The CTO Playbook

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.

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 stageIf 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.

What if speed as a CTO has less to do with urgency and more to do with discipline?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 Bastien Duret, CTO at a French-American company building web-based products in the clinical trials space, to unpack what “moving fast” really means in complex technical environments.As CTOs, we’re taught to value urgency. But when you’re debugging memory leaks across fragmented Android devices or responding to a vendor outage that brings your entire service down, speed starts to look different. The real question becomes when to stem the bleeding and when to slow down long enough to actually learn.We get into what that shift looks like in practice, how leadership changes when problems become learning opportunities, how postmortems build long-term velocity, and why incident response reveals the true operating system of your team.If you’re responsible for uptime, technical strategy, and building resilient teams, this episode will challenge how you think about speed, progress, and sustainable execution.You’ll Learn:[00:00] Introduction[04:32] Why fragmented Android devices force you to rethink what quality really means[06:48] How crash reports expose flawed assumptions you didn’t see[08:21] The difference between fixing pain fast and learning from the mistake[09:47] What to do when a vendor outage takes down your entire service[11:18] The tension between contractual SLAs and your own uptime standards[18:36] Why firefighting feels productive but fuels repeat failures[28:14] How postmortems turn incidents into long-term acceleration[39:52] The mindset shift from frantic execution to smooth accelerationClinical research shouldn’t be limited to a handful of sites. See how Inato helps sponsors reach more diverse patients, faster.You can connect with Bastien 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.

What if redefining one simple phrase could change how your entire organization delivers value?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.Why does the definition of ‘done quietly’ determine whether engineering effort turns into real business impact? In this episode, I share a coaching story from a CTO leading a busy organization where motion looked like momentum, but nearly everything stalled just before completion. The teams were working hard, yet features lingered in limbo, ownership blurred, and frustration built across engineering and product.There is a mental model that reframes software delivery using a familiar sports analogy, showing why writing code or merging branches doesn’t move the scoreboard. Impact only happens when work reaches production, is absorbed by the organization, and enables the next move. This lens exposes how excessive work in progress stretches timelines, fragments focus, and erodes fulfillment for senior engineers.I talk about what changes when leaders stop tracking activity and start insisting on outcomes. For anyone responsible for CTO leadership, engineering productivity, or scaling teams without burning them out, this conversation challenges how you measure progress and where you apply pressure.You’ll Learn:[00:00] Introduction[01:12] How teams stay busy yet fail to move the business forward when finishing is unclear[02:08] What happens when too much work in progress creates motion without results[03:07] Why writing code and merging branches do not equal business impact[03:56] How the basketball scoreboard analogy reshapes what done really means[05:14] The leadership question that exposes activity over outcomes[06:41] What changes when nothing new starts until something is fully done[08:27] How redefining done restores ownership, focus, and team satisfactionFind 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.

What if the most dangerous thing we build as leaders is certainty?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 sit down with fellow technology leader Joe Thompson, to examine how ethical technology leadership shows up in the smallest day-to-day decisions, not the mission statements. A CTO mindset shifts once it becomes clear that the products being shipped shape how people work, think, and feel long after the roadmap is finished. Responsibility enters the work through a design-led lens that starts with user research and carries through product strategy grounded in usability, accessibility, and cognitive load.Earlier in my career, optimizing metrics felt sufficient. That belief changed after seeing software become a primary work tool for thousands of people who had little choice but to live inside it every day. Tech for good emerges here as a leadership posture rather than a side initiative, rooted in intention, influence, and awareness. Digital transformation sharpens that responsibility further, with the power to narrow or expand who technology truly serves as analog channels steadily disappear.If you’re navigating scale, pressure, and trade-offs as a technical leader, this episode is an invitation to slow down, ask better questions, and lead with impact rather than assumption.You’ll Learn:[00:00] Introduction[03:01] Why design-led products start with user research, not features[04:27] How optimizing for one metric creates invisible usability and accessibility debt[07:12] When you realize your software becomes someone’s full-time work environment[23:04] Why teams ship products without thinking through real-world user impact[29:18] How engagement algorithms shape behavior and quietly reward harmful patterns[31:07] What ethical leadership looks like without lecturing or moral grandstanding[35:02] Why AI feels revolutionary while productivity barely moves[42:21] Where tech leaders should start when thinking about impact and responsibility[47:00] How values, influence, and intent guide better technology decisionsResources Mentioned:No Silver Bullet Essence - Accident in Software Engineering by Brooks F. | ArticleYou can connect with Joe and his work through his LinkedIn here.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.

