The CTO Playbook

In this episode, it’s a CTO Christmas Tale! You'll learn the importance of steady leadership, how to manage tech debt effectively, the risks of rushing features, and why balanced teamwork leads to success.

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:

[00:50] Two CTOs prepare for a funding race  

[01:34] Rallying the team with bold demands  

[02:13] Adopting a steady approach with a coach’s advice  

[02:52] Rushing features led to technical chaos  

[03:29] AI assistant mocks poor planning  

[04:04] Team fixes festive tech mishaps  

[04:35] Holiday hackathon fails disastrously  

[05:21] Leadership inspires calm and efficient teamwork  

[05:58] Demo glitches with embarrassing bugs  

[06:30] Smooth presentation wins investor funding  

[07:28] Reveals coach’s lessons for steady progress  

[08:24] Both CTOs learn valuable leadership lessons 

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.

Alena Ipanova is an expert in cultural intelligence and intercultural leadership.

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're going to learn what cultural intelligence is and why it matters for CTOs, how to assess and improve self-awareness as a leader, ways to bridge cultural differences within global teams, strategies for adapting communication styles effectively, and the importance of continuous learning and feedback in fostering inclusivity and collaboration.



Alena is an Intercultural Leadership and Team Development Trainer and Coach. She helps leaders and teams develop Cultural Intelligence, build inclusive workplaces, and create high-performing teams.

With 15 years of experience and a background in psychology, coaching, and intercultural leadership, Alena combines research with best practices from her work across industries. Her goal is to support leaders and teams in developing a global mindset and an inclusive company culture.

Alena’s work is centred on her clients' real needs. She aims to provide solutions that continue to help them long after each project ends. Alena approaches diversity, equity, and inclusion (DEI) by considering not only visible differences but also cognitive diversity, psychological safety, and practices that promote a sense of belonging and teamwork.

In her personal life, Alena is an adventurous traveller and curious learner, always interested in people and cultures. She lives with her family in a new country each year.

Timestamps:

[03:00] What cultural intelligence means

[05:10] Misconceptions about cultural differences

[07:15] Challenges of working in multicultural teams

[09:25] Why self-awareness is essential for leaders

[12:40] How feedback improves self-awareness

[15:30] Common pitfalls in cultural leadership

[17:45] Differences between personal and organizational norms

[20:20] Signs of poor cultural awareness in teams

[22:50] Simple exercises for self-assessment

[25:15] How the global disk assessment works

[27:30] Bridging communication gaps in diverse teams

[29:50] How team culture mapping improves dynamics

[32:05] Building relationships through informal check-ins

[34:15] Why curiosity matters in cultural intelligence

[36:20] Adapting communication styles to different contexts

[38:10] How to improve team meetings with better questions

[40:05] Practicing and unlearning old communication habits

[42:30] Importance of leaders modelling inclusive behaviour

[44:15] Encouraging curiosity in diverse teams

[45:45] How to leverage cultural diversity for better outcomes

If you would like to connect with Alena you can book a call with her and follow her on LinkedIn.

Resources Mentioned:

Cultural Intelligence | 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.

Adrian Stanek is a seasoned CTO and leadership mentor known for his practical insights on leading teams effectively.

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're going to learn the four key traits that make a leader worth following, how to use credibility and vision to lead effectively, why dictating deadlines is a sign of poor leadership, how to handle resistance within a team, and the surprising reason why great leaders focus on enabling their teams rather than commanding them.

Adrian Stanek is a veteran CTO with a 24-year track record in the tech industry, specializing in elevating SMBs and startups. His 15-year tenure as a strategic leader has been marked by cultivating modern engineering cultures and guiding companies into Cloud-Native practices. A mentor, senior consultant, speaker, and newsletter author, Adrian is a driving force in tech, passionate about continuous learning and the power of DevOps.

