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Most CEOs hire the wrong CTO—not because of a talent shortage, but because they don't know what they're actually looking for.



In this episode, Adam sits down with returning guest Warren Beazley—known across the UK tech scene as The CTO Recruiter. With nearly 30 years in the industry and a track record of 96%+ retention rates, Warren specializes in helping founder-led and investor-backed companies make one of the most pivotal hires in their org: a world-class CTO.

You’ll learn why most CTO searches fail before they begin, how top CEOs are quietly mapping their talent pipelines long before they’re hiring, and the exact behavioral tools Warren uses to identify true leadership fit—not just technical skill. Whether you’re a CEO hiring your first tech exec or a CTO positioning yourself for your next role, this episode reveals how high-stakes technical hiring actually works behind the scenes. Expect sharp insights on filtering through noise, diagnosing culture clashes before they happen, and why gut instinct is no longer enough.

You’ll Learn:

• How elite CEOs reverse-engineer their CTO hires for long-term fit
• Why mapping your talent market beats relying on inbound candidates
• How Warren’s “12-month success review” technique clarifies role expectations
• What most CEOs get wrong about job specs—and how to fix it
• How behavioral surveys predict executive compatibility before it’s too late
• How to test for strategic thinking without asking cliché interview questions
• What to do when you’re not the candidate’s first choice—and how to tell
• How to spot red flags in resumes that even experienced recruiters miss
• Why most hiring failures aren’t about skills—they’re about culture mismatches

Timestamps:

[00:00] Introduction

[00:37] Why the CTO hiring market is still tough in 2025

[05:07] What makes hiring CTOs more like poker than chess

[07:15] The difference between founder-led vs investor-led hiring

[10:18] Why great CEOs pivot and redefine their own role

[12:16] Why most companies don’t know who their top candidates are

[14:03] Employed vs. unemployed CTO hiring strategy

[15:00] How to pitch your company to elite CTOs

[16:13] Why money isn’t the main motivator for great candidates

[17:41] The “12-month success review” for defining your ideal hire

[20:00] Why job ads fail and how to create story-driven ones

[22:03] Mapping the market to uncover passive candidates

[25:00] The challenge of filtering hundreds of resumes

[27:00] How structured interviews speed up good hiring

[29:16] What your resume should reveal—but probably doesn’t

[31:14] Culture and compatibility: the real reasons hires fail

[33:00] How behavioral surveys predict long-term fit

[36:03] Using personality data to shape interview questions

[38:06] Why a 3-day decision window makes or breaks offers

[40:01] Setting salary expectations early to avoid breakdowns

[42:15] Open feedback channels that improve CTO retention

[45:03] What really happens when a great hire walks away

You can learn more about Warren's work on his website. or you can book a FREE 10 Minute call to understand if his hiring blueprint would work for you.

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!

What if the part of you causing burnout is the same one that got you where you are?

In this episode, Adam sits down with Rob Kalwarowsky—executive coach, TEDx speaker, and author of Capitalizing on Chaos—to explore how high performers can stop white-knuckling their leadership journey and start transforming from within. Rob has helped tech execs and founders all over the world how to fast-track deep change through his FIRE method, a unique four-step framework that rewires how we lead, scale, and relate to chaos itself.

If you’ve ever looked “successful” on the outside while feeling stuck, burned out, or quietly miserable on the inside, this conversation will hit home. You’ll hear Rob’s deeply personal journey from MIT engineer to global coach, how internal family systems reshaped his leadership philosophy, and why chaos might be the exact catalyst you need. Expect mindset rewiring, counterintuitive truth bombs, and tools to break through the next ceiling in your growth.

This one’s not just about business. It’s about the human behind the title.

You’ll Learn:

• How Rob’s FIRE method rewires leadership by turning inner chaos into strategic clarity
• Why imposter syndrome signals deeper misalignment, not personal failure
• What Internal Family Systems reveals about the voices that shape executive behavior
• How high achievers unknowingly sabotage themselves by clinging to “productive” masks
• Why logical self-talk fails—and what actually works to shift emotional patterns
• What guilt and overachievement often hide in leadership dynamics
• How emotional check-ins create trust and coherence in your inner team
• Why leaning into chaos can unlock innovation, not just survival
• How to evolve your leadership identity without losing your edge

Timestamps:

[00:00] Introduction

[06:13] The cost of a “perfect” life

[08:42] The role of coaching and therapy in real growth

[11:41] What Internal Family Systems therapy reveals

[13:21] Why mindset hacks don’t solve deep issues

[15:11] Even destructive inner voices have a purpose

[16:27] Rob’s 6-minute self-leadership exercise

[16:53] Step 1 of the FIRE method: find your reason

[17:32] Step 2: ignite the masks and uncover inner blocks

[21:56] Step 3: rapidly transform your identity

[25:04] Step 4: expand and evolve your leadership

[26:17] Why fear shuts down innovation

[28:00] How to lead teams through disruption

[30:10] Chaos opens new possibilities for growth

[31:33] Summary of the FIRE method

[32:57] The importance of guided transformation

[35:55] Why leadership growth is deeply personal

Resources Mentioned:

How to Handle a Bad Boss | TEDx Talk

Saboteur Assessment | Website

Internal Family Systems by Dr. Richard Schwartz | Website

Movie: Inside Out

If you want the first 2 chapters of Capitalizing on Chaos for FREE, sign up for Robs newsletter!