Are you running faster with AI, or just running blind?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.Most teams don’t lack data, they lack understanding. Today, I sit down with CTO Jason McGhee, who has spent years inside analytics, machine learning, and product teams asking the hard question: why is the data changing?AI in analytics works best when it supports human judgment instead of replacing it. A hybrid approach keeps people involved while AI assists with complex tasks, making decisions clearer and systems easier to reason about. Moving faster with AI increases risk when teams cannot explain why the data is changing.Both recurring reports and one-off investigations break down without context. Dashboards often fail as real deliverables because they separate numbers from explanation. Insight becomes more actionable when it is shared alongside the data itself. Screenshots, slide decks, and disconnected tools add friction, making validation harder and discouraging deeper questions from leaders.If you care about data-driven decision making, want a more honest relationship with machine learning outputs, or are figuring out how generative AI fits into real-world business analytics, this conversation sharpens how you think about data, trust, and momentum as a technology leader.You’ll Learn:[00:00] Introduction[02:45] Why more data doesn’t help if you can’t explain what changed[05:12] How keeping humans in the loop changes AI analytics failure modes[09:48] Why dashboards break down once they leave the builder’s hands[14:32] How AI turns big analytical questions into auditable steps[20:41] Why one-off and recurring reports need shared intuition to work[27:18] How screenshots and slide decks quietly block data validation[34:55] Why faster AI increases the risk of running in the wrong direction[43:07] How mixing structured data with Slack adds missing business context[57:26] The leadership cost of treating analytics as outputs, not understandingFor more information you can also visit writ.so.You can connect with Jason on his personal LinkedIn or his business 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.

What if the strongest part of your engineering organization isn’t your tech stack, but the culture you protect every day?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’m joined by CTO Pasha Jam, who has grown an engineering team from three people to 110, expanded internationally, and navigated company acquisitions while keeping culture a central focus. We define what a healthy engineering culture looks like, and why it consistently outperforms strategy and process.Culture became a priority after working in environments that were difficult to enjoy, even when the products and compensation were strong. Psychological safety is explored through the lens of engineering teams, including the ability to ask questions, raise risks, challenge decisions, and fail without fear.Culture’s impact on hiring, onboarding, and communication across teams in multiple countries is explored, along with why people who leave often say they miss the culture and sometimes choose to return.If you’re responsible for engineering teams and want to think more intentionally about culture, leadership, and long-term team health, this episode offers practical perspective grounded in lived experience.You’ll Learn:[00:00] Introduction [05:18] Why job dissatisfaction often traces back to culture instead of pay or products[06:42] What psychological safety looks like when engineers challenge decisions without fear[11:07] How empowerment leads teams to take ownership without being pushed[24:21] Why fixing incidents together matters more than assigning blame[28:36] How putting people before process changes commitment and delivery[30:14] Why micromanagement quietly erodes trust and culture[33:09] What it looks like when leaders carry culture forward without seeking credit[35:27] Why culture must evolve as teams scale and contexts changeResources Mentioned:Agile Manifesto | WebsiteNeed car repairs but not the upfront cash? If you're in the UK, get approved in seconds and pay interest‑free over time, apply with Bumper today and stay on the road.You can connect with Pasha Jam on his LinkedinFind 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.

