Deep Dives: Managing Upwards & Sideways
For CTOs and tech leaders who want more than just the headlines
1st July 2025 | Online - 3pm (BST)
CTO Craft: Deep Dives – Where Real Leadership Challenges Get Real Answers
Deep Dives are targeted, high-impact virtual events crafted specifically for senior technology leaders. Each session addresses the most pressing and complex challenges you face, combining expert insights with actionable strategies you can put to use right away.
While open to all senior technology leaders, Deep Dives are designed with CTO Craft Campus members in mind, reflecting the real-world challenges and growth areas surfaced within the Campus community. What’s more, Campus members get free access to every session as part of their membership.
Deep Dives will be hosted regularly, offering an ongoing opportunity to sharpen your leadership toolkit alongside a trusted peer group.
Our first session focuses on one of the most powerful levers in your leadership: your team – your CEO and peers across the organisation. Managing upwards and sideways isn’t just about alignment; it’s about building trust, shaping strategy, and amplifying your influence across the business.
You’ll walk away with:
- Clear frameworks for strengthening relationships with senior stakeholders
- Practical approaches to navigating cross-functional dynamics
- Strategies for making your voice heard where it matters most
This is more than a conversation – it’s a deep, actionable exploration of what it means to lead at the executive level.
New to CTO Craft Campus?
CTO Craft: Deep Dives are just the beginning.
Join CTO Craft Campus for just £399/year and get free access to every Deep Dive (normally £199 each) – plus a whole lot more designed to accelerate your leadership journey.
With Campus, you’re not just attending events – you’re joining a year-round support system built exclusively for senior technology leaders. Your membership gives you:
- Unlimited access to 500+ on-demand leadership videos
- A growing library of self-paced leadership courses
- Over 5,000 curated articles, frameworks, and real-world playbooks
- A private Slack community of experienced tech leaders
- Exclusive discounts, early access, and other member-only perks
Whether you’re building your first leadership team or stepping into the C-suite, Campus gives you the tools, insights, and network to grow faster and lead smarter.
Ready to make the most of what CTO Craft has to offer? Campus is where it all comes together.
Expert Speakers
Dr. Lee-Jon Ball
CTO, CTO Craft
Adelina Chalmers
Founder, The Geek Whisperer
Giorgos Ampavis
Tech Exec/Advisor
Philippe Guenet
Founder, Henko
Holly Donohue
Fractional CPO, Product Rebel
Dan Smith
CTO Coach
Themes we’ll explore…
Mapping team relationships
Navigate and strengthen relationships with executive peers to build alignment and trust.
Handling crises
Lead decisively through uncertainty and high-stakes situations.
Executive presence
Develop the presence, communication, and influence needed to lead with authority.
Strategy
Engage in strategic thinking and contribute effectively to business direction.
Building visibility
Ensure your work and leadership are recognised by stakeholders at every level.
Boardroom impact
Communicate with confidence in the boardroom and contribute to governance and vision.
Agenda
15:00-15:05
Introduction & Welcome
15:05-15:35
Keynote: Storytelling
Dr. Lee-Jon Ball, CTO, CTO Craft
We’re kicking things off with a skill every leader needs but rarely gets formal training in: storytelling. Lee-Jon shares how he used it to reshape an entire company, influencing everything from salaries and team structure to product strategy.
In this keynote, you’ll learn how storytelling can serve as a leadership tool, helping you shape vision, build alignment, and drive strategic clarity across your organisation.
Expect insights from real-life transformations and walk away with ideas you can apply to your own leadership style.
15:35-16:05
Projecting Engineering as a Profit Centre
Adelina Chalmers, Founder, The Geek Whisperer
Still fighting the “cost centre” label? You’re not alone. In this talk, Adelina explores what truly defines engineering team performance and how to create the conditions that let it shine.
She’ll share practical tools to help shift perceptions and position engineering as a commercial engine, not just a delivery team. We’ll look at how to make impact visible, how to speak the language of value, and how to lead your team towards greater alignment, accountability, and influence.
16:05-16:35
Making Boardroom Impact with Strategy Map for Tech Leaders
Philippe Guenet, Founder, Henko
What actually gets heard in a boardroom? Philippe will walk through how strategy maps can help tech leaders frame their work in a way that clicks with the business and keeps you in the conversation.
Drawing from years of experience and real use cases, he’ll explore how you can bridge the divide between tech and business by speaking in a shared strategic language and why tech leaders need to lead that conversation.
16:35-16:45
Break
16:45-17:15
WTF is a Product Strategy Anyway?
Holly Donohue, Fractional CPO, Product Rebel
Product strategy is often misunderstood or missing altogether. Holly delivers a candid breakdown of what strategy really means in practice, how to build one that sticks, and what to avoid when trying to align the business around it.
You’ll hear stories from the trenches, tackle common pitfalls, and come away with a clearer idea of what strategy looks like in the wild, plus tips to help your team get behind it.
17:15-17:35
Mastering the Role of a Strategic CTO
Dan Smith, CTO Coach
The CTO role today demands more than technical oversight; it requires a profound ability to influence and strategically position technology as a core driver of business growth.
Dan Smith, an executive coach and M&A advisor, shares invaluable insights on how strategic CTOs can effectively engage with both board governance and executive leadership teams.
Expect practical strategies for communicating complex technical issues to non-technical stakeholders to make abstract concepts relatable, and balancing the presentation of both risks and opportunities.
You’ll gain actionable strategies and a deeper understanding of the essential communication, leadership, and organisational dynamics needed to drive impactful technological change.
17:35-17:55
Aligning Tech with Business Goals: A Guide to Strategic Engineering
Giorgos Ampavis, Tech Exec/Advisor
This talk focuses on connecting day-to-day engineering with business outcomes. Giorgos shares frameworks and tactics to align cross-functional teams, measure progress, and ensure engineering is seen as a true strategic partner.
He’ll explore how to turn vague business goals into clear engineering priorities and how that clarity can transform your team’s output, influence, and ability to scale.
17:55-18:00
Closing Remarks
TechManagerWeekly
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Curated weekly by Andy Skipper, Founder and Chief Coach at CTO Craft.