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.

Most CTOs fail not because of bad decisions, but because they stop asking why.

In this episode, I sit down with Massimo Belloni, Head of Machine Learning and Data Science at Docplanner, to discuss what real technical leadership looks like when the answers aren’t obvious.

We dig into bold CTO leadership, why engineering leadership is mostly about people, and how curiosity in leadership builds trust faster than authority ever will. Massimo shares hard-earned lessons from leading ML teams across industries, and why the job isn’t about being the smartest person in the room, but creating conditions where teams thrive.

If you’re navigating CTO mindset shifts, managing high-performing engineering teams, or feeling the quiet weight of imposter syndrome in tech leadership, this conversation will land. We talk about invisible leadership work, asking better questions, and why progress only makes sense in hindsight.

Iif you’re leading through complexity and change, this episode is your reminder: certainty isn’t the goal, clarity is.

You’ll Learn:

[00:00] Introduction

[02:14] How Massimo realized leadership is about people, not technical mastery

[05:48] Why trying to be the smartest person in the room backfires

[09:37] What changes when you lead systems you don’t fully understand

[13:22] Why most leadership problems aren’t actually technical

[17:54] How asking why builds trust faster than giving answers

[22:41] Why strong teams come from safety, not fearlessness

[27:36] How invisible leadership work compounds over time

[33:18] The question Massimo uses to measure leadership progress

[38:47] Why leadership only makes sense in hindsight

Resources Mentioned:

The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or Apple

Steve Jobs Stanford Commencement Speech | YouTube

You can connect with Massimo on LinkedIn and learn more about his work on his substack here.

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

Daf Yomi Berachos Daf 10 by R’ Eli Stefansky