Lessons Learned Over 21 Years: A Journey Through IT Project Management
Welcome to the very first installment of my blog series, where I will be sharing the hard-earned lessons from my 21-year career in IT project management. From my early days as a Systems Analyst at Unilever HPC to navigating the high-stakes world of Department of Defense consulting, and ultimately leading large-scale SAP migrations and IT security projects, I’ve encountered just about every pitfall a project manager can face.
By Tom Jones, IT Project Manager
Welcome to the very first installment of my blog series, where I will be sharing the hard-earned lessons from my 21-year career in IT project management. From my early days as a Systems Analyst at Unilever HPC to navigating the high-stakes world of Department of Defense consulting, and ultimately leading large-scale SAP migrations and IT security projects, I’ve encountered just about every pitfall a project manager can face.
But here’s the kicker—I didn’t just survive; I learned.
Over the next 21 blog posts, I’ll take you through one lesson learned per year, starting in 2004 when I took my first consulting job in Washington D.C. This journey is for aspiring and seasoned project managers alike, giving you insights into avoiding mistakes I (and many others) have made.
Along the way, I’ll also introduce you to ezRACI, a project management tool that has evolved to solve many of the very problems I’ll be discussing. While I won’t hit you over the head with promotions, I’ll make sure you understand why having the right tools and frameworks can mean the difference between success and failure in project execution.
The 21-Part Series: Lessons Learned from the Field
Here’s what you can expect in the coming weeks:
2004 – Lesson 1: The ‘Requirements Freeze’ Myth
How I learned the hard way that requirements are never truly frozen—and how to manage scope creep effectively.
2005 – Lesson 2: When ‘Agile’ is Just a Buzzword
Navigating projects where Agile is misunderstood or misapplied and how to bridge the gap between theory and reality.
2006 – Lesson 3: Vendor Promises vs. Delivery Reality
The importance of contractual safeguards and how to manage vendor expectations.
2007 – Lesson 4: Change Management is Not Just Training
Why project failures often have nothing to do with technology but everything to do with people’s resistance to change.
2008 – Lesson 5: The Risks of Over-Customization
How customizing an SAP system to death nearly sunk a project—and what I would do differently today.
2009 – Lesson 6: The CIO Wants a Dashboard… Now What?
Executive expectations vs. project feasibility—and how to translate tech talk into business results.
2010 – Lesson 7: Surviving Your First IT Audit
How a lack of documentation and accountability can bring a multi-million dollar project to a halt.
2011 – Lesson 8: The Stakeholder You Forgot Will Come Back to Haunt You
The dangers of not identifying all key stakeholders early on—and how to avoid costly surprises.
2012 – Lesson 9: When ‘Go-Live’ is a Disaster
What happens when a system launch cripples an organization—and how to build a bulletproof cutover plan.
2013 – Lesson 10: The IT-Security Tug-of-War
Balancing business agility with security compliance—why IT security is a project enabler, not an obstacle.
2014 – Lesson 11: The Art of the Executive Status Report
What I learned about telling the truth vs. sugarcoating when reporting to leadership.
2015 – Lesson 12: The RACI Matrix Saved My Project
How clear role definitions prevented a project from descending into chaos.
2016 – Lesson 13: Offshore Teams: A Blessing and a Challenge
How to manage global teams without losing your mind or your project timeline.
2017 – Lesson 14: The Day My Project Budget Was Slashed
How to pivot when leadership pulls the rug out from under your financials.
2018 – Lesson 15: Why You Need a Project ‘Kill Switch’
Knowing when to stop a failing project is just as important as knowing how to execute it.
2019 – Lesson 16: Surviving a Merger or Acquisition Project
How company culture shifts affect IT projects and what you can do to stay ahead of the curve.
2020 – Lesson 17: Crisis Mode – Managing IT Projects During a Pandemic
The sudden shift to remote work, unprecedented security challenges, and redefining productivity.
2021 – Lesson 18: Shadow IT – Your Biggest Threat?
What happens when departments build their own solutions without IT’s involvement—and how to manage it.
2022 – Lesson 19: The ‘Citizen Developer’ Revolution
How low-code/no-code platforms are changing the project landscape.
2023 – Lesson 20: AI in Project Management – Hype or Reality?
