episode of Technical Debt: Design, Risk, and Beyond, we look at technical debt from a place it’s rarely discussed - the CEO’s desk. My guest is David Cruz, Founder & CEO of Elmaextro, certified business coach, and thought leader in governance, resilience, and information risk. David’s journey spans operational leadership during major crises, advisory work with CEOs and leadership teams, and years spent translating information risk into strategic and architectural consequences. We explore a core idea that challenges common assumptions: technical debt often doesn’t start with bad code or poor tooling. It starts with leadership blind spots: unclear decision rights, postponed decisions, fragmented ownership, and a tendency to frame information risk as "an IT problem". In our conversation, we unpack how decision debt accumulates at the executive level and quietly hardens into architectural fragility. David explains why "risk-informed" leadership is not about being cautious, but about clearly defining a risk profile, making tradeoffs explicit, and aligning systems to what truly matters for the business. We discuss why consensus can become a liability, how dashboards often obscure rather than clarify risk, and why resilience depends more on disciplined leadership practices than on complex frameworks. David also shares practical guidance for non-technical CEOs: how to govern digital and information risk without jargon, why technology leaders must communicate in business terms, and how a simple one-page briefing can replace dozens of confusing reports. The episode closes with a powerful leadership question every executive should ask themselves: What is the most sensitive information in my organisation, where does it live, who has access to it, and why? This conversation is for CEOs, founders, CTOs, and architects who want to understand technical debt not just as a technical issue, but as a leadership and governance challenge with long-term consequences. You can learn more about David’s work at Elmaextro.com. Check David's free ebook - The CEO's 7 Steps Playbook. Use a coupon to get a free access to David's course: 29DQ3A2 Send a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    38 min

  2. FEB 2

    Technical debt under real constraints: fintech leadership in emerging markets with Erioluwa Asiru

    In this episode of Technical Debt: Design, Risk and Beyond, Maxim Silaev speaks with Erioluwa Asiru, CTO at CircleFunds, about what technical debt really looks like inside a fast-growing fintech operating in an emerging market. CircleFunds is digitising traditional thrift savings in Nigeria: a problem that turns out to be far more complex than “building an app.” Erioluwa shares how early architectural decisions were shaped by human behavior, cultural practices, and the reality that some processes are initially "technically impossible" to digitise without breaking trust. The conversation explores how technical debt rarely appears in one place. Instead, it emerges as a blend of architectural shortcuts, shifting product logic, regulatory pressure, and team dynamics in an environment that changes faster than most systems can adapt. Erioluwa explains the early warning signs, such as constant firefighting, repeated fixes, and system instability, that signal debt accumulation long before failure is visible from the outside. We also dive into leadership tradeoffs: how to balance speed with system health, how to ask engineers for compromises without losing trust, and why many long-term technical problems are rooted in product and leadership decisions rather than code. Erioluwa shares her perspective on intentional debt, architectural simplicity, documentation as a first-class artifact, and why infrastructure debt is the one category she would never knowingly accept. The episode closes with a practical discussion on AI in fintech engineering: where it accelerates delivery, where it becomes dangerous, and why critical financial systems still demand human judgment, strong standards, and rigorous testing. This conversation is a grounded look at technical debt as a leadership and risk problem, shaped by pressure, ambiguity, and real-world constraints. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    38 min

  3. JAN 26

    How Technical Debt creeps in: leadership, AI, and long-term cost with Rob Broadhead

    In this episode of Technical Debt: Design, Risk and Beyond, Maxim Silaev is joined by Rob Broadhead, a technology leader with more than 30 years of experience across enterprise systems, startups, and consulting. Together, they explore how technical debt actually creeps into systems: not through bad engineering, but through reasonable decisions made under pressure. Rob shares early-career scars, leadership failures without happy endings, and hard-earned lessons about how debt becomes normalised inside teams. A large part of the conversation focuses on modern tooling and AI. While AI promises speed, Rob explains how “vibe coding” and unreviewed AI output can quietly amplify existing problems: shifting debt from code into architecture, design, and assumptions. When teams stop asking the right questions, systems slow down, trust erodes, and recovery becomes expensive. This episode also dives into leadership responsibility: why strong teams still fail, how lack of authority distorts decision-making, and why delaying cleanup for “one more release” almost always backfires. If you are a CTO, architect, or technical leader navigating growth, AI adoption, or mounting complexity, this conversation will feel uncomfortably familiar. Topics covered: Where technical debt is really bornHow bad patterns become “normal”AI as an accelerator of existing habitsEarly non-technical warning signs of dangerous debtWhy cleanup efforts fail — and how to avoid thatLeadership habits that prevent debt from becoming a way of lifeConnect with Rob on his website. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    43 min

  4. 12/05/2025

    How to assess technical debt: strategic, product, and architectural: TSB Bank case study

    In this episode of Technical Debt: Design, Risk and Beyond, hosts Maxim Silaev and Nikita Golovko break down one of the most widely documented technical-debt disasters in modern enterprise IT: the failed 2018 TSB Bank migration. More than two million customers lost access to their accounts, systems malfunctioned for weeks, and leadership was forced to answer to regulators. But behind the headlines lies a deeper lesson: technical debt exists at multiple layers: strategic, product, and architectural, and TSB’s collapse showed how these debts compound when communication fails. Maxim and Nikita unpack: Strategic debt: rushed timelines, misaligned goals, and a pressured migration from Lloyds to Sabadell’s platformProduct debt: incomplete integrations, insufficient testing, and delivery pressure that forced release of known defectsArchitectural debt: brittle interfaces, undocumented dependencies, and an infrastructure designed for a different business contextCommunication debt: silos between leadership, engineering, and vendors, amplifying risk until it became unavoidableDrawing from their own experience assessing technical debt for organizations, the hosts explain how to recognize early warning signs, measure debt at every level, and communicate risks effectively to leadership. TSB is more than a failure story, it is a blueprint for understanding how technical debt grows, how it hides, and how it can paralyze an entire company when left unmanaged. Next episode: How to quickly evaluate the technical debt volume in your organization. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    13 min

