64: What Got You Here Won’t Get You There — CTO Leadership with Catherine Stagg-Macey

7 snips

Oct 6, 2025

Catherine Stagg-Macey, an executive coach for technical experts transitioning into leadership, shares her insights on the struggles of moving from individual contributor to team leader. She highlights why being the smartest person in the room can become a hindrance and explores the damaging 'hero' culture that leads to burnout. Catherine discusses the importance of recognizing triggers, testing new leadership behaviors, and how upbringing influences leadership styles. The conversation also touches on the potential role of AI in coaching.

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INSIGHT

Technical Skill Stops Scaling

Technical expertise stops scaling when leadership demands people skills and delegation.
Catherine Stagg-Macey highlights that being the smartest person in the room is insufficient at scale.

ANECDOTE

25 Meetings A Week Trap

One client had 25 meetings a week because he didn't trust his team to avoid mistakes.
That micromanagement trapped him in detail work and left no time for strategic thinking.

INSIGHT

The Superhero Culture Cycle

Chronic firefighting creates an addictive 'superhero' culture that rewards crisis fixing.
That modelling trains teams to expect constant rescue instead of building sustainable systems.

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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

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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.