Timestamps:

[03:05] Adrian’s journey to becoming a leader

[04:15] Why leadership roles often catch people by surprise

[05:45] The biggest mistake new leaders make

[07:10] The importance of learning from your team

[08:30] How to recognize poor leadership habits

[10:05] Why IT leadership structures are changing

[11:30] The ideal team size for effective leadership

[12:45] Balancing different leadership styles in teams

[14:00] The challenges of managing hybrid and remote teams

[15:20] How to spot when leadership is failing

[17:00] Understanding the role of deadlines in leadership

[18:45] Why leaders should focus on removing roadblocks

[20:30] The difference between managing and leading

[22:15] Dealing with dominant personalities in teams

[24:00] Why strong personalities can benefit a team

[25:40] How to create a positive team culture

[27:05] Using credibility to build trust as a leader

[28:45] Why role modelling is essential in leadership

[30:20] How a clear vision motivates teams

[31:55] The storytelling framework for leaders

[33:15] Why leadership is about enabling others

[34:40] Challenges leaders face with resistance

[36:10] How to turn resistance into momentum

[37:55] Why leadership must be consistent

[39:30] The role of intrinsic motivation in team success

[41:05] How to balance technical and leadership responsibilities

[42:40] When to shift fully into a leadership role

[44:15] Why CTOs must bridge business and technology gaps

[46:00] The importance of aligning with your vision

[47:30] How to create meaningful challenges for your team

[49:10] Why effective leaders always prioritize clarity

[51:00] Adrian’s advice for new CTOs

Discover all of Adrian’s offerings by clicking here.

Resources Mentioned:

snackableCTO | Substack

snackableCast | 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, you'll learn how to communicate effectively as a CTO, master nonverbal cues, build trust with your team, and handle crises with clear communication.

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:

[04:45] The impact of mismatched communication cues  

[06:10] Understanding your audience as a technology leader  

[07:25] Why tone matters in delivering important messages  

[08:45] Using nonverbal cues like eye contact and body language  

[10:20] The role of empathy in effective communication  

[12:05] How listening helps build trust with your team  

[13:40] Tips for conducting successful one-on-ones  

[15:00] Why asking open-ended questions improves feedback  

[16:25] The importance of letting others speak first in meetings  

[18:15] Encouraging silent team members to share their opinions  

[20:05] Leveraging anonymous feedback tools for honest insights  

[21:30] How survey tools can gauge team morale  

[23:10] Common mistakes in team status meetings  

[24:45] Benefits of asynchronous communication for status updates  

[26:20] Choosing the right audience for your communication  

[28:10] Effective strategies for communicating major changes  

[30:05] Preparing for high-stakes meetings with agendas  

[31:50] Using storytelling to make messages stick  

[33:35] Building trust through transparency and honesty  

[35:10] The impact of systemic communication in engineering  

[36:45] Workflow communication tools for better project management  

[38:30] Preparing your team for unexpected emergencies

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.

Gareth Thomas is a seasoned CTO with over 25 years of experience building and leading tech teams.

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're going to learn why Gareth decided to step away from coding to focus on leadership, his strategies for creating high-performing teams without burning out engineers, the biggest mistake tech leaders make when managing people, how empathy plays a crucial role in leading tech teams and why promoting from within can be a game-changer for scaling your business.

Gareth Thomas is a creative technology executive with deep expertise in both product strategy and engineering leadership, backed by extensive CIO/CTO and board-level experience. He has proven to have the ability to lead large, cross-functional teams and harness AI to drive innovation, accelerate product development, and scale businesses in high-growth sectors such as pharma, insurance, digital health, and financial services.

Timestamps:

