I'm Toby Corballis, Founder and CEO at Strategic Flow Ltd, and your host on a journey through the world of fascinating global and business problems being worked on and thought about by some extremely clever people from the worlds of business and academia. Join me to find out how people are solving seemingly intractable problems!
Wicked Problems Podcast
Claim This Podcastby Toby Corballis
5.0(1 reviews)
50 episodes
Updated Daily
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42
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
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YouTube68
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Podcast Overview
I'm Toby Corballis, Founder and CEO at Strategic Flow Ltd, and your host on a journey through the world of fascinating global and business problems being worked on and thought about by some extremely clever people from the worlds of business and academia. Join me to find out how people are solving seemingly intractable problems!
Language
🇺🇲
Publishing Since
9/19/2019
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Recent Episodes
July 8, 2026
Why AI Implementation Fails When Organisations Move Faster Than They Can Govern
<p>This long-form episode of Wicked Problems is a practical conversation about AI adoption after the initial hype. Toby Corballis and Marcellus Lindsay look beyond the promise of automation and ask what happens when AI is introduced into organisations that cannot yet govern its cost, risk, data, accountability or human impact.<br /> <br /> The discussion moves between real-world implementation, change leadership, AI literacy, trust, hallucinations, token costs, agentic AI, and the familiar pattern of technology running ahead of organisational capability. The point is not that leaders should avoid AI. It is that they need enough understanding to ask better questions before they scale it.<br /> <br /> Marcellus brings the perspective of a consultant implementer: someone who can work with senior leaders while also understanding what happens on the ground. Together, he and Toby argue for controlled speed, domain expertise, human-in-the-loop review, and governance that helps organisations move quickly without building on flawed foundations.</p> <p><strong>Key themes</strong><br /> - AI governance, risk and accountability as leadership responsibilities, not technical afterthoughts.<br /> - Why many corporate AI initiatives fail to produce clear return on investment.<br /> - The gap between exponential technology change and slower organisational change.<br /> - How AI hallucinations, confidence and error rates create hidden implementation risk.<br /> - Why human trust in AI can exceed human trust in other people.<br /> - Token pricing, cost controls and the danger of unbounded AI usage at scale.<br /> - The role of domain expertise in judging where AI should and should not be applied.<br /> - Why agentic AI needs stronger guardrails than simple chat-based experimentation.<br /> - How flawed assumptions early in a programme compound into expensive failure later.<br /> - Why AI literacy should be basic, practical and principle-based for senior leaders.</p> <p> </p> <p>To register intrerest in one of the forthcoming webinars mentioned, <a title="Webinar Sign-up" href= "https://strategicflow.io/ai-governance-webinar/" target="_blank" rel="noopener">sign up at Strategic Flow</a></p>
June 24, 2026
Digital Transformation in Professional Services: What Consultants See That You Don't with Winnie Barnwell
<p dir="ltr">Is your firm spending money on new software when the real problem is hiding in plain sight, inside the processes, handovers, and habits your team has quietly built around a broken system?</p> <p dir="ltr">In this episode, Toby Corballis is joined by Winnie Barnwell, a digital transformation consultant and project and change manager who works primarily with law firms and professional services businesses. Winnie brings a structured, diagnostic approach to operational improvement, helping organisations understand not just what is going wrong, but why, and what to do about it in a way that actually sticks.</p> <p dir="ltr">Winnie's work sits at the intersection of workflow design, system implementation, and change management. She is frequently brought in when a firm knows something is not working but lacks the clarity to define the problem, let alone fix it. Her focus is always on getting the process right before reaching for the technology.</p> <p><strong> </strong></p> <p dir="ltr"><strong>What We Cover</strong></p> <ul> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why clients almost always misdiagnose their own problems, and what the real root cause usually turns out to be</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">How discovery sessions and probing questions surface the issues that sit beneath the symptoms</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">The law firm losing 18 hours a week on admin, and why the answer had nothing to do with changing their software</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why a consultant does not need to know your specific CRM, and what they actually need to understand instead</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">The cost of delay: how to quantify the financial impact of an unresolved problem and use it to prioritise</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Cross-pollinating methods across industries, and when bringing in a specialist really does make sense</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Translation as a core consulting skill, from C-suite to accounts, and why speaking the right language to the right person is everything</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Building solutions that work for everyone, including the people who are not comfortable with technology</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">What a consultant's working week actually looks like, from discovery through to Friday playback sessions</p> </li> </ul> <p><strong> </strong></p> <p dir="ltr">Whether you are a practice manager trying to make sense of a system that never quite does what it should, a leader considering a costly technology migration, or a consultant looking to sharpen your diagnostic process, this conversation will give you a clearer framework for finding the real problem and making change that lasts.</p> <p><strong> </strong></p> <p dir="ltr"> </p> <p dir="ltr"><strong>Chapters</strong></p> <p dir="ltr">00:00 — Episode begins</p> <p dir="ltr">00:15 — Introduction</p> <p dir="ltr">01:41 — What Winnie does: digital transformation and workflow consultancy</p> <p dir="ltr">02:41 — The discovery process: diagnosing root causes, not symptoms</p> <p dir="ltr">04:06 — Do consultants need to know your software?