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Worked thinking for hard technical decisions

Long reads for technical leaders. Each one follows a real problem through to a decision, and leaves you with something to use on your own.

Latest · Security & compliance · 16 min readBuild a compliance operating system with NIST CSF 2.0A practical guide for engineering leaders. We’ll follow one fictional startup from a customer’s security questionnaire to a working set of controls, evidence and decisions.Includes a workbook you can tailorRead the articleNovember 5, 2026

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Technical leadership · 9 min readDo you have an execution problem, or a clarity problem?Some plans stall because delivery is hard. Others stall because the decision underneath them was never made. Telling the two apart changes what you do next.Includes a worksheet for your own decisionRead the articleOctober 8, 2026