Your most powerful decision engine isn’t your data, your dashboards, or your AI, it’s your gut.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.There is a topic that most technical leaders quietly wrestle with: gut instinct. Not as mysticism. Not as guesswork. But as a real decision-making tool for modern CTO leadership.This episode is all about why your instincts are often your experience compressed into a feeling, when you should trust that signal, and when you absolutely shouldn’t. You’ll hear real coaching stories from seasoned CTOs navigating technical leadership, roadmap trade-offs, scaling engineering teams, and high-stakes calls where the data wasn’t enough.We’ll talk about how engineering leadership changes when you treat instinct like a cached function, fast, powerful, but sometimes stale, and how to validate it without killing its speed. This episode is for startup and enterprise technology leaders who want sharper judgment, fewer regret-filled postmortems, and more confidence saying, “Something about this feels off, and here’s why.”If you’ve ever ignored your gut and paid for it later, or trusted it blindly and been burned, this conversation will give you a practical way forward. It’s about building better instincts, not just better systems.You’ll Learn:[00:00] Introduction[01:02] Why seasoned CTOs sense problems before they can explain them[03:18] How ignoring gut signals leads to overcommitment and roadmap failure[05:07] What gut instinct really is — experience compressed into a signal[07:26] When instinct fails in new or emotionally charged situations[09:41] How to spot where your instincts are strong, weak, or distorted[12:12] Treating instinct like a cached function — fast but fallible[16:34] Using gut instinct as a warning without turning it into dogma[20:18] How data can validate instinct without slowing decisions[24:47] A playbook for sharpening instinct under pressureFind 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.

Most CTOs fail not because of bad decisions, but because they stop asking 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.In this episode, I sit down with Massimo Belloni, Head of Machine Learning and Data Science at Docplanner, to discuss what real technical leadership looks like when the answers aren’t obvious.We dig into bold CTO leadership, why engineering leadership is mostly about people, and how curiosity in leadership builds trust faster than authority ever will. Massimo shares hard-earned lessons from leading ML teams across industries, and why the job isn’t about being the smartest person in the room, but creating conditions where teams thrive.If you’re navigating CTO mindset shifts, managing high-performing engineering teams, or feeling the quiet weight of imposter syndrome in tech leadership, this conversation will land. We talk about invisible leadership work, asking better questions, and why progress only makes sense in hindsight.Iif you’re leading through complexity and change, this episode is your reminder: certainty isn’t the goal, clarity is.You’ll Learn:[00:00] Introduction[02:14] How Massimo realized leadership is about people, not technical mastery[05:48] Why trying to be the smartest person in the room backfires[09:37] What changes when you lead systems you don’t fully understand[13:22] Why most leadership problems aren’t actually technical[17:54] How asking why builds trust faster than giving answers[22:41] Why strong teams come from safety, not fearlessness[27:36] How invisible leadership work compounds over time[33:18] The question Massimo uses to measure leadership progress[38:47] Why leadership only makes sense in hindsightResources Mentioned:The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or AppleSteve Jobs Stanford Commencement Speech | YouTubeYou can connect with Massimo on LinkedIn and learn more about his work on his substack here.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.

The real reason invoices don’t get paid has nothing to do with accounting.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.Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this episode I sit down with entrepreneur Maximiliaan van Kuyk to discuss why trust in business payments is breaking down, and what CTOs can do about it.Drawing on years of experience across startups, agencies, and global markets, Maximiliaan explains why accounts receivable is no longer just a finance function, but a leadership and systems problem. They explore how late invoice payments persist not because people are malicious, but because incentives are misaligned, and accountability is invisible.You’ll hear why consistency beats confrontation, how social accountability in business can outperform legal threats, and why CTOs should care deeply about cash flow management even if they never touch invoicing.If you’ve ever felt the quiet frustration of waiting to get paid, or watched payment delays impact runway, morale, or growth, this conversation will reshape how you think about trust systems, AI in accounts receivable, and the future of getting paid on time.You’ll Learn:[00:00] Introduction[02:18] Why getting paid is really a trust problem, not a money problem[06:41] How chasing payments drains founders emotionally and why it usually lands leadership[10:52] What happens when small businesses become accidental lenders, and why the system works against them[15:37] Why consistent follow-ups beat confrontation and legal threats when recovering unpaid invoices[21:04] Why late payments persist even with contracts and how incentives shape behavior[27:56] How social accountability changes payment behavior faster than reminders or credit scores[34:48] Why reputation only works when it’s visible, and what hidden payment history enables[41:22] Why CTOs need to understand cash flow risk even if they never touch invoicing[48:09] How tracking payment behavior could reshape trust, partnerships, and who gets hiredYou can connect with Maximiliaan on Instagram or find his work on his website here.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.

