#leadership

Articles tagged with #leadership

Your Transformation Isn't Failing. Your Evidence Is.
There's one question that quietly ends more transformation programs than bad architecture ever will. "What changed for the business?" It usually arrives in budget season. The team has been working har
Oct 2, 202611 min read2
You Aren't Choosing an AI Tool. You're Choosing Who Gets Paged at 2 AM.
Part of AI Leadership in the Real World — how leaders turn scattered pilots into governed, adopted, measurable capability. TLDR: A support agent doing 50,000 chats a month needs ~3.5 FTE and $500k+/y
Sep 6, 202616 min read7
AI Made Prototyping Free. That Is Exactly Why Your Portfolio Strategy Matters Now.
TLDR: 60 ideas on a board. 4 product teams to build them. $1.2M in annualized run cost for pilots that produced $340K in measurable value. The week we made tradeoffs visible was the week AI stopped be
Aug 9, 202617 min read7
AI-Assisted Engineering: Faster to Build Isn't Cheaper to Own
AI-Assisted Engineering: Faster to Build Isn't Cheaper to Own TL;DR: In METR's 2025 randomized study, experienced open-source developers took 19% longer when using AI tools, even though they believed
Jul 31, 202611 min read7
Platform Strategy That Ships: 90-Day Bets, Kill Criteria, and the Only AI That Mattered
TL;DR: Across separate 90-day cycles (2018, 2023, 2025), we shipped platform bets that hit real adoption in 90 days (telemetry: ~20 DAU / ~150 MAU; Backstage IDP: ~30 DAU / ~500 MAU) and a CI bet that
Jul 24, 202612 min read10