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.

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 your most important leadership skill had nothing to do with technology, and everything to do with how people feel?



In this episode, I’m joined by Wesley Eugene, SVP at HIT Global and former CIO at IDEO. Wesley’s career has taken him from building computers in college to leading technology and transformation for some of the world’s most innovative companies. At HIT Global, he’s helping usher in a new way of thinking about tech leadership with a framework built entirely around human-first principles.

We talk about the moments in his career that drove home the power of trust, relationships, and empathy in technology. Wesley shares how human-centered design, storytelling, and a focus on real-world experiences can transform how leaders guide their teams and serve their customers. This is a conversation about leading people, not just managing processes.

You’ll Learn:

• The leadership shift that happens when you treat experience as your North Star
• Why telling better stories with data wins more than just arguments
• The surprising power of empathy as a competitive edge in tech leadership
• How radical candor transforms the way feedback is given and received
• The quiet damage of outsourcing critical customer experiences
• What it feels like to lead through a global crisis with trust as your main currency
• The link between human-centered design and faster, smoother transformations
• Why going analog can unlock your most creative and strategic thinking
• How to anchor digital transformation in moments that truly matter to people

Timestamps:

[00:00] Introduction

[05:58] Starting in tech through service desk work and early career moves

[08:56] Driving digital transformation and workforce reskilling at Aflac

[09:58] Leading secure remote transitions during the pandemic through trust and relationships

[12:57] Frameworks that shaped leadership including TBM and radical candor

[17:49] Immersion in human-centered design at Aflac and IDEO

[21:01] Realizing the importance of designing for real-world user experiences

[25:02] Breaking down the Human First playbook principles

[34:09] The role of unplugging and analog thinking in creativity and leadership

Resources Mentioned:

Technology Business Management Council | Website

Radical Candor by Kim Scott | Book or Audiobook

Radical Respect by Kim Scott | Book or Audiobook

Want to learn how to lead with empathy, design, and story at the core? You can connect with Wesley on LinkedIn, where he is building the Humanising IT™ movement; training, certifying, and coaching the next generation of human-first tech leaders.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

What if the very habits that once made you successful are now holding you back?

In this episode, I talk with Dr. Ravi Iyer, a physician, scientist, and leader with over four decades of experience in medicine, research, and hospital leadership. His work has taken him from studying molecular immunology at Harvard to serving as Chairman of a Department of Medicine, and his career has been driven by one relentless question: how do you make life work when it doesn’t?

We dig into why our brains cling to patterns, how those patterns can trap even the smartest leaders, and what it really takes to see beyond the “menu” of our past playbooks so we can actually taste the meal of life. This is a conversation about awareness, choice, and breaking free from default thinking, both in leadership and in life.

You’ll Learn:

• The real reason even accomplished leaders cling to outdated playbooks
• What happens when life stops matching the patterns you’ve always relied on
• The link between an amoeba’s behavior and human decision-making
• Why subconscious “choices” are actually compulsions in disguise
• How success can lock you into strategies that block future growth
• The two forces powerful enough to break a leader’s mental resistance
• Why chasing novelty can become just another limiting pattern
• The quiet damage of confusing the “menu” for the actual “meal” of life
• How to use sensory deprivation to break stale relational or leadership habits
• What it feels like to lead from the space that contains all your options

Timestamps:

[00:00] Introduction

[03:02] The lifelong question that shaped a career in science and medicine

[06:46] How pattern matching drives human behavior and decision-making

[11:41] Lessons from a grandfather on reframing problems and breaking patterns

[17:08] Why subconscious choices limit freedom and success

[24:54] How successful playbooks create plateaus in leadership growth

[28:01] The “menu vs meal” analogy and the search for real experience

[33:42] Using sensory deprivation to reset relationships and leadership habits

[39:24] Applying new data collection methods to break organizational patterns

[42:51] Why personal experience should guide your ultimate playbook

Get a FREE copy of Dr. Ravi Iyer’s digital books here.

If you want to connect more with Dr. Ravi, follow him on LinkedIn.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Stop Doing These 14 Things If You Want to Be a Great CTO



I’m not adding to your to-do list—I’m flipping it. These are the habits that keep you reactive, overwhelmed, or straight-up invisible to the rest of the exec team. I walk through the traps that I see CTOs fall into again and again, from packing your calendar like a bad game of Tetris to leading every decision and chasing every shiny trend. These aren’t theories. They’re mistakes I’ve coached dozens of tech leaders through—and screwed up myself too.

