#288 – February 22, 2026
skills that worked before start to hurt instead of help
The shift to managing managers
8 minutes by Kevin Goldsmith
Moving from managing a team to managing managers is a sharp shift that catches many leaders off guard. Skills that worked before, like staying close to the work, start to hurt instead of help. The real job becomes sharing context so managers can make good decisions without constant approval. When leaders hold too tight, decisions slow down and their own growth stalls.
Unblocked: The context layer for AI-driven development
sponsored by Unblocked
Give AI agents the knowledge of your most experienced engineers. Unblocked builds context from your team’s code, PR history, conversations, documentation, planning tools, and runtime signals to surface what matters for the task at hand – while resolving conflicts and respecting permissions. Ship faster with AI outputs that reflect how your system actually works.
How to beat decision fatigue
9 minutes by Phil McKinney
Fatigue doesn't drain your brain like a battery. It quietly lowers your standards, pushing you toward whatever takes the least effort. Doctors prescribe more unnecessary antibiotics as the day goes on. Nurses miss doses. Analysts grow less accurate. The fix is to schedule hard decisions early, set rules in advance for when you're tired, and treat recovery as part of good judgment, not a reward for finishing work.
14 more lessons from 14 years at Google
12 minutes by Addy Osmani
Good engineering is less about individual skill and more about how teams make decisions, share ownership, and remove friction. Vague plans, slow decisions, and unclear team boundaries quietly kill more projects than bad code ever does. Trust, small changes, and clear ownership let normal people do extraordinary things consistently. AI makes output cheap, so judgment about what to build and what to cut matters more than ever.
Feeling fast, delivering slow
12 minutes by Dalia Havens
AI tools make individual developers faster, but most organizations see no real gains because the underlying processes aren't ready. Common blockers include weak test coverage, poor code context, slow review cycles, and tool sprawl. Developers often feel more productive while actually delivering slower. Fixing the fundamentals, like better testing, clearer architecture, and stronger review practices, is what turns AI into real organizational value.
Question behind the question
11 minutes by Wes Kao
Every question has a surface layer and a deeper concern underneath. Spotting that hidden concern, the "question behind the question," helps you give answers that actually satisfy people. When answers keep missing the mark, pause and think about what the person truly needs, whether that's reassurance, better evidence, or clearer logic. Sharing context when you ask questions yourself works the same way, making it easier for others to give you useful replies.
And the most popular article from the last issue was: