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.

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 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.