You need troublemakers

#363 – November 12, 2026

good collaboration often requires someone willing to challenge the status quo

You need troublemakers
4 minutes by Maarten Dalmijn

Good collaboration often requires someone willing to challenge the status quo. When teams stay in their silos, they make decisions that serve their own area but hurt the company overall. Asking hard questions across departments creates friction but leads to better outcomes. The best troublemakers push back without burning bridges, keeping the long-term goal in focus.

AI & The Rise of Intelligent Operations
sponsored by Celonis

Having driven over $2 billion in revenue for Microsoft AI, Noelle Russell shares how to build trust and inclusion as you look to responsibly scale AI.

You can’t change your boss
2 minutes by Jacob Kaplan-Moss

Jacob points out that trying to give your boss feedback rarely works and can backfire badly. Power flows downward at work, so your boss has little reason to listen and may even punish you for speaking up. Good bosses who welcome feedback exist, but they usually seek it out themselves. If your boss is difficult, your real options are to adapt or move on.

We handed testing to AI. Here is what stayed human.
6 minutes by Roman Nikolaev

A team facing a QA crunch built an AI testing assistant that now handles 75–85% of test execution per ticket. It sorts the queue each morning, checks acceptance criteria using the cheapest method available, and hunts for edge cases. Humans still make every final call. The team is keeping up, but only just, and the expectation is that QA will shift toward building better systems around AI rather than adding more testers.

Building vs splitting: A model for growing an engineering org
6 minutes by Daniel Pupius

Small engineering teams feel planning pressure early, but splitting evenly into sub-teams often creates coordination overhead and locks in boundaries before the work is stable. Daniel suggests a better approach is "budding": keep one fluid core team, and only spin off a small group when a workstream shows clear, ongoing ownership signals like its own bug queue or recurring requests. The core team stays intact and flexible until the product shape is clear, then dissolves naturally into the teams that grew from it.

Every upgrade has a downgrade
9 minutes by Jurriaan Kamer

Every upgrade quietly fires the old thing from jobs it was doing without anyone noticing. AI tools promise speed and scale, but erode deep thinking, product quality, and human service. Return-to-office mandates restore connection but cost trust and flexibility. Before rolling out any big change, name the real trade-off honestly, then design experiments that protect what matters most.

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