The CTO Playbook

Zoe Cunningham is a director at Softwire and author of Networking Know-How.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

In this episode, you will learn what most people get wrong about networking and why it’s so misunderstood. Zoe talks about simple ways to build genuine connections without feeling awkward, how introverts can excel at networking with the right approach, how to prepare for networking events to make them more enjoyable, and why investing in networking now pays off in the long run.

Zoe Cunningham is an award-winning technology professional and currently a Director of Softwire Technology, voted the #1 Best Place to Work in the UK 2023. She won Business Leader of the Year at the UK Women in IT Awards 2019 and has been selected by the BBC as the Brightest Woman in Britain. 

Zoe has published three books, including "Networking Know-How" the tech leaders’ handbook for building a network and extending their professional reach.

Timestamps:

[05:09] Why networking is often misunderstood  

[07:59] How to build genuine one-on-one connections  

[10:33] Why networking is crucial for career growth  

[13:54] Misconceptions about elevator pitches  

[16:41] How to make networking less transactional  

[24:06] Tips for boosting confidence at networking events  

[27:22] Easy phrases to break the ice during networking

Check out Zoe’s book “Networking Know-How” and find her on LinkedIn.

Resources Mentioned:

CTO Craft | Website

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam interviews Adem Bilican, the CTO at Relai, the App, about Bitcoin's value and its potential as a global currency. Adem discusses the technological advancements in Bitcoin, such as the Lightning Network, and offers insights into overcoming barriers to adoption.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Adem Bilican, is the co-founder and CTO at Relai, Europe's number one Bitcoin app. We provide an app for your mobile phone that users can use to easily buy and sell Bitcoin while keeping full ownership.

Timestamps:

6:15 Improving mobile wallets to boost Bitcoin user adoption.

20:50 Using renewable energy for more efficient Bitcoin mining.

25:35 Leveraging Bitcoin’s capped supply to increase long-term value.

29:10 Introducing the Lightning Network for instant Bitcoin transactions at zero cost.

38:30 Ensuring user control with self-custodial wallets in the Relai app.

44:50 Securing your Bitcoin wallet with reliable backup and restore options.

Get the Relai App to help you buy and manage your Bitcoin and follow Adem on X.

Resources Mentioned:

Mastering Bitcoin by Andreas Antonopoulos | Book or Audiobook

Mastering the Lightning Network by Andreas Antonopoulos | Book

Bitcoin Nashville | Website

Plan B Forum in Switzerland (Oct 2024) | Website

Bitaxe Mining Device | Website

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam discusses how CTOs can transition from firefighting to strategic leadership by following a structured, disciplined approach.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Timestamps:

5:19 Create time blocks for strategic work to avoid constant firefighting.

9:51 Build trust by empowering your team through delegation.

16:07 Focus on documenting why and how, not just what, to improve processes.

23:38 Block off time for your top priority and protect it fiercely.

Resources Mentioned:

Michael Lopp | LinkedIn

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam interviews Dipak Mistry, a senior architect with 25 years of experience. Dipak shares his structured approach to presentations, emphasizing the importance of storytelling, conflict and resolution, and a clear narrative to make technical information more relatable and engaging.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Dipak Mistry helps small, medium and corporates business's grow and become efficiently sustainable by aiming to deliver value and achieve each business's mission. Dipak delivers a Technology Presentation Training Program that helps IT Professionals elevate their careers and in turn give great presentations that is specialized for different audiences.

Timestamps:

5:27 Know your audience to tailor the presentation effectively.

13:04 Build presentations with consistency for easier decision-making.

19:51 Focus on the key objective of the presentation to avoid distractions.

27:39 Use a structured framework to create clear and impactful presentations.

33:12 Get pre-approval from stakeholders to streamline decision-making.

Visit the Unity Edge Website and follow Dipak on LinkedIn.

Resources Mentioned:

The Golden Circle by Simon Sinek | Ted Talk

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam interviews Carol Palombini, a psychologist and leadership coach specializing in psychological safety. Carol offers insights on how fostering psychological safety can drive team innovation and what leaders can do to create safe, effective work environments.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Carol Palombini is a seasoned Psychologist and Tech Leadership Coach. Her passion lies in being a catalyst for transformation among tech leaders who face challenges such as communication issues, imposter syndrome, burnout, and the intricate demands of tech leadership roles.

Timestamps:

3:30 Assessing for a team's psychological safety.

8:06 Foster healthy conflict for innovation and team growth.

15:30 Create a psychologically safe environment by managing emotions.

19:08 Conduct exit interviews to uncover reasons for talent loss.

29:02 Reward and recognize behaviours that foster psychological safety.

Build your dream team with personalized solutions that actually get results. Book a complimentary 30-minute call with Carol.

Also, be sure to follow Carol on LinkedIn.

Resources Mentioned:

re:Work With Google | Archived Website

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam dives into the challenges of transitioning from a technical leader to a strategic CTO, outlining a five-step playbook to help navigate this journey successfully. He also shares insights on overcoming common obstacles and embracing a leadership mindset.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Timestamps:

8:45 Make fewer decisions by delegating responsibilities.

12:33 Adopt a learning mindset for your new role.

18:47 Learn the language of the business to succeed.

27:35 Empower your team by stepping back from technical details.

