Migration, tooling choices, and outcomes

What if leadership isn’t about managing people, but about owning decisions?

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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.