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 shift from one-on-one coaching to group leadership, how to reduce politics and knowledge gaps in large engineering teams, how to build a high-trust leadership environment, and how to implement an open-door policy for better team alignment.

Timestamps:

[00:00] Introduction  

[00:45] What leading leaders means  

[01:30] Lessons from top CEOs on leadership  

[02:15] Defining a small engineering organization  

[03:00] Why politics emerge in growing teams  

[03:45] The impact of trust and information gaps  

[04:30] The challenge of repeating yourself as a leader  

[05:15] Why large organizations create communication bottlenecks  

[06:00] NVIDIA's leadership model with 60 direct reports  

[06:45] How Airbnb’s CEO manages leadership without one-on-ones  

[07:30] Group coaching vs individual coaching  

[08:15] The benefits of shared leadership problem-solving  

[09:00] How open feedback reduces internal politics  

[09:45] Why peer support strengthens leadership teams  

[10:30] Creating strong alignment among engineering leaders  

[11:15] How shared context improves decision-making  

[12:00] Why engineering leadership needs a structured approach  

[12:45] The importance of experience in leadership roles  

[13:30] How ad hoc one-on-ones still play a role  

[14:15] Transitioning engineering leadership to a group model  

[15:00] Why equalized voices improve engineering management  

[15:45] Avoiding loudest voice domination in meetings  

[16:30] Encouraging collaboration instead of top-down directives  

[17:15] Setting up team-wide planning and retros  

[18:00] Ensuring transparency in data and decision-making  

[18:45] Teaching leaders how to think critically  

[19:30] Preventing leadership silos with open discussions  

[20:15] Helping new leaders adapt to group leadership  

[21:00] Why weekly one-on-ones may still be necessary  

[21:45] Balancing structured and flexible leadership approaches  

[22:30] Implementing an open-door policy for transparency  

[23:15] Why leadership alignment is critical for scaling  

[24:00] Spotting and eliminating unchecked politics  

[24:45] Supporting new leaders through mentorship  

[25:30] Why strong engineering leadership improves team morale  

[26:15] How to prevent groupthink in leadership teams  

[27:00] Keeping leadership teams engaged and evolving  

[27:45] Steps to successfully transition to a group coaching model

Want to start a podcast like this one? Book your free podcast planning call here.

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!

Kevin Howren is the Chief Product and Technology Officer at NPACT, where he has led major organizational changes, doubling the customer base and scaling SaaS assets under management from $50 billion to over $100 billion.



In this episode, you're going to learn why managing change is more about people than processes, how to overcome resistance and build trust in an organization, the key to keeping momentum during long-term transformations, how to make tough personnel decisions while maintaining morale, and why knowing when to stop making changes is just as important as knowing when to start.

With over 25 years in technology, Kevin Howren has consistently driven transformative change through deep technical expertise and strategic vision. His career has been shaped by a commitment to innovation, operational excellence, and building high-performing teams, turning complex challenges into opportunities for growth.

He has led the post-acquisition transformation of NPACT, guiding engineering, product, AI, and infrastructure teams to achieve remarkable results. This includes doubling the customer base and increasing SaaS assets under management from $50 billion to $100 billion. His approach has always been centered on aligning technology and business strategies, ensuring that every decision supports long-term growth and sustainability. Whether modernizing the technology stack, enhancing cross-departmental collaboration, or mentoring senior leaders, his focus remains on driving continuous improvement and delivering value to the organization and its customers.

Before NPACT, he served as Head of Client Technologies at BBC Systems, where he oversaw the development and transitioning of key products and technology infrastructure, managing UI/UX engineering and product teams to enhance user experience and streamline operations. One of his key achievements was reducing production rollbacks by 78% through implementing innovative development processes and adopting modern technologies.

Timestamps:

[00:00] Introduction

[02:10] Doubling the customer base and scaling SaaS assets

[03:15] The biggest challenge in change management

[04:02] Why small wins matter more than big changes

[05:20] Keeping momentum during long-term projects

[06:18] Handling unexpected challenges in transformation

[07:30] The role of people in organizational change

[08:45] Managing resistance and trust in leadership

[09:50] How to navigate layoffs and team restructuring

[11:05] The importance of redeploying talent

[12:30] Avoiding morale issues during transitions

[13:45] Why rushing changes can backfire

[14:55] Balancing process, technology, and people changes

[16:02] The impact of company culture on change

[17:15] Why some changes fail despite careful planning

[18:30] How to prioritize changes effectively

[19:45] Building trust through early wins

[20:55] Involving teams without slowing decisions

[22:10] The importance of leadership accountability

[23:20] Predicting how change will unfold

[24:35] Why honesty about difficulties builds trust

[25:45] Learning from failures and moving forward

[26:58] Recognizing signs of change fatigue

[28:05] How to slow down change to prevent burnout

[29:15] Making change stick before introducing new changes

[30:25] Celebrating wins to reinforce progress

[31:40] Avoiding unnecessary changes

[32:50] Recognizing when it’s time to stop making changes

[34:05] How company culture shapes change success

[35:20] The role of communication in keeping teams engaged

Want to start a podcast like this one? Book your free podcast planning call here.

