Essays about organizations, technology, product, incentives, and the occasionally irrational ways humans build companies.
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- The 5W’s of Software Products: A framework for assigning the five accountabilities every successful software initiative needs.
- TCF: The Origin Story: A firsthand history of how Europe’s Transparency and Consent Framework came to be.
- Eleven Ways The Ground Beneath Software Development Has Shifted: How AI is reshaping software development and what valuable engineering work now looks like.
- Plan Heavy vs Ship Light: How organizational incentives push teams toward coordination and planning instead of shipping.
- The NIH Tax: How “Not Invented Here” Quietly Kills Your Margin and Your Roadmap: How reflexively building in-house quietly damages margins, speed, and product roadmaps.
Organizations & Strategy
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Cutting your way to growth
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Why cost-cutting only creates growth when it follows a coherent strategy.
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The Laws and Razors That Rule Everything Around Me
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A practical guide to recurring principles that explain behavior at work and in life.
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A Barrel With No Ammunition
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Why ambitious transformations fail when leaders do not fund the capabilities they require.
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Plan Heavy vs Ship Light
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How organizational incentives push teams toward coordination and planning instead of shipping.
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Act Your Size
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Why startups should resist adopting big-company processes before they have earned them.
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Obvious Rules to Live By, for Corporate Sanity
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Straightforward rules for making organizations less wasteful, irrational, and unpleasant.
Product & Execution
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Why Dates are Hard
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How uncertainty, dependencies, and novel work make software timelines difficult to predict.
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The NIH Tax: How “Not Invented Here” Quietly Kills Your Margin and Your Roadmap
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How reflexively building in-house quietly damages margins, speed, and product roadmaps.
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Deliverables vs. Outcomes: A Classic Corporate Tragedy
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Why shipping outputs is not the same as creating meaningful customer or business impact.
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The 5W’s of Software Products
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A framework for assigning the five accountabilities every successful software initiative needs.
Leadership & Work
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On Building Resilience in a Startup
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What resilience looks like inside a startup and how to practice it without empty slogans.
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Why should they stay? How having a clear employee value proposition can help you snag top talent
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How a clear employee value proposition helps companies attract and retain strong talent.
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Meetings and Coronavirus-induced WFH
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Lessons for making meetings more intentional when an organization suddenly shifts to remote work.
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Wil.README
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A guide to Wil’s expectations, communication style, decision-making, and leadership philosophy.
Technology & AI
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Eleven Ways The Ground Beneath Software Development Has Shifted
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How AI is reshaping software development and what valuable engineering work now looks like.
Adtech & the Internet
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TCF: The Origin Story
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A firsthand history of how Europe’s Transparency and Consent Framework came to be.