https://billsimmons.net/ A weekly brief on AI transformation inside mission-driven organizations: what is real, what it costs, and what it does to the people doing the work. en-us Wed, 30 Sep 2026 15:15:59 +0000 https://billsimmons.net/writing/post.html?slug=confession-or-invitation-to-discussion https://billsimmons.net/writing/post.html?slug=confession-or-invitation-to-discussion Tue, 15 Sep 2026 12:00:00 +0000 Written with Jason Malec after an AI detector flagged his post: one of them posts only human writing, the other mixes in AI, and both ask where AI belongs in writing. https://billsimmons.net/writing/post.html?slug=how-to-know-ai-transformation-is-real https://billsimmons.net/writing/post.html?slug=how-to-know-ai-transformation-is-real Tue, 08 Sep 2026 12:00:00 +0000 The test is subtraction: pull the AI out and see whether the workflow still stands. Three signs of real change, none of which need an adoption metric. https://billsimmons.net/writing/post.html?slug=the-hard-parts-are-still-hard https://billsimmons.net/writing/post.html?slug=the-hard-parts-are-still-hard Tue, 25 Aug 2026 12:00:00 +0000 Coding agents made building a tool easy. Doing it safely, keeping secrets out of the open, and keeping it running still takes architecture. https://billsimmons.net/writing/post.html?slug=adoption-is-the-wrong-metric https://billsimmons.net/writing/post.html?slug=adoption-is-the-wrong-metric Tue, 18 Aug 2026 12:00:00 +0000 One person building with AI never shows up as adoption. What has actually changed in a year is the better measure. https://billsimmons.net/writing/post.html?slug=context-window-management https://billsimmons.net/writing/post.html?slug=context-window-management Tue, 11 Aug 2026 12:00:00 +0000 Six months ago it was prompt engineering. Today it is context window management, and the failures are manageable. https://billsimmons.net/writing/post.html?slug=why-a-ceo-posts-about-ai https://billsimmons.net/writing/post.html?slug=why-a-ceo-posts-about-ai Thu, 06 Aug 2026 12:00:00 +0000 Policy follows use, not the other way around. Three things a CEO can do today that were impossible nine months ago. https://billsimmons.net/writing/post.html?slug=record-a-skill-easy-button https://billsimmons.net/writing/post.html?slug=record-a-skill-easy-button Tue, 04 Aug 2026 12:00:00 +0000 Turn it on, talk through the task, hit done. Claude writes the skill file and the automation is ready to run. https://billsimmons.net/writing/post.html?slug=donor-appeals-ai-detection https://billsimmons.net/writing/post.html?slug=donor-appeals-ai-detection Tue, 28 Jul 2026 12:00:00 +0000 Detection tools stopped being unreliable. What that changes for nonprofits writing appeals with AI. https://billsimmons.net/writing/post.html?slug=no-server-no-developer https://billsimmons.net/writing/post.html?slug=no-server-no-developer Tue, 21 Jul 2026 12:00:00 +0000 Scheduled jobs now run on someone else's servers. The last piece of infrastructure a small nonprofit never had just disappeared. https://billsimmons.net/writing/post.html?slug=clarity-is-the-new-barrier https://billsimmons.net/writing/post.html?slug=clarity-is-the-new-barrier Thu, 16 Jul 2026 12:00:00 +0000 The barrier to building software used to be a language barrier. Now it is clarity. https://billsimmons.net/writing/post.html?slug=kivu-translation https://billsimmons.net/writing/post.html?slug=kivu-translation Tue, 14 Jul 2026 12:00:00 +0000 A skill file that knew how people actually speak in Kivu turned weeks of translation into a few hours. https://billsimmons.net/writing/post.html?slug=salesforce-is-not-your-backup https://billsimmons.net/writing/post.html?slug=salesforce-is-not-your-backup Wed, 08 Jul 2026 12:00:00 +0000 Six to eight weeks to maybe recover your donor history. So we built our own nightly backup instead. https://billsimmons.net/writing/post.html?slug=do-not-overprompt-fable-5 https://billsimmons.net/writing/post.html?slug=do-not-overprompt-fable-5 Tue, 07 Jul 2026 12:00:00 +0000 Fable 5 