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

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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!

Ever wondered what it really takes to produce a high-quality tech podcast from scratch—while wrangling kids, late nights, and a studio in your basement?

In this rare behind-the-scenes solo episode of The CTO Playbook, Adam pulls back the curtain on the exact gear, workflows, and production team that bring each episode to life. You’ll get a candid tour of his setup—from boom mics and soundproofing hacks to lighting rigs, software automation, and the husband-and-wife editing duo who shape the final sound. Whether you're a tech leader curious about content creation, or just a gear nerd wondering how to level up your own audio-video presence, this episode delivers a crisp, tactical walkthrough of what goes into building a professional podcast from the ground up.

You’ll Learn:

• How low-tech soundproofing methods can dramatically boost audio quality
• Why lighting—not camera quality—is the secret weapon for pro-looking video
• What Adam’s minimalist mic and soundboard setup reveals about smart gear investment
• How in-ear monitors solve a hidden distraction problem in podcasting
• How to repurpose MIDI buttons and OBS for seamless video scene control
• What behind-the-scenes editing reveals about capturing a guest’s true voice
• How a modular, portable gear setup enables studio-quality content on the road
• Why recording late at night might be your best move for consistency and clarity
• How to transform a standing desk into a high-performance media station
• What working with a small production team unlocks in creativity and output quality

Timestamps:

[00:00] Introduction

[00:25] Purpose of this behind-the-scenes episode

[01:27] Who produces the podcast

[02:19] Why episodes are recorded at night

[03:00] Microphone and audio gear overview

[04:00] How the audio is routed and optimized

[05:05] Acoustic treatment in the room

[06:00] Webcam, monitor, and lighting overview

[07:15] Lighting gear and why it's travel-friendly

[08:25] Background lighting setup

[09:25] Software used to control lighting

[10:22] OBS setup and live scene switching

[11:45] Using Riverside and production handoff

[13:08] Desk setup and standing comfort

[14:10] Music used and its personal connection

[15:00] Using the setup for coaching calls

Want to start a podcast like this one? Book your free podcast planning call here.

Resources Mentioned:

Shure SM7B Microphone | Website

Elgato Low Profile Wave Mic Arm | Website

Sennheiser IE 200 In-Ear Monitors | Website

RØDECaster Duo | Website

Amaran 100X S | Website

Aputure Light Dome Mini III | Website

Keep It by Justin J. Moore and Mortiz Houwen | 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!

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.

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

Victor Nicollet is an expert in mechanical sympathy for software, focusing on how software design can better align with the hardware it runs on for smarter, faster systems.

In this episode, you're going to learn what mechanical sympathy is and why understanding your hardware can massively improve software performance, how to predict when software should be optimized instead of waiting for users to feel pain, why abstraction layers can hurt performance and how to navigate escape hatches when needed, the importance of building broad but shallow systems to keep software fast and manageable, and when it makes sense to build your own tools instead of buying or using existing ones.

Timestamps:

[00:00] Introduction

[02:00] What mechanical sympathy means for software

[07:00] Building a custom language for supply chain optimization

[09:00] Real-time analysis and scaling big data

[11:00] When to optimize before pain shows up

[13:00] Diagnosing hidden performance issues

[15:00] How hardware understanding drives smarter software

[17:00] Fighting abstraction layers to regain speed

[20:00] Data size matters more than you think

[23:00] Using smaller memory layouts for faster performance

[26:00] Lossy compression vs real-time performance needs

[29:00] Structuring broad but shallow systems

[31:00] Using optimized black boxes the right way

[34:00] Where glue code bottlenecks appear

[37:00] Build vs buy decisions based on real needs

[39:00] Why Lokad had to create its own data format

[41:00] Storing petabytes for supply chain forecasting

[44:00] Summarizing the 7-step optimization strategy

Resources Mentioned:

Lokad | Website

If you want to learn more from Victor, follow him on LinkedIn.

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.

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

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.

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.

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

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

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

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

Timestamps:

[05:09] Why networking is often misunderstood  

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

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

[13:54] Misconceptions about elevator pitches  

[16:41] How to make networking less transactional  

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

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

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

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

Resources Mentioned:

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

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

Timestamps:

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

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

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

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

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

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

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

Resources Mentioned:

Mastering Bitcoin by Andreas Antonopoulos | Book or Audiobook

Mastering the Lightning Network by Andreas Antonopoulos | Book

Bitcoin Nashville | Website

Plan B Forum in Switzerland (Oct 2024) | Website

Bitaxe Mining Device | Website

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

Join The CTO Playbook Slack Community to learn more about how to be a great CTO!

