15 Years of FireOak: Reflections, Lessons Learned, and Why I Still Love This Work
Fifteen years in, I’ve worked across dozens of countries, supported bold missions, and learned a lot. Here are a few lessons and why I still love this work.
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What Does a Fractional CIO Actually Do? (A Day in the Life)
A Fractional CIO's day rarely revolves around technology alone. From AI strategy and cybersecurity to governance, budgeting, and executive decision-making, the role is about helping organizations make better long-term technology decisions.
Getting Ready for AI Starts with Cleaning Up Your Knowledge
AI won’t organize your knowledge for you — it will amplify what’s already there. Learn why strong knowledge management is the foundation of AI readiness.
AI isn't magic. But it can be transformational.
AI isn’t a silver bullet. But when grounded in strategy, clear workflows, and well-organized knowledge, it can be a powerful force for small teams.
The Most Overlooked Risk in Small Orgs? What You Don't Know.
In small organizations and growing teams, the biggest risk isn’t your tech stack — it’s the undocumented knowledge hiding in plain sight. Learn how to identify and fix these invisible risks.
Knowledge Management in 2025: What's Emerging, What's Evolving, What Matters Most
KM in 2025 is more dynamic, distributed, and people-centered than ever. This isn’t just a trends list — it’s a look at what’s really changing and why it matters.
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IT vs. Yacht Chefs: A Below Deck-Inspired Guide to Tech Leadership
Ever feel like your job in IT is a mix of high-stakes chaos, impossible requests, and zero daylight? Turns out we have a lot in common with yacht chefs. Inspired by too much Below Deck, here’s a cheeky comparison between IT leadership and the unsung heroes of the galley.
What is a Fractional CIO? An Executive Guide to Strategic Technology Leadership
What is a Fractional CIO? Learn how strategic technology leadership helps growing organizations align technology with business goals.
Your First 5 Steps Toward AI Readiness (No Magic Required)
AI doesn’t require a magic wand — just a smart strategy. Here are 5 clear, practical steps to help your organization get ready for AI in a way that actually works.
Every Technology Decision Is An Organizational Decision
Technology environments rarely become complicated overnight. They grow one well-intentioned decision at a time. Thoughtful technology strategy helps organizations make intentional decisions that support long-term goals instead of creating unnecessary complexity.
Data Loss Prevention Best Practices
Data Loss Prevention (DLP) is more critical than ever — but it doesn’t have to be complex. Here are five updated best practices for 2025 to help your team protect sensitive data without slowing down.
Don't Let Knowledge Walk Out the Door: 5 Knowledge Retention Tips
Worried about losing critical know-how when someone leaves your team? These 5 practical steps will help you retain institutional knowledge before it disappears.
