Newsletter – 26 June – Leadership

👋 Welcome to your fortnightly dose of curated content — built for the CTO Craft community.

We’ve handpicked the latest videos, insights, and updates to help you grow as a leader and stay connected. Want this straight to your inbox every time? Become a member and never miss an update!

In Focus This Week: Leadership

It takes more than a job title to thrive as a tech leader – especially in today’s fast-moving, high-pressure world.

This week, we’ve pulled together a set of videos focused on exactly that: the skills, mindset shifts, and community connections that help leaders grow beyond the title. From navigating change to building peer support, to tackling the tough stuff like retention and difficult conversations – it’s all here.

Explore this week’s highlights below, and don’t forget, all of this and much, much more is available on-demand in Campus.

What does it take to be a Successful CTO?

The best CTOs balance technical know-how with commercial awareness – but that’s only part of the story. They’re also strategic, empathetic, and focused on building teams and cultures where both people and products can thrive. It’s all about finding the sweet spot between tech, strategy, and leadership.

Henry Draper: Retention in Focus: Why 41% of Tech Leaders Want to Leave

This year’s survey revealed a big challenge – 41% of respondents are considering leaving their roles. The top reasons? Lack of trust in leadership, poor culture, inadequate pay, and limited growth opportunities. It’s a wake-up call for the tech industry.

Zoe Cunningham: Leadership: The Value of Doing, Not Just Knowing

You can read all the books in the world, but real leadership lessons come from doing. Hear how practical experience – and sometimes just staying silent – can reveal more about your team than any textbook ever could.-

Jon Topper: The Power of Change – Done Right

Good change management isn’t about surprise announcements. It’s about bringing your team along for the journey. Hear how involving people early, answering tough questions upfront, and making change feel familiar can transform how your organisation embraces new ideas.

Jen Fry: Tough Conversations: 3 Things to Remember

Avoiding difficult conversations only makes things worse – for everyone. In this video, hear why self-reflection, giving people space to express emotions, and sticking to your key points can make tough talks less overwhelming… and far more effective.

Alice Driscoll: A Simple Technique for Tough Conversations

Saying something difficult? Focus on facts, not accusations. Learn how sharing your observations, the impact they had, and keeping things personal (without judgement) can help tricky conversations feel more constructive – and far less confrontational.

These videos are just a small taste of what’s waiting for you in CTO Craft Campus. Members get full access to the entire video library — including the full Compensation Survey series, past conference sessions, exclusive leadership content, and so much more.

Whether you’re after quick, actionable insights or deep-dive learning, Campus is packed with resources to support you at every stage of your leadership journey.

Want to Grow Your Leadership? Start with Coaching & Mentoring Circles

If you’re ready to grow your leadership skills or want a space to share challenges with people who get it, Coaching & Mentoring Circles are for you.

They offer a supportive platform to learn from peers, tap into expert guidance, and build connections that help you lead with more confidence. Whether you’re navigating tough decisions or looking for fresh perspectives – Circles are where real, honest conversations happen.

Want to hear more? Check out these clips below:

How do you approach decision-making when coaching CTOs?

Dr Lee-Jon Ball, Non-Executive Director,  CTO Craft

What is a Mentoring Circle?

Joel Chippindale, CTO Coach

Ready to Level Up? Do it with CTO Craft

Great leadership doesn’t happen in isolation. At CTO Craft, we believe building your network, sharing real experiences, and learning from others is what helps you grow – not just as a leader, but as part of the wider tech community.

Whether it’s through our events, mentoring circles, or honest conversations with people who’ve been in your shoes, CTO Craft is here to support your leadership journey – every step of the way.

Hear why connecting with this community makes all the difference:

Why attend CTO Craft Events?

Alice Driscoll, Conflict Expert

The CTO Craft Connection

Zoe Cunningham, Director – Softwire

ICYMI: Deep Dives: Managing Upwards & Sideways

Our brand-new Deep Dives series is taking place next week, and it’s packed with sessions to help you lead across the org – not just within your team. 

From using storytelling to shape strategy, to making engineering a profit centre, to decoding product strategy and aligning with the board – this one’s all about leading sideways and upwards.

Big names, real talk, and practical tools you can actually use. Oh, and did we mention? Deep Dives are free for Campus members.

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