The CTO Playbook

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 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.

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 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.

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 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.

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 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.

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 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.

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 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.

What if the real lever isn’t the tech 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 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.

Logic alone won’t land; people react to change emotionally.

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.

Are you optimizing for starting work instead of finishing?

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.

What if the playbook that built your career suddenly stopped working and nobody told you?

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.