The CTO Playbook

Join The CTO Playbook Slack Community to connect with other CTOs!In this episode, you'll learn the top mistakes founder engineers make when starting a business, why early technical decisions can have long-term business consequences, how to choose co-founders with complementary strengths, the importance of understanding business fundamentals as a technical founder, and strategies for picking the right tech stack for your startup's needs.Dr. Georgios Christou graduated from Carnegie Mellon University with a dual degree in Cognitive Science and Computer Science, he also has a Master’s and Ph.D. in Computer Science from Tufts University. Since 2003, he has worked at Cyprus College and holds the rank of Associate Professor. Dr. Christou founded and was the director of the Games Research Center of European University Cyprus, through which a computer game development start-up company emerged. Dr. Christou was also the coordinator of perhaps the only Microsoft-branded degree in the world, Microsoft's Bachelor in Information Systems.Dr. Christou moved to the Cyprus International Institute of Management where he held a dual role, as the Chair Associate Professor of Computer Science and the Chief Technology Officer of eCREDO Ltd., a Fintech company in Cyprus. He was responsible for the Technology strategy of the company. Currently, Dr. Christou is a freelance consultant for Fintech companies.Dr. Christou has many publications in scientific journals, as well as presentations at international conferences. His research examines the ways that video games can serve as social “third-places” and how this can be designed. He also examines the nature of player experience, the motivations that pull us towards playing video games, and the ways that we interact with them, as novices and as experienced players. The insights into these behaviours have been used towards creating entertaining e-Health experiences as well as novel interactions, such as playing video games through brain-computer interfaces.Timestamps:[04:06] Combining academia and industry experience[05:26] The challenges of a failed startup[07:04] Importance of product velocity[08:26] Creating early income streams[10:11] Choosing better co-founders[12:20] Balancing communication styles[13:46] Complementary knowledge in co-founders[15:22] Common mistakes in startup presentations[17:37] Learning from startup competition feedback[19:29] Lessons from Amazon's business strategy[21:00] The impact of early tech choices[22:36] Matching the tech stack to the niche[23:38] Overhauling poorly chosen technologies[26:08] Planning for long-term scalability[27:31] Managing decision-making complexity[28:26] Avoiding the sunk cost fallacy[30:01] The importance of asking the right questions[33:09] Flexibility in choosing tech stacks[34:40] Parallel tech stacks for different domains[35:37] Learning the business side of startupsFollow Dr. Georgios Christou on LinkedIn to learn more.Resources Mentioned:The E-Myth Revisited by Michael E. Gerber | Book or AudiobookFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Stephan Schmidt is a CTO coach and the author of “Amazing CTO”.In this episode, you're going to learn why hiring the right people is the foundation of success and how to assess candidates effectively. Stephan shares his strategy for running weekly one-on-one meetings and why they should focus on alignment rather than status updates. You'll also hear about the importance of trust in leadership and practical ways to build it within your team. He explains why surprises undermine leadership and how to present ideas and decisions without creating resistance. Finally, Stephan emphasizes the value of early and consistent delegation as a tool for scaling leadership and empowering team members.As a CTO and CPTO Coach, Stephen helps CTOs, CPTOs, VPs of Engineering, Heads of Development, and other tech leaders to master their challenges and achieve their goals. With over 25 years of experience as a CTO, consultant, and executive in various startups and enterprises, he has a wide range of skills and insights to share with clients. Stephen’s coaching services include training workshops, one-on-one sessions, and fractional/ interim management. He focuses on topics such as people management, communication, recruiting, leadership, lean start-up, e-commerce, and bridging business and technology. He is passionate about working with people and developing them, as well as explaining technology in a clear and engaging way. Stephen is currently coaching several CTOs and tech managers from different industries and countries, and he enjoys seeing them grow and succeed.Timestamps:[00:00] Introduction[05:05] Early career and becoming a manager[07:44] First training on people management[09:15] Learning from a great boss at eBay[11:05] Building trust with junior developers[13:07] Shifting decisions to the team[16:22] Managing through late-night crises[18:11] Importance of hiring the right people[20:04] Common mistakes in one-on-ones[22:07] Best practices for weekly one-on-ones[23:15] Aligning remote teams effectively[25:35] Benefits of skip-level meetings[27:12] Spending 50% of the time on people[29:02] Helping employees identify career goals[30:20] The role of trust in leadership[32:22] Avoiding surprises in leadership[34:06] Overcommitting to solutions for success[36:38] Focusing on effectiveness over efficiency[39:07] Writing clear job descriptions[41:04] People-first vs process-first management[43:06] Why surprises harm team alignment[45:09] Stephan’s advice for new CTOsFind your Dream CTO Job with Inkmi.Connect with Stephan through LinkedIn.Resources Mentioned:Amazing CTO | WebsiteTurn the Ship Around by L. David Marquet | Book or AudiobookFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!David Wascha is a seasoned product and tech leader with experience at Microsoft, MOO, Travelex and Zoopla.In this episode, you're going to learn when to combine product and tech leadership roles and when not to, why the distinction between tech-enabled and deep tech businesses matters for leadership structure, how to avoid tension and misalignment between product and tech teams, the importance of representing and advocating for all functions as a leader, and practical strategies for new CTOs to build trust and effectively lead cross-functional teams.Timestamps:[08:23] Lessons learned from mistakes at Microsoft[11:00] Transitioning to product-focused roles[13:45] Adopting customer-focused strategies at Microsoft  [16:10] Moving to the UK and joining MOO  [17:32] Differences in product management between the US and UK  [19:08] Expanding MOO’s product lines and markets  [20:44] First combined product and tech leadership role  [23:13] When to combine product and tech roles  [24:35] Distinguishing between tech-enabled and deep tech businesses  [25:31] Avoiding tension between product and tech teams  [27:09] Challenges with re-platforming[29:12] Handling legacy systems and updates  [31:04] Balancing product and tech priorities  [32:27] The importance of titles and team representation  [34:16] Managing relationships with other executives  [36:25] Challenges of stakeholder management  [37:46] The cost of misalignment in leadership  [39:12] Tips for avoiding executive misalignment  [40:27] Building trust as a new tech leader  To learn more from Dave, connect with him on LinkedIn.Resources Mentioned:MOO | WebsitePhotobox | WebsiteFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Discover essential strategies for streamlining your recruiting process. Learn how to create compelling job ads, evaluate candidates effectively, and design an outstanding onboarding experience. Explore the importance of employer branding and the role of headhunters. Gain insights into group interviews and coding assessments. Get tips on enhancing candidate experience and communicating rejection feedback. Uncover the value of a coordinated recruiting approach and training teams on effective hiring skills.

