The CTO Playbook

• 32: How to Run 1:1s That Actually Improve Performance

  Join The CTO Playbook Slack Community to connect with other CTOs!In this episode, you'll learn how to structure effective one-on-one meetings with engineers, how to maintain alignment between individual performance and company goals, how to use a rolling agenda for tracking progress, and how to transition from weekly check-ins to quarterly and annual reviews seamlessly.Timestamps:[00:00] Introduction[00:38] Importance of one-on-one meetings for engineers[01:22] How often should you meet with individual contributors[02:14] Weekly vs. biweekly or monthly meetings[03:06] Why weekly meetings maintain momentum[04:02] When to adjust meeting frequency[04:48] Balancing meeting length and effectiveness[05:32] What to cover in one-on-one meetings[06:20] The role of trust and rapport in leadership[07:05] How to start meetings with open-ended questions[07:52] Why listening is a key leadership skill[08:36] Avoiding status updates in one-on-ones[09:20] Helping engineers improve communication skills[10:02] Teaching engineers how to listen effectively[10:48] Steering conversations toward personal growth[11:36] How to shift focus from output to experience[12:24] Using silence to encourage deeper responses[13:10] The importance of writing things down[14:00] How to structure a rolling agenda document[14:46] Benefits of an open agenda for tracking topics[15:30] Using action items to track progress[16:14] How a personal development plan fits in[17:02] Why mission statements help guide career growth[17:48] Real examples of how writing things down improves performance[19:20] Using notes to build confidence in employees[20:10] Preparing for performance improvement plans[20:58] How to guide conversations in one-on-ones[21:42] Understanding different learning styles[22:28] The VARK model: visual, auditory, read/write, kinesthetic[23:12] Adapting coaching based on learning style[24:02] Asking the right questions for better engagement[24:50] How different learning styles impact communication[25:36] Structuring quarterly reviews for performance tracking[26:22] How to align quarterly reviews with company goals[27:10] The four key sections of a quarterly review[27:56] Why quarterly reviews remove surprises in evaluations[28:44] Rolling up quarterly insights into annual reviews[29:30] Making promotions and salary adjustments smoother[30:18] Five key takeaways for leading individual contributorsFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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• 31: The Fatal Flaw of 10x Developers (Here’s What Actually Matters)

  Join The CTO Playbook Slack Community to connect with other CTOs!Matt Watson is the CEO of FullScale and previously bootstrapped an SaaS company to $35 million ARR before a $150 million exit.In this episode, you're going to learn what skills CTOs need to become CEOs, why understanding sales and marketing is crucial for tech leaders, how to delegate effectively to focus on big-picture strategy, why communication and collaboration are key to scaling engineering teams, and what AI’s role is in shaping the future of software development.Matt Watson is the founder and former CTO of one of the early SaaS companies, VinSolutions, which he bootstrapped in 2003 to $35 million ARR before a $150 million exit in 2011. In 2018, he founded FullScale to help himself and others scale their teams with talent from the Philippines at 70% less cost. He also hosts the Product Driven podcast and writes a weekly newsletter about the gap between business and software engineering.Timestamps:[00:00] Introduction[05:30] Starting a company by solving a real problem[07:15] Bootstrapping an SaaS business to $35 million ARR[08:40] Challenges of building a product without a playbook[10:20] Different types of CTO roles[11:50] Why startup CTOs need a product mindset[13:05] The natural transition from CTO to CEO[14:30] What makes a good CTO[15:40] The importance of sales and marketing for CTOs[17:00] Selling to developers is harder than it seems[18:30] Why engineers struggle with delegation[19:50] The real reason 10x developers exist[21:10] How bureaucracy slows down engineering[22:35] Why startups move faster than big companies[24:00] Software corrosion and how products degrade over time[25:30] Why big companies struggle with innovation[27:00] The hidden cost of maintaining legacy software[28:40] Teaching the next generation of developers[30:20] The impact of AI on software development[31:50] How AI is changing the role of engineers[33:15] AI adoption rates among software developers[34:50] Why junior developers benefit most from AI[36:10] The balance between using AI and learning fundamentals[37:45] Why developers need to improve communication skills[39:00] The key to becoming a successful CTO[40:30] Why being the best known is more important than being the bestOffshore your tech team with the talented engineers at FullScale.Connect with Matt on LinkedIn.Resources Mentioned:Product Driven Podcast with Matt Watson | Spotify or AppleVinSolutions | WebsiteStackify | WebsiteGitHub Copilot | WebsiteFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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• 30: How to Align Data, Teams, and Strategy for Business Success: Ritavan's Framework

