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 performance

Resources Mentioned:

OODA Loop | Wikipedia

The Joel Test: 12 Steps to Better Code | Website

Notion | Website

Knolling | Website

Tom Sachs’ 10 Bullets | Website

Time Enough for Love by Robert Heinlein | Book or Audiobook

Joyful Militancy: Building Thriving Resistance in Toxic Times by Carla Bergman and Nick Montgomery | Book or Audiobook

Eve Online | Video Game

Kanban Tool | Website

Find 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.

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 moves

Resources Mentioned:

The Software Architect Elevator: Redefining the Architect's Role in the Digital Enterprise by Gregor Hohpe | Book

Architectural Decision Records (ADR) | Website

GitHub | Website

Astro | Website

CodeMotion Conference | Website

jsday - The Italian JavaScript Conference | Website

Italian Agile Days Conference | Website

Dive 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.

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 value

If you want to support the work Nic mentioned, become a member of the Bat Conservation Trust.

Resources Mentioned:

CTO Craft | Website

UK National Data Repository (NDR) | Website

Bat Conservation Trust | Website

Falklands Conservation | Website

Lovable AI | Website

Base44 | Website

If 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.

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.

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

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 for

Resources Mentioned:

NIST AI Risk Management Framework | Website

Download 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.

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.

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 acceleration

Clinical 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.

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 satisfaction

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.

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 decisions

Resources Mentioned:

No Silver Bullet Essence - Accident in Software Engineering by Brooks F. | Article

You 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.

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 understanding

For 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.

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 change

Resources Mentioned:

Agile Manifesto | Website

Need 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 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.

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 pressure

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.

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 hindsight

Resources Mentioned:

The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or Apple

Steve Jobs Stanford Commencement Speech | YouTube

You 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.

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 hired

You 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.

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 everything

You 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.

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 progress

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.

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 yourself

You 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.

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 balance

You 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.

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 seasons

Resources Mentioned:

Fjord’s Mountain Mission: Avalanche Safety Children’s Book by Caroline Elliott | Book

You 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.

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 loops

Resources Mentioned:

Radical Product Thinking by Radhika Dutt | Book or Audiobook

It’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.

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 last

Resources Mentioned:

Digital Transformation Success by Michael Schank | Book

You 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.

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 strategy

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.

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 platforms

You 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.

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 layer
• What happens when nobody knows what a great AI company looks like yet
• The link between defense and medical devices and hardware-plus-software products
• The damage of skipping investor updates and simple monthly KPIs
• What it feels like to raise when only one to three percent get a check
• The reason pre-diligence and checklists come before the pitch
• What happens when agentic workflows scale without safety guardrails

Timestamps:

[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 trust

Connect 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.

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 Matthew Carr, who does interim work and often comes in as the firefighter when a company has taken a wrong turn. He lays out why people come first, processes second, and technology follows.

He started in classic ASP and built a loyalty program for the heating and engineering sector. Real-time results beat long compile cycles and changed how he delivered. A private-equity buyout couldn’t get the startup’s tech delivered, so he sat one-to-one with everyone to map the problems. Turns out, fixing broken delivery isn’t about new tools. It’s about people, trust, and having the guts to act fast.

You’ll Learn:

• The reason putting people first makes process work and technology follow
• What happens when you plan three sprints ahead and tie outcomes to business value
• The link between quick wins and winning trust in the first 30 days
• The damage of being six to twelve months off on deliverables after a PE acquisition
• What it feels like to inherit a program that hasn’t shipped in 18 months
• The link between weekly iterations, monthly demos, and a product becoming a bedrock of the business
• The reason trust, leadership, and alignment are the core enablers of the people pillar
• What happens when you play their game first by showing a six-week plan the board can approve
• The reason “believe in yourself” is the sharpest one-line tip for new CTOs

Timestamps:

[00:00] Introduction

[05:12] Why people come first before process and technology

[10:46] Lessons from early development work in classic ASP and loyalty programs

[15:58] How a private equity acquisition exposed major delivery delays

[21:37] Running a massive retrospective and uncovering 110 problems

[28:04] The importance of quick wins and building trust in the first 30 days

[33:41] Planning three sprints ahead and reporting outcomes instead of outputs

[38:22] Turning around a project that hadn’t shipped in 18 months

[45:09] How weekly iterations and monthly demos rebuilt momentum

[51:28] The one-line advice Matthew gives every new CTO

Learn more from Matthew 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.

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 Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.

We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.

