Episodes

  • 93: From SDLC to ADLC: How Engineering Teams are Actually Adopting AI

    93: From SDLC to ADLC: How Engineering Teams are Actually Adopting AI
    Apr 28 2026

    A CTO hired a star engineer to push AI adoption forward, and within months, the team had lost its momentum, the new hire, and any sense of where they actually were.


    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.


    Almost every CTO Adam speaks to right now is carrying the same thing: exhaustion beneath loud pressure. The board wants speed. Investors want an AI strategy. The voice in their own head says everyone else has worked something out that they haven't.


    The pressure to go faster with AI is usually the signal that the real work is somewhere else. Adam has watched organizations try to leap from pure experimentation to mature AI practice through a single hire, and watched what breaks when they do.


    The fastest engineering teams aren't tuning the engine first. They're upgrading the brakes and tires, the testing automation, the review systems, and the people around the work, before they touch raw speed.


    Tune in to learn about the three-stage pattern of AI adoption, two contrasting examples that show what acceleration actually costs, and the three postures that separate the CTOs making real progress from the ones spending money to look busy.


    You’ll Learn:


    [00:00] Introduction

    [01:08] Why CTOs feel behind even when they’re moving fast

    [02:48] The three stages of AI adoption and where most teams get stuck

    [05:12] Why skipping stages creates friction that slows the whole team

    [08:34] How lack of standards turns fast progress into team-wide frustration

    [15:06] Why slowing down in the right way is what actually moves teams forward

    [23:11] How to spot your team’s real stage and decide what to do next


    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.
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    25 mins
  • 92: The CTO Playbook: How to Build Trust, Consistency, and Psychological Safety in Engineering Teams

    92: The CTO Playbook: How to Build Trust, Consistency, and Psychological Safety in Engineering Teams
    Apr 20 2026
    The difference between a good CTO and a trusted one often comes down to a personal playbook.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.Sam Boswell is the CTO of Terralayr, an energy tech company focused on solving global energy storage challenges. With a background in high-risk infrastructure and scaling engineering teams, he brings a practical lens to how leadership actually works.At the center of that philosophy is a simple idea. Engineers don’t follow leaders because they’re the most technically brilliant person in the room. They follow leaders who are consistent.That consistency doesn’t happen by accident. It comes from a personal playbook. A set of lived principles that shape how decisions are made, how problems are approached, and how people are treated.We get into how that playbook forms over time, why documenting how you think matters more than most leaders realize, and what happens inside teams when that consistency is missing.The result is a grounded look at leadership that moves beyond theory. It shows what it takes to build trust, create safety, and lead in a way people actually want to follow.You’ll Learn:[00:00] Introduction[05:12] The shift from coding to leading people[07:45] Turning ideas into outcomes without touching the code[12:18] Why consistency earns trust faster than brilliance[15:42] Writing as a tool for clearer thinking and better leadership[18:36] What breaks inside teams when leadership is inconsistent[22:04] The power of a personal user manual for faster trust[26:31] There’s always a move, even when you feel stuck[30:12] Small principles that compound into better decisions[36:48] Psychological safety as the foundation of real performanceResources Mentioned:OODA Loop | WikipediaThe Joel Test: 12 Steps to Better Code | WebsiteNotion | WebsiteKnolling | WebsiteTom Sachs’ 10 Bullets | WebsiteTime Enough for Love by Robert Heinlein | Book or AudiobookJoyful Militancy: Building Thriving Resistance in Toxic Times by Carla Bergman and Nick Montgomery | Book or AudiobookEve Online | Video GameKanban Tool | WebsiteFind more from Sam 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.
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    44 mins
  • 91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge

