Show Notes
What if leadership isn’t about managing people, but about owning decisions?
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 joined by Michael Di Prisco, who describes himself as “a software engineer struggling to realize that he became a tech leader”.
Michael was pretty reluctant to become an engineering manager and leave the keyboard, but he started moving outside his comfort zone one step at a time. He gradually found a balance where he still writes code, but it is not expected of him.
We explore how authority and responsibility actually work inside a team. He explains why every engineer should understand the business, and what changed when he started delegating code instead of doing everything himself. That shift did not slow the team down. The quality of their coding was becoming better, and people could focus on what they wanted to do more.
We also get into documenting technical debt and how his team reached a point where they solved more debt than they created. If you are thinking about the move into leadership, this is a grounded look at what that shift might actually involve.
You’ll Learn:
[00:00] Introduction [02:05] Stepping into leadership felt like losing his edge as an engineer [06:45] A small move outside your comfort zone can shift your entire career path [08:30] Coding stopped being expected and started becoming a deliberate choice [12:10] Teams can improve when a tech lead stops doing all the coding and starts delegating [16:20] The hidden gap between responsibility and authority most teams never fix [20:15] Engineers make weaker decisions when they don’t understand the business [24:40] Letting go of best practices can reveal what actually works in your context [27:10] Documenting technical debt can lead to actually reducing it over time [31:25] Small steps and honest feedback often outperform big career moves
Resources Mentioned:
The Software Architect Elevator: Redefining the Architect's Role in the Digital Enterprise by Gregor Hohpe | Book Architectural Decision Records (ADR) | Website GitHub | Website Astro | Website CodeMotion Conference | Website jsday - The Italian JavaScript Conference | Website Italian Agile Days Conference | Website
Dive deeper into Michael’s ideas on software engineering and leadership on his blog.
Find more from Michael 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.
More from The CTO Playbook
Most leaders treat impostor syndrome as something they need to overcome. But what if the belief that you're not good enough is actually serving a purpose?
AI has made building software dramatically faster. The problem is that the rest of the engineering system hasn’t caught up. AI agents can now produce code, tests, documentation, migrations, and pull requests at a pace most engineering organisations weren’t designed to handle. But when everything around code review accelerates, review becomes the bottleneck. Pull requests pile up, reviewers spend more time reconstructing intent, and experienced engineers can end up reduced to repeatedly saying yes or sending work back for fixes.
AI adoption is getting easier for everyone. The harder question is whether you're using it to optimise the game you're already in, or to build a position that changes the game.
AI isn't just changing how engineers work. It's forcing technology leaders to rethink what makes management valuable.
Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.