Resources Mentioned:

Crossing the Chasm by Geoffrey A. Moore | Book or Audiobook

What Got You Here Won't Get You There by Marshall Goldsmith and Mark Reiter | Book or Audiobook

Turn The Ship Around! by L. David Marquet | Book or Audiobook

The Five Dysfunctions of a Team by Patrick M. Lencioni | Book or Audiobook

The CTO Playbook episode on The 2 Most Critical Components of a CTO Career with Andy Skipper | Spotify or Apple

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam interviews Daniel Walters, a seasoned CTO coach and consultant. Daniel shares his experiences on leading change within organizations, focusing on collaboration, dynamic reteaming, and the emotional impact of restructuring.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Daniel Walters is a Technology Strategy Consultant and CTO coach based in Auckland, New Zealand. With over 25 years of experience in technology leadership across various sectors, he specializes in systems thinking, technology strategy, and situational leadership.

Daniel has held leadership roles, including CPTO at Weirdly and CTO/CIO at Seek Asia, and has consulted for notable organizations like Kiwi Rail and New Zealand Super Funds. While in Malaysia he successfully established a development centre for Experian Marketing Services. He was part of a small team at Prestariang that won a concession to replace Malaysia's immigration systems nationally (MYR8.6bn). He also helped integrate JobsDB and Jobstreet into Seek to successfully fend off global competitors whilst raising the quality of product experiences for candidates and hirers.

Daniel started his career in his hometown of Melbourne, Australia where he was part of Hitwise' leadership that oversaw growth and eventual sale (USD240m). His blog 'Great CTOs Focus on Outcomes' is dedicated to supporting CTOs' success.

Timestamps:

4:15 How to use empathy to lead change effectively.

10:05 Strategies for CTOs' to implement dynamic reteaming successfully.

15:22 Why internal hiring is crucial for fostering innovation.

20:48 Leveraging team identity to boost morale and performance.

26:11 The 90-day strategy for assessing organizational needs.

32:34 How to avoid common pitfalls in restructuring as a CTO.

39:19 Why empathy should drive your leadership decisions.

To get more tips check out Daniel's Blog: Great CTOs Focus on Outcomes on Substack and connect with Daniel on LinkedIn.

Resources Mentioned:

Six Simple Rules by Yves Morieux and Peter Tollman | Book or Audiobook

Team Topologies by Matthew Skelton and Manuel Pais | Book or Audiobook

Domain-Driven Design by Eric Evans | Book

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam interviews John Broome, a seasoned product leader with over 20 years of experience. John shares insights on generative AI, collaboration between CTOs and CPOs, and the importance of being customer-centric in product management.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

John Broome is a product and operations practitioner having worked in customer service, development, sales, marketing and project management for the past 20 years. Spending most of his time managing products and UX leadership throughout finance, gaming, e-commerce and now hospitality. John is currently the CPO and COO at Chico Hotel Solutions in Stockholm, helping hotels to increase revenues, reduce costs and improve their guest experience.

Timestamps:

3:39 Bridging the gap between business goals and product strategy.

10:46 Prioritizing customer needs over what they say they want.

16:33 Constructing effective teams despite budget constraints.

24:56 Collaborating to avoid idle engineers and wasted resources.

33:33 Balancing the capacity for product and technical development.

38:08 Leveraging generative AI as a tool, not a replacement.

51:01 Holding product managers accountable for prioritization decisions.

Connect with John on LinkedIn

Resources Mentioned:

Chico Hotel Solutions | Website

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

If you are finding this podcast helpful, please rate and review so other CTOs can join the conversation.

In this episode, Adam explores the different types and stages of a CTO's journey, offering insights and practical strategies to help you identify your strengths and align with your organization's needs.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Timestamps:

3:15 Understand the stages of CTO growth.

4:30 Determine what type of CTO your organization needs now.

7:20 Assess your strengths and weaknesses using a SWOT analysis.

10:24 Identify the gaps between your skills and organizational demands.

13:06 Consider coaching and feedback to accelerate your growth.

Resources Mentioned:

The Startup CTO's Handbook by Zach Goldberg | Book

The Unicorn CTO: Daniel Jarjoura's Startup CTO Growth Cycle | Website

SaaS Academy | Website

Realforce | Website

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, Adam speaks with Andy Skipper, the founder of CTO Craft and a seasoned CTO coach. Andy delves into the benefits of coaching for new CTOs, the growth of the CTO Craft community, as well as offers advice for navigating leadership challenges.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

CTO Craft helps thousands of CTOs and Senior Engineering Leaders build skills, experience and resilience, to survive the pressures and demands of the most senior technology role in modern business, as well as provide real commercial impact within their organizations. CTO Craft helps both new and experienced CTOs by providing a safe space for learning and growth among one of the largest peer networks of senior engineering leaders in the world.

Alongside the free community, they help hundreds of CTOs through private mastermind Circles, one-to-one CTO coaching, conferences and other resources. The CTO Craft mission is to increase the success of technology-enabled startups and scale-ups by providing CTOs with the skills and support they need.

Prior to coaching and mentoring new leaders, Andy held CTO roles at Made.com, Comic Relief, and interim roles at dozens of companies such as JustPark, Intu, Threads Styling, Living Maps, Spyscape, VONQ and The School of Life, and has advised and invested in several massively successful businesses in the UK, as well as many VC firms and accelerators.

Timestamps:

3:00 Addressing leadership gaps through coaching.

10:36 Emotional intelligence improvements in personal life.

16:39 Convincing CEOs about coaching benefits.

20:28 Value of external mentoring groups.

24:03 Networking opportunities at CTO events.

29:11 Managing personal expectations in leadership roles.

31:50 Importance of CTOs focusing on the first team.

Stay connected with Andy on LinkedIn

Resources Mentioned:

CTO Craft | Website

CTO Craft Events | Website

CTO Craft | YouTube

Patrick Lencioni's Books | Amazon

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.