Conversations Roadshow by CTO Craft
London, let’s talk tech leadership...
- 20th October, 2026
- etc. venues Monument
An intimate half-day gathering for CTOs and senior tech leaders to share experiences, explore challenges, and build lasting connections.
What is the Conversations Roadshow?
A half-day peer gathering for senior engineering leaders, born out of the CTO Craft community. Small rooms, real problems.
The format is consistent: small-group roundtables, peer-led discussion, experienced facilitators who’ve held the role themselves. The content isn’t. Attendees, facilitators, and topics are shaped by what’s live for engineering leaders in London right now.
Each session is built around honest conversation, real problem-solving, and the kind of connections that keep going after the afternoon ends..
Small group discussions
12-15 CTOs and senior tech leaders per table, creating space for real exchange.
Peer-led conversation
Interactive roundtables and deep-dive sessions built around shared challenges and experience.
No slides, real conversation
No long keynotes or sales pitches. Just open, honest dialogue and practical insight.
Is this event right for you?
Conversations is built around one thing: the quality of the room.
Peers at similar stages, with similar-shape teams and similar problems on their desks – guided by facilitators who’ve held the role themselves. The conversations work because everyone is operating at the same level, and because someone experienced is steering.
It’s intended for senior engineering leaders who:
- Hold a senior engineering leadership title – CTO, VP Engineering, Head of Engineering, Director of Engineering, or equivalent
- Currently lead an engineering team
- Are in role at a single company, or recently between roles
If that’s you, you’ll get a lot out of it. If it’s not quite, but you think the room is a fit, get in touch.
Your facilitators
Tom Howlett
Claire Donald
Mike Jones
Thomas in’t Veld
Oge Opara-Nadi
Daniel Wagner-Hall
Blanca Garcia Gil
Joel Chippindale
Hywel Carver
Prakriti Karthauser
Claire Barrett
Agenda
12:00pm – 1:00pm
Arrival and welcome
1:00pm – 1:15pm
Welcome remarks
1:15-2:15pm
Pick your table. Choose from our roundtables, each exploring a different leadership challenge. Bring your questions, share your experiences, and learn from peers who’ve been there.
AI and Burnout
AI was supposed to take work off our plates. Instead, many teams feel busier, more fragmented, and more exhausted than before. This session starts with the tension a lot of leaders are already feeling: if AI is driving productivity gains, why does work still feel heavier – and why are so many teams closer to burnout, not further from it?
In the room, we’ll unpack where that pressure is actually coming from. Not just the usual causes of burnout, but the newer forms AI is introducing: higher output expectations, constant context-switching, decision fatigue, tool sprawl, and the quiet pressure to always be “AI-enabled.” We’ll look at how these dynamics are showing up across teams, where AI is genuinely reducing load, and where it’s simply accelerating the pace without removing the strain. You’ll leave with a clearer way to spot the difference between useful AI adoption and burnout by automation.
Expect a practical framework for identifying where AI is helping, where it’s adding invisible workload, and what to change so your team gets the gains without paying for them in exhaustion.
Joel Chippindale - CTO Coach @ Monkey's Thumb
Blanca Garcia Gil - Transformational Coach @ StaffPlusEngineer.com
Leading Through Uncertainty: Adapting Your Leadership Style When Everything Keeps Changing
Tech leaders are being asked to lead through constant change while dealing with the same uncertainty as everyone else. AI pressure, restructures, shifting priorities, and tighter expectations mean the old “steady leadership style” often stops working fast.
This roundtable is an honest discussion about what situational leadership actually looks like in practice. We’ll unpack how leaders adapt their approach depending on context – from supporting overstretched teams during uncertainty to managing upwards during organisational pressure, while still protecting their own capacity. Expect practical conversation rather than leadership theory: the signals leaders use to change style, where people get stuck trying to lead consistently through inconsistent environments, and the trade-offs that come with different approaches. Leave with a clearer way to recognise what your team needs in different moments – and a more practical framework for adjusting your leadership style without losing trust, clarity, or yourself in the process.
Claire Donald - CPTO @ Rational Partners
More Human Than Ever: Empathy, leadership and AI
As AI takes on more cognitive work, leaders face a harder question: which parts of leadership should never be delegated? When efficiency is easy to scale, qualities that require time, presence and genuine attention become more valuable – and more visible when they’re missing. In this fishbowl discussion, Oge Opara-Nadi and Hywel Carver will explore empathy as a leadership capability rather than a soft skill.
