Deep Dives: Managing Upwards & Sideways

For CTOs and tech leaders who want more than just the headlines

1st July 2025 | Online - 3pm-7pm (BST)

CTO Craft: Deep Dives – Where Real Leadership Challenges Get Real Answers

Deep Dives are purpose-built online events created to help senior technology leaders tackle the most critical, nuanced challenges in their roles. Each Deep Dive is a focused half-day session that blends high-impact talks with practical, workshop-style elements – giving you tools you can apply immediately.

In our first Deep Dive, we’re set to focus on one of the most powerful levers in your leadership toolkit: 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.

Keynote

Dr. Lee-Jon Ball

CTO, CTO Craft

Storytelling as a compass

Strategies for transforming when your board and executive team have little faith.

In this talk, Dr. Lee-Jon Ball uses a real example of a technology division turnaround, where he had to get a board’s attention, create tension, and show a cohesive strategy to overcome where they are now.

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.

Unlock Even More with CTO Craft Campus

Want to get the most out of CTO Craft: Deep Dives? Join CTO Craft Campus for just £399/year – and you’ll get free access to Deep Dives (usually £199 each), plus a lot more.

With Campus, you’re not just saving money – you’re investing in your long-term leadership growth. Your membership includes:

  • Full 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
  • Discounts, early access, and more member-only perks

It’s the smartest way to level up as a tech leader—whether you’re deep in the weeds or eyeing the C-suite.

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Curated weekly by Andy Skipper, Founder and Chief Coach at CTO Craft.