    91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge
    Apr 13 2026
    What if leadership isn’t about managing people, but about owning decisions?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.I’m joined by Michael Di Prisco, who describes himself as “a software engineer struggling to realize that he became a tech leader”.Michael was pretty reluctant to become an engineering manager and leave the keyboard, but he started moving outside his comfort zone one step at a time. He gradually found a balance where he still writes code, but it is not expected of him.We explore how authority and responsibility actually work inside a team. He explains why every engineer should understand the business, and what changed when he started delegating code instead of doing everything himself. That shift did not slow the team down. The quality of their coding was becoming better, and people could focus on what they wanted to do more.We also get into documenting technical debt and how his team reached a point where they solved more debt than they created.If you are thinking about the move into leadership, this is a grounded look at what that shift might actually involve.You’ll Learn:[00:00] Introduction[02:05] Stepping into leadership felt like losing his edge as an engineer[06:45] A small move outside your comfort zone can shift your entire career path[08:30] Coding stopped being expected and started becoming a deliberate choice[12:10] Teams can improve when a tech lead stops doing all the coding and starts delegating[16:20] The hidden gap between responsibility and authority most teams never fix[20:15] Engineers make weaker decisions when they don’t understand the business[24:40] Letting go of best practices can reveal what actually works in your context[27:10] Documenting technical debt can lead to actually reducing it over time[31:25] Small steps and honest feedback often outperform big career movesResources Mentioned:The Software Architect Elevator: Redefining the Architect's Role in the Digital Enterprise by Gregor Hohpe | BookArchitectural Decision Records (ADR) | WebsiteGitHub | WebsiteAstro | WebsiteCodeMotion Conference | Websitejsday - The Italian JavaScript Conference | WebsiteItalian Agile Days Conference | WebsiteDive deeper into Michael’s ideas on software engineering and leadership on his blog.Find more from Michael 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.
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    39 mins
  • 90: Data Is a Leadership Problem, Not a Technical One — A Playbook for CTOs

    90: Data Is a Leadership Problem, Not a Technical One — A Playbook for CTOs
    Apr 6 2026
    Most teams don’t have a data problem; they have a decision problem.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.Nic Granger, Chief Information and Financial Officer at the North Sea Transition Authority, joins me to share her perspective from the intersection of data, finance, and transformation in a highly complex, regulated industry.Nic leads a multidisciplinary portfolio spanning digital, data, and core services, with a focus on enabling better decisions across the energy transition.We get into why data strategy is fundamentally a human challenge, not just a technical one, and how data-driven decision making only works when people can actually access and trust the data. You’ll hear how data leadership shifts when the goal isn’t dashboards, but real-world outcomes like energy security and decarbonization.We also unpack why jumping straight to AI in business often misses the point, and what it really takes to build strong data foundations that support scale. If you’re responsible for digital transformation or shaping CTO strategy, this will likely reframe how you think about value, not just volume.You’ll Learn:[00:00] Introduction[03:15] The value of data has nothing to do with the data itself, and what it actually comes down to[07:30] Nic's realization that turning petabytes into value is a people problem, not a technology problem[10:05] The mistake most organizations make with data is jumping to AI before they've solved anything[13:00] What decades of vital data trapped in unreadable PDFs look like, and what AI is doing about it[16:45] Making industry data freely available unlocked competition from smaller players and academia in ways nobody expected[21:20] Your team is probably already asking the right data questions; you just have to listen for them[27:45] The reason Nic's team swapped the word "process" for "workflow" and what the language shift actually changed[31:20] Digitizing a paper trolley process revealed hidden data that now predicts industry trends[37:00] The one thing Nic says every CTO should prioritize in the next 90 days to unlock data valueIf you want to support the work Nic mentioned, become a member of the Bat Conservation Trust. Resources Mentioned:CTO Craft | WebsiteUK National Data Repository (NDR) | WebsiteBat Conservation Trust | WebsiteFalklands Conservation | WebsiteLovable AI | WebsiteBase44 | WebsiteIf you want to support the work Nic mentioned, become a member of the Bat Conservation Trust. Find more from Nic Granger 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.
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    38 mins
  • 89: Engineering Velocity for CTOs: How Superhuman Moves Fast Without Sacrificing Quality

    89: Engineering Velocity for CTOs: How Superhuman Moves Fast Without Sacrificing Quality
    Mar 30 2026

    If your team feels busy but nothing meaningful gets delivered, this might explain why.