You’ll Learn:

• The real reason packing your calendar wall-to-wall kills strategic thinking
• What happens when you delegate tasks but not decisions
• The quiet damage of assuming your team understands the company vision
• Why translating tech into business outcomes changes your exec team influence
• The simple phrase that makes hard feedback easier to hear and act on
• What it feels like to stop chasing trends and start trusting fundamentals
• The surprising link between avoiding trade-offs and leadership gridlock
• How overusing jargon weakens your clarity and authority
• What most CTOs get wrong about culture—and how to fix it
• Why punishing mistakes kills innovation faster than any bad process

Timestamps:

[00:00] Introduction

[03:06] Why filling every hour kills your ability to lead

[04:15] The problem with working without strategic alignment

[05:01] Delegating tasks vs delegating decisions

[06:41] What happens when people don’t understand the vision

[07:50] How to translate engineering into business language

[08:55] Why leading with opinion weakens your credibility

[10:00] The cost of chasing every shiny trend

[11:00] You can’t scale if you lead everything alone

[12:58] How to have hard conversations and handle feedback

[13:54] Why jargon destroys clarity and influence

[14:50] What culture is actually made of

[15:36] Stop punishing mistakes if you want innovation

[16:31] The danger of forcing rigid frameworks

[17:29] How indecision leads to gridlock

[18:49] Quick-fire recap of the 14 habits to stop

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Are you managing your individual contributors in a way that fuels growth, performance, and alignment?

In this episode, I’m talking with Faris Aranki, founder of Shiageto Consulting, about leading individual contributors through regular one-on-one meetings. Faris brings a wealth of experience from his career in strategy consulting and leadership coaching. We dive into a proven system for structuring these meetings to keep performance management simple, effective, and human-centered.

We explore how to align individual performance with company goals, why weekly check-ins are crucial, and how to integrate these meetings into your larger performance frameworks. Faris also shares how building rapport and listening actively can lead to stronger relationships with your team, ensuring that growth is both continuous and aligned with the broader mission.

You’ll Learn:

• The real reason weekly one-on-ones are critical for individual contributor success
• Why a rolling agenda document is your most powerful tool in building trust and accountability
• How to use silence strategically in one-on-one meetings to encourage deeper conversation
• The quiet damage of neglecting active listening in engineering teams
• What it feels like to lead with empathy and get results without micromanaging
• How to align individual performance with company goals through simple, structured conversations
• The surprising link between personal development plans and long-term organizational success
• Why you should avoid status updates in one-on-ones and focus on personal growth
• How asking the right questions based on learning styles can level up your coaching approach

Timestamps:

[00:00] Introduction

[06:30] The impact of the rolling agenda document on trust and accountability

[08:00] How to structure one-on-ones to focus on personal growth and alignment

[10:15] The role of silence in encouraging deeper conversations

[12:00] How active listening can strengthen team communication and trust

[16:30] Using the VARK model to tailor coaching to individual learning styles

[19:10] How to integrate weekly, quarterly, and annual meetings into a performance management system

[22:50] The benefits of focusing on experience over output in one-on-one meetings

[25:00] Handling performance improvement plans and documentation for legal clarity

[28:30] How to use one-on-ones to build influence and promote personal development

[32:00] The importance of aligning individual goals with company objectives

[34:50] Best practices for conducting quarterly and annual performance reviews

Resources Mentioned:

The Five Dysfunctions of a Team by Patrick Lencioni | Book or Audiobook

Leaders Eat Last by Simon Sinek | Book or Audiobook

Hanlon's Razor | Principle

Movie: Moneyball

You can connect with Faris on LinkedIn or take the Shiageto effectiveness assessment here.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Are you managing individual contributors the best way possible?



In this episode, I sit down with Peter Wong, a seasoned CTO, to discuss how to lead individual contributors effectively with a structured and personalized approach. You’ll hear how weekly one-on-one meetings, a simple but powerful rolling agenda, and understanding how each person learns can take performance management from stressful to seamless.

We dive into how this method helps you align your team with company goals, nurture personal growth, and create trust—ensuring the continuous development of your engineering team, one conversation at a time. This approach ensures clarity and consistency, allowing your team to thrive.

