Tales from the Roundtable: AI won’t close the skills gap
You’re reading a guest article written by Georgina Shute, a tech leader, facilitator, and ADHD coach who helps teams navigate complexity and build environments where people thrive.
How CTOs can build teams that keep evolving
Renee Hawkins and Matthew Skelton
This roundtable, facilitated by Matthew Skelton and Renee Hawkins, explored how the skills gap in technology cannot be closed by AI alone. Human connection remains essential for effective learning and organisational growth, and tech leaders must build teams that continuously evolve without chasing short-lived trends or wasting resources on ineffective strategies.
People bridge the critical gap between business and technology, with human translators proving more valuable than documentation or processes alone.
AI serves as an enabler rather than a replacement, enhancing team capabilities while avoiding the "throwing over the wall" problem that creates new silos.
Tech leaders succeed by creating environments where teams connect around a common purpose, learn from past challenges, and develop meta-skills that adapt to change.
The discussion highlighted the importance of building learning environments where people thrive, balancing innovation with practical application in a way that works for diverse minds and evolving technologies. With participants from various industries and backgrounds, the conversation was packed with real-world insights into challenges that tech leaders are grappling with right now.
Some conversations just stick with you, and this roundtable was one of them. CTO Craft Con brings together tech leaders to share the realities of leadership, tech, and culture in a way that really matters. It’s a space for honest conversations, practical strategies, and connections that make a difference. With interactive formats, roundtables are designed to be useful, not just interesting, and if this session was anything to go by, it’s clear why people keep coming back.
With around 30 people in the room, two facilitators, and four key discussions, the session was a mix of expert insights, lively group conversations, and real talk about the challenges tech leaders face in keeping up with an ever-changing world.
Georgina Shute — Founder of KindTwo and the Procrastination Breaker Framework™
As the chair of this discussion, my role was to keep the conversation flowing, make sure everyone had space to contribute, and help tie together the themes emerging from different tables. The setup was simple but effective: an overview, some incredible expertise, and a space for people to dig in at their tables before coming back to share what stood out.
The energy in the room was great — people wanted to contribute, and the mix of slides, discussions, and open-ended questions kept the conversation going, so much so that a few people didn’t want to stop (and nearly missed lunch!).
This wasn’t just about upskilling; it was about how we build organizations that can keep up, how we avoid making the same mistakes we’ve made before, and how leadership isn’t about knowing all the answers but about creating the space for the right conversations.
Why these conversations matter
Discussions like these aren’t just valuable or a great chat; they’re foundational to our success in industry.
As someone who works closely with neurodivergent leaders, I see firsthand how rapidly evolving workplaces create both opportunities and challenges. Without these open, collaborative discussions, we risk designing systems and processes that leave some of the brightest minds behind.
For neurodivergent professionals, the skills conversation is even more crucial. We often thrive in environments that prioritize deep thinking, problem-solving, and creative problem structuring, areas that automation can enhance but never replace. But traditional career pathways aren’t always designed for the way our brains work. If we don’t actively shape the conversation on upskilling and innovation, we end up with learning models that don’t fit, and teams that aren’t able to leverage the full potential of individual differences (because they aren’t sure how!).
Key themes and takeaways
The discussions revolved around the challenges and opportunities associated with developing the path from learning something new to actually using it. We also explored how we keep pace with technological change.
Some of the most thought-provoking insights included:
People bridge the gap between business and technology
Alignment isn’t achieved solely through documentation or frameworks. Individuals who can translate business needs into technology solutions — and vice versa — play a critical role in helping organizations build products people actually want (with happier people!).
AI as an enabler, not a replacement for human connection
AI can assist in automating tasks and optimising workflows, but real learning happens through people. The value of human experience, problem-solving, and collaboration remains irreplaceable. It’s not a case of choosing between AI and human learning; integrating AI to enhance, rather than replace, critical thinking and relationship-building in teams is what’s needed. While AI is a game-changer for automation and efficiency, it cannot replace the nuanced, context-driven decision-making and relationship-building that define successful teams.