What if the biggest challenge in scaling your organization isn’t execution, but knowing where you actually are?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 James Webster, former Amazon engineer and founder of Sheep CRM, to unpack a deceptively simple idea that cuts through years of confusion around operational maturity. James introduces his Three Mountains model, a practical way for CTOs to assess reality without ego, optimism, or wishful thinking.We talk about what CTO leadership really looks like during hypergrowth, why engineering leadership breaks when teams skip stages, and how misaligned expectations quietly derail even strong organizations. Drawing from James’s experience inside Amazon and years working with scaling teams, we explore why clarity beats speed, and why naming constraints honestly is a leadership advantage, not a liability.If you’re navigating startup scaling, leading teams through change, or trying to align technology with business reality, this conversation will help you reset your internal compass.This episode is about perspective, precision, and building from where you are, not where you wish you were.You’ll Learn:[00:00] Introduction[01:08] Why scaling fails when leaders misread where they actually are[02:21] How Amazon hypergrowth reshaped James Webster’s view of pace and pressure[03:37] Why constant role change breaks traditional playbooks[14:26] Why thinking too far ahead undermines real transformation[41:12] How repeated problems signal when process really matters[42:18] Why “sloppy” processes beat perfection early on[43:34] How optimism bias keeps leaders from seeing reality[47:09] Why losing your position on the map becomes dangerous at speed[48:22] How choosing the right problem changes everythingYou can connect with James on LinkedIn and learn more about his work on his website here.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.

What if the real blocker in your certification isn’t the rules at all, but how you’re playing the game?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.What really happens when you treat compliance like a fixed checklist and then get hit with yet another vague delay? I take you into the moment a CTO realized that being technically right still left him carrying months of uncertainty on his shoulders. That crack in his old mental model opened the door to seeing regulation as a human system shaped by people instead of boxes to tick.The same compliance posture can lead to totally different timelines depending on relationships, incentives, and how you show up in the room. Instead of obsessing over perfection, the focus shifts to mapping the people in the process and asking sharper questions that actually move things forward. By the end of this episode, you’ll see how small moves of influence can change a certification journey that once felt completely out of your hands.You’ll Learn:[00:00] Introduction[01:12] Why the real certification roadblock is rarely the checklist[03:56] What changes when you treat compliance as a human system instead of binary rules[05:22] The question that flips frustration into influence and momentum[07:18] How a single shift in communication makes leadership lean in[08:42] The reason two identical compliance postures get wildly different timelines[09:31] How mapping people instead of tasks reveals hidden bottlenecks and unstuck paths[11:54] What a high-stakes UK implementation showed about friction-free compliance[14:38] Why aligned incentives accelerate timelines faster than documentation ever will[17:42] Where influence replaces waiting and CTOs move from reactive to strategic[18:22] Five steps that turn regulatory uncertainty into predictable progressFind 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.

