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 if the future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?



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 check out Adam's CTO coaching company here.

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 if the real lever isn’t the tech at all?



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 check out Adam's CTO coaching company here.

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.

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



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 check out Adam's CTO coaching company here.

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.

Are you optimizing for starting work instead of finishing?



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 check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!

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



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 check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!

Would you say yes to leading through chaos with no plan, little information, and no guarantee of success?



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 check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!

What if the biggest reason your team feels stuck isn’t money, but the weight of your own code?



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 check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!

What if the only difference between freezing in chaos and staying calm is how much practice you’ve done before the storm hits?



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 check out Adam's CTO coaching company here.

Build your own CTO Playbook at our website — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Proactivity isn’t an all-or-nothing game.



In this episode, I break down the myth that leaders are either “proactive” or “reactive” and share why even small, flickering moments of foresight can put you ahead. I get into what happens when you’re forced into reactive mode and how to inject just a bit of proactivity into those moments so they don’t derail you. I talk about the “pressure off” test, those quiet weeks when your defaults show up, and how to use them to reset your habits. I wrap up with five practical steps you can start this week to shift from constant firefighting to being seen as a steady, strategic leader.

You’ll Learn:

• The real reason proactivity isn’t a fixed leadership trait
• What a flickering light bulb can teach you about staying ahead
• Why just 5% more foresight each week changes how your team sees you
• How to inject proactive moves into high-pressure, reactive situations
• The quiet damage of coasting during “pressure off” weeks
• What the “pressure off” test reveals about your default leadership mode
• Practical ways to prepare for outages and crises before they happen
• The surprising link between military “go bags” and tech leadership readiness
• How to turn firefighting moments into long-term strategic wins
• Five simple steps to build steady, visible proactivity into your week

Timestamps:

[00:00] Introduction

[05:00] Busting the myth of proactive vs reactive leadership

[06:14] The flickering light bulb analogy for building proactivity

[07:55] Injecting proactive actions into reactive situations

[09:59] Building your leadership “go bag” for crises

[11:42] The pressure off test and why quiet weeks matter

[13:50] Using downtime to reset strategic habits

[14:56] Five steps to increase consistent proactivity

[18:45] Why small, steady choices outweigh perfection

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Build your own CTO Playbook at our website — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

What if the hardest part of being a CTO isn’t about the technology at all, but learning to lead without a map?



In this episode, I’m joined by Etienne de Bruin, founder of Seven CTOs and CTO Levels, and co-author of the upcoming book Liquid. For more than a decade, Etienne has worked with CTOs navigating the shift from hands-on coding to executive leadership.

We talk about the moment he realized his value wasn’t in the code anymore, how he built a peer network to fill the gaps he couldn’t see, and the pivotal lessons that shaped his approach to coaching. Etienne also shares the thinking behind Liquid, exploring how CTOs can find balance between chaos and rigidity while mastering the four “sentinels” every tech leader needs to succeed.

You’ll Learn:

• What it feels like to be pushed or pulled out of the codebase as a CTO
• The real reason Etienne founded Seven CTOs and why most early members walked away
• How ontological coaching changes the way CTOs solve problems and influence outcomes
• The quiet damage of solving the wrong problem when your influence goes unchecked
• The four “sentinels” every CTO must master to earn trust at the executive table
• Why balancing “boiling” chaos and “frozen” rigidity can make or break a tech team
• The surprising link between financial fluency and a CTO’s long-term success
• How the Levels framework reveals capability gaps that stall growth
• What happens when a CTO builds genuine alignment with sales and product leaders

Timestamps:

[00:00] Introduction

[06:58] The challenge of stepping away from coding into leadership

[14:00] Building a startup and the moment to stop coding

[17:57] Creating Seven CTOs and the need for peer groups

[27:15] How ontological coaching transforms CTO problem solving

[37:14] The core role of a CTO and the importance of financial fluency

[45:11] The concept of Liquid and navigating boiling vs frozen states

[47:59] The four sentinels every CTO must manage

[53:54] Using the Levels framework to diagnose capability gaps

You can connect with Etienne on LinkedIn.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.