Alan Williamson

Observations on software, leadership,
and thinking like a CTO

  • 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.

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    The Shiny Object Trap: Don’t forego the basics

  • 2025 in review

    With the 1st of January now rolling us into 2026, it’s time for my annual review of the year that has just closed. Another beautiful sunny day here in Virginia, warm and blue skies as I sit down and reflect on some of the stats and journals I have maintained this year. Read Post ⇢

    2025 in review

  • The Inevitable V3 Rewrite

    Software rarely finds its feet until version three. Version one is an idealistic guess. Version two is a survival patch. Version three is the rewrite where you finally delete the noise and build what is actually needed. Real stability comes from subtraction, a lesson every architect learns the hard way. Read Post ⇢

    The Inevitable V3 Rewrite

  • Double NAT, 40 Terabytes, and a Christmas Miracle

    I spent my Christmas downtime replacing a fragile, port-forwarded network with a resilient Tailscale mesh. I managed to overcome double NAT headaches to sync Synology units peer-to-peer, fixed the inevitable MTU “black holes,” and automated the DSM 7 sandboxing hurdles to build a private, encrypted family network. Read Post ⇢

    Double NAT, 40 Terabytes, and a Christmas Miracle

  • “This ain’t no technological breakdown”

    Honoring British rock legend Chris Rea, I recall 1989: a 16-year-old student in Paisley, wrestling with the guilt of spending my living grant on “The Road to Hell” vinyl. Purchased for £5.99 at Woolworths, it became the defining soundtrack of my university years. Thirty-five years later, the joy remains. RIP. Read Post ⇢

    “This ain’t no technological breakdown”

  • The CTO’s Year-End Audit: Are You Building Your Vision or Just a Backlog?

    December is the only quiet time you have. Don’t waste it clearing your inbox. Use this silence to audit your architecture against your Vision Document. Move beyond simple feature roadmaps and focus on building strategic capabilities. If your environment doesn’t support your 2026 goals, fix it now before the chaos returns. Read Post ⇢

    The CTO’s Year-End Audit: Are You Building Your Vision or Just a Backlog?

  • Morphing into James McAvoy

    Playing with AI to transform a selfie into a stylistic portrait inspired by James McAvoy’s movie “Pose.” After describing the desired photo detail to Gemini Pro, they generated an impressive monochrome image. The process evolved into animating the image, showcasing a novel technique for creating unique personalized visuals. Read Post ⇢

    Morphing into James McAvoy

  • Change Management

    As a CTO, effective change management is crucial for delivering solutions to users who may resist significant changes. Develop a detailed project plan outlining responsibilities, timelines, and success criteria. Communicate extensively with stakeholders, providing training on new systems to ensure users understand the changes. Over-communicate throughout the process for success. Read Post ⇢

    Change Management

  • Only takes a minute

    Navigating the rapidly changing technology landscape can be stressful. It’s essential to engage in regular, small learning increments, such as 15 minutes daily, to build knowledge over time. Embrace a self-learning model without pressure, prioritize your time effectively, and share your insights to reinforce understanding. Progress comes from consistent, bite-sized efforts. Read Post ⇢

    Only takes a minute

  • Quality

    Quality is a multifaceted concept recognized through tangible attributes, such as performance, reliability, and aesthetics. In software, quality is critical, impacting user experience and operational safety. By adhering to quality dimensions and maintaining vigilance in development, teams ensure high standards, preventing failures and fostering client trust essential for business sustainability. Read Post ⇢

    Quality

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.