Together, the room will unpack where empathy belongs in decision-making, whether it can conflict with accountability, and where leaders should consciously choose human judgement over AI. Participants are invited to join and leave the conversation throughout, shaping the discussion with their own experiences and perspectives. You’ll leave with practical ways to recognise, develop and apply empathy in your organisation – and a clearer sense of where human leadership creates value that AI can’t replicate.
Oge Opara-Nadi - VP of Engineering @ Hey Savi
Hywel Carver - CEO @ Skiller Whale
Leading Technology in Rapidly Evolving Environments
This executive roundtable will examine the opportunities and pressures facing today’s technology leaders. Discussions will focus on innovation, operational scale, and strategic decision-making in rapidly evolving environments. Attendees can expect a high-value exchange of perspectives, experiences, and practical leadership insights.
What Strong Leadership Looks Like Now
Focused on leadership resilience and team wellbeing, this session will explore how organisations can support performance in high-pressure technology environments. Senior leaders will discuss sustainable leadership, accountability, and maintaining engagement during periods of rapid change.Further details will be announced soon, but this session will examine what strong leadership looks like in modern technology businesses. Leaders will share experiences around decision-making, team performance, and leading through periods of growth and change. Expect practical takeaways and thoughtful discussion throughout.
2:15pm – 2:45pm
Networking Break
2:45pm – 3:45pm
Pick your table. Choose from our roundtables, each exploring a different leadership challenge. Bring your questions, share your experiences, and learn from peers who’ve been there.
The Human Side of Better Decisions
The quality of our decisions depends on the perspectives we invite in – but even the right decision can fall flat if people don’t understand, trust or feel connected to the process behind it. In this session, we’ll explore how diverse teams make stronger decisions and why self-awareness is the foundation of effective leadership.
We’ll place particular emphasis on the value of diversity of thought – moving beyond the idea that it’s simply a “good thing to have” and demonstrating, through practical examples, how bringing together different perspectives can lead to better decisions, uncover blind spots and produce stronger outcomes. We’ll also examine how leaders can intentionally create space for different viewpoints and the impact effective communication has on trust, engagement and team performance. You’ll leave with practical techniques for bringing diverse perspectives into decision-making, along with a simple framework for communicating decisions clearly, confidently and in a way that people can genuinely get behind. Most importantly, you’ll gain a tangible understanding of how diversity of thought directly improves the quality of decisions and the results teams achieve.
Prakriti Kartgauser - Head of Infrastructure @ L&G
Beyond Technical Expertise: Staying Valuable in an AI-First World
The skills that have traditionally defined career progression – technical expertise and management capability – are increasingly being augmented, and in some cases replaced, by AI. So where does that leave us, and what will organisations value most next?
In this session, we’ll explore why creative thinking, product judgement and leadership are becoming the capabilities that set people apart. Drawing parallels with the challenges CEOs already face, we’ll examine how the role of leaders is evolving from directing work to creating the conditions for teams to thrive. We’ll also look ahead to a future where organisations operate more like autonomous vehicles: teams are empowered to build and move quickly, while senior leaders focus on guiding, mentoring and unlocking their full potential.
You’ll leave with a practical lens for identifying which skills will become more valuable in an AI-first world, and a clearer understanding of where to invest your time and energy to remain relevant, influential and impactful. More information will follow soon, but this session will centre on building and sustaining strong cultures in modern technology organisations. Leaders will discuss how to create alignment, maintain engagement through change, and foster environments where teams can thrive. The conversation will offer practical approaches and real-world experiences from those leading through growth and transformation.
Sasha Bilton - CTO @ Anomalous
One Data Stack, Two Consumers: Building Data Foundations That Humans and Agents Can Both Rely On.
At this point it is clear that AI infrastructure is a critical part of the tech stack you are responsible for, and that people will want to connect their AI systems to your different data generating systems for e.g customer metrics or marketing performance data.
But how aware are you of the data architecture necessary to do this safely without causing data gaps or, even worse, wrong insights?
Discussions about data stacks have been the remit of analytics teams in the past, but there is much more at stake now that agents are consumers as well and are lacking the critical context that an analyst has.
This session is built around three questions that sit at the heart of that architecture:
- How do you build data foundations robust enough for both humans and AI to rely on — and where do semantic and context layers fit into that?
- How do you structure information so it is genuinely accessible across your organisation, not just to the people who built it?
- Who owns the rules for how that information evolves as your business changes?