[03:10] Gareth’s journey from software engineer to CTO  

[04:23] Why he moved from coding to leadership  

[05:54] How burnout shaped his approach to managing teams  

[07:06] Creating high-performing tech teams without burnout  

[08:31] The power of empathy in leading tech teams  

[09:45] Why managing people is not taught to new leaders  

[10:53] How to avoid common leadership pitfalls  

[12:04] Navigating the loneliness of the CTO role  

[13:20] Balancing the needs of the C-suite with engineering  

[14:58] The “us vs. them” mindset in leadership  

[16:15] Promoting from within to build strong teams  

[17:34] Identifying key players early on  

[18:45] Gareth’s method for assessing team satisfaction  

[20:09] Spotting early signs of employee dissatisfaction  

[21:35] Building trust with one-on-one conversations  

[22:57] The importance of “fire jumpers” in tech teams  

[24:10] How senior engineers solve complex problems  

[25:33] The challenge of managing remote teams  

[26:58] Bridging the gap between tech and business teams  

[28:12] The value of experienced individual contributors  

[29:44] Justifying high salaries for top engineers  

[30:59] Why coding experience is critical for CTOs  

[32:16] Problems with non-technical CTOs  

[33:35] The intuition that comes with deep coding experience  

[34:51] Building a company culture around mentorship  

[36:05] Improving the interview process for better hires  

[37:29] Reducing bias in hiring decisions  

[38:47] Scaling teams while keeping a flat structure  

[39:58] Using empathy to retain top talent  

[41:22] Rethinking hiring strategies in tech  

[42:38] Advice for new CTOs facing leadership challenges  

[43:55] The rise of the individual contributor role  

[45:10] Creating clear career progression paths  

[46:28] Empowering engineers with ownership  

[47:40] Leveraging internal promotions for growth  

[48:59] Gareth’s thoughts on leadership training  

[50:15] Aligning tech goals with business strategy  

Want to hear more from Gareth? Check out the Tech-Captains Podcast.

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.

Zach Goldberg is a seasoned CTO and author of “The Startup CTO's Handbook”.

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're going to learn the key lessons Zach gained from leading multiple startup engineering teams, common mistakes CTOs make when managing growth, how to build a culture of continuous learning and high performance, why external thought leadership matters for tech leaders, and much more.

Zach Goldberg is an executive coach, the author of the 10k+ GitHub star book, “The Startup CTO’s Handbook” and the CTO of Gruntwork. Zach graduated from the University of Pennsylvania Magna Cum Laude with a degree in Computer Science and Engineering. He’s been the CTO of seven startups including WiFast, Sticks and Brains, AutoLotto, Trellis Technologies, GrowFlow, Towards Equilibrium Inc. and most recently Gruntwork, as well as an Entrepreneur in Residence at Tencent and an Associate Product Manager at Google.

Timestamps:

[01:34] Zach shares his journey from engineer to CTO  

[02:47] The origins of The Startup CTO's Handbook  

[05:11] Key lessons learned from managing engineering teams  

[06:18] Balancing management responsibilities in growing teams  

[07:39] Different challenges with various management styles  

[10:22] The value of culture in retention and hiring  

[12:02] Creating a culture of learning in tech teams  

[13:21] Ensuring managers support learning opportunities  

[15:31] Measuring coaching success with feedback loops  

[17:11] Why skip-level meetings can improve transparency  

[19:12] Benefits of connecting with lower-level team members  

[23:05] Encouraging documentation and writing skills  

[24:33] Why writing is a valuable skill for tech leaders  

[27:18] Writing documentation for different user perspectives  

[28:38] How consuming your own product builds empathy  

[30:36] Practical examples of fostering empathy in engineering  

[32:30] Zach’s advice for new CTOs entering growth organizations  

[33:30] How to handle mistakes and setbacks as a leader  

[34:44] Value of CTO coaching and leadership development

Want Zach Goldberg’s advice? Book a discovery call today to get an introduction to what Executive Leadership Coaching can help you achieve. 

Find Zach through The Startup CTO Coach’s Website and on LinkedIn.

Resources Mentioned:

The Startup CTO's Handbook by Zach Goldberg | Book or Audiobook

Turn the Ship Around! by David Marquet | Book or Audiobook 

Extreme Ownership by Jocko Willink and Leif Babin | Book or Audiobook

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.

Thorgeir Einarsson is a seasoned CEO and advisor who has helped hundreds of tech startups secure funding and navigate acquisitions.

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're going to learn why CTOs play a crucial role in fundraising and M&A deals, common mistakes CTOs make that can kill a deal, the importance of transparency during technical due diligence, how AI is changing the expectations for tech leaders, and why a CTO’s communication skills are as important as their technical knowledge.

Thorgeir Einarsson is the founder of Elevera Advisers and has created, built and sold tech companies in Europe, the US, Asia and Africa for the last 35 years. Thorgeir co-founded Pitchago in 2020, which is an innovative SaaS platform for incubators & entrepreneurs to self-assess their startups and build a level-up action plan.

Timestamps:

[05:00] Introduction to Thorgeir’s background in fundraising  

[06:33] Differences between M&A and raising capital  

[08:01] Role of a CTO during M&A and fundraising  

[09:33] Importance of preparation in fundraising  

[10:10] Changes in the CTO role with AI advancements  

[10:33] Should a non-founder CTO act like a founder?  