You’ll Learn:

• Why weekly one-on-one meetings are more powerful than lengthier sessions
• The real reason a rolling agenda can transform your leadership approach
• How to foster trust and build rapport by simply listening more than speaking
• What happens when you tailor your questions to how each person learns
• The surprising link between performance management and building personal connections
• Why writing things down in meetings isn’t just a formality—it’s a trust-builder
• The quiet damage of skipping regular check-ins with your team
• What it feels like to have an annual review with zero surprises
• The key to making performance feedback feel like a natural progression
• How to use small actions like weekly meetings to drive big results over time

Timestamps:

[00:00] Introduction

[05:25] How to build trust through active listening in one-on-ones

[06:45] Tailoring questions to different learning styles for better coaching

[08:05] The value of writing things down in meetings

[09:20] Structuring one-on-one meetings for maximum impact

[11:15] Keeping feedback focused on personal growth

[12:40] The power of regular check-ins for performance momentum

[14:05] Linking weekly meetings to quarterly and annual reviews

[15:35] Using the VARK model to understand how your team learns

[17:10] Handling performance improvement plans effectively

[21:00] Simplifying annual reviews with structured feedback

[22:45] Making performance reviews a natural progression

[28:05] The role of a structured approach in leadership

[30:10] Why a rolling agenda document is a game-changer

You can connect with Peter and learn more about his work through his LinkedIn and website.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Are you getting the most out of your individual contributors?

In this episode, I sit down with Matan Kubovsky to dive into the art of managing individual contributors through weekly one-on-one meetings. Matan shares his experience and a proven system for leading teams with consistency, clarity, and alignment. This method isn’t just about project updates—it’s about shaping growth and connecting each person’s role to the broader organizational mission.



We cover how to structure meetings, build trust, and set the right cadence to keep momentum going. Matan also discusses how to track progress with a rolling agenda and how to use the VARK learning model to tailor coaching to the team’s learning styles. Whether leading a small team or guiding team leads, this episode is packed with actionable insights to make performance management smoother and more effective.

You’ll Learn:

• The real reason weekly one-on-ones are the most powerful tool for individual contributor growth
• What happens when you set the right cadence for meetings and stick to it
• The surprising link between active listening and building trust with your team
• Why silence in meetings can be your secret weapon to get more from your team
• How to use the VARK model to tailor coaching and accelerate learning
• The quiet damage of losing momentum by meeting less than once a week
• What it feels like to lead with clarity by aligning individual performance with company goals
• Why recording your one-on-one meetings can build confidence and create valuable evidence
• The key difference between a mission statement and a personal development plan
• How to avoid the performance review “surprise” by keeping a rolling agenda document

Timestamps:

[00:00] Introduction

[06:30] Why many engineering teams lack performance management skills

[08:05] The problem with annual performance reviews

[09:35] How feedback frequency impacts team performance

[11:10] The Start/Stop/Continue framework explained

[13:25] The need for weekly one-on-one meetings with individual contributors

[16:05] Why silence in meetings can drive more meaningful conversations

[19:15] How to help engineers improve their listening and communication skills

[21:40] The importance of shifting focus from output to experience in meetings

[25:00] Why keeping a rolling agenda document is essential for tracking progress

[30:20] How to structure quarterly reviews and set goals for the next quarter

Resources Mentioned:

McKinsey Research | Website

You can connect with Matan through his Linkedin or schedule a meeting to learn more here.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Being busy isn’t your problem—being absent is.



In this special episode, Adam dives into the hidden cost of not showing up—at work, at home, and especially as a leader. If you’ve ever coasted through a Zoom call, half-listened to a teammate, or checked your phone while spending time with your kids, this one will hit hard.

Adam pulls back the curtain on what it really means to lead with presence—not perfection—and how that simple act can radically transform trust, engagement, and team performance. You’ll hear personal stories, hard-won lessons, and five tactical steps to build a leadership style grounded in consistency and connection. Whether you're burned out or just trying to level up, this episode delivers the wake-up call (and the playbook) you didn’t know you needed.

You’ll Learn:

• How showing up with full presence activates trust, connection, and influence
• Why “being there” isn’t the same as actually being present
• What distracted leadership signals to your team—and how it erodes performance
• How to create friction against distractions and train consistent focus
• Why celebration is a strategic act—not a soft one
• How to structure 1:1s that deepen trust and engagement
• What a simple “thank you” does to long-term team motivation
• Why consistency beats charisma in high-stakes leadership
• How to audit your calendar for high-impact presence opportunities
• What missed moments teach us about recommitment and integrity

Timestamps:

[00:00] Introduction

[02:20] Why presence matters more than perfection

[03:08] The real meaning of “showing up”

[03:47] Story: daughter calls out her dad for not watching

[04:29] Story: child notices when phone is put away

[05:07] Why absence creates disconnection—even in the same room

[05:35] What presence looks like in a professional setting

[06:10] How presence builds or destroys trust

[06:45] Story: transforming a demoralized team through consistency

[07:56] The role of showing up in changing team culture

[08:25] Why presence includes celebrating wins

[08:58] Story: the 15-minute celebration that stuck

[09:50] Why being noticed beats being rewarded

[10:36] What makes consistency so difficult

[11:05] The support systems that enable presence

[12:02] Step 1: know where presence matters most

[12:22] Step 2: create friction for distraction

[12:45] Step 3: celebrate outcomes deliberately

[13:04] Step 4: practice active presence in 1:1s

[13:30] Step 5: acknowledge your misses and recommit

Resources Mentioned:

The CTO Playbook Platform | Website

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

Join The CTO Playbook Slack Community to connect with other CTOs!