You’ll Learn:

• The reason logic-only change pitches backfire
• What happens when leaders move faster than teams
• The link between the metric you reward and the behavior you get
• What it feels like to run layoffs twice
• The reason pre-mortems work
• What happens when you don’t set indicators early
• The link between purpose, alignment, and smoother execution
• What happens when a key trainer is missing
• The damage of losing clarity at the top

Timestamps:

[00:00] Introduction

[05:18] Why logic fails when leading change

[10:42] The emotional side of resistance and uncertainty

[15:56] How leaders move faster than their teams

[20:11] The blind spot that halted a global SAP rollout

[26:27] Why bad metrics destroy good behavior

[31:03] Cultural barriers that derail transformation

[36:49] The pre-mortem method for spotting hidden risks

[42:08] The eight-step change playbook

Resources Mentioned:

Master the Change Maze by Giorgia Prestento | Book

Giorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.

You can connect more with Giorgia 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.

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 Joakim von Prónay, an engineer and psychologist by education and a coach by passion.

We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.

You’ll Learn:

• The reason long-term planning works when it’s roughly right instead of precisely wrong
• What happens when teams are incentivized to start work instead of finish it
• The link between delivery predictability and real prioritization and accountability
• The damage of treating roadmaps like a Gantt chart exercise
• What it feels like when every question defaults to “ask the boss” instead of talking directly
• The reason fragmented steering creates conflicting directions
• The link between a single “central rule” and measurable goals

Timestamps:

[00:00] Introduction

[06:14] Why high-performing teams are so rare

[09:27] The danger of planning for perfection

[15:46] Why teams start work instead of finishing it

[19:32] The power of predictability and real accountability

[25:40] When collaboration breaks down into escalation

[31:58] What fragmented steering really looks like

[38:45] The rule that defines true strategy

[46:23] A Spotify story and the engineer’s warning

[51:17] How alignment turns insight into action

Connect more with Joakim 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.

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 Catherine Stagg-Macey, an executive coach who works with technical experts turned leaders. She knows firsthand what it’s like to move from coding and spreadsheets into managing people, and the struggle that comes with it.

We get into what happens when being the smartest person in the room is no longer enough, the patterns that keep leaders trapped in the systems they built, and the hard pivot it takes to step into a new kind of leadership.

You’ll Learn:

• The reason smart technical leaders hit a wall when old habits stop working
• What happens when you try to manage people with the same mindset you used to write code
• The link between control, trust issues, and being stuck in endless meetings
• The damage of wearing the “superhero cape” and building a culture of firefighting
• Why skepticism is common when leaders are first asked to work with a coach
• The pivotal moment that led Catherine from consulting success to a coaching career
• How childhood patterns and early work experiences quietly shape leadership behaviors
• The role of feedback, or the lack of it, in pushing leaders toward breaking points
• Why creating distance from your triggers opens space for better choices

Timestamps:

[00:00] Introduction

[06:15] Breaking patterns of overwork and constant meetings

[08:55] The lure and cost of playing the workplace superhero

[10:20] Catherine’s pivot from consulting success to coaching

[16:05] When rock bottom moments force change

[20:15] Early warning signs leaders ignore before burnout

[26:45] Identity shifts required to let go of old leadership habits

[30:10] Recognizing triggers and unconscious behavior patterns

[41:20] How upbringing and culture shape leadership reactions

[53:00] Building range as a leader in times of uncertainty

Resources Mentioned:

Conversations at the Edge | Website

You Didn’t Chase Leadership. Leadership CHASED You. Join Catherine’s Inner Circle.

Unlock your leadership superpower, discover what your leadership style is with Catherine’s Leadership Style Quiz.

You can connect with Catherine on LinkedIn and listen to her podcast 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.

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 Corey Hart, a crisis operator who’s built a career on scaling massive humanitarian and operations projects under extreme pressure. He’s said yes to projects most people would run from, from helping New York City respond to a sudden influx of asylum seekers to standing up global call centers and navigating cruise ship operations post-lockdown.

We get into how he prepares for the unknown, what it takes to build trust in the middle of a storm, and why surrounding yourself with the right people makes the difference between collapse and momentum.

