The CTO Playbook

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.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Timestamps:  [00:00] 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 conversationsFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Andre Louca is a former CTO who became the CEO of a deep tech startup focused on AI and computer vision.  Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you'll 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 technologyTo learn more from Andre, connect with him on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Eric Johannsen is an engineering leader, author, and father of triplets who has helped lead multiple startups to successful exits.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you're going to learn what cultural 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 creativityLearn more from Eric on his website and follow him on LinkedIn.Eric's BooksThe Gods We Make by Eric Johannsen | BookThe Gods We Seek by Eric Johannsen | BookJi-min by Eric Johannsen | BookFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you’ll 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 itWant to start a podcast like this one? Book your free podcast planning call here.Follow Sarah Greasley on LinkedIn Resources Mentioned:CTO Academy | WebsiteRadical Candor by Kim Scott | Book or AudiobookDisagree & Commit by Justin Kuester | KindleFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Discover the art of transforming leadership in large engineering teams. Learn how to mitigate politics and knowledge gaps to foster a high-trust environment. Uncover the innovative shift from one-on-one coaching to group leadership techniques used by top CEOs. Explore strategies to enhance communication and align teams effectively. Embrace the power of shared problem-solving and the importance of structured leadership approaches to improve decision-making and management in growing organizations.

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.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you’ll learn why managing change is more about people than processes; how to overcome resistance and build trust in an organisation; how to sustain momentum during long-term transformations; how to make tough personnel decisions while maintaining morale; and why knowing when to stop making changes is as important as knowing when to start.With over 25 years in technology, Kevin Howren has driven transformative change through deep technical expertise and strategic vision. He is committed to innovation, operational excellence, and building high-performing teams, turning complex challenges into growth opportunities.He led the post-acquisition transformation of NPACT, guiding engineering, product, AI, and infrastructure teams to achieve significant results, including doubling the customer base and increasing SaaS assets under management from $50 billion to $100 billion. He consistently aligns technology and business strategy to support long-term growth and sustainability. Whether modernising the technology stack, improving cross-departmental collaboration, or mentoring senior leaders, his focus is on continuous improvement and delivering value to the organisation and its customers.Before NPACT, he was Head of Client Technologies at BBC Systems, overseeing product and infrastructure development and leading UI/UX engineering and product teams. A key achievement was reducing production rollbacks by 78% through innovative processes and 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 engagedWant to start a podcast like this one? Book your free podcast planning call here.Follow Kevin on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Discover the world of CTO coaching and its transformative impact on leadership. The discussion highlights common challenges faced by CTOs and shares personal journeys from technical roles to executive positions. Dive into the five unique CTO archetypes: the firefighter, the seasoned technologist, and more. Learn how structured coaching can boost confidence, tackle stress, and enhance strategic influence. Real-life stories illustrate the importance of investing in personal growth and navigating the complexities of leadership.

Dan Gwalter is a fractional consultant and former IT director who helps businesses navigate growth challenges.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you're going to learn why 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 practiceKickstart 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 explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Discover the art of effective one-on-ones to boost engineer performance! Learn how to structure meetings for maximum impact, focusing on active listening and rapport-building. Explore the benefits of a rolling agenda and documentation for tracking progress. Transition seamlessly from regular check-ins to comprehensive quarterly reviews. Enhance personal development with tailored learning strategies and actionable insights that align individual goals with company missions.

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