Everyone seems to be talking about context engineering. That was certainly the case in our recent discussions for the upcoming edition of the Technology Radar (volume 33, due early November 2025). And although we ran into the term on the Technology Podcast just a few weeks ago, we thought it would be useful to try and tackle exactly what people are talking about when they talk about context engineering. We know context is important when it comes to AI, but what does it mean to engineer it?

On this episode of the Technology Podcast, host and Thoughtworks CTO Rachel Laycock is joined by Thoughtworkers Alessio Ferri and Bharani Subramaniam to discuss what context engineering is, how it's being done and what it tells us about the evolution of AI. This certainly won't be the last word — ours or anyone else's — on context engineering, but it might help clarify and cement your understanding as the term comes to dominate technology conversations.

Although the concept of the 'citizen developer' isn't new, with the rise of AI the relationship between those building software without much technical experience and seasoned software developers is becoming more significant. That's not to say there's conflict exactly, but there are often competing interests and demands — which can lead to tension, organizational friction and governance challenges.

On this episode of the Technology Podcast, host Ken Mugrage facilitates a debate (of sorts) between Christopher Hastings, Global Tech Product Lead at Thoughtworks (and citizen developer) and Scott Davies, Head of Technology for Thoughtworks Europe (very much in the developer camp). They discuss the needs and interests of both sides, how to avoid regressing to the dark ages of shadow IT and how citizen developers can be properly empowered by engineering teams.

Managing technological change in an organization — particularly a large and complex one — has always been challenging. But thanks to the rapid adoption of AI in all kinds of spheres, from knowledge management to software development to content creation, it's becoming more difficult than ever. How do you strike a balance between governance and safety and autonomy and empowerment? How should teams be structured and how should they work together?

In this episode of the Technology Podcast, Matthew Skelton and Manuel Pais — authors of the influential Team Topologies book — join hosts Birgitta Böckeler and Ken Mugrage to discuss what AI means for organizational design. They discuss how AI is changing team capabilities, what it means for cognitive load and knowledge sharing and how to ensure there's structure and control without constraining experimentation and creativity.

With the second edition of Team Topologies set to be published in September 2025, Matthew and Manuel used the conversation to explore the evolution of their ideas and what they've learned from working with and listening to the stories of many different organizations around the world.

Learn more about Team Topologies: https://teamtopologies.com/

Generative AI can be incredibly powerful when it comes to legacy modernization. Not only can it help us better understand a large, aging codebase, it can even help us reverse engineer a legacy system when we don't have access to the complete source code. Doing it, though, requires a specific approach that's being described as 'context engineering'.

This is something we've been exploring a lot in recent months at Thoughtworks. On this episode of the Technology Podcast, Thoughtworks' lead for AI-enabled software engineering, Birgitta Böckeler, and tech principal Chandirasekar Thiagarajan join hosts Ken Mugrage and Neal Ford to discuss how it works.

They explain the process, the tools and what the work is teaching them about both generative AI and legacy modernization.

Read Birgitta's blog post on reverse engineering with AI: https://www.thoughtworks.com/insights/blog/generative-ai/blackbox-reverse-engineering-ai-rebuild-application-without-accessing-code

How should businesses go about actually navigating AI? It's one thing to strategize and generate new ideas, but what needs to be done to put it into practice in a way that's effective and commercially impactful?

In this episode of the Technology Podcast, new host Nigel Dalton is joined by his Thoughtworks colleague May Xu — Head of Tech for Thoughtworks APAC — and Simon Noonan, CTO at Australian business software company MYOB.

Thoughtworks has been working closely with MYOB for a number of years now; May and Simon explain how they collaborate and offer their perspectives on everything from leadership to architecture in a world where AI has become imperative.

Learn more about Thoughtworks' partnership with MYOB: https://www.thoughtworks.com/clients/myob

In an age of vibe coding and LLMs, do we really need to care about documentation? Do we need to spend time and energy producing it — time when we could just be shipping code? Of course we do; particularly if we want to communicate and share software with other humans.

To discuss documentation in 2025, Technology Podcast host Lilly Ryan is joined by Heidi Waterhouse, a very special guest with an esteemed and varied career in technical communcation.

In this episode, Lilly and Heidi tackle the challenges of documentation in a world increasingly infused with AI-generated code and text, explore whether prompt engineering is really just technical writing in disguise and examine the difficulties of writing for highly specific audiences.

They also cover Heidi's Progressive Delivery, an upcoming book about bridging the gap between software delivery and business value. It's due to be released in the latter part of 2025 and written alongside James Governor, Kim Harrison and Adam Zimman.

Find out more about Heidi Waterhouse by visiting her website: https://heidiwaterhouse.com/

Learn more about Progressive Delivery: https://itrevolution.com/product/progressive-delivery/

The technology industry has embraced specialisms — not just in different fields or job roles, like web development or security, but even in terms of particular platforms or stacks. But are we losing something as every tech professional is forced to push themselves into increasingly smaller niches?

Martin Fowler and Unmesh Joshi think so. They've been thinking a lot about the importance of what they call "Expert Generalists" — professionals who "can dissect unfamiliar challenges, spot first-principles patterns and make confident design decisions with the assurance of a specialist."

In this episode of the Technology Podcast, Martin and Unmesh join hosts Prem Chandrasekaran and Lilly Ryan to discuss how they came to identify the importance of expert generalists and why it was important to not just talk about the issue, but to explicitly name it. They also explore how they believe the industry can cultivate and encourage expert generalists, despite an entrenched tendency to overlook their value.

Read Martin and Unmesh's article, written with Gitanjali Venkatraman: https://martinfowler.com/articles/expert-generalist

Back in 1994, Peter Deutsch and his colleagues at Sun Microsystems identified what they described as the "eight fallacies of distributed computing" — flawed assumptions that often get made when teams move from monolithic to distributed software architectures. In recent years, software architecture experts and regular writing partners Neal Ford and Mark Richards have identified a further three new fallacies of distributed computing: versioning is easy; compensating updates always work; and observability is optional.

In this episode of the Technology Podcast, Neal and Mark join host Prem Chandrasekaran to talk through these three new fallacies, before digging deeper into other important issues in software architecture, including modular monoliths and governing architectural characteristics. Listen for a fresh perspective on software architecture and to explore key ideas shaping the discipline in 2025.

Learn more about the second edition of Neal and Mark's Fundamentals of Software Architecture: https://www.oreilly.com/library/view/fundamentals-of-software/9781098175504/