wants a mission and a review, not a detailed prompt. Four habits that flip. https://billsimmons.net/writing/post.html?slug=fable-5-orchestrator-quote https://billsimmons.net/writing/post.html?slug=fable-5-orchestrator-quote Thu, 02 Jul 2026 12:00:00 +0000 An engineer at one of the big five on what Fable 5 actually hands off. https://billsimmons.net/writing/post.html?slug=grant-money-on-the-table https://billsimmons.net/writing/post.html?slug=grant-money-on-the-table Tue, 30 Jun 2026 12:00:00 +0000 The pipeline was never thin for lack of opportunities. The search was too expensive to run often. https://billsimmons.net/writing/post.html?slug=the-real-barrier-to-ai https://billsimmons.net/writing/post.html?slug=the-real-barrier-to-ai Fri, 26 Jun 2026 12:00:00 +0000 Most organizations don't have a technology problem. They have a leadership problem wearing a technology costume. https://billsimmons.net/writing/post.html?slug=dignity-lives-in-the-person https://billsimmons.net/writing/post.html?slug=dignity-lives-in-the-person Fri, 26 Jun 2026 12:00:00 +0000 Dignity lives in the person, not the position. What leaders owe people on the way across. https://billsimmons.net/writing/post.html?slug=complaining-well https://billsimmons.net/writing/post.html?slug=complaining-well Tue, 23 Jun 2026 12:00:00 +0000 The best prompts don't sound like instructions. They sound like honest complaints. https://billsimmons.net/writing/post.html?slug=ceos-running-coding-agents https://billsimmons.net/writing/post.html?slug=ceos-running-coding-agents Tue, 16 Jun 2026 12:00:00 +0000 Fifty funders researched by an AI org chart: an orchestrator, ten researchers, two reviewers. https://billsimmons.net/writing/post.html?slug=i-stopped-reading-ai-newsletters https://billsimmons.net/writing/post.html?slug=i-stopped-reading-ai-newsletters Tue, 09 Jun 2026 12:00:00 +0000 I built an agent to do the watching and reading for me. The template is free on GitHub. https://billsimmons.net/writing/post.html?slug=four-sources https://billsimmons.net/writing/post.html?slug=four-sources Mon, 01 Jun 2026 12:00:00 +0000 Diamandis, Mollick, Nate B. Jones, Mindstream. https://billsimmons.net/writing/post.html?slug=ai-boardroom-second-opinion https://billsimmons.net/writing/post.html?slug=ai-boardroom-second-opinion Tue, 19 May 2026 12:00:00 +0000 A multi-agent system designed to disagree: the second opinion a chatbot can't give you. https://billsimmons.net/writing/post.html?slug=vibeware-the-critics-are-right https://billsimmons.net/writing/post.html?slug=vibeware-the-critics-are-right Tue, 12 May 2026 12:00:00 +0000 The critics are right about the failures. The discipline is what separates the builds. https://billsimmons.net/writing/post.html?slug=synchronized-swimming https://billsimmons.net/writing/post.html?slug=synchronized-swimming Tue, 05 May 2026 12:00:00 +0000 Solo tools solve problems. Orchestrated ones transform the organization. https://billsimmons.net/writing/post.html?slug=use-ai-to-fix-the-plumbing https://billsimmons.net/writing/post.html?slug=use-ai-to-fix-the-plumbing Tue, 28 Apr 2026 12:00:00 +0000 You don't need agents yet. You need the pipes between the systems you already have. https://billsimmons.net/writing/post.html?slug=sam-walton-og-vibe-coder https://billsimmons.net/writing/post.html?slug=sam-walton-og-vibe-coder Tue, 21 Apr 2026 12:00:00 +0000 He knew the problem cold and directed the build. The yellow legal pad is now a conversation. https://billsimmons.net/writing/post.html?slug=the-ai-isnt-the-asset https://billsimmons.net/writing/post.html?slug=the-ai-isnt-the-asset Tue, 14 Apr 2026 12:00:00 +0000 Owned infrastructure that happens to be AI-built, and the Donor Brief Builder open build. https://billsimmons.net/writing/post.html?slug=35-days-1-million-zero-developers https://billsimmons.net/writing/post.html?slug=35-days-1-million-zero-developers Tue, 07 Apr 2026 12:00:00 +0000 The post that started it: what a 25-person nonprofit shipped with an AI coding agent.