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

Timestamps:

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

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

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

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

Resources Mentioned:

Michael Lopp | LinkedIn

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

Join The CTO Playbook Slack Community to learn more about how to be a great CTO.

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

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

Timestamps:

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

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

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

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

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

Visit the Unity Edge Website and follow Dipak on LinkedIn.

Resources Mentioned:

The Golden Circle by Simon Sinek | Ted Talk

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

Join The CTO Playbook Slack Community to learn more about how to be a leader!

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

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

Timestamps:

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

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

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

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

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

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

Also, be sure to follow Carol on LinkedIn.

Resources Mentioned:

re:Work With Google | Archived Website

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

Join The CTO Playbook Slack Community to learn more about the five-step playbook!

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

Timestamps:

8:45 Make fewer decisions by delegating responsibilities.

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

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

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

Resources Mentioned:

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

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

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

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

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

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

Join The CTO Playbook Slack Community to learn more about empathic, dynamic reteaming!

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

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

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

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

Timestamps:

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

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

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

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

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

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

39:19 Why empathy should drive your leadership decisions.

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

Resources Mentioned:

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

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

Domain-Driven Design by Eric Evans | Book

Find more from Adam on LinkedIn and YouTube and 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 the rise of citizen builders is reshaping software creation, why leadership now demands alignment over control, how to measure real impact across teams, and what it takes to scale safely in a world of AI-assisted development.

Timestamps:

[00:00] Introduction

[02:00] Overview of the 4-part structure in this episode

[02:54] Principle one: everyone can build — but can they build right?

[04:53] Principle two: redefining junior vs senior in a cross-functional world

[05:38] What growth actually looks like beyond technical skill

[06:20] Principle three: abstraction saves time, understanding prevents disaster

[07:08] AI tools vs foundational knowledge

[07:47] Why elite builders accelerate others

[08:39] Principle four: direction beats control

[09:23] Teaching others how to make decisions

[09:57] Broadcasting context until it feels repetitive

[10:18] Principle five: organizational design is system design

[11:03] Avoiding the productivity dip during scaling

[11:36] Conway’s Law and communication-driven design

[12:34] Principle six: measure velocity, not busyness

[14:00] The power of aligned data visibility

[14:44] Dashboards that trigger strategic pivots

[15:20] Principle seven: developer experience is now your product

[16:00] Builders outside engineering — even the CEO

[16:36] The danger of unchecked shadow IT

[17:10] What guardrails are you offering citizen builders

[18:01] Principle eight: outcomes are the new OKRs

[18:49] Why measuring customer activation changed everything

[19:26] Shifting priorities when you focus on real outcomes

[20:00] Principle nine: solve across the organization

[20:43] Rethinking engineering as a business-wide competency

[21:08] Empowering non-engineers to solve with software

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 learn more about startups and scale ups!

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

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

Timestamps:

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

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

16:33 Constructing effective teams despite budget constraints.

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

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

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

51:01 Holding product managers accountable for prioritization decisions.

Connect with John on LinkedIn

Resources Mentioned:

Chico Hotel Solutions | Website

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

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

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

Timestamps:

3:15 Understand the stages of CTO growth.

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

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

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

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

Resources Mentioned:

The Startup CTO's Handbook by Zach Goldberg | Book

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

SaaS Academy | Website

Realforce | Website

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

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

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

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

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

Timestamps:

3:00 Addressing leadership gaps through coaching.

10:36 Emotional intelligence improvements in personal life.

16:39 Convincing CEOs about coaching benefits.

20:28 Value of external mentoring groups.

24:03 Networking opportunities at CTO events.

29:11 Managing personal expectations in leadership roles.

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

Stay connected with Andy on LinkedIn

Resources Mentioned:

CTO Craft | Website

CTO Craft Events | Website

CTO Craft | YouTube

Patrick Lencioni's Books | Amazon

Find more from Adam on LinkedIn and YouTube.

In this episode, Adam interviews Warren Beazley, a seasoned CTO recruiter, about how tech leaders can effectively communicate their professional identity and attract ideal clients. Warren shares insights into leveraging LinkedIn for networking, strategic job searching, and the importance of personal branding.

Based in the UK, Warren is one of the best CTO recruiters, even going by the tagline "The CTO Recruiter". Warren has been hiring CTOs since 1997 and has an extensive network, a proven methodology, and a desire to help. He has hired against every brief he has had since 2015!

Connect with Warren on LinkedIn and book a 15 min Intro Call!

Resources Mentioned:

Edison Hill Search | Website

Find more from Adam on LinkedIn and YouTube.