What if your team's biggest problem isn't talent, it's the rules you've never written down?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'm talking with Gerald Chablowski, a lead developer based in Thailand whose journey from archaeology and history into tech leadership gives him a very human lens on engineering. I’m drawn to the way he thinks less about shiny tools and more about how people organize themselves, how rules get explained, and how work actually feels. His experience leading teams across different countries and cultures makes him obsessed with one question: what happens when we use structure to protect humans instead of control them.Too many engineering teams are playing a game where nobody can see the rulebook, then wondering why everything feels chaotic. Here we get brutally honest about what happens when goals change every week, when leaders “delegate” but still pull every string, and when trust gets treated like a slogan instead of something you earn in tiny daily moments. You’ll hear how simple constraints like clear rules, small pull requests, and real documentation can unlock creativity instead of killing it, especially in environments where people are scared to challenge the plan. You’ll Learn:[00:00] Introduction[03:48] Why tech only matters when it serves people, not the other way around[06:19] What happens when a team works without clear rules or shared understanding[09:14] The reason trust is built through tiny daily behavior, not speeches or titles[11:47] How unclear systems force developers into chaos even when rules technically exist[14:52] Why documentation becomes leverage when knowledge needs to outlive individuals[17:01] The leadership mistake that made a senior dev refuse to work with him[23:08] What learning hard physical skills teaches about leadership discomfort[28:19] How asking people to rewrite a task in their own words exposes hidden gaps fast[34:22] Why tiny pull requests transform code quality when systems enforce them[42:08] How relying on juniors teaches humility and system thinking faster than doing it all yourselfYou can connect with Gerald and his work on his 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.

What if your biggest advantage as a CTO has almost nothing to do with technology at all?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 Rory Herriman, US CTO at Zip Co, whose thirty year career runs from the military through large enterprises to high growth fintech. Rory brings a playbook forged in real world pressure, from learning to stay calm under fire to realizing that the job is as much about business impact as it is about systems and code. That journey taught him to care less about flashy problems and more about culture, fundamentals and the people he is working with every day.We get honest about what it feels like when you're the one carrying the unspoken weight of every decision while everyone else assumes you've got it handled. It is very easy to slip into chasing hype or focusing on the wrong signals when the real leverage is in resilient fundamentals and a clear link between decisions and business impact. We explore what it actually looks like to stand on that bedrock, keep things fluid around your people, and lean into a near-term future where humans and AI are working side by side. And you'll see why leading this way makes the CTO journey feel a lot less lonely and a lot more sustainable.You’ll Learn:[00:00] Introduction[04:14] How military calm under pressure becomes one of a CTO’s most transferable advantages[08:02] Why the real job isn’t technology but understanding business impact at a deep level[13:03] What shifts when you stop being the smartest technologist and start leading through people[17:06] The humbling moment that proved one org chart can’t fix cultural differences[19:48] Why a strong bedrock of fundamentals makes everything else faster and easier[24:58] How treating people and systems as symbiotic unlocks execution instead of friction[28:54] The power of fluid teams that move to the work rather than waiting for work to come to them[33:04] What changes when a CTO stops chasing the future and starts shaping it[46:12] The reason AI isn’t cost-cutting, but a resource multiplier that expands what humans can do[50:28] What hybrid human + AI teams look like inside an organization right now[55:02] Why excellence, velocity and integrity aren’t trade-offs but a three-part operating balanceYou can connect with Rory and his work on his LinkedIn and his 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.

What if your calmest moment showed up in the middle of a crisis?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 Caroline Elliott, who has made life and death calls in avalanche rescue and now brings that same rescue mindset into high pressure corporate teams. She trained in mountain rescue as a ski patroller, then joined an elite unit in France as a dog handler working avalanches, rubble, gas explosions, and large area searches. In this episode, I pull her mountain stories into the world of tech leadership so you can see what avalanche work can teach us about leading under pressure.We get into what happens to your body when a crisis hits and your team reads every signal you send. I want you to notice how a brief reset and calm language can turn spikes of stress into something you can grow from. And you'll see why staying just a little calmer than the room can change everything when the pressure hits.You’ll Learn:[00:00] Introduction[04:12] Why the body’s first response to crisis can shut down your ability to think clearly[09:47] How a three-second reset changes the entire tone of a high-pressure moment[14:58] The reason stress spreads through a team faster than any words you say[21:36] What happens when leaders use calm language to anchor people who are already overwhelmed[27:44] How a simple breathing sound becomes a reliable reset for staying functional under pressure[33:51] A dog’s reaction in avalanche rescue reveals how humans read stress signals from leaders[39:22] The surprising link between positive reinforcement and team performance when stakes are high[46:05] What shifts inside a team when leaders stay just slightly calmer than the room[51:10] Why caring for your people becomes the deciding factor in whether they’ll stay through hard seasonsResources Mentioned:Fjord’s Mountain Mission: Avalanche Safety Children’s Book by Caroline Elliott | BookYou can connect with Caroline on Instagram or through her website here, where she is happy to do an intro call to discuss how she can help your team.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.

