Engineering Leadership: Hard Truths for Tech Leaders
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Why your best engineers leave, how bad org structures quietly destroy teams, and what separates engineering leaders who scale from those who stall.
How to Lead Engineering Teams Without Technical Knowledge
Health warning: This article may not make you feel happy, it may not suit you to read this article. I am not even sure I necessarily believe everything I am saying here – but I do believe in personally reflecting on the challenging questions being posed in this article to try make myself a better […]
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Why Bolting AI onto Existing Org Structures Always Fails
There is an old urban legend, immortalised as one of the original Darwin Award nominations, about a man who bolted a JATO unit to a 1967 Chevrolet Impala. JATO stands for Jet Assisted Take Off. It is a solid fuel rocket designed to give heavy military transport aircraft the extra thrust they need to leave […]
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The Message Mangler: Why Leaders Make Decisions on Fiction
There’s a silent killer sitting in most large organisations. It doesn’t appear on any risk register, it doesn’t show up in your sprint velocity charts, and it certainly won’t announce itself in your next all-hands. It operates quietly, in the gap between what actually happened and what gets reported upward. Meet the Message Mangler. 1. […]
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The Full Context Product: How Agentic AI Redefines the Relationship Between Teams and the Software They Own
A variation on the dark factory thesis. Humans remain, humans are accountable, and what changes is everything else. 1. The Team That Memory Built There is a certain kind of organisational structure that forms not by design but by accumulated necessity. Take a low code onboarding system. It changes twice a year. It breaks twice […]
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Corporate Heckling: Why Low-Context Oversight Fails Teams
There is a peculiar sport played in large organisations. It looks like leadership and sounds like governance, hiding behind frameworks, maturity models, and operating rhythms. But in reality it is something far less noble. It is corporate heckling. Corporate heckling is what happens when a function narrates from the sidelines with low context and high […]
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Decision Debt: Why Good Teams Become Approval Factories
1. The Symptoms Come First Start with the experience rather than the diagnosis, because the diagnosis only lands once the pain is familiar. A feature that two people could decide in an afternoon now requires six, and none of them can say with certainty who actually owns the call. Nobody in the building can tell […]
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How Product Team Structures Inflate Engineer Performance Ratings
There is a product team performance bias hiding in plain sight inside every organisation that has moved to product aligned engineering, except that it does not show up as a number on a dashboard, a flag in a talent calibration session, or a red line in an engagement survey. It accumulates quietly, year on year, […]
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Why AI Pilots Fail to Reach Production (And How to Fix It)
Gartner says 40% of agentic AI projects will fail by 2027. I think they’re being optimistic. Walk into almost any large enterprise right now and you’ll find the same scene: a glossy AI pilot, a proud press release, a steering committee meeting monthly to “track progress,” and an absolutely zero percent chance that any of […]
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The Antidote: How to Be Kind, Be Funny, and Still Tell the Truth
Or: What to do after you have spent years writing posts that scare people. There is a pattern in my writing that I have only recently started to see clearly. The Handoff post was about how leaders abdicate. The 10 Nil post was about a team getting thrashed and not knowing why. The heckling post […]
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I Have Two Outlooks on a NASA Spacecraft and Neither Works
1. Ground Control to Major Redmond In early April 2026, four astronauts aboard the Orion spacecraft radioed Mission Control. They were travelling at over four thousand miles per hour, more than thirty thousand miles from Earth, on NASA’s first crewed lunar mission in more than fifty years. The hardware that got them there represents the […]
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Why Kindness Is the Most Important Quality in a Leader (And Without It, Nothing Else Works)
I have spent a long time thinking about what separates the leaders who build things that outlast them from the ones who leave wreckage where organisations used to be. There are thousands of frameworks, countless MBA modules, and an entire industry devoted to answering that question, and most of them are wrong, or at least […]
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The Difference Between Leadership and Management: Why Leaders Create Discomfort and Managers Mask it
1. Management and Leadership Are Not the Same Thing There is a fundamental confusion in how organizations talk about leadership, because we use the word interchangeably with management and we should not. Management is the art of moving things from point A to point B; it is process, it is orderly, and you can measure […]
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