In this episode, Adam interviews Steven Renwick, who dives deep into the relationship between the CEO and CTO in early-stage startups. Steven shares his journey with Adam at Satago, emphasizing the importance of vision alignment and efficient software deployment.

Steven Renwick is a British technology entrepreneur living in Berlin, with a unique combination of experience in healthcare, fintech and technology. He is a product-focused CEO/founder with a passion for building businesses that actually make a difference in people's lives. In an earlier life, he started out working as a consultant in the pharmaceutical and biotechnology industry, advising on IP valuation, deal structuring, and M&A.

In November 2021 he co-founded Tilores, a start-up that specializes in helping tech scale-ups to radically transform their data infrastructure efficiency using Tilores, their entity resolution technology, while dramatically cutting prototyping time and decreasing operating costs. With Tilores, scale-ups can achieve unlimited processing scalability without adding a single machine or headcount to the tech budget.

Steven founded Satago in 2012 to help SMBs use technology to improve credit control and cash flow, before pivoting the company into a fintech business providing invoice finance through software. He raised ~£5M (debt & equity) to develop the business from VCs and Angels and grew the team to 16 people. He exited Satago in 2017. The company is currently listed on the Alternative Investment Market (AIM) in London.

Connect with Steven on LinkedIn

Resources Mentioned:

Tilores | Website

Satago | Website

Palantir | Website

GraphQL | Website

Find more from Adam on LinkedIn and YouTube.

Welcome to the CTO Playbook! I'm Adam Horner, your host, with over 30 years in the tech industry and more than a decade as a CTO. In this podcast, we cover essential topics, strategies, and practical advice to help CTOs excel. Join me as we explore my journey, share insights from industry leaders, and build your unique CTO playbook. Whether you're navigating the rapid changes in technology or handling growing responsibilities, you're not alone. Tune in for valuable resources, community support, and expert interviews.

In this episode, Adam shares his journey to becoming a CTO, the challenges he faced, and the reasons for starting this podcast. He also emphasizes the importance of building a personalized CTO playbook and the evolving role of the CTO.

Resources Mentioned:

Synova Tech | Website

Find more from Adam on LinkedIn and YouTube.

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

Zacharias Beckman is a technology leader and creator of the Customer Obsessed Delivery Playbook.

In this episode, you're going to learn what the Customer Obsessed Delivery Playbook is and why having a checklist is critical for complex software projects, how event storming and steel threads can help prevent costly surprises in software delivery, how Zac used lessons from government projects, cruise lines, and iPhone launches to shape a better approach to technical delivery, why a visual “subway map” model can make software development easier to navigate, and how to keep customer needs front and center throughout an entire project.

Timestamps:

[00:00] Introduction

[01:57] Why software projects need a checklist approach

[03:04] Mistakes early in Zac’s career that led to building a playbook

[05:08] The role of structure and guardrails in complex delivery

[06:04] Creativity versus consistency in engineering playbooks

[07:45] Giving teams flexibility to experiment

[09:55] Evolution of the playbook from large companies to startups

[11:03] How startups and big companies use the playbook differently

[12:58] How the playbook can uncover process gaps in existing teams

[16:30] Inspiration behind using a subway map for software delivery

[18:01] Problems Zac saw in government projects that sparked change

[19:12] Miscommunication between customers and tech teams

[20:55] How R&D uncertainty compares to building cars or bridges

[22:05] How to structure checkpoints and quality gates in delivery

[23:04] Why event storming is a crucial early exercise

[24:09] Zac’s first experience with event storming on cruise ships

[25:40] Why cruise ships are a major software engineering challenge

[26:40] How event storming reveals hidden complexity

[27:35] Importance of having business and tech teams in event storming

[28:01] What a steel thread is and why it matters

[29:12] Differences between a steel thread and an MVP

[30:02] Building end-to-end scaffolding before scaling

[31:05] Real-world example of a steel thread fixing a telco iPhone launch

[32:33] How Lightbend proved their solution in six weeks

[33:30] Why building the full system first is a mistake

[34:02] What a target state architecture is

[35:10] Why you need an incremental path to a target state

[36:05] Risks of pulling future features into early development

[36:58] Why customer needs often change during projects

[37:40] How to avoid failed big bang product launches

[38:00] How to keep the customer visible throughout delivery

[39:05] How event storms connect to engineering artifacts

[40:20] Avoiding translation errors from customer to code

[41:00] Testing outputs based on original customer events

[42:45] The importance of empirically measuring project outcomes

[43:50] Why teams must create their own processes

[44:30] How to tie product features to measurable business outcomes

The best way to connect with Zac is by subscribing to his Substack and reading his Blog.

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 win support for a tough proposal, avoid getting blindsided in meetings, use informal conversations to map your allies and blockers, and turn neutral teammates into advocates.