What if goals are the real 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.In this episode, I’m joined by Radhika Dutt, an engineer who studied electrical engineering at MIT. She wrote Radical Product Thinking and is now working on a new book exploring why goals and OKRs backfire, and what to do instead.Targets can look great on paper while the foundation quietly erodes beneath them, leaving leaders focused on green dashboards instead of genuine learning. Together we unpack how shifting from goal setting to puzzle setting can unlock motivation, creativity, and alignment, using a simple framework that turns experiments into smarter decisions. By the end, you’ll see why puzzle setting beats targets when progress actually matters.You’ll Learn:[00:00] Introduction[04:12] The story of how chasing perfect targets blinded a company to a crumbling foundation[05:47] Why leaders often get good news first and the truth too late[06:32] The hidden reason goal-setting traps teams in the wrong solutions[07:15] How puzzle thinking rewires teams to stay in the problem space longer[33:04] What happens when you replace optimization with exploration[35:41] Why surfacing bad news early helps leaders make smarter choices[37:18] How one company built real trust by modeling puzzle-solving from the top[38:21] The three questions that turn metrics into learning loopsResources Mentioned:Radical Product Thinking by Radhika Dutt | Book or AudiobookIt’s soul-sucking to chase arbitrary targets. OHLs—Objectives, Hypotheses, and Learnings—shift the focus to learning, experimentation, and real progress. These templates help you break up with OKRs (without a career limiting move) and reclaim meaning at work.If you want to connect more with Radhika, follow her 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.

What if the real bottleneck isn’t people or tech but the thing between them?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’m joined by Michael Louis Schank, author of Digital Transformation Success. He’s spent years in the trenches at Accenture, Bank of America, EY, and Citi, then struck out on his own to codify what actually works. We dig into his process inventory framework and how it transforms complexity into clarity without wishful thinking.Most transformations stumble not because teams are bad, but because complexity breeds chaos. The fix starts with mapping what the business actually does, naming owners, and tying change to those specific processes. No buzzwords, just the hard work that kills the telephone game and keeps scope, design, and testing honest. And you’ll see why getting the map right beats chasing shiny tools.You’ll Learn:[00:00] Introduction[10:52] Why alignment and systems thinking are the two foundations every transformation depends on[13:17] What happens when business and tech speak different languages and how to finally bridge that gap[19:40] The real reason “easy buttons” and buzzwords keep derailing enterprise change[27:05] How a simple process inventory turns chaos into clarity across teams[31:14] What mapping COBOL systems taught one bank about risk and modernization[33:42] Why ignoring side effects in process change can quietly destroy entire workflows[43:05] How visualizing current state exposes waste and redundancy no one noticed before[45:11] The hidden danger of optimizing what should’ve been deleted in the first place[56:09] What transformation leaders get wrong about ownership, and the one fix that makes it lastResources Mentioned:Digital Transformation Success by Michael Schank | BookYou can connect with Michael on his 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.