  5. 11/10/2025

    Interserve case: when communication debt becomes a security breach

    What happens when a company’s biggest vulnerability isn’t its software, but its communication? In this episode of Technical Debt: Design, Risk and Beyond, hosts Maxim Silaev and Nikita Golovko explore the collapse of Interserve, a UK-based outsourcing and construction giant that suffered a major data breach in 2020, exposing the personal data of over 100,000 employees and resulting in a £4.4 million fine from the Information Commissioner’s Office. The breach was more than a phishing email gone wrong. It was the inevitable outcome of years of architectural neglect, fragmented systems, poor training, and missing communication between business and technology. Maxim breaks down the technical side: outdated software, legacy infrastructure, weak identity management, and a dangerous overreliance on trust assumptions: classic security debt. Nikita then connects the dots to organizational behavior: silos, misaligned incentives, and a culture where IT was reactive instead of strategic. Together they uncover: The forms of technical and organizational debt that led to Interserve’s downfall;How communication debt amplifies security risk;The hidden “single points of failure” in both systems and decision-making;How AI and automation could have helped detect risks earlier;Why architecture and culture must evolve together.Interserve’s story is a case study in how security failures are often symptoms, not causes, the result of decades of accumulated technical and human debt. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    17 min

  6. 10/09/2025

    Secure boot: debt, trust, and the future of firmware security

    Secure Boot was designed to solve one of the most fundamental security problems in computing: how to ensure that only trusted software starts your machine. But like any architectural decision, it came with its own trade-offs, and its own technical debt. In this episode of Technical Debt: Design, Risk and Beyond, Maxim Silaev and Nikita Golovko explore Secure Boot as a case study in how solving one kind of debt often creates another. Maxim explains how the pre-Secure Boot world fragmented BIOS loaders, vendor-specific boot hacks, and no shared trust model, which was itself a form of technical debt waiting to explode. Nikita then breaks down how Secure Boot centralized trust and improved integrity, while introducing new risks: reliance on external signing authorities, firmware lock-ins, and single points of failure. Together, they unpack: How Secure Boot actually works, and why the world before it was pure architectural chaosWhy "centralized trust" solved one problem but created anotherHow dependency on Microsoft’s signing keys became an industry-scale riskWhat communication failures between OEMs, OS vendors, and users taught us about architectural assumptionsHow AI might help us audit and secure firmware chains in the futureWhether you’re in firmware, architecture, or security, this episode shows how even the most well-intentioned design can accumulate invisible debt, and why architecture is as much about people and trust as it is about code. Next episode: How to design architecture specifically to minimize technical debt from the start. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    15 min

  7. 09/29/2025

    Technical debt beyond technology with Simon Copsey

    Technical debt is not just about code!  it is the visible symptom of deeper organisational issues. When companies try to move faster than their systems, teams, or leadership structures allow, debt shows up in technology but originates elsewhere. In this episode of Technical Debt: Design, Risk, and Beyond, we will talk with Simon Copsey, a management and technology leader who writes and consults on how technical debt reflects strategy, culture, and communication. Simon shares why debt is felt far beyond engineering, how to spot the hidden debts beneath the surface, and what leaders can do to prevent debt from eroding trust and agility. 📍 Connect with Simon: Website: curiouscoffee.clubLinkedIn: linkedin.com/in/simoncopsey🎧 Join us to explore how looking at technical debt through an organisational lens changes the way we understand and manage it. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    28 min

  8. 09/15/2025

    Technical debt in frontend with Christian Joecker

    Frontend moves fast — but with every new framework, testing shortcut, or design compromise, teams risk piling up technical debt that quickly becomes visible to users and costly to the business. In this episode of Technical Debt: Design, Risk, and Beyond, we talk with Christian Joecker, a web developer and UX designer with over 10 years of experience helping companies like BMW, Volkswagen, United Airlines, and the Fraunhofer Institute build and scale digital products. Christian shares his perspective on: Why frontend debt is different from backend or infrastructure debtHow the constant wave of frameworks creates long-term risksThe role of testing and documentation in avoiding costly mistakesLessons from integrating new features into legacy stacksThe one piece of advice he’d give his younger self about handling technical debt📍 Connect with Christian: Website: https://jocker.devLinkedIn: https://www.linkedin.com/in/christianjoecker🎧 Tune in for practical stories and insights into frontend debt — why it’s visible, why it matters, and how to manage it before it manages you. Send us a text Reach us @ LinkedIn: https://www.linkedin.com/in/maxim-silaev https://www.linkedin.com/in/dr-nikita-golovko

    23 min
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About

We talk to experienced architects and technology leaders about the architectural choices they’ve made — the good, the bad, and the costly. From scaling systems to integrating legacy platforms, from misaligned domains to governance gaps, we discuss how architecture impacts technical debt.You’ll hear honest stories of architectural missteps, what teams learned from them, and how they built systems designed not just to work, but to last.

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