[12:36] Why investors worry about non-founder CTOs  

[14:34] Due diligence process explained  

[15:23] What to include in a technical presentation  

[16:53] Should you hide flaws during due diligence  

[18:24] How startups handle imperfect technology  

[20:14] Learning from past M&A deals

[21:28] How a CTO can sell their vision effectively  

[23:17] Focus on solving real problems with technology  

[24:04] Why a CTO should communicate the company vision  

[25:31] Examples of successful CTOs in M&A deals  

[26:49] The importance of reading the room during negotiations  

[28:49] Challenges of dealing with different tech stacks in M&A  

[29:45] Why CTOs need to have a bit of attitude  

[30:24] Avoiding the “not invented here” mindset  

[31:59] How a CTO’s openness impacts M&A success  

[33:18] Influence of a CTO in deal negotiations  

[34:36] Balancing technical and business perspectives  

[36:00] When is a complete technology rewrite necessary?

[37:08] The evolving importance of the CTO role  

[39:20] How AI is changing the software industry  

[41:05] Global trends and their impact on CTOs  

[43:48] Building a scenario-based product roadmap  

[45:06] Preparing for uncertain market conditions  

[46:00] How to decide on a major tech overhaul  

[47:51] Why the CTO should work closely with the CEO  

[49:59] Introduction to Pitchago’s assessment tool  

[50:45] How Pitchago helps with funding readiness

[52:59] How CTOs can become better communicators  

Get a thorough 360-degree Pitchago Assessment of your venture in just 5 minutes for free! 

Find Thorgeir Einarsson on LinkedIn

Resource Mentioned:

Pitchago | Website

Elevera Advisers | Website

Three Types of Online Attacks with Mikko Hypponen | TEDx Talk

Fighting Viruses, Defending The Net with Mikko Hypponen | TEDx 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 talks about how to create a strong engineering strategy and prioritize creating roadmaps that align with company goals while effectively communicating your strategy to the entire team.

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:

[02:19] Aligning the engineering strategy with company goals  

[06:00] Creating a roadmap for the engineering strategy

[13:40] Building a process roadmap  

[24:03] Prioritizing and executing the engineering strategy 

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 and Todd talk about why tech and product leaders need to expand their roles in today's market, why many startups struggle with tech debt and product debt, how AI is reshaping the responsibilities of engineers and CTOs, what the future holds for fractional CTO roles, and what Todd thinks about the shifting demands on tech leaders and the future of the CTO role.

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.

Todd is an experienced CPTO now doing fractional work, startup advisory, and working on his own SaaS platform. Todd offers consulting services for businesses seeking responsible growth and transformation. He is also working on a customer data platform that will unlock the true potential of AI and CRM in the new technology landscape.

Timestamps:

[06:19] The challenges of scaling tech teams during hypergrowth  

[12:09] Why smaller teams can achieve more with the right structure   

[24:18] How fractional roles fit into today’s tech leadership landscape

[27:10] The evolution of the CTO role and what’s next for leaders  

[37:10] The future of no-code and low-code tools 

[41:53] The importance of financial training for tech leaders  

[45:35] Predictions for the role of CTOs over the next decade

Connect with Todd on 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.

Magnus Lenngren is an engineering leader and a three-time unicorn builder.

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'll find out how to scale remote-first engineering teams effectively, the key challenges leaders face when growing teams quickly, the biggest mistakes to avoid during hypergrowth, why strong company culture is critical in scaling, and how to keep employees engaged and productive in a remote setting.

Magnus is an experienced CTO and Director of Engineering, skilled at scaling engineering teams, especially in Fintech, with experience at Collector Bank, Klarna, and now Mews among others. Magnus is also an investor, having led Collector’s corporate venture capital division. Magnus is currently focused on scaling Mews’ remote engineering teams.

Timestamps:

[11:05] How to scale remote teams effectively  

[16:28] Benefits of building a remote-first team  

[22:13] Providing co-working spaces for remote employees  

[35:17] Using new hires for onboarding other employees  

[41:05] Applying the Conway/Yawnoc strategy to reshape teams  

[46:22] Mistakes leaders make when scaling fast  

[51:03] Focusing on continuous improvement over fixed metrics  

[57:13] Balancing efficiency with hyper-growth challenges

Connect with Magnus on 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.