    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.


    Loïc Houssier, an engineering leader with two decades of experience across startups, scale-ups, and global companies, joins me today to explore how engineering velocity really works beyond output metrics.


    We get into why decision-making speed is often a better indicator of performance than output, and how long feedback loops kill momentum, even in teams that look productive on the surface. You’ll hear how product-led SaaS organizations sustain speed without sacrificing quality, and why reducing the cycle from idea to impact matters more than optimizing coding time.


    Loïc shares how career ladders and incentives shape behavior in ways most leaders overlook, along with a practical way to spot whether your team is truly fast or just performing speed. We also unpack how user empathy becomes a strategic advantage, not just a design principle.


    If you’re trying to scale without losing control, this will change how you think about speed, decisions, and what actually drives results.


    You’ll Learn:


    [00:00] Introduction

    [8:52] Why velocity isn't really about writing code faster, and where the time is actually going

    [17:00] The costly mistake Loïc made at DocuSign that he'd still fix if he could go back

    [21:55] The career ladder is slowly shaping engineer behaviour, and most CTOs aren't using that deliberately enough

    [31:55] Moving fast without losing quality; what aligned autonomy looks like in practice, and the hiring filter that makes it possible

    [38:57] How Superhuman's founder uses game design thinking, a 100ms rule, and an 11-star standard to build experiences people actually feel


    Save 4 hours every week with Superhuman Mail.


    Find more from Loïc Houssier 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.
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    49 mins
  • 88: The CTO Role Has Changed — Why Doing More Isn’t the Answer

    88: The CTO Role Has Changed — Why Doing More Isn’t the Answer
    Mar 24 2026

    Why does the CTO role feel heavier after you start winning?


    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.


    Many leaders in CTO leadership roles are shipping products, raising funding, and hiring well, yet describing a new weight in the role. Decisions feel more loaded. Progress becomes harder to define. The work carries more consequence even when the calendar looks the same.


    The modern Chief Technology Officer now sits at the intersection of strategy, narrative, and emerging AI strategy expectations. Boards want direction. Executive teams want clarity. The scope expands faster than it is redefined. Pressure no longer replaces pressure. It stacks. That stacking changes the nature of technology leadership.


    This episode focuses on leadership orientation as the skill that restores executive clarity. Orientation answers two questions before speed: where you are, and which way you are facing. Without it, motion creates confusion at scale.

    

    For startup and scale-up leaders navigating CTO career growth, this reframes heaviness as a threshold moment that requires recalibration before acceleration.


    You’ll Learn:


    [00:00] Introduction

    [00:46] Why feeling heavier after success can mean the role itself has shifted into a new level of leadership

    [02:12] What it means when momentum is strong but you are no longer sure where the role is taking you

    [03:18] How the CTO role crosses a threshold from execution into something more abstract and executive

    [05:32] Why stacked pressures are changing the nature of the work rather than simply increasing it

    [06:34] How expanded scope and collapsing time to credibility create hidden cognitive load

    [09:42] What the treadmill metaphor reveals about working harder without changing your position

    [11:02] Why reorienting before accelerating is the maturity move most CTOs resist

    [14:32] The four diagnostic questions that expose where you are still leading from old metrics

    [15:47] Three practical orientation shifts that reduce friction and restore clarity in real time


    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

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    17 mins
  • 87: AI Governance for CTOs: Turning AI Risk Into Competitive Advantage