Timestamps: 

[00:00] Introduction

[01:04] A failed pitch story and key lesson

[02:18] The importance of having a playbook

[02:55] Why great ideas get shot down

[03:12] Stage 1: Test the waters

[04:40] How early insights shape your pitch

[05:30] Stage 2: Understand the numbers

[06:00] Identify veto players and the majority needed

[06:45] Plan around timing and meetings

[07:30] The power of loud voices in group settings

[08:10] Stage 3: Strengthen your supporters

[08:50] Ask for feedback, not support

[09:30] Involve people by including their suggestions

[09:50] Win over key skeptics

[10:20] Turning opponents into advocates

[10:50] Leverage respected voices in the group

[11:15] Why being heard matters more than being right

[11:35] Coaching for executive communication

[12:10] Why logic often loses to emotion

[12:50] How storytelling wins the room

[13:20] Stage 4: Engage the neutrals

[13:50] Connect your idea to their priorities

[14:15] Use win-win framing for middle-ground people

[14:40] Avoid turning neutrals into opponents

[15:00] Use social proof to tip the balance

[15:30] Stage 5: Presentation and decision

[16:20] Call out contributors by name

[16:45] Make it feel like the next logical step

[17:00] Keep the decision meeting short and smooth

[17:45] How to avoid meeting debates and delays

[18:00] Creating watercooler moments in remote work

[18:30] How to test ideas before remote meetings

[19:25] Follow-up strategy after remote conversations

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!

Andre Louca is a former CTO who became the CEO of a deep tech startup focused on AI and computer vision. 

In this episode, you'll learn what it takes to move from CTO to CEO, how to set yourself up for success in the new role, what mindset shifts are needed to lead a company, and how to make tough decisions without losing trust.

Timestamps:

 [00:00] Introduction

[05:00] Understanding customer needs

[07:00] Becoming the CTO of Work Analytics

[09:00] Using cloud computing to accelerate processing times

[11:00] Corate's IP and technology structure

[13:00] Becoming the CEO of Corate

[15:00] Ensuring product readiness before transitioning to CEO

[17:00] Dealing with role transitions and maintaining approachability

[19:00] Dealing with surprises and the learning curve of being CEO

[21:00] Learning from sales and marketing experts

[23:00] Transitioning skills from CTO to CEO

[25:00] Setting and achieving continuous goals

[27:00] Using short-term goals to drive energy and performance

[29:00] Celebrating milestones with the team

[31:00] Importance of analyzing decisions analytically

[33:00] Making difficult decisions with a rational approach

[35:00] Balancing technical leadership and business leadership

[37:00] Networking and relationship-building with the board

[39:00] Gaining trust from non-technical board members

[41:00] Importance of delivering results and building credibility

[43:00] Coaching and accepting help from others

[45:00] Focusing on the business, not just technology

To learn more from Andre, connect with him 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!

Eric Johannsen is an engineering leader, author, and father of triplets who has helped lead multiple startups to successful exits.

In this episode, you're going to learn what cultural transformation really means and why it matters, how to spot when company culture is blocking progress, how Eric won over skeptics during high-stakes mergers, how he overcame imposter syndrome early in his career, and the single biggest mistake he made during a transformation—plus what he learned from it.

Timestamps:

[00:00] Introduction

[00:55] Finding balance between work and family

[02:10] What is cultural transformation?

[02:55] Misalignment between culture and strategic goals

[04:05] Eric’s early experience with resistance to change

[05:30] Imposter syndrome during Eric’s first job

[06:50] Overcoming resistance through communication

[07:55] Field trips to understand user problems

[09:20] Improving communication at DOMA Financial

[10:25] Building trust through consistency and safety

[12:30] Admitting mistakes and building trust

[13:35] Developing confidence

[14:10] Early career mistakes in leadership

[16:10] Integration of different work cultures

[17:10] Challenges of post-merger cultural blending

[19:00] Achieving success through cultural transformation

[20:05] Creating a culture of empowerment and communication

[22:15] Importance of humility and listening

[24:00] Encouraging participation and transparency

[25:55] Using metrics to show progress

[27:45] Psychological safety and overcommunication

[29:55] Managing risk without stifling creativity

Learn more from Eric on his website and follow him on LinkedIn.

Eric's Books

The Gods We Make by Eric Johannsen | Book

The Gods We Seek by Eric Johannsen | Book

Ji-min by Eric Johannsen | Book

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!

Sarah Greasley is an IBM Distinguished Engineer turned CTO with over 40 years in tech, known for leading large-scale transformation projects at companies like IBM, Direct Line, and AWS.

In this episode, you’ll learn how to lead complex tech projects without getting lost in details, make tough calls when short-term goals clash with long-term needs, and understand why managing technical debt is a leadership issue, not just an engineering one. Sarah shares practical ways to align thousands of people, how language, culture, and clarity impact success.

Sarah was EMEA Director for Solution Architecture at AWS, leading a 1,300-person team, supporting over 612,000 customers, and driving AI, diversity, and inclusion initiatives. Before that, she was Group CTO at Direct Line Group, delivering tech strategy, architecture, and £100m+ programs, transforming the business for 5 million UK customers and doubling gender diversity in tech. Earlier, Sarah was IBM Technical Director and Distinguished Engineer, creating architectures for major financial services clients.

