The CTO Playbook

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

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



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

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

You’ll Learn:

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

Timestamps:

[00:00] Introduction

[05:58] Saying yes to unpredictable challenges

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

[11:58] Handling moments when operations nearly collapse

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

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

[20:06] Creating trust and making failure safe

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

[27:00] Unlikely outcomes from saying yes

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

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

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

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

Resources Mentioned:

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

You can connect with Corey on LinkedIn and his website.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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

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



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

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

You’ll Learn:

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

Timestamps:

[00:00] Introduction

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

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

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

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

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

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

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

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

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

Resources Mentioned:

Swimming in Tech Debt by Lou Franco | Book

Crossing the Chasm by Geoffrey Moore | Book or Audiobook

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

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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

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



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

You’ll Learn:

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

Timestamps:

[00:00] Introduction

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

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

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

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

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

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

[15:46] Rebuilding trust and technology at Realforce

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

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

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

Resources Mentioned:

Start with Why by Simon Sinek | Book

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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

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



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

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 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 explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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

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

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 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 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.

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



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

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

In this episode, I’m talking with 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 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 managing individual contributors the best way possible?

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 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 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.