Thomas and Mike will bring their own views from decades of leadership in tech & data, and challenge the room to bring theirs. Expect a practical, peer-led discussion grounded in real-world scenarios. And leave with a clearer picture of where your data architecture stands today, whether it’s AI-ready, and if not, what are the next steps you can run with your team immediately.
Thomas in't Veld- CEO + Founder @ Tasman Analytics
Mike Jones - CPTO @ Tasman Analytics
Effective Leadership in Uncertain Times
Details will be shared shortly, but this roundtable will focus on what effective leadership looks like in today’s technology landscape. Senior leaders will come together to discuss leading through uncertainty, managing change, and building high-performing teams. Expect an open, insight-led conversation with practical takeaways from leaders shaping the future of the industry.
Cultural Change Without the Buzzword
Designed for senior technology leaders, this roundtable will explore the demands of leadership in complex and fast-moving organisations. Topics will include navigating uncertainty, leading cultural change, and developing resilient, high-performing teams. Expect open discussion and actionable insights from experienced peers.
3:45pm – 4:15pm
Networking Break
4:15pm – 5:15pm
Pick your table. Choose from our roundtables, each exploring a different leadership challenge. Bring your questions, share your experiences, and learn from peers who’ve been there.
Board Whispering
Teams rarely struggle because people are lazy or incapable. More often, delivery slows because of invisible friction, unclear ownership, mismatched expectations, or leadership habits that no longer scale.
In this facilitated CTO conversation, we will explore what team efficiency really means in start-up and scale-up environments, and why predictability often breaks down even when everyone is working hard. Together, we will surface common patterns across people, process, and systems, and discuss where CTOs have the greatest leverage to reduce friction without adding unnecessary complexity. This is a reflective, peer-led discussion designed to help participants recognise shared challenges, exchange perspectives, and leave with clearer ways of thinking about their own teams.
Claire Barrett - Founder @ APIsFirst
Building the Engineering Talent Pipeline in the Age of AI
Scaling an engineering team isn’t just about hiring more people – it’s about making the right hiring decisions at the right time. Do you wait for experienced engineers who can hit the ground running, or invest in junior talent with long-term potential? How do you build a team that can deliver today while creating the leadership and technical capability you’ll need tomorrow?
As organisations grow, the challenges evolve. The ideal team structure changes, communication becomes more complex, and hiring decisions have a greater impact on engineering velocity, culture, and execution. Finding the right balance between senior and junior talent, knowing when to specialise, and building clear progression pathways are all critical to scaling successfully.
In this roundtable, we’ll discuss how CTOs and engineering leaders are approaching team growth, workforce planning, and organisational design. We’ll explore strategies for hiring at different stages of scale, identifying candidates with the potential to grow alongside the business, and developing engineers into future technical and people leaders.
You’ll leave with practical ideas for scaling engineering teams sustainably, creating the right mix of experience and potential, and building an organisation that continues to perform as it grows.
Daniel Wagner-Hall - Director of Tech Ed @ Code Your Future
An Honest Conversations About a Changing Industry
Join fellow technology leaders for an open discussion on the opportunities and challenges shaping today’s industry. From innovation and growth to leadership and decision-making, this roundtable is designed to encourage honest conversations, shared learning, and practical takeaways from peers across the sector.
Leadership When the Decisions Get Hard
This leadership roundtable will bring together senior professionals for an honest conversation about leading in today’s technology landscape. From managing change and supporting teams to making difficult decisions, attendees will gain practical insights and fresh perspectives from leaders facing similar challenges.
Culture and Communication
Culture continues to play a defining role in successful organisations, particularly during periods of growth and change. This session will bring leaders together to share experiences around engagement, communication, and building environments where teams feel supported, motivated, and aligned.
5:15pm – 5:30pm
Closing Remarks
Venue
etc. Venues Monument
8 Eastcheap, London, EC3M 1AE
We’ll be gathering at etc. venues Monument, a contemporary event space in the heart of the City of London. With bright, well-designed meeting rooms and a calm, professional atmosphere, it provides an ideal setting for focused discussion and practical peer exchange.
Register Now
What your ticket includes
Networking lunch
Facilitated small-group leadership roundtables
Practical peer discussion on real challenges (no slides, no panels)
Joining a curated room of senior tech leaders
Insights you can take straight back to your organisation
Refreshments throughout the afternoon
Due to the intimate nature of this event, availability is extremely limited.
Our event partners
London
Berlin
Stockholm
New York
Stockholm
Stockholm