👋 Hi, I’m Aaron Held

Why Your Strategic Planning Fails (And How to Fix It) I’ve seen more agile planning sessions derailed by politics than by any technical challenge. It always starts the same way. You get the right people in a room—Product, Engineering, Sales, Finance—and for a moment, it feels like a powerful alliance focused on building the future. A spy’s guide to strategy helped me realize these sessions unfold in three acts: Alliance, Competition, and Endgame. ...

I got into management because I saw myself as a player-coach. I could create software and make my teams more effective. The most rewarding part? Shielding creative people from bad direction and then watching them delivering results. Success gave me more influence to shape process and continue to help my teams be their best. Chris Dixon’s recent, high-profile shift from “Management” back to “Engineer” made me pause. He’s a true champion of the possible who had an outsized impact on my early career, and his move forced me to think about my own direction. ...

Introduction For over 25 years, I’ve blogged through countless iterations of my writing and technical processes. Recently, I’ve found something that makes writing enjoyable again: Claude Code. This isn’t another “AI will replace writers” story. It’s about how AI can enhance creative expression by handling the tedious parts of content creation. Crucially, it helps me overcome the final hurdle: actually publishing. Most of my posts start as first drafts that never see the light of day. Now, my Robot Buddy guides me through the entire process, from idea to execution. In this post, I’ll walk you through my complete workflow from initial idea to published post, showing exactly how Claude Code integrates with Hugo, my static site generator of choice. You’ll see real screenshots, actual commands, and the genuine collaborative process that happens when human insight meets AI assistance. ...

Is the Economy derailing your Agile Transformations? Economic uncertainty hits. Layoffs are all over the news and productivity suffers. Every time, I see people wanting to blame the loss or productivity on budget cuts and layoffs. That is the short term impact, but I see longer term harm playing out. Teams that were thriving on collaborative decision-making suddenly go quiet. The same people who were debating sprint priorities and pushing back on requirements start waiting for marching orders from above. ...

𝗣𝗹𝗲𝗮𝘀𝗲 𝗿𝗲𝗮𝗱 𝗶𝗻 𝘁𝗵𝗲 𝘃𝗼𝗶𝗰𝗲 𝗼𝗳 𝗥𝗼𝗱 𝗦𝗲𝗿𝗹𝗶𝗻𝗴 𝘈 𝘲𝘶𝘪𝘦𝘵 𝘴𝘶𝘣𝘶𝘳𝘣𝘢𝘯 𝘦𝘷𝘦𝘯𝘪𝘯𝘨. 𝘈 𝘮𝘢𝘯, 𝘢 𝘴𝘤𝘪𝘦𝘯𝘵𝘪𝘴𝘵, 𝘢𝘵 𝘵𝘩𝘦 𝘷𝘦𝘳𝘺 𝘱𝘪𝘯𝘯𝘢𝘤𝘭𝘦 𝘰𝘧 𝘩𝘪𝘴 𝘧𝘪𝘦𝘭𝘥. 𝘏𝘦 𝘩𝘢𝘴 𝘨𝘪𝘷𝘦𝘯 𝘵𝘩𝘦 𝘸𝘰𝘳𝘭𝘥 𝘢 𝘸𝘦𝘢𝘱𝘰𝘯 𝘰𝘧 𝘶𝘭𝘵𝘪𝘮𝘢𝘵𝘦 𝘱𝘰𝘸𝘦𝘳, 𝘢 𝘵𝘰𝘰𝘭 𝘩𝘦 𝘣𝘦𝘭𝘪𝘦𝘷𝘦𝘴 𝘸𝘪𝘭𝘭 𝘦𝘯𝘴𝘶𝘳𝘦 𝘱𝘦𝘢𝘤𝘦. 𝘏𝘦 𝘴𝘭𝘦𝘦𝘱𝘴 𝘴𝘰𝘶𝘯𝘥𝘭𝘺, 𝘩𝘪𝘴 𝘤𝘰𝘯𝘴𝘤𝘪𝘦𝘯𝘤𝘦 𝘶𝘯𝘵𝘳𝘰𝘶𝘣𝘭𝘦𝘥 𝘣𝘺 𝘵𝘩𝘦 𝘵𝘦𝘳𝘳𝘪𝘣𝘭𝘦 𝘧𝘰𝘳𝘤𝘦 𝘩𝘦 𝘩𝘢𝘴 𝘶𝘯𝘭𝘦𝘢𝘴𝘩𝘦𝘥. 𝘉𝘶𝘵 𝘵𝘰𝘯𝘪𝘨𝘩𝘵, 𝘢 𝘴𝘵𝘳𝘢𝘯𝘨𝘦𝘳 𝘸𝘪𝘭𝘭 𝘬𝘯𝘰𝘤𝘬 𝘰𝘯 𝘩𝘪𝘴 𝘥𝘰𝘰𝘳. 𝘈 𝘴𝘮𝘢𝘭𝘭 𝘮𝘢𝘯, 𝘢 𝘳𝘦𝘱𝘰𝘳𝘵𝘦𝘳, 𝘸𝘪𝘵𝘩 𝘢 𝘴𝘦𝘦𝘮𝘪𝘯𝘨𝘭𝘺 𝘴𝘪𝘮𝘱𝘭𝘦 𝘨𝘪𝘧𝘵 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘴𝘤𝘪𝘦𝘯𝘵𝘪𝘴𝘵’𝘴 𝘺𝘰𝘶𝘯𝘨 𝘴𝘰𝘯. 𝘐𝘵 𝘪𝘴 𝘢𝘯 𝘢𝘤𝘵 𝘰𝘧 𝘤𝘢𝘴𝘶𝘢𝘭 𝘮𝘢𝘭𝘪𝘤𝘦, 𝘰𝘳 𝘱𝘦𝘳𝘩𝘢𝘱𝘴, 𝘢 𝘱𝘳𝘰𝘧𝘰𝘶𝘯𝘥 𝘴𝘵𝘢𝘵𝘦𝘮𝘦𝘯𝘵. 𝘍𝘰𝘳 𝘸𝘩𝘢𝘵 𝘩𝘦 𝘭𝘦𝘢𝘷𝘦𝘴 𝘪𝘴 𝘢 𝘭𝘰𝘢𝘥𝘦𝘥 𝘳𝘦𝘷𝘰𝘭𝘷𝘦𝘳. ...