Timestamps:

[0:00] Introduction

[03:30] Moving from IBM to Direct Line Group

[05:10] The importance of purpose in career decisions

[06:30] Handling complexity between program goals and enterprise needs

[08:00] Leading with alignment in large organizations

[09:45] Reading between the lines in communication

[10:50] Different meanings of risk in insurance

[12:00] Learning to ask better questions instead of having all the answers

[13:30] Losing technical expertise and shifting to architectural thinking

[15:00] Cloud migration challenges at Direct Line

[16:30] Building scalable cloud solutions with performance testing

[17:55] Moving away from legacy mainframes

[18:50] Lessons from working on ATMs in the 1980s

[20:00] Building future leaders and emotional intelligence in teams

[21:30] Managing technical debt during high-stakes changes

[23:00] Human capital and specialist knowledge in legacy systems

[24:20] Aligning org structure with tech for adaptability

[25:40] Using analogies to explain technical debt

[27:10] The role of allies in building inclusive cultures

[28:30] Subtle meeting dynamics and how to navigate them

[29:50] Writing inclusive job specs that attract more women

[31:10] The importance of visible female role models

[32:20] Emotional intelligence as a leadership skill

[33:40] Thinking beyond tech: money and the business view

[35:00] Learning to let go and trust your team

[36:20] Building consensus in large enterprises

[37:40] The value of “disagree and commit”

[40:40] Structural changes that enable diversity and inclusion

[41:45] Leaving IBM after 33 years and embracing change

[43:00] First three things to do as a new CTO

[44:30] Owning your schedule and not apologizing for it

Want to start a podcast like this one? Book your free podcast planning call here.

Follow Sarah Greasley on LinkedIn

Resources Mentioned:

CTO Academy | Website

Radical Candor by Kim Scott | Book or Audiobook

Disagree & Commit by Justin Kuester | Kindle

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!

Stop Doing These 14 Things If You Want to Be a Great CTO



I’m not adding to your to-do list—I’m flipping it. These are the habits that keep you reactive, overwhelmed, or straight-up invisible to the rest of the exec team. I walk through the traps that I see CTOs fall into again and again, from packing your calendar like a bad game of Tetris to leading every decision and chasing every shiny trend. These aren’t theories. They’re mistakes I’ve coached dozens of tech leaders through—and screwed up myself too.

You’ll Learn:

• The real reason packing your calendar wall-to-wall kills strategic thinking
• What happens when you delegate tasks but not decisions
• The quiet damage of assuming your team understands the company vision
• Why translating tech into business outcomes changes your exec team influence
• The simple phrase that makes hard feedback easier to hear and act on
• What it feels like to stop chasing trends and start trusting fundamentals
• The surprising link between avoiding trade-offs and leadership gridlock
• How overusing jargon weakens your clarity and authority
• What most CTOs get wrong about culture—and how to fix it
• Why punishing mistakes kills innovation faster than any bad process

Timestamps:

[00:00] Introduction

[03:06] Why filling every hour kills your ability to lead

[04:15] The problem with working without strategic alignment

[05:01] Delegating tasks vs delegating decisions

[06:41] What happens when people don’t understand the vision

[07:50] How to translate engineering into business language

[08:55] Why leading with opinion weakens your credibility

[10:00] The cost of chasing every shiny trend

[11:00] You can’t scale if you lead everything alone

[12:58] How to have hard conversations and handle feedback

[13:54] Why jargon destroys clarity and influence

[14:50] What culture is actually made of

[15:36] Stop punishing mistakes if you want innovation

[16:31] The danger of forcing rigid frameworks

[17:29] How indecision leads to gridlock

[18:49] Quick-fire recap of the 14 habits to stop

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!

Are you managing your individual contributors in a way that fuels growth, performance, and alignment?

In this episode, I’m talking with Faris Aranki, founder of Shiageto Consulting, about leading individual contributors through regular one-on-one meetings. Faris brings a wealth of experience from his career in strategy consulting and leadership coaching. We dive into a proven system for structuring these meetings to keep performance management simple, effective, and human-centered.

We explore how to align individual performance with company goals, why weekly check-ins are crucial, and how to integrate these meetings into your larger performance frameworks. Faris also shares how building rapport and listening actively can lead to stronger relationships with your team, ensuring that growth is both continuous and aligned with the broader mission.