What AI is actually good at in project management (and what it’s not).
2024 – Lesson 21: The Future of IT Project Management
Where the industry is heading—and what I wish I had known back in 2004.
Why You Should Follow This Series
Each article will provide real-world project management advice, blending leadership insights, process improvements, and practical tools like ezRACI that help avoid these mistakes altogether. My goal is to ensure that you don’t have to learn these lessons the hard way—like I did.
So buckle up. The next 21 weeks are going to be a wild ride through IT project war stories, leadership insights, and actionable strategies to make your projects more successful.
See you in the next post where I break down Lesson 1: The ‘Requirements Freeze’ Myth—and why your project requirements are never really frozen.
Disclaimer: This blog is written from the perspective of Tom Jones, a fictional IT Project Manager, and is intended for informational and educational purposes. While based on real-world project management principles, all anecdotes and characters in these posts are entirely fictitious. Any resemblance to actual persons or events is purely coincidental. The blog also references ezRACI, a project management tool designed to help teams succeed in project execution. However, these opinions are solely those of the fictional character and do not constitute an official endorsement.
About Tom Jones
Tom Jones: A Veteran IT Project Manager Navigating the Complexities of Enterprise Technology
Tom Jones is a seasoned IT Project Manager with over two decades of experience leading complex enterprise technology initiatives. Based in South Florida, Tom has built a reputation as a pragmatic, results-driven leader who thrives on solving intricate business and IT challenges. His expertise spans project management, IT security, large-scale system migrations, and process optimization, making him a trusted figure in the industry.
Early Life and Education
Tom was born and raised in Pennsylvania, eventually attending Penn State University, where he earned a Bachelor of Science in Management Information Systems (MIS) in 2003. His passion for technology and business integration was evident early on, as he quickly grasped the nuances of systems architecture and project execution. His ability to bridge the gap between technical teams and business stakeholders became a defining characteristic of his career.
Professional Journey
Tom's career began at Unilever HPC as a Systems Analyst, where he got his first taste of large-scale enterprise operations. However, he quickly sought new challenges and moved to Washington, D.C., to work as a Consultant for the Department of Defense. This experience exposed him to high-stakes, mission-critical projects where precision and security were paramount.
Over the years, Tom took on increasingly demanding roles, managing SAP migrations, IT security projects, and various large-scale initiatives across industries. His ability to navigate high-pressure environments and deliver results led him to leadership roles in project management, where he excelled in driving teams toward successful project completion.
Leadership Philosophy
Tom's leadership style is rooted in accountability, transparency, and strategic execution. He believes that successful project management isn't just about timelines and budgets—it’s about aligning business objectives with technology solutions while fostering a culture of collaboration and continuous improvement. His direct, no-nonsense approach has earned him the respect of peers, executives, and technical teams alike.
Entrepreneurial Ventures and ezRACI
In recent years, Tom has expanded his expertise into entrepreneurship, co-founding ezRACI, a SaaS platform designed to streamline compliance, audit trails, and project management workflows. Recognizing the inefficiencies in traditional project management tools, he sought to develop a solution that integrates collaboration features like Slack and MS Teams, industry-specific templates, and intuitive dashboards for workload optimization. His goal with ezRACI is to help teams achieve clarity, accountability, and efficiency in their IT projects.
Personal Life
Beyond his professional accomplishments, Tom is a devoted husband and father of two elementary school-aged children. He enjoys spending time with his family, coaching his kids' sports teams, and keeping up with the latest industry trends. His wife, who works at the local library, shares his appreciation for continuous learning and knowledge-sharing. Together, they have built a life centered around personal growth, resilience, and community.
Legacy and Vision
With over 21 years in the industry, Tom Jones remains a passionate advocate for effective project management and IT governance. Through his blog, he shares lessons learned, war stories from past projects, and insights on optimizing workflows in modern enterprises. Whether leading large IT transformations or mentoring the next generation of project managers, Tom's mission remains the same: to drive efficiency, innovation, and lasting impact in the world of enterprise technology.
As he continues to build ezRACI into a premier project management tool, Tom is committed to reshaping how teams collaborate, execute projects, and maintain compliance in an ever-evolving digital landscape.