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.