You’ll Learn:

• The real reason weekly one-on-ones are critical for individual contributor success
• Why a rolling agenda document is your most powerful tool in building trust and accountability
• How to use silence strategically in one-on-one meetings to encourage deeper conversation
• The quiet damage of neglecting active listening in engineering teams
• What it feels like to lead with empathy and get results without micromanaging
• How to align individual performance with company goals through simple, structured conversations
• The surprising link between personal development plans and long-term organizational success
• Why you should avoid status updates in one-on-ones and focus on personal growth
• How asking the right questions based on learning styles can level up your coaching approach

Timestamps:

[00:00] Introduction

[06:30] The impact of the rolling agenda document on trust and accountability

[08:00] How to structure one-on-ones to focus on personal growth and alignment

[10:15] The role of silence in encouraging deeper conversations

[12:00] How active listening can strengthen team communication and trust

[16:30] Using the VARK model to tailor coaching to individual learning styles

[19:10] How to integrate weekly, quarterly, and annual meetings into a performance management system

[22:50] The benefits of focusing on experience over output in one-on-one meetings

[25:00] Handling performance improvement plans and documentation for legal clarity

[28:30] How to use one-on-ones to build influence and promote personal development

[32:00] The importance of aligning individual goals with company objectives

[34:50] Best practices for conducting quarterly and annual performance reviews

Resources Mentioned:

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

Leaders Eat Last by Simon Sinek | Book or Audiobook

Hanlon's Razor | Principle

Movie: Moneyball

You can connect with Faris on LinkedIn or take the Shiageto effectiveness assessment here.

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!

Are you managing individual contributors the best way possible?



In this episode, I sit down with Peter Wong, a seasoned CTO, to discuss how to lead individual contributors effectively with a structured and personalized approach. You’ll hear how weekly one-on-one meetings, a simple but powerful rolling agenda, and understanding how each person learns can take performance management from stressful to seamless.

We dive into how this method helps you align your team with company goals, nurture personal growth, and create trust—ensuring the continuous development of your engineering team, one conversation at a time. This approach ensures clarity and consistency, allowing your team to thrive.

You’ll Learn:

• Why weekly one-on-one meetings are more powerful than lengthier sessions
• The real reason a rolling agenda can transform your leadership approach
• How to foster trust and build rapport by simply listening more than speaking
• What happens when you tailor your questions to how each person learns
• The surprising link between performance management and building personal connections
• Why writing things down in meetings isn’t just a formality—it’s a trust-builder
• The quiet damage of skipping regular check-ins with your team
• What it feels like to have an annual review with zero surprises
• The key to making performance feedback feel like a natural progression
• How to use small actions like weekly meetings to drive big results over time

Timestamps:

[00:00] Introduction

[05:25] How to build trust through active listening in one-on-ones

[06:45] Tailoring questions to different learning styles for better coaching

[08:05] The value of writing things down in meetings

[09:20] Structuring one-on-one meetings for maximum impact

[11:15] Keeping feedback focused on personal growth

[12:40] The power of regular check-ins for performance momentum

[14:05] Linking weekly meetings to quarterly and annual reviews

[15:35] Using the VARK model to understand how your team learns

[17:10] Handling performance improvement plans effectively

[21:00] Simplifying annual reviews with structured feedback

[22:45] Making performance reviews a natural progression

[28:05] The role of a structured approach in leadership

[30:10] Why a rolling agenda document is a game-changer

You can connect with Peter and learn more about his work through his LinkedIn and 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!

Are you getting the most out of your individual contributors?

In this episode, I sit down with Matan Kubovsky to dive into the art of managing individual contributors through weekly one-on-one meetings. Matan shares his experience and a proven system for leading teams with consistency, clarity, and alignment. This method isn’t just about project updates—it’s about shaping growth and connecting each person’s role to the broader organizational mission.



We cover how to structure meetings, build trust, and set the right cadence to keep momentum going. Matan also discusses how to track progress with a rolling agenda and how to use the VARK learning model to tailor coaching to the team’s learning styles. Whether leading a small team or guiding team leads, this episode is packed with actionable insights to make performance management smoother and more effective.

You’ll Learn:

• The real reason weekly one-on-ones are the most powerful tool for individual contributor growth
• What happens when you set the right cadence for meetings and stick to it
• The surprising link between active listening and building trust with your team
• Why silence in meetings can be your secret weapon to get more from your team
• How to use the VARK model to tailor coaching and accelerate learning
• The quiet damage of losing momentum by meeting less than once a week
• What it feels like to lead with clarity by aligning individual performance with company goals
• Why recording your one-on-one meetings can build confidence and create valuable evidence
• The key difference between a mission statement and a personal development plan
• How to avoid the performance review “surprise” by keeping a rolling agenda document

Timestamps:

[00:00] Introduction

[06:30] Why many engineering teams lack performance management skills

[08:05] The problem with annual performance reviews

[09:35] How feedback frequency impacts team performance

[11:10] The Start/Stop/Continue framework explained

[13:25] The need for weekly one-on-one meetings with individual contributors

[16:05] Why silence in meetings can drive more meaningful conversations

[19:15] How to help engineers improve their listening and communication skills

[21:40] The importance of shifting focus from output to experience in meetings

[25:00] Why keeping a rolling agenda document is essential for tracking progress

[30:20] How to structure quarterly reviews and set goals for the next quarter

Resources Mentioned:

McKinsey Research | Website

You can connect with Matan through his Linkedin or schedule a meeting to learn more here.

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