#24 | Sunday reads for EMs

My favourite reads of the week to make your Sunday a little more inspiring.

Nov 30, 2025

👋 Hey, it’s Stephane. This is a new series in which every Sunday I share with you my favourite reads of the week. To accelerate your growth see: 50 Notion Templates | The EM’s Field Guide | CodeCrafters | Get Hired as an EM | 1:1 Coaching

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Invert, Always Invert (
James Stanier
)

tl;dr: Instead of asking “how do we succeed?” ask “how would this absolutely fail?” and then systematically avoid those failure modes. This applies beautifully to rollouts, architectural decisions, and estimation.

How Startups Lose Their Edge (
PostHog
)

tl;dr: Culture dilutes through management layers. Each hire makes hires slightly different from what you meant, and concessions compound. Worth reading if your org is scaling - the warning signs here are specific enough to recognize in your own team.

The Hitchhiker’s Guide to Measuring Engineering ROI (
Itzy Sabo
)

tl;dr: Most CTOs freeze when asked “what’s engineering’s ROI?” because they counter with DORA metrics that don’t translate to revenue. This piece offers two concrete formulas: Operating Efficiency (existing customer revenue ÷ KTLO costs) and Growth Efficiency (new customer revenue ÷ CapEx investment).

Startup Engineering Team Organisation (Marc G Gauthier)

tl;dr: A walkthrough of how engineering team structures evolve and break: from technical teams, to squads, to chapters, to platform teams, to one-shot projects. Worth reading if you’re at 15-50 engineers and sensing your current structure is about to hit its ceiling.

Leading in Low-Trust Times (Subbu Allamaraju)

tl;dr: Listen first, acknowledge reality, be transparent even when it’s unpopular, then co-develop direction collaboratively. A great read if you’re managing through a period your team didn’t choose; the core framework (authenticity as antidote to cynicism) is sound.