https://charleslehman.com/blog/ Essays on product craft, leadership, and making sense of how things work. en-us Sun, 20 Sep 2026 22:41:42 GMT https://charleslehman.com/blog/play-the-smaller-game/ https://charleslehman.com/blog/play-the-smaller-game/ Wed, 08 Jul 2026 18:00:00 GMT Mbappé learned football in a cage. Pickleball sharpened my tennis. The constrained game teaches what the full game can't - and side projects are how PMs get their reps. Product Learning Sports https://charleslehman.com/blog/not-behind-on-ai/ https://charleslehman.com/blog/not-behind-on-ai/ Sat, 28 Feb 2026 18:00:00 GMT You haven't missed the AI wave. But the window is closing. Here's the simplest way to start, no technical skills required. AI Productivity https://charleslehman.com/blog/anthropic-humble-product/ https://charleslehman.com/blog/anthropic-humble-product/ Mon, 02 Feb 2026 18:00:00 GMT AskUserQuestion inverts the AI prompt paradigm. The model prompts you. What product teams can learn from Anthropic optimizing for outcomes over optics. Product AI https://charleslehman.com/blog/feedback-loop-problem/ https://charleslehman.com/blog/feedback-loop-problem/ Mon, 19 Jan 2026 18:00:00 GMT Fast feedback lies. Slow feedback strands you. Product management gets both. Product Leadership Strategy https://charleslehman.com/blog/best-people-to-work-with/ https://charleslehman.com/blog/best-people-to-work-with/ Mon, 10 Nov 2025 18:00:00 GMT The best people to work with say "you're right, I didn't see that" easily. They hold ideas loosely and adjust fast. Leadership Collaboration Culture https://charleslehman.com/blog/jeep-product-lessons/ https://charleslehman.com/blog/jeep-product-lessons/ Thu, 02 Oct 2025 18:00:00 GMT The Germans made the fatal mistake of confusing simplicity with stupidity. Product Design Strategy https://charleslehman.com/blog/strava-social-media-that-works/ https://charleslehman.com/blog/strava-social-media-that-works/ Tue, 23 Sep 2025 18:00:00 GMT How Strava became the best social network by making effort the engine. Social Media Fitness Technology https://charleslehman.com/blog/conversation-never-have/ https://charleslehman.com/blog/conversation-never-have/ Thu, 07 Aug 2025 18:00:00 GMT Fifteen years ago today, my father died. This is about the father-shaped space in understanding the world, and the conversations that continue even after death. Personal Grief Family Loss https://charleslehman.com/blog/music-software-development/ https://charleslehman.com/blog/music-software-development/ Mon, 21 Jul 2025 18:00:00 GMT Your favorite artist drops a new album, but instead of being a finished product set in stone, it launches like software - with version updates, beta releases, and user-submitted bug reports. Music Technology Innovation https://charleslehman.com/blog/hill-country-flooding/ https://charleslehman.com/blog/hill-country-flooding/ Mon, 07 Jul 2025 18:00:00 GMT The river will flow again. We'll make new memories. But for now, we grieve what we lost, and we take care of each other. Community Grief Texas Natural Disasters https://charleslehman.com/blog/netscape-lessons/ https://charleslehman.com/blog/netscape-lessons/ Tue, 01 Jul 2025 18:00:00 GMT How the company that created the modern internet dominated everything, then disappeared - and what that means for product builders today. Product History Lessons https://charleslehman.com/blog/sonos-meltdown-product-lessons/ https://charleslehman.com/blog/sonos-meltdown-product-lessons/ Sun, 15 Jun 2025 18:00:00 GMT In 2024, Sonos delivered a masterclass in how to erode user trust. Here are the critical product management lessons every PM needs to learn from their $2B mistake. Product Lessons User Experience https://charleslehman.com/blog/marty-cagan-product-creator/ https://charleslehman.com/blog/marty-cagan-product-creator/ Wed, 28 May 2025 18:00:00 GMT The traditional product manager role is becoming obsolete, and AI just massively sped up that timeline. Here's what that means for the future of product creation. Product AI Leadership https://charleslehman.com/blog/10x-product-manager/ https://charleslehman.com/blog/10x-product-manager/ Tue, 20 May 2025 18:00:00 GMT The mythical 10x engineer is making way for a new star: the 10x product manager. AI is making this happen. Product AI Leadership https://charleslehman.com/blog/time-traveling-product-manager/ https://charleslehman.com/blog/time-traveling-product-manager/ Tue, 06 May 2025 18:00:00 GMT A candid look at how great product management is less about heroic moments and more about moving thoughtfully through different time dimensions. Product Leadership https://charleslehman.com/blog/product-tools-2025/ https://charleslehman.com/blog/product-tools-2025/ Tue, 15 Apr 2025 18:00:00 GMT A decade in product has taught me what tools actually create leverage. Here's what's working in 2025. Product Tools https://charleslehman.com/blog/real-engineering-conversations/ https://charleslehman.com/blog/real-engineering-conversations/ Wed, 09 Apr 2025 18:00:00 GMT A decade of working with engineers has taught me what truly matters in the age of AI - and it's not what you might think. Engineering AI Product https://charleslehman.com/blog/high-agency-ai-product/ https://charleslehman.com/blog/high-agency-ai-product/ Thu, 03 Apr 2025 18:00:00 GMT Real talk about building AI products in 2025. Skip the trends, focus on what matters, and ship what users actually need. AI Product