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Showing posts from April, 2026

AI & Systems Debt

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If there's one AI article you read today, make sure it's this one: https://www.forbes.com/sites/jasonwingard/2026/04/23/vibe-coding-will-break-your-company This isn't an anti-AI or AI-is-terrible take. This is a real & grounded take on the very real problem that AI is allowing us to move faster that the decision-time is compressed. Over the course of my career, I learned that the shift towards "seniority" isn't just that you have more of the core skills and are faster and better. It's that you become wiser about when to use those skills. You ask fundamental questions like: What new problems do we create by solving this? If we build this, who will maintain it? If we build this, will this distract us from our priorities? If we build this will we set some new expectations that we'll have to uphold? Just because something has value doesn't mean it doesn't create a form of debt in the long run. And these were all important to consider before  G...

Rude Q&As

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There's a scene from the movie Big, I always think back to: Tom Hanks' character is sitting in his first big important meeting about a new toy launch, and he stops everyone in their tracks by saying "I don't get it... what's fun about playing with a building?" His question isn't meant to be antagonistic. It's honest, it's earnest, and (most importantly) it gets right to the point. One of the challenges we run into in our adult corporate lives is leaning so heavily on politeness that we introduce ambiguity ("we" should get this done...), and we combat that ambiguity with frameworks (OKRs, KPIs, SMART goals, etc.) But sometimes, we need a bit of Tom Hanks in the mix. That's the power of the Rude Q&A - a document that captures all the blunt, direct, and even rude questions. It's great for after the ideation, research, analysis, refinements and iterations. It challenges, stress-tests, detects contradictions, revalidates assumption...

80% of scenarios, 80% of the time

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I'm starting to think generative AI is a proxy for revealing skills gaps. Regardless of field, if you are a high performing, critical thinking, strategic and effective individual then AI is a time saving augmentor of your existing capabilities. Your high degree of skill lets you use AI tactically. You quickly iterate with prompts, better orchestrate, evaluate outputs, and immediately identify when you've been received a quality output. Alternatively, you will quickly revert to the traditional non-AI way of doing things if needed while offloading the more discreet and deterministic tasks to AI. And all that is great... If you're great at what you do. On the flip side, AI has also allowed for us all to easily fake that we are skilled in areas where we've not spent any time honing our craft. To our untrained eye, AI has given us passable-quality outputs that are in need of a trained eye to call out the risks, challenges, issues, or problems. At best, despite our lack of sk...

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