Conversations Roadshow by CTO Craft
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Conversations Roadshow by CTO Craft

London, let’s talk tech leadership...

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 of around 10 or more
  • 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.

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

Tech

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.

Leadership

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.

Culture (communication/cultural dynamics)

This roundtable will explore how leadership and workplace culture continue to evolve across the technology sector. Discussions will cover everything from engagement and collaboration to navigating uncertainty and organisational change. Attendees can expect practical perspectives and honest conversations from leaders facing similar challenges.

Leadership

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.​

Tech

Full details will be announced shortly, but this roundtable will explore the realities of technology leadership today. Bringing together experienced leaders from across the sector, the discussion will focus on scaling teams, navigating rapid change, and making strategic decisions in an increasingly complex environment. Expect a candid conversation grounded in practical experience, shared challenges, and lessons learned at the forefront of tech leadership.

Leadership

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.

Wellness

This roundtable will explore the human side of leadership in fast-moving technology environments. Through open discussion, attendees will share perspectives on resilience, wellbeing, accountability, and sustaining high-performing teams under pressure. Expect practical insights and honest reflections from leaders balancing people, performance, and business priorities.

Culture

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.

Leadership

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 startup 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

Tech

 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

 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

This session will address the growing importance of culture in driving organisational performance and long-term success. Through peer discussion, leaders will explore alignment, communication, and fostering environments that support innovation and collaboration at scale.

Culture

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

Your facilitators

Ready to join the Conversation?

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.

First 10 tickets available for just £199 – act fast!

Register Now

Tech Leader Ticket

£249

+VAT

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

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