https://www.promptingtheorg.blog Practical conversations about what AI changes for engineering leadership and management. https://www.promptingtheorg.blog/2026/05/local-genius-collective-drag-ai-tooling-at-scale.html https://www.promptingtheorg.blog/2026/05/local-genius-collective-drag-ai-tooling-at-scale.html Wed, 13 May 2026 00:00:00 GMT I was discussing with some old friends recently about on call not specific incidents, more how to shap the burden across a large team. Someone mentioned in their company a few engi... https://www.promptingtheorg.blog/2026/05/ai-fluency-new-non-negotiable-hiring.html https://www.promptingtheorg.blog/2026/05/ai-fluency-new-non-negotiable-hiring.html Wed, 06 May 2026 00:00:00 GMT I have been talking to people in my network lately hiring managers, staff engineers, a few founders and a phrase keeps surfacing in different words but with the same spine: if some... https://www.promptingtheorg.blog/2026/05/ai-spend-volatility-what-changed-and-what-leaders-can-control.html https://www.promptingtheorg.blog/2026/05/ai-spend-volatility-what-changed-and-what-leaders-can-control.html Sun, 03 May 2026 00:00:00 GMT Engineering organizations are hitting a planning wall that spreadsheets were not built for. Headcount curves are familiar: slow ramps, predictable bands, and finance models that mo... https://www.promptingtheorg.blog/2026/04/when-minimum-span-arrived-faster-than-i.html https://www.promptingtheorg.blog/2026/04/when-minimum-span-arrived-faster-than-i.html Sun, 26 Apr 2026 00:00:00 GMT I was in a leadership forum this week when the conversation turned to span of control. Not in the abstract. In numbers. There is a new floor forming: a minimum expectation that man... https://www.promptingtheorg.blog/2026/03/from-story-points-to-decision-throughput.html https://www.promptingtheorg.blog/2026/03/from-story-points-to-decision-throughput.html Mon, 30 Mar 2026 00:00:00 GMT I was in planning recently when someone asked, "How many points can we commit to next sprint?" For years, that question was normal. Useful, even. It gave us a shared language for f... https://www.promptingtheorg.blog/2026/03/from-reporting-grind-to-leadership-time.html https://www.promptingtheorg.blog/2026/03/from-reporting-grind-to-leadership-time.html Sun, 29 Mar 2026 00:00:00 GMT A few weeks ago, I had one of those leadership moments that felt productive on paper and pointless in reality. I had spent over an hour stitching together Jira updates, GitHub acti... https://www.promptingtheorg.blog/2026/03/performance-reviews-in-age-of-ai.html https://www.promptingtheorg.blog/2026/03/performance-reviews-in-age-of-ai.html Mon, 09 Mar 2026 00:00:00 GMT As Engineering Managers, we’ve always known that impact beats throughput. The best leaders in our industry already look past the raw volume of PRs or the velocity of a sprint to fi... https://www.promptingtheorg.blog/2026/03/the-150-ratio-is-pod-dead-and-horde.html https://www.promptingtheorg.blog/2026/03/the-150-ratio-is-pod-dead-and-horde.html Fri, 06 Mar 2026 00:00:00 GMT The 1:50 Ratio: Is the "Pod" Dead and the "Horde" Rising? For decades, the "Rule of 7" (plus or minus two) has been the gold standard for engineering management. The logic was simp... https://www.promptingtheorg.blog/2026/02/when-ai-feels-like-extra-work.html https://www.promptingtheorg.blog/2026/02/when-ai-feels-like-extra-work.html Fri, 27 Feb 2026 00:00:00 GMT I had a realization this week: I barely opened my LLM this week, and for the first time in months, I felt like I was falling behind. In the past few months I have been surrounded b... https://www.promptingtheorg.blog/2026/02/playing-chess-simul-are-ai-agents.html https://www.promptingtheorg.blog/2026/02/playing-chess-simul-are-ai-agents.html Sat, 21 Feb 2026 00:00:00 GMT We were promised that AI would be the "Easy Button" for engineering. Instead, I’m seeing something else: my highest performing leads and managers are reporting a level of fatigue t... https://www.promptingtheorg.blog/2026/02/the-cohesion-crisis.html https://www.promptingtheorg.blog/2026/02/the-cohesion-crisis.html Fri, 20 Feb 2026 00:00:00 GMT Ever since becoming a leader my North Star has been velocity. Each day I’ve tried to optimize sprints, CI/CD pipelines, and stand ups to solve one problem: how do we ship faster? N... https://www.promptingtheorg.blog/2026/02/headcount-vs-tokens.html https://www.promptingtheorg.blog/2026/02/headcount-vs-tokens.html Tue, 17 Feb 2026 00:00:00 GMT As I work through another planning cycle, the ritual remains the same: the spreadsheet opens, the roadmap is prioritized, and we start the negotiation for more "heads." In my world... https://www.promptingtheorg.blog/2026/02/are-engineering-managers-obsolete-in-ai-world.html https://www.promptingtheorg.blog/2026/02/are-engineering-managers-obsolete-in-ai-world.html Mon, 16 Feb 2026 00:00:00 GMT So far in my career, our value as leaders was measured by how well we manage the machine optimizing for velocity, smoothing out team dynamics, and ensuring predictable delivery of... https://www.promptingtheorg.blog/2026/02/prompting-ai-adoption-for-skeptical-engineers.html https://www.promptingtheorg.blog/2026/02/prompting-ai-adoption-for-skeptical-engineers.html Fri, 13 Feb 2026 00:00:00 GMT We’ve all seen the headlines. "AI will replace the junior engineer”. "The 10x engineer is now a 100x engineer." In leadership meetings almost every conversation comes back to veloc... https://www.promptingtheorg.blog/2026/02/promptingtheorg.html https://www.promptingtheorg.blog/2026/02/promptingtheorg.html Wed, 11 Feb 2026 00:00:00 GMT For a decade, my job as an Engineering Leader was about clarity and predictability. I optimized for the team's velocity, coached managers on team dynamics, helped engineers maximis... https://www.promptingtheorg.blog/2026/02/the-just-in-time-manager-and-1-1-gemini-gem.html https://www.promptingtheorg.blog/2026/02/the-just-in-time-manager-and-1-1-gemini-gem.html Wed, 11 Feb 2026 00:00:00 GMT We’ve all been there. The calendar notification pings. You finish your previous meeting (which ran over by three minutes), and as the Zoom window for your next 1:1 pops up, you’re...