</p> <p dir="ltr">07:04 — Case study: the law firm losing 18 hours a week</p> <p dir="ltr">09:00 — When the fix is organisational, not technological</p> <p dir="ltr">11:45 — The cost of delay: quantifying unresolved problems</p> <p dir="ltr">14:59 — Cross-pollinating methods across industries</p> <p dir="ltr">17:18 — Translation as a consulting skill</p> <p dir="ltr">20:28 — Building anti-discriminatory solutions</p> <p dir="ltr">24:52 — A day in the life of a digital transformation consultant</p> <p><strong> </strong></p> <p dir="ltr"><strong>Resources</strong></p> <p dir="ltr">Wicked Problems</p> <p dir="ltr"><a href= "https://wickedproblems.fm">wickedproblems.fm</a></p> <p><strong> </strong></p> <p dir="ltr">Yonda Limited</p> <p dir="ltr"><a href= "http://www.yondalimited.com/">yondalimited.com</a></p> <p><strong> </strong></p> <p dir="ltr">Winnie Barnwell on LinkedIn</p> <p dir="ltr"><a href= "https://www.linkedin.com/in/winnie-barnwell/">linkedin.com/in/winnie-barnwell</a></p> <p><strong> </strong></p> <p dir="ltr">Yonda Limited on LinkedIn</p> <p dir="ltr"><a href= "https://www.linkedin.com/company/yonda-limited/">linkedin.com/company/yonda-limited</a></p> <p><strong> </strong></p> <p dir="ltr">McKinsey — The Art of the Root Cause Analysis</p> <p dir="ltr"><a href= "https://www.mckinsey.com">mckinsey.com</a></p> <p> </p>
June 10, 2026
Moldable Development and Glamorous Toolkit: How to Make Your Software System Explain Itself
<p dir="ltr">Are your engineering decisions based on what your system actually does, or on what your team believes it does?</p> <p dir="ltr">Most software teams are navigating in the dark. Developers spend more than half their time reading code, yet reading doesn't scale, and it rarely produces accurate decisions. As AI tools generate code faster than ever, the problem is getting worse, not better. This episode challenges the assumption that delegating understanding to AI is the answer.</p> <p dir="ltr">Tudor Girba is the co-creator of Moldable Development and the Glamorous Toolkit, and a co-founder of Feenk, the research company behind both. With decades of experience working on some of the most complex legacy system challenges in enterprise software, Tudor brings a rigorous, engineering-discipline lens to a problem the industry has largely left unaddressed: how do you make a system legible, without reading it line by line?</p> <p dir="ltr">Tudor is also co-authoring a book with Simon Wardley called Rewilding Software Engineering, written openly and available free at moldabledevelopment.com. The work sits at the intersection of software engineering, decision-making, and organisational change, and is increasingly relevant to anyone responsible for large or ageing codebases.</p> <p><strong> </strong></p> <p dir="ltr"><strong>What We Cover</strong></p> <ul> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why reading code is the single largest cost in software development, and why no one talks about optimising it</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">How moldable development works, and why it is closer in spirit to test-driven development than to conventional documentation</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why AI cannot replace human understanding of a system, and what happens when teams try to make it do so</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">How asking an LLM to build you a tool produces better results than asking it to answer your question directly</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why a diagram drawn by a human about a system is a belief, not a fact, and what the difference costs you</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">How Feenk helped an organisation find an entire system they did not know they had, two weeks into an engagement</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why only 26 percent of software modernisation efforts succeed, and what the outliers are doing differently</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">What it looks like to migrate more than 20 legacy systems in under a year, every time, without failure</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">How the Glamorous Toolkit enables thousands of custom, context-specific development tools to compound over time</p> </li> <li dir="ltr" aria-level="1"> <p dir="ltr" role="presentation">Why Tudor believes we are nowhere near the peak of human ability, and why perception is the bottleneck, not intelligence</p> </li> </ul> <p dir="ltr"> </p> <p dir="ltr">Whether you are a CTO navigating a legacy modernisation programme, a senior engineer trying to reduce the time your team spends reading unfamiliar code, or a technology leader being asked to rely more heavily on AI for engineering decisions, this episode will give you a clearer framework for where human understanding must remain, and the tools that make it possible.</p> <p><strong> </strong></p> <p dir="ltr"><strong>Chapters</strong></p> <p dir="ltr">00:00 — Reading Code Is the Biggest Cost Nobody Is Optimising</p> <p dir="ltr">02:26 — What Moldable Development Actually Solves</p> <p dir="ltr">07:17 — Why LLMs Miss 20-30% of Your System, and What to Do Instead</p> <p dir="ltr">09:23 — Diagrams Are Beliefs, Not Facts</p> <p dir="ltr">10:12 — Make the System Draw Itself</p> <p dir="ltr">13:26 — The User Interface Insight That Changes Everything</p> <p dir="ltr">18:37 — Verifying AI Output Against Reality</p> <p dir="ltr">21:04 — The Data Pipeline That Did Not Move for Three Years</p> <p dir="ltr">24:03 — 26% Success Rate: Why Modernisation Efforts Fail</p> <p dir="ltr">25:13 — The Bottleneck Is Perception, Not Intelligence</p> <p><strong> </strong></p> <p dir="ltr"><strong>Resources</strong></p> <p dir="ltr">Wicked Problems Podcast</p> <p dir="ltr"><a href= "https://wickedproblems.fm">https://wickedproblems.fm</a></p> <p dir="ltr">Feenk (Tudor Girba's company)</p> <p dir="ltr"><a href="https://feenk.com">https://feenk.com</a></p> <p dir="ltr">Moldable Development (book and resources)</p> <p dir="ltr"><a href= "https://moldabledevelopment.com">https://moldabledevelopment.com</a></p> <p dir="ltr">Glamorous Toolkit</p> <p dir="ltr"><a href= "https://gtoolkit.com">https://gtoolkit.com</a></p> <p dir="ltr">Rewilding Software Engineering (book, written in the open with Simon Wardley)</p> <p dir="ltr"><a href= "https://moldabledevelopment.com">https://moldabledevelopment.com</a></p>
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