In our latest Digital Lighthouse episode, Zoe Cunningham is joined by Daniel Whitston, CTO of AutogenAI.

The adoption of AI tools is on the rise, with a large number of them utilising the large-scale language model, GPT-3. While these models can solve difficult problems, they tend to be trained on a large corpus of the entire internet and may not capture an individual company’s voice or values. Daniel discusses how CTOs can embrace and use AI large language models in their company, and shares how AutogenAI is bringing AI-generated outputs closer to company needs. Read the transcript at: www.softwire.com/insights/daniel-whitston-cto-how-ive-embraced-ai-and-large-language-models

Daniel Whitston, CTO: How I’ve embraced AI and large language models

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For the 20th anniversary of Design Matters, Debbie Millman revisits past interviews with technology pioneers Bill Moggridge, Jason Kottke, Anil Dash, and Kevin Kelly. These excerpts reflect on how technology emerged, how it shapes the way we live, and how these early thinkers imagined the future unfolding.

20th Anniversary celebration with technology pioneers Bill Moggridge, Jason Kottke, Anil Dash, and Kevin Kelly

For the 20th anniversary of Design Matters, Debbie Millman revisits conversations with theatre designers David Korins, Ina Mayhew, David Rockwell, Es Devlin, and Dane Laffrey. From Broadway landmarks to innovative film and live performance design, these excerpts reveal how sets and spaces shape emotion, deepen story, and draw audiences into the moment.

20th Anniversary celebration with theatre designers David Korins, Ina Mayhew, David Rockwell, Es Devlin, and Dane Laffrey

Why do technology projects get so messy even when they start with clear plans and enthusiastic teams? And what can leaders do to navigate the chaos in the middle?

In this episode, Zoe Cunningham speaks with Rachael Morgan, an experienced Head of Technology. She has worked in different industries from the NHS, betting and gaming, and is currently in finance. 

They explore the messy middle of tech delivery. Drawing on experience across the NHS, Sky Betting and Gaming, and now Flutter, Rachael explains why delivery challenges rarely come from the technology itself, but from people, process choices, and the complexity of real organisational ecosystems.

Rachael shares practical insights from leading six global data engineering teams, including how to strike the right balance of process, how to understand and use individual strengths within a team, and why continuous communication is essential when navigating uncertainty.

🔎 You’ll learn:
• What the “messy middle” is and why every technology project encounters it
• Why humans, not technology, are the real drivers of delivery success
• How process frameworks help, hinder, and grow unintentionally over time
• The risks of over-processing and under-processing in regulated environments
• How leaders can use metrics and communication to spot real delivery risks early
• Why understanding your team and understanding yourself sit at the core of effective leadership
• How reflection helps leaders manage emotion, complexity, and decision making

💡 Whether you lead engineering teams, manage digital projects, or work anywhere near technology delivery, this conversation offers practical and thoughtful guidance for handling complexity with confidence.

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Timestamps
00:00 – Introduction
01:11 – Rachael’s career journey through NHS, gaming, and data leadership
03:52 – What the “messy middle” means in tech delivery
07:07 – Why technology is binary but delivery is human
08:47 – Process frameworks, complexity, and making the right choices
11:30 – How much process is “just enough”?
14:18 – Learning from other leaders and industries
20:01 – Is Agile the answer?
21:18 – Humans are messy, and that is a strength
23:56 – Understanding individuals and leadership at scale
24:48 – How to tell normal problems from real project danger
28:11 – Why leaders must understand themselves

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#TechLeadership #DigitalDelivery #EngineeringManagement #ProjectDelivery #RachaelMorgan #TheDigitalLighthouse #ZoeCunningham #FlutterEntertainment #MessyMiddle #Softwire

Navigating the messy middle of technology projects with Rachael Morgan

In celebration of the 20th anniversary of Design Matters, Debbie Millman shares excerpts from interviews with typographers and lettering artists Marian Bantjes, Oded Ezer, Jessica Hische, Tobias Frere-Jones, Matthew Carter, and Kris Holmes, reflecting on legibility and expression, how letters behave, the discipline of refinement, and how type has evolved from hand-crafted processes to the digital tools we use today.

20th Anniversary celebration with typographers and lettering artists Marian Bantjes, Oded Ezer, Jessica Hische, Tobias Frere-Jones, Matthew Carter, and Kris Holmes

For the 20th anniversary of Design Matters, Debbie Millman revisits previous episodes with activists and advocates Gloria Steinem, Anita Hill, Cindy Gallop, Sonya Passi, and Dr. Joy Buolamwini. These excerpts highlight conversations about power, accountability, and the urgent work of dismantling inequality across culture, institutions, and technology.

20th Anniversary celebration with activists and advocates Gloria Steinem, Anita Hill, Cindy Gallop, Sonya Passi, and Dr. Joy Buolamwini

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The Digital Lighthouse is a podcast for CTOs and other tech leaders looking to navigate their organisation through endless disruption and turbulence. Packed full of real life stories and insights, this podcast serves as your guiding light - wherever you are in your journey and whatever challenges you face.

Daniel Whitston, CTO: How I’ve embraced AI and large language models

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