Alan Williamson

Observations on software, leadership,
and thinking like a CTO

  • Planning for the inevitable end

    Software maturity requires planning for the inevitable death of your users. You must implement marketing kill switches, clear data retention policies, and account delegation. Stop annoying grieving families by automating bereavement reporting and protecting user namespaces. Building these mechanisms proves your organization handles every user stage with the respect deserved.

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    Planning for the inevitable end

  • The Shiny Object Trap: Don’t forego the basics

    Software quality declines as leaders chase shiny features while ignoring basic reliability. Outlook fails at calendar imports. PowerPoint uses ancient tools. This complexity creates security risks. You must audit your core tasks and fix friction first. Do not add new code until the fundamentals work every time. Reliability is everything. Read Post ⇢

    The Shiny Object Trap: Don’t forego the basics

  • Reclaiming Focus: The Lost Art of Downtime

    Modern software builds traded the forced tea time of Borland Turbo C for complex YAML pipelines and noisy distributed failures. To avoid burnout and logic errors, you must reclaim your time to think. Build a fake commute, step away from the screen, and go make a proper cup of tea. Read Post ⇢

    Reclaiming Focus: The Lost Art of Downtime

  • The Silent Decay to Legacy

    Software does not age, but the world around it does. Digital systems become legacy when knowledge is lost and environments shift. To avoid the “stagnant” phase, engineering teams must dedicate 30% of their effort to maintenance. Investing in health today is the only way to prevent a museum tomorrow. Read Post ⇢

    The Silent Decay to Legacy

  • The Hidden “If” in Everything

    Our lives are governed by the humble “if” statement. From stubborn car updates to the inner workings of AI, these two letters dictate our reality. Software logic often lacks empathy. We must surface these buried rules and ensure product managers, not developers, define the conditions that govern our daily lives. Read Post ⇢

    The Hidden “If” in Everything

  • The Realities of Software Releases: More Than Just a Button

    Releasing software is more than a button click. It is a high stakes moment where code meets the friction of the real world. From the landing gear moment of scale to the clean floor data paradox, here is why going live is complex and why we never release on Fridays. Read Post ⇢

    The Realities of Software Releases: More Than Just a Button

  • Think like a CTO – Japanese Edition

    Think Like a CTO has been translated and published into another language, Japanese. Read Post ⇢

    Think like a CTO – Japanese Edition

  • How AI Agents Will Change Ecommerce

    The rise of the machine customer marks the end of the browser era. To win, platforms must move beyond UI and provide deterministic, AI ready APIs. Making your site agent friendly is no longer optional; it is your new competitive advantage. Read Post ⇢

    How AI Agents Will Change Ecommerce

  • The Flaws in AI Customer Support Systems

    My recent Logitech support experience highlights why context is king. A solid AI speech agent was ruined by a human handover that started from scratch. AI should be a connected workflow, not an isolated silo. If your latest improvement makes the service slower, you have failed the integration test. Read Post ⇢

    The Flaws in AI Customer Support Systems

  • Rock me Amadeus (& Elvis)

    Watching the new Amadeus series led me down a rabbit hole where I found a striking parallel between Mozart and Elvis. Both icons died broke, but their widows, Constanze and Priscilla, became the first accidental CEOs. They professionalized the legacies, cleared massive debts, and pioneered celebrity tourism to save the brands. Read Post ⇢

    Rock me Amadeus (& Elvis)

the leg-end that is, Alan Williamson.

For over 20 years, I’ve shared my thoughts whenever the muse strikes. It’s unpredictable, honest, unedited, and occasionally witty. I’m living the best years of my life, working harder than ever, and enjoying every second.