    87: AI Governance for CTOs: Turning AI Risk Into Competitive Advantage
    Mar 17 2026
    What if the biggest risk in your AI strategy isn’t the technology, but the assumptions you never question?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.Today I’m joined by Jill Heinze, an AI Foresight and Strategy Architect who helps mid-size organizations turn AI risk management into sustainable competitive advantage. With a background spanning academic librarianship, market research, digital product strategy, and executive AI governance, Jill has built responsible AI frameworks for Fortune 500 clients and led the creation of a formal governance committee inside a major consultancy.Many executive teams default to speed and competitive pressure when shaping AI strategy, often without structured reflection on downstream impact. Jill explains how anticipatory thinking and structured empathy exercises surface risks that technical teams rarely identify in isolation. She introduces her anticipatory AI horizons and outlines how reframing responsible AI from compliance overhead to strategic discipline strengthens long-term positioning.If you are a CTO balancing board expectations, generative experimentation, and operational deployment, this episode sharpens your thinking around AI leadership, foresight, and building technology that accounts for the human systems it touches.You’ll Learn:[00:00] Introduction[03:18] Why generative AI felt like a whole new animal and the moment that forced a rethink of responsible deployment[05:12] The pattern of we need to be first we need to be fast and what that urgency costs organizations[06:47] How direct user research exposes risks teams never see when they focus only on the technical problem[09:08] What shifts when you treat risk evaluation as part of every AI proof of concept instead of a brake on progress[12:14] The reason some risks are endemic to generative AI itself and how that reframes acceptable use cases[17:36] Why checklists create false confidence and how thinking in horizons changes the way you design and deploy[33:02] The question how do you know that’s true and why challenging embedded assumptions can alter the trajectory of a project[40:18] Where to start if you already have a live AI system and a concern you can’t quite articulate[44:07] The grounding question every CTO should ask before the next AI initiative what are we hurrying up forResources Mentioned:NIST AI Risk Management Framework | WebsiteDownload The Four AI Horizons Guide or schedule a free consultation with Jill Heinze.Find more from Jill on her LinkedIn, YouTube, and Website. 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.
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    45 mins
  • 86: Why Communication Is Now a Core Skill for CTOs and Senior Engineering Leaders

    86: Why Communication Is Now a Core Skill for CTOs and Senior Engineering Leaders
    Mar 10 2026

    What if the most underused asset in your tech organization is your voice?


    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, I sit down with Kathleen Lucente, founder and CEO of Red Fan Communications, to explore why communication is now a core leadership capability for enterprise technology leaders.


    Stepping into the role of business leader changes everything, and learning to speak the language of finance is essential inside the boardroom. The most effective CTOs build influence across the C-suite by understanding how the CFO, CMO, CEO, and head of sales each think about value.


    Kathleen reflects on her career in high-tech PR, from journalism at EDN to shaping innovation narratives at IBM Research and advising companies through IPO moments. Her experience shows how authority is built long before a keynote or media interview.

    

    If you’re focused on CTO leadership, executive communication, and increasing your influence in the enterprise, this conversation will challenge how you think about your role and your voice.


    You’ll Learn:


    [00:00] Introduction

    [01:32] Seeing yourself as a business leader shifts your authority inside the enterprise

    [02:18] Speaking finance earns real credibility in the boardroom

    [03:07] Building trust across the C-suite meaningfully changes your impact

    [04:12] Ignoring competitor visibility weakens your overall strategic presence

    [10:24] Early work with engineers exposed deep communication gaps

    [14:38] Turning complex tech into stories business leaders value

    [21:17] Innovation stories must clearly connect to business priorities

    [29:46] Thought leadership can significantly accelerate a CTO's career

    [37:52] Strong communication systems build influence long before you take the stage


    If you’re a CTO approaching a high-stakes transition, whether that’s an IPO, major funding round, acquisition, or significant market repositioning, click here and take our FREE brand positioning assessment to benchmark your company’s messaging and discover if there are gaps between your leadership, marketing, and sales teams that need attention.


    You can connect with Kathleen on her 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.
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    44 mins