Join The CTO Playbook Slack Community to connect with other CTOs!Roman Labunsky is the co-founder and CTO of an early-stage cybersecurity startup based in Israel.In this episode, you're going to learn how Roman's experience leading a military tech unit during wartime shaped his approach to building resilient teams and processes. You will discover strategies for managing onboarding and handovers under extreme constraints, the value of starting simple to scale effectively, and why clear communication and adaptability are key to succeeding in high-pressure environments.Roman is the CTO and co-founder of a cybersecurity startup specializing in third-party risk management. He is 40 years old, married and a father to a 2-year-old girl. Roman lives in Israel with his family and two dogs.He has been in the tech industry for over two decades, holding various engineering roles including software developer, team lead and software architect in both startups and enterprises across the security space. Between 2017 and 2023, he served as VP of R&D for a startup in the Kubernetes security space, where he led the company through growth and eventual closure when funding ran out.Over the past year, Roman co-founded and served as CTO of a technological military unit in the Israeli Defense Force. With the unit now firmly established, he is focusing on his startup.Timestamps:[03:00] Roman’s journey into tech leadership[05:20] Building a new military tech unit[07:35] Early challenges in a high-stakes environment [09:56] Adapting to military operations during wartime[12:10] Overcoming bureaucratic barriers for faster delivery[14:54] Managing short-term volunteers effectively[17:07] Why traditional onboarding didn’t work[18:13] The role of documentation in smooth transitions[20:07] Setting a two-day onboarding goal[22:23] Standardizing processes for efficiency[24:18] The importance of automation for rapid delivery[26:30] Navigating bureaucracy as the war progressed[27:54] Conducting offboarding interviews for improvements[30:37] Challenges of leading large-scale projects[31:54] Starting simple with team structures[34:24] Avoiding imported processes and frameworks[35:10] The reality of rewriting code in early startups[36:58] Streamlining recruitment for large-scale hiring[39:26] Balancing risk and speed in recruitment[42:33] Choosing tools that teams will actually use[45:07] Delegating decisions to the teams[46:43] Fixing breakages instead of overplanning[48:12] Importance of communication for alignmentConnect with Roman on LinkedIn.Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!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.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 check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Alena Ipanova is an expert in cultural intelligence and intercultural leadership.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 outcomesIf you would like to connect with Alena you can book a call with her and follow her on LinkedIn.Resources Mentioned:Cultural Intelligence | WebsiteFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Adrian Stanek, a seasoned CTO and leadership mentor with 24 years in tech, shares invaluable insights on effective leadership. He discusses the four key traits that make a leader worth following, emphasizing the importance of credibility and vision. Adrian highlights common pitfalls new leaders face, such as dictating deadlines, and stresses the value of enabling teams rather than commanding them. He also explores the evolving dynamics of leadership in the IT sector and the impact of hybrid work environments on team collaboration.

Join The CTO Playbook Slack Community to connect with other CTOs!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.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 emergenciesFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Gareth Thomas is a seasoned CTO with over 25 years of experience building and leading tech teams.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 check out Adam's CTO coaching company Synova Tech.