  Join The CTO Playbook Slack Community to connect with other CTOs!Ritavan is a machine learning expert, author of Data Impact, and has worked in industries such as banking, energy, and real estate.In this episode, you're going to learn how to avoid complexity traps in data-driven decision-making, how to leverage unique advantages to create real business value, why alignment across teams is critical for success, the importance of simplifying processes to reduce inefficiency, and the role of data in driving growth while maintaining focus on customer needs.Ritavan is an entrepreneurial technology leader with a decade of experience focused on data-driven business impact. He has authored peer-reviewed papers, given invited talks at global conferences, and holds an international patent. Known for his first principles approach to building and scaling data-driven solutions across industries, Ritavan combines deep technical expertise with strategic vision and an execution-focused mindset. His latest book offers actionable insights to accelerate data-driven impact for non-software native businesses.Timestamps:[00:00] Introduction[06:30] Working with large volumes of data in diverse fields[07:45] The challenge of scoping problems in the real world[09:00] Lessons learned from his time at Societe Generale[10:25] Identifying and solving real-world problems in data[11:40] Impact of working in high-stakes environments like energy markets[12:55] The importance of owning P&L in business[14:05] Ritavan’s journey into real estate technology and venture capital[15:35] Scaling businesses from seed to post-series B[16:45] The challenge of growing in legacy businesses[17:50] A different approach to solving problems in traditional industries[19:05] The role of technology in modern businesses[20:15] Defining leverage and its role in business growth[21:35] Aligning teams for maximum impact[23:00] How military strategies inform business alignment[24:25] The power of clarity in decision-making[25:40] How to use data to drive alignment across teams[26:50] Simplifying processes to avoid overcomplication[28:10] The need for refactoring systems at every level[29:25] Avoiding complexity and streamlining operations[30:30] The risk of inefficiency when complexity builds up[31:45] How simplification leads to better optimization[32:50] The importance of optimizing after simplifying[34:05] Iterative optimization in business processes[35:15] Building an empirically valid model of your business[36:30] Balancing stochasticity and regularity in decision-making[37:40] The importance of continuously evolving business strategies[39:00] Why satisficing is suboptimal and how to avoid it[40:20] The need to maximize every opportunity for growth[41:35] Transitioning from a scarcity to an abundance mindset in business[42:50] The difference between industrial and data-driven paradigms[44:05] How airlines are an example of using data for customer loyalty[45:15] Why traditional models in energy markets need rethinking[46:30] Case study: Octopus Energy’s approach to consumer involvement[47:50] Streamlining processes for customer involvement and efficiency[49:00] Importance of leveraging data for more efficient consumption[50:10] Rethinking industries by going back to first principles[51:25] Why businesses must evolve with modern tools and technology[52:40] Maximizing impact through data-driven business strategiesIf you want to stop being just a consumer of AI products and start being a producer of data impact to delight your customers and grow revenue profitably, pre-register for Ritavan’s new book, Data Impact.Follow Ritavan on LinkedIn.Resources Mentioned:Data Impact by Ritavan | WebsiteThe Collapse of Complex Societies by Joseph Tainter | Book or AudiobookWhat Your Business Can Learn From Peter Drucker | ArticleFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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• 29: How to Scale a Developer-First Startup with Daniel Jarjoura

  Join The CTO Playbook Slack Community to connect with other CTOs!Daniel Jarjoura is the Managing Director at Avolta, specializing in helping engineering-led companies prepare for mergers and acquisitions.In this episode, you'll learn the importance of building products that solve broad problems for developers, how to use open source as a growth tool while monetizing through premium services, why GitHub metrics can help predict future success, how to scale from a developer-led market to enterprise sales, and the 18-24 month process to plan for a successful M&A exit.Daniel Jarjoura specializes in 'developer-first' companies, open source, AI, cloud, infrastructure and cybersecurity. Prior to his current role, Daniel served as a CTO advisor for four years and founded The Unicorn CTO, a community and leadership training program dedicated to CTOs. A software engineer by training, Daniel began his career managing tech, product and support teams before transitioning into entrepreneurship. Over the last 12 years, he launched two companies: Startup42, one of France’s first tech startup accelerators, and H2 Innovate, an innovative platform offering on-demand expertise. Additionally, Daniel founded and directed the entrepreneurship department at EPITA, a leading software engineering school in France, for ten years.Timestamps:[00:00] Introduction[05:00] Startup42: A tech startup accelerator for engineers[07:00] Challenges faced by engineer-led startups[09:00] Business model for Startup42[12:05] Lessons learned when transitioning to a second company[14:00] Shifting towards advisory work for CTOs and developers[16:00] Due diligence and M&A transactions in small cap companies[19:00] The importance of scaling to enterprise sales[21:10] Developer-first companies and the importance of solving broad problems[24:00] Evaluating market demand and finding alternatives[26:10] The difference between developer-first and VC-compatible companies[29:00] How to determine if your company is ready for VC funding[31:00] Open source as a tool for growth[36:05] The evolution of open source and its business model[39:00] The challenges of scaling developer-first companies[42:00] How to approach sales in a developer-first startup[44:30] Scaling from selling to developers to selling to enterprises[47:00] How cultural differences affect sales strategies in the US and Europe[50:00] How to position your company for an exit[52:00] The importance of getting noticed by the right acquirers[54:10] Strategies for attracting M&A attention[56:00] The 18-24 month preparation for a successful M&A exitConnect with Daniel on LinkedInResources Mentioned:The Unicorn CTO | WebsiteGitHub | WebsiteGitLab | WebsiteMongoDB | WebsiteAngelList | WebsiteDatadog | WebsiteH2 Innovate | WebsiteStartup42 | LinkedInEPITA | WebsiteFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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• 28: The No.1 Reason Startups Fail and How to Avoid It with Dr. Georgios Christou

  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.

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