Engineering Leadership Reading List - September 2025

This month's Engineering Leadership Reading List for September 2025 confronts organizational transformation and power shifts. The Last Days of the Managerial Class provocatively argues that AI and remote work fundamentally undermine justifications for middle management layers, enabling flatter structures with direct communication between executives and individual contributors. While perhaps overstated, the article forces engagement with genuine questions about which coordination and translation functions remain valuable versus which exist primarily through organizational inertia.

Practical planning frameworks provide counterweight through 5 Steps from Features to Outcome Roadmap, offering concrete methodology for transitioning teams from output-focused feature lists toward outcome-oriented planning. The framework acknowledges organizational realities whilst pushing teams toward more strategic thinking, demonstrating that better planning processes don't require wholesale organizational disruption to deliver value.

September captures tension between revolutionary rhetoric about AI-driven organizational transformation and practical incrementalism of improving existing processes. The reading list documents both perspectives: voices arguing current structures are obsolete alongside voices offering pragmatic improvements within current constraints. Where truth lies depends heavily on specific organizational contexts, timelines, and which aspects of management work prove automatable versus irreducibly human.

As always, the Quantum Fax Machine Propellor Hat Key will guide your browsing. Enjoy!

Links

Regards,
M@

[ED: If you'd like to sign up for this content as an email, click here to join the mailing list.]

Originally published on quantumfaxmachine.com and cross-posted on Medium.

hello@matthewsinclair.com | matthewsinclair.com | bsky.app/@matthewsinclair.com | masto.ai/@matthewsinclair | medium.com/@matthewsinclair | xitter/@matthewsinclair |