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.

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https://www.linkedin.com/in/maxim-silaev
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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 born
• How bad patterns become “normal”
• AI as an accelerator of existing habits
• Early non-technical warning signs of dangerous debt
• Why cleanup efforts fail — and how to avoid that
• Leadership habits that prevent debt from becoming a way of life

Connect with Rob on his website.

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https://www.linkedin.com/in/maxim-silaev
https://www.linkedin.com/in/dr-nikita-golovko

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 platform
• Product debt: incomplete integrations, insufficient testing, and delivery pressure that forced release of known defects
• Architectural debt: brittle interfaces, undocumented dependencies, and an infrastructure designed for a different business context
• Communication debt: silos between leadership, engineering, and vendors, amplifying risk until it became unavoidable

Drawing 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.

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https://www.linkedin.com/in/maxim-silaev
https://www.linkedin.com/in/dr-nikita-golovko

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.

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https://www.linkedin.com/in/maxim-silaev
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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 chaos
• Why "centralized trust" solved one problem but created another
• How dependency on Microsoft’s signing keys became an industry-scale risk
• What communication failures between OEMs, OS vendors, and users taught us about architectural assumptions
• How AI might help us audit and secure firmware chains in the future

Whether 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.

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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.club
• LinkedIn: 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.

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https://www.linkedin.com/in/dr-nikita-golovko

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 debt
• How the constant wave of frameworks creates long-term risks
• The role of testing and documentation in avoiding costly mistakes
• Lessons from integrating new features into legacy stacks
• The one piece of advice he’d give his younger self about handling technical debt

📍 Connect with Christian:

• Website: https://jocker.dev
• LinkedIn: 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.

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https://www.linkedin.com/in/maxim-silaev
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Everyone has their own definition of "architecture". For some, it is diagrams. For others, it is documentation, a set of rules, or technical excellence. Some see it as task-setting, others as an evolving discipline. But what does IT architecture really mean in practice?

In this episode of Technical Debt: Design, Risk and Beyond, hosts Maxim Silaev and Nikita Golovko unpack the many faces of architecture. Drawing on real-world stories, they explore how architecture is more than static rules: it is a living, dynamic process shaped by communication, assumptions, and culture.

Together they discuss:

• Why architecture is not "done" once, but evolves with teams and products
• Architecture-as-code: what it is and why it matters
• How wrong assumptions or poor requirements become architectural debt
• Architecture in unexpected places: team structures, product roadmaps, even AI systems
• The human side: communication and technical excellence as architectural pillars

In this episode, Maxim reflects on communication and cultural alignment, while Nikita brings an AI perspective, showing how architecture shifts when data and automation take center stage.

Whether you’re a developer, architect, or product leader, this episode challenges the way you think about architecture, not as a static document, but as an active force that shapes every decision and every debt.

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https://www.linkedin.com/in/maxim-silaev
https://www.linkedin.com/in/dr-nikita-golovko