AI and the ‘throwing over the wall’ problem
We’ve seen this before. Whether it was between development and testing, or marketing and engineering, each shift created new silos and barriers to collaboration, and now, it’s happening again with AI. The assumption that AI can simply be ‘handed off’ without careful integration echoes past mistakes, and teams need to be intentional in how they incorporate AI into workflows. I remember my first job where the Project Management Office sat in a glass box at the end of the room, always watching, writing… it always felt like a huge barrier stood between us.
Treating AI as a separate entity rather than an integrated part of workflows introduces the same barriers and risks, and these must be addressed.
Learning from our past to prepare for the future
A big theme emerged: the importance of looking back at past challenges to better plan for the future. Tech leaders have seen patterns repeat — whether it’s the handover challenges between development and testing, the struggles of aligning business and technology, or now, the shift to AI-enabled workflows. We need to take those lessons forward to avoid reinventing the same problems.
This is where the balance of strong opinions, loosely held, comes in. Leaders need conviction, but also the humility to adapt as new information arises. What worked five years ago may not work now, and what works today won’t necessarily be the answer tomorrow. The best leaders create spaces where this kind of critical thinking and adaptation can thrive.
The role of the tech leader: Enabling, connecting, and planning for the future
The discussion also highlighted that tech leadership is not about having all the answers — it’s about fostering an environment where people can connect around a common purpose and navigate complexity together.
In reality, this role is rarely held by just one person. Successful teams are often guided by multiple ‘connectors’ who see across boundaries, connect ideas, and enable others with the right tools, processes, and conversations to move forward together. The ability to plan for the future doesn’t mean predicting the next big thing, but creating the structures and cultures that allow teams to adapt to whatever comes next.
How teams keep learning and evolving without wasting time: Challenges and solutions
The discussion also explored practical strategies for developing learning models that really work — balancing agility with long-term capability-building:
Avoiding ‘skills gravity’ — With constant change, there is a need to focus on adaptable, meta-skills rather than chasing short-lived trends. Organizations must invest in learning approaches that evolve with emerging technologies.
Innovation vs. duplication — Rapid innovation can lead to wasteful duplication. Companies need structured yet flexible approaches to upskilling that encourage collaboration and cross-functional knowledge-sharing.
Internal tech conferences as a catalyst for alignment — One of the most compelling ideas was the power of internal tech conferences to bridge gaps between IT and business. Creating regular, structured forums for sharing ideas can significantly enhance alignment and engagement.
Why I care as a coach and facilitator
As a coach who works with high-achieving neurodivergent leaders, these topics are more than just theoretical; they shape real careers, teams, and lives. My clients often have the potential to drive some of the most innovative ideas forward.
That’s why facilitation matters. A well-run discussion isn’t just information sharing; it helps people make sense of complexity, find clarity in uncertainty, and leave feeling empowered to take action.
The best facilitators do more than guide conversations; they create spaces where people feel safe to explore new ideas, challenge assumptions, and build meaningful connections.
At this roundtable, I saw that happening. Participants weren’t just sharing insights; they were listening, reflecting, and thinking about how to apply these ideas in their own organizations. And that’s what good facilitation is all about — helping people unlock their own best thinking.
The roundtable underscored the importance of aligning technical and business teams in a dynamic, scalable, and human-centric way. The discussions highlighted the need to balance speed with thoughtful upskilling, ensuring that organizations stay ahead of the curve without constantly chasing the latest tech fads.
The key question remains: How do we build teams that keep learning and evolving in a way that really works?
This roundtable set the stage for deeper exploration into this challenge, and I’m excited to see how these insights translate into real-world action.
Start this conversation in your organization
The skills gap won't close itself, and AI isn't the answer. Real transformation happens when leaders create space for teams to connect, learn, and evolve together.
Let's facilitate this discussion with your teams. Whether you require a focused 90-minute session or want to invest in a half-day or full-day deep dive, we'll tailor the experience to deliver maximum value — Leadership roundtable - Skills pathways for fast flow.
