The CTO Playbook

Join The CTO Playbook Slack Community to connect with other CTOs! 



In this episode, you'll learn what CTO coaching is, who it’s for, the impact it can have, and how to find the right coach for your goals. Adam Horner shares common CTO challenges, the skills needed to succeed at the executive level, and a framework for accelerating leadership growth.

Timestamps:

[00:00] Introduction  

[02:10] Common struggles CTOs face  

[03:45] How coaching provides clarity and accountability  

[05:00] My own CTO journey and early challenges  

[06:30] The impact of not having a coach  

[08:15] Five common CTO archetypes  

[08:30] The firefighter CTO  

[09:50] The senior developer turned CTO  

[11:00] The seasoned technologist ready to lead  

[12:20] The plateaued CTO  

[13:30] The rocket ship CTO  

[15:00] The challenge of getting stuck in execution  

[16:20] Story of a CTO who shifted from feature delivery to strategic leadership  

[18:00] What makes my coaching different  

[19:45] The CTO maturity model  

[21:00] Skills that CTOs often lack compared to other executives  

[22:30] The importance of communication, finance, and strategy  

[24:00] Coaching vs. teaching vs. mentoring  

[25:30] The real cost of not investing in coaching  

[27:00] Story of a CTO who resisted coaching and almost lost his role  

[29:30] What happens when CTOs invest in coaching  

[30:45] How coaching builds confidence and influence  

[32:00] The impact of coaching on stress and burnout  

[33:15] How to know if coaching is right for you  

[34:30] When is the best time to get a coach  

[35:45] How to find the right CTO coach  

[36:30] Step-by-step playbook for choosing a coach  

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! 

Dan Gwalter is a fractional consultant and former IT director who helps businesses navigate growth challenges.

In this episode, you're going to learn why Dan left a high-paying corporate job to build a career he actually enjoys, how to craft a strong personal brand on LinkedIn that attracts clients, why conversations—not sales pitches—are the key to building a thriving consulting business, the simple process Dan uses to keep a steady stream of clients without stress, and how he balances work and life while making a great living.

Dan Gwalter has been running a successful Fractional Consulting business for over a decade, helping professionals break free from traditional career constraints. With a focus on creating stability and maximizing flexibility, he has built a model that allows consultants to get paid for the value they create rather than just the hours they work.

Through The Fractional Formula, Dan provides structured guidance for those looking to transition into fractional consulting. His program includes seven weeks of live training in small groups, unlimited one-on-one coaching, and a full year of ongoing mentoring and support. Many participants have landed their first clients within weeks, proving that a well-executed strategy can lead to rapid success.

Dan’s approach is built on practical experience, offering a clear path for professionals who want to move from day-rate contracting to managing a portfolio of high-value clients. His expertise helps others design careers that prioritize both financial security and personal freedom.

Timestamps:

[00:00] Introduction

[03:04] The pressure of chasing prestige and power

[04:48] Experiencing the downside of an IPO

[06:25] Walking away from a high-paying job

[07:58] The challenges of starting as a consultant

[09:41] Dealing with inconsistent income

[11:12] The mistake of relying only on referrals

[12:35] Why networking isn’t about selling

[13:52] How asking the right questions leads to opportunities

[15:04] The power of building a reputation

[16:20] Why job security is a myth

[17:41] The importance of a clear niche

[19:03] How to structure a LinkedIn profile for consulting

[20:15] The biggest mistake consultants make on LinkedIn

[21:42] How to write a LinkedIn profile that attracts clients

[23:16] Why storytelling is key to standing out

[24:40] How to get into high-value conversations

[25:52] Why most LinkedIn content fails

[27:04] The key to writing content that brings clients

[28:36] The simple way to generate inbound leads

[30:02] Why selling isn’t about pitching

[31:14] How to start sales conversations naturally

[32:45] The importance of solving problems upfront

[34:12] The best way to structure a sales call

[35:25] How to stay top-of-mind with potential clients

[37:02] Why continuous business development is essential

[38:36] How to balance client work and marketing

[39:58] The danger of relying on just a few clients

[41:20] How to avoid feast and famine cycles

[42:45] Why consulting is about relationships, not transactions

[44:12] The mindset shift that leads to long-term success

[45:30] Why most consultants undercharge for their expertise

[47:04] The power of saying no to the wrong clients

[48:20] How Dan built a business that fits his lifestyle

[50:02] What a work-life blend looks like in practice

Kickstart your fractional career in 30 minutes with Dan’s No-Nonsense Leadership.

Follow Dan 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, 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 contributors

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!

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 best

Offshore your tech team with the talented engineers at FullScale.

Connect with Matt on LinkedIn.

Resources Mentioned:

Product Driven Podcast with Matt Watson | Spotify or Apple

VinSolutions | Website

Stackify | Website

GitHub Copilot | Website

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!

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 strategies

If 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 | Website

The Collapse of Complex Societies by Joseph Tainter | Book or Audiobook

What Your Business Can Learn From Peter Drucker | Article

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!

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 exit

Connect with Daniel on LinkedIn

Resources Mentioned:

The Unicorn CTO | Website

GitHub | Website

GitLab | Website

MongoDB | Website

AngelList | Website

Datadog | Website

H2 Innovate | Website

Startup42 | LinkedIn

EPITA | Website

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, 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 startups

Follow Dr. Georgios Christou on LinkedIn to learn more.

Resources Mentioned:

The E-Myth Revisited by Michael E. Gerber | Book or Audiobook

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!

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 CTOs

Find your Dream CTO Job with Inkmi.

Connect with Stephan through LinkedIn.

Resources Mentioned:

Amazing CTO | Website

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

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!

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 | Website

Photobox | Website

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, you'll learn how to streamline your recruiting process, craft compelling job ads, evaluate candidates effectively, and create an exceptional onboarding experience.



Timestamps:

[03:48] Deciding when to hire

[04:27] Importance of employer branding

[05:32] Creating a role description

[06:13] Writing a job advert

[07:09] Talent sourcing strategies

[07:56] Using recruiters effectively

[08:48] The role of headhunters

[09:48] CV screening tips

[10:22] Benefits of group interviews

[11:02] Designing coding assessments

[12:08] Architectural and standards evaluations

[12:46] Assessing cultural fit

[13:16] The pressure release test

[14:22] Crafting effective interview questions

[14:57] Using situational achievement assessments

[15:45] Typical interview stages

[16:33] Selling the role during final interviews

[17:38] Tracking candidate funnel metrics

[18:16] Scoring and benchmarking candidates

[18:59] Blind voting in group interviews

[19:56] Enhancing candidate experience

[20:45] Communicating rejection feedback

[21:52] Tools for managing recruiting processes

[22:28] Making and presenting job offers

[23:39] Engaging new hires before start date

[24:35] Structuring onboarding processes

[25:58] Leveraging probation periods

[26:54] The value of a coordinated recruiting approach

[27:34] Investing in the recruiting process

[28:04] Training teams on recruiting skills

[28:51] Defaulting to no hire when unsure

[29:20] Creating an amazing onboarding experience

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!

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 alignment

Connect 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 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 check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!

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

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 check out Adam's CTO coaching company Synova Tech.

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 emergencies

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!

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.

Join The CTO Playbook Slack Community to connect with other CTOs!

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

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 check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!

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

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 check out Adam's CTO coaching company Synova Tech.

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.

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 

Join The CTO Playbook Slack Community to connect with other CTOs!

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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.

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. 

Join The CTO Playbook Slack Community to connect with other CTOs!

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.