You’re leading everyone else—but are you quietly abandoning yourself?



This episode features executive coach and former engineer Natalya Tarasova, who brings a rare blend of technical credibility, Eastern philosophy, and mountaineering metaphors to the world of tech leadership. With a background in physics, machine learning, and organizational coaching, Natalya doesn’t just talk about change—she’s lived it through multiple career pivots and international moves. Her perspective is especially powerful for high-performing CTOs who’ve built their careers on delivering results but feel disconnected from their own needs.

In this conversation, Adam and Natalya break down why so many senior tech leaders are brilliant at leading others but terrible at leading themselves. You’ll learn how to recognize when you’ve put yourself last for too long, how to approach inner transformation with the same strategy you’d use for scaling a system, and why burnout often hides behind high output. Expect unconventional insights on emotional regulation, breathing as a leadership tool, the myth of waiting until you’re “ready,” and how to rewire your mental architecture for sustainable impact. This episode is a must-listen if you’re ready to stop sprinting and start leading from stillness.

You’ll Learn:

• How high performers unknowingly sabotage themselves by avoiding stillness
• Why “putting yourself first” is essential—not selfish—for sustainable leadership
• How to use mountaineering metaphors to map out complex personal growth
• What breathing techniques reveal about nervous system regulation under stress
• How to shift from reactive change to intentional transformation
• Why visualizing your “inner mountain” creates clarity in career transitions
• How to identify the emotional weight you're carrying that’s slowing your progress
• What Eastern philosophy teaches about integrating body, mind, and identity
• How to coach others more effectively by first learning to coach yourself
• Why most CTOs delay change until they feel “ready”—and why that’s a trap

Timestamps:

[00:00] Introduction

[04:58] What constant career change reveals about personal adaptability

[06:36] The hidden cost of being too externally focused

[09:08] Are you a victim of change or a driver of it

[10:18] How to take control of your state and response

[12:30] Why CTOs say they don’t know how to put themselves first

[14:56] Using a mountain metaphor to visualize growth

[17:05] Why high achievers struggle to slow down

[18:16] The role of stillness in understanding motion

[20:12] Why breathwork is the fastest reset for high performers

[23:12] How to prepare for the next phase of your leadership

[25:11] How to know when it’s time to move

[27:09] What leaders need to leave behind to grow

[28:12] Change is not linear—it’s a spiral

[30:01] What most high performers miss when working on themselves

[31:07] Why change starts with rewiring your identity

[33:00] Giving yourself permission to fail and learn

[35:03] Why emotional empathy can’t be intellectualized

[37:06] How embodied wisdom changes your leadership presence

[39:04] The hidden power of integrating personal and professional growth

[41:05] How self-leadership creates ripple effects across teams

[42:12] The 4-step change framework for CTOs

[44:05] Why timing your next change is a skill, not luck

You can connect with Natalya on LinkedIn and learn more about her company, Tarasova Coaching on its website.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

Your KPIs aren’t just underperforming—some of them are actively lying to you.

In this episode, Adam sits down with Lior Gerson, co-founder and CEO of Target Board, a company that's redefining how tech leaders track and prove their impact. With two decades of experience leading both e-commerce and SaaS companies, and advising giants like Macy’s and Sephora, Lior brings a brutally honest take on why most CTOs are flying blind when it comes to metrics—and how to fix it.

This conversation is a no-BS breakdown of the most overlooked lever in engineering leadership: meaningful, actionable KPIs. You’ll learn how to turn your data into a defensive shield, why most dashboards are vanity theater, and what it actually takes to align your metrics with strategic business outcomes. If you’re a CTO tired of being reactive—or worse, irrelevant—this is your wake-up call. Expect a tactical playbook for building real visibility, accountability, and leverage inside your org.