Ever tried to explain a technical decision and felt the room silently check out?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.Why do brilliant ideas so often get lost in translation? There is one simple metaphor that changes everything. In this episode, I share the story of a growth-stage CTO who could see a scale crisis coming, but couldn’t get his co-founders to see it too. It took one unexpected image, a floating city at sea, to finally bridge the gap.Why does the old “building” analogy fail? How does reframing your stack as something alive, modular, and adaptable change the whole conversation? The right metaphor doesn’t just explain your system, it earns you buy-in. Because oftentimes, leading isn’t about simplifying the truth, it’s about telling the right story.You’ll Learn:[00:00] Introduction[01:47] Why technical insight isn’t enough when your team can’t see the urgency you do[03:18] How one metaphor turned a frustrating explanation into an instant lightbulb moment[04:41] What happens when you frame your platform as a living, floating system instead of a fixed foundation[06:52] The reason most architectural metaphors fail modern software and what replaces them[08:36] How a single story helped a CTO win over skeptical co-founders and a cautious CFO[09:24] Why the right analogy frees you to teach complexity without losing the room[10:48] How to build metaphors that empower non-technical leaders to see real platform value[11:51] The mindset shift that turns architecture into leadership and communication into strategyFind 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.

When your CTO dies and no one can read the code, you realize the real problem was never the software.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 Matteo Di Battista and Marcello Modica, two Italian innovators who’ve spent decades helping companies escape the grip of outdated ERP systems. From IBM mainframes to cloud-native development, they’ve seen how technical debt and siloed knowledge can quietly strangle growth.We get into what happens when your tech stack outlives your people, why monoliths breed fragility, and how breaking systems into small, pluggable services changes everything. It’s not just about new tools—it’s about a new kind of teamwork that keeps knowledge alive even when key players leave.Because modernization isn’t just a tech upgrade—it’s a survival strategy.You’ll Learn:[00:00] Introduction[05:32] Why monolithic ERP systems quietly trap companies in technical debt[09:47] What happens when a CTO’s death exposes a company’s hidden knowledge silos[12:18] The moment you know it’s time to modernize your software before it collapses[15:44] How low-code and visual tools can close the gap between design and delivery[18:56] Why developers are becoming replaceable, and what that means for software teams[23:51] How building a shared development community protects both companies and clients[26:28] The real reason developers resist change even when innovation would make life easier[33:42] What the new network API standard means for identity, payments, and fraud prevention[45:37] How converting old databases into REST APIs transforms legacy systems into living platformsYou can connect on LinkedIn with both Matteo and Marcello, and their work though wavemaker.com and oneclickapp.it.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.

What if the future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?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’m joined again by my friend Thorgeir Einarsson, almost a year since we last spoke, to unpack how AI funding and investor expectations have shifted from hype cycles to hard realities. Thor runs PGO, a service that helps founders get truly investment-ready with real pre-diligence instead of lipstick on a pig.Pre-seed and seed are brutal right now, and traction beats vibes. Investors are placing smaller, option-like bets at the AI application layer while steering clear of generic models. Hardware is back where it matters, from defense tech to medical devices, when firmware and software meet close to the metal. We trace the PE-ification of VC: rolling up vertical SaaS, “AI-firing” them, and rebuilding moats from customer bases and domain data. Thor flags a blind spot worth building for: AI safety and guardrails for agentic workflows. Then we get practical: preparation beats performative decks, checklist-driven pre-diligence forces the hard questions, and the playbook is simple… know yourself, know your co-founders, keep investors updated, and track the numbers.You’ll Learn:The reason many VCs focus on the AI application layerWhat happens when nobody knows what a great AI company looks like yetThe link between defense and medical devices and hardware-plus-software productsThe damage of skipping investor updates and simple monthly KPIsWhat it feels like to raise when only one to three percent get a checkThe reason pre-diligence and checklists come before the pitchWhat happens when agentic workflows scale without safety guardrailsTimestamps:[00:00] Introduction[05:42] Why AI investment has shifted from hype to hard reality[12:18] The brutal truth about pre-seed and seed fundraising in 2025[18:33] Why investors are betting smaller at the AI application layer[25:47] How defense tech and medical devices are bringing hardware back[32:11] The rise of “AI-firing” old SaaS companies and the PE-ification of VC[40:26] The missed opportunity in AI safety and agentic workflow guardrails[48:59] How founders can prepare for due diligence the right way[56:22] Why investor updates and clear KPIs determine long-term trustConnect more with Thorgeir 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.