You’ll Learn:

• The reason Corey says yes to high-stakes projects others avoid
• What happens when you’re asked to launch a humanitarian response overnight
• The link between early onboarding and a culture of openness and candor
• The damage of overcomplicating operations when speed is critical
• What it feels like to land in a crisis with little info and no certainty
• Why bringing compliance and tech in early turns them into strategists
• The role of trust in holding teams together under extreme pressure
• How living autopsies fix problems in real time, not after the fact
• The mindset shift that turns specialists into early-stage leaders
• Why tracking from day one helps you see around corners in chaos

Timestamps:

[00:00] Introduction

[05:58] Saying yes to unpredictable challenges

[07:02] Scaling New York’s asylum seeker response

[11:58] Handling moments when operations nearly collapse

[14:02] Filtering signal from noise in crisis decision-making

[17:56] Building openness and candor into team culture

[20:06] Creating trust and making failure safe

[22:01] Why saying yes builds momentum and possibility

[27:00] Unlikely outcomes from saying yes

[31:00] Keeping operations simple and avoiding scope creep

[33:02] Tracking data early to guide decisions under pressure

[35:00] Bringing compliance and tech in early to shape solutions

[37:56] Knowing when and how to step out of a crisis project

Resources Mentioned:

Podcast Episode The CEO’s Playbook for Hiring the Right CTO with Warren Beasley | YouTube

You can connect with Corey on 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.

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 Lou Franco, author of Swimming in Tech Debt and a veteran software engineer who’s been a founding engineer at three successful startups, a principal engineer at Trello through its Atlassian acquisition, and now an advisor to software teams.

We trace his journey from early lessons in fintech and startup acquisitions to the moments that exposed just how costly ignored tech debt can be. Lou shares what he learned from engineers on the ground, how small fixes can deliver outsized productivity gains, and why culture and process matter just as much as code when tackling debt.

You’ll Learn:

• The reason most engineering teams carry hidden tech debt without clear solutions
• What happens when day-to-day friction drags down delivery speed and morale
• The ROI of small, focused fixes that start paying back almost immediately
• The damage that builds when debt is ignored until it hits a breaking point
• The link between a product’s lifecycle stage and the right level of debt reduction
• Why dedicated engineering-led time creates accountability and better outcomes
• How visible progress metrics help leadership see the value of paying down debt
• The risk of jumping too fast into shiny new tech that stalls out in production
• The role of culture, style guides, and clear values in preventing runaway debt

Timestamps:

[00:00] Introduction

[05:01] Early lessons on tech debt in fintech and startups

[07:02] The exit interview that exposed ignored debt

[08:59] Small fixes that delivered immediate productivity gains

[11:00] When debt grows into brick walls and forced rewrites

[14:01] Building team culture and values to tackle debt

[16:59] Splitting engineering-led time from product-led work

[23:00] Measuring debt payoff with metrics and visibility

[29:01] Leading indicators of productivity and developer experience

[36:59] High-risk systems, regressions, and measured approaches

Resources Mentioned:

Swimming in Tech Debt by Lou Franco | Book

Crossing the Chasm by Geoffrey Moore | Book or Audiobook

You can connect with Lou on LinkedIn and find his book 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.

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 trace the moments that shaped why I coach. From digging strangers out of an avalanche in Switzerland to carrying the weight of a teammate down Mont Blanc on one ski, survival and leadership kept pointing to the same truth: preparation creates calm. I talk about teaching kung fu to kids and bankers, seeing culture hold Palantir together at breakneck speed, and stumbling through my own startup without a coach. Later, I describe rebuilding both technology and trust at Realforce when fear was running high. All of it comes back to this: even the strongest leaders need someone in their corner, and that’s why I built The CTO Playbook.

You’ll Learn:

• The reason practice beats panic when pressure hits
• The link between small wins and the breakthrough confidence they create
• The damage of trying to figure everything out alone without guidance
• What it feels like to rebuild trust and safety in a fearful team
• Why culture becomes the glue when growth outpaces structure
• The moment persistence matters more than raw talent in leadership and coaching
• How scaling without culture can tip a company into chaos

Timestamps:

[00:00] Introduction

[06:00] Avalanche rescue and the calm that comes from practice

[08:59] Skiing Mont Blanc and carrying the load so the team could get home

[10:48] Kung fu teaching and the breakthrough power of persistence

[13:00] Coaching adults and the hidden gaps even senior leaders face

[13:52] Lessons from Palantir and why culture holds during chaos

[14:55] Startup founder struggles and the cost of going it alone

[15:46] Rebuilding trust and technology at Realforce

[18:00] Why I coach and how Simon Sinek’s Golden Circle frames it

[21:00] The five CTO archetypes every tech leader falls into

[26:00] Basecamp, Elevate, and Ascent explained as the CTO Playbook journey

Resources Mentioned:

Start with Why by Simon Sinek | Book

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.

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.