You’ll Learn:

• How bad KPIs create blind spots—and how to replace them with metrics that drive results
• Why most dashboards fail to align with business outcomes (and what to do instead)
• How to use KPIs as a defensive shield to prove your value as a CTO
• What engineering leaders can learn from consumer companies about data discipline
• Why many CTOs unconsciously resist accountability—and how that holds teams back
• How to build a metric system that connects engineering output to revenue
• Why founder-led companies often ignore metrics—and what fractional CTOs must do differently
• How to identify whether your team is measuring for impact or just checking boxes
• What makes a KPI actually meaningful (hint: it’s not speed or story points)
• How to avoid the DORA trap and surface the metrics your exec team actually cares about

Timestamps:

[00:00] Introduction

[00:52] Why KPIs are critical infrastructure, not just reports

[01:28] Common CTO struggles with metrics and alignment

[03:54] The shock of entering a $100M SaaS company with no metrics

[05:32] The impact of analytical leadership on performance

[06:18] Why understanding other C-level roles gives CTOs an edge

[07:12] How fractional CTOs prove impact fast

[08:48] Why engineering teams resist accountability and tracking

[10:51] How internal pressure forces KPI adoption

[11:23] Using metrics as a defensive shield in leadership

[12:42] How lazy KPI systems fail ambitious CTOs

[14:11] Why every team needs different metrics to improve

[15:28] Why most BI teams can’t deliver what CTOs need

[16:42] How Target Board replaces data teams in days

[17:52] Why DORA metrics don’t move the business needle

[19:07] Connecting metrics to revenue and business outcomes

[20:26] Why paychecks depend on the metrics people ignore

[22:13] What causes misalignment between execs and data

[23:31] How OKRs can sabotage team performance

[25:01] Why full metric visibility empowers better decisions

[27:01] Automating metric modeling across platforms

[28:13] The hardest part of using KPIs effectively

[29:58] The mindset shift needed to use metrics well

[31:09] What data can’t fix when politics blocks accountability

[32:28] A step-by-step playbook for KPI-driven execution

You can connect with Lior and his company on Linkedin.

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

Join The CTO Playbook Slack Community to connect with other CTOs!

"Compliance doesn’t make you good—so how do you really know if your tech team is any good at all?"



In this episode, Adam sits down with Andy Graham, former CTO with 30 years of M&A and enterprise tech leadership, and Dane Eldridge, serial entrepreneur and CEO of Stackup. Together, they’ve built a deceptively simple tool that’s flipping the script on how tech leaders assess their teams—and uncover hidden risks before they explode.

You’ll learn why most CTOs are unknowingly flying blind, how to detect the silent killers of innovation (like misaligned architecture or fuzzy definitions of "automation"), and how a single 30-minute assessment can surface the unknown unknowns holding your business back. Whether you're a scaleup CTO, a board member trying to evaluate tech health, or a founder wondering if your dev team is as strong as they say—they break down the real reason so many companies move slow, and how to fix it. You'll walk away with a new lens on language, leadership, and the hidden liabilities inside most tech functions.

You’ll Learn:

• How benchmarking reveals hidden risks and weak spots in your tech function
• Why compliance frameworks can create a false sense of confidence
• How to detect misalignment between your tech strategy and business goals
• What most CTOs miss about the real cost of technical debt during scale-up
• Why “automation” means different things to different teams—and why that’s dangerous
• How to use Stackup’s 30-minute assessment to surface unknown unknowns
• What poor communication habits are silently sabotaging CTO credibility
• How to use objective scoring to drive strategic investment and track improvement over time

Timestamps:

[00:00] Introduction

[04:41] Common pitfalls in developer-turned-CTOs

[06:33] Triggers for assessing your tech function

[08:00] How Stackup surfaces unknown unknowns

[09:23] Real-world horror stories that drive urgency

[10:07] Why misaligned language leads to costly misunderstandings

[11:56] When tech due diligence reveals million-dollar mistakes

[13:35] What technical debt really costs in scaleups

[14:20] Why early architecture choices are critical

[16:14] Planning upgrades with trigger points

[17:45] How Stackup supports smarter, faster decisions

[20:39] Why slowness doesn’t show up on the P&L

[26:15] Using storytelling to align leadership around tech

[28:01] What Stackup assesses in just 30 minutes

[29:47] Simple questions that reveal massive security flaws

[31:08] Why shiny tools like AI won’t fix misalignment

[33:22] How to counter hype with strategy and expectations

[35:31] When to use Stackup as a new or evolving CTO

[37:59] Proving your tech value with objective results

[39:13] Why Stackup delivers reports in video and podcast formats

[41:19] Running the assessment quarterly to track growth

[43:12] Focusing on just four priorities for maximum ROI

[45:10] How the scoring system ensures objectivity

[47:31] Why most leaders want to improve—transparently

[49:12] Upcoming AI-powered CTO assistant and benchmarking

[52:06] Using Stackup data to shape strategy and performance

You can follow Andy and Dane on LinkedIn and learn more about their work here.

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