25 Years of SharePoint: First Projects, Hard Lessons, and How Far We’ve Come 

SharePoint turns 25 this year. Which, in technology years, is practically ancient. 
Over that time, SharePoint has been a lot of things: 
 – A document library. 
 – An application platform. 
 – An intranet. 
 – A workflow engine. 
 – Occasionally… a source of mild panic during deployments. 

At Cloudwell, our team’s experience with SharePoint stretches back almost to the beginning. To mark the anniversary, we asked a few of the Cloudwell team to reflect on their very first SharePoint projects — what they built, what they learned, and how far the platform (and all of us) have come. 

What follows is part nostalgia, part technical archaeology — and a reminder that while the tools have changed dramatically, the problems we solve haven’t. 

2004: When “Customization” Meant Flash and Web Parts 

Pat McGown, Co-Founder and CEO 

Shortly after SharePoint 2003 was released, Pat’s team set out to deliver preconfigured SharePoint environments tailored to different use cases — a concept that still feels very familiar today. 

Pat’s first project involved building a custom web part that loaded an interactive Macromedia Flash radar map. The map visualized events by connecting to a web service fed by data from a SharePoint list. 

Yes — Flash. 
Yes — custom web parts. 
Yes — SharePoint lists powering real-time visuals. 

What this taught us: 

Even in its earliest days, SharePoint wasn’t “just document management.” It was already a platform — one that teams were stretching to meet real business and operational needs. 

How we’d do it today:

Modern APIs, SPFx, Power BI, and real-time dashboards — with zero Flash and far fewer browser crashes. 

2009: Manual Deployments and the Art of Not Breaking Production 

Chris Alechko, Co-Founder and CIO 

Chris was working on HarmonieWeb, a humanitarian support project tied to DoD initiatives supporting communities in Afghanistan. The platform: MOSS 2007. 

His responsibility? Developing web parts and customizations for the portal — and manually constructing manifest files and WSP packages by hand to deploy them. 

One wrong character in a manifest file could mean hours (or days) of troubleshooting. 
One unhandled error could take down an entire page — or the whole site. 

“Man how far we’ve come!” 

What this taught us: 

Early SharePoint development demanded discipline. Packaging, error handling, and deployment processes weren’t “nice to have” — they were survival skills. 

How we’d do it today: 

SPFx, source control, CI/CD pipelines, and guardrails that prevent a single typo from ruining everyone’s afternoon. 

2011: Search, Test Data, and Proofing the Invisible 

Troy Palacino, Head of Product Development 

Troy’s first SharePoint project didn’t look flashy on the surface — but it solved a critical problem. 

He built a tool for generating dummy users and loading content to test and proof integrations with the indexing side of SharePoint Search. 

This work happened behind the scenes, but it was essential for validating that search worked the way users expected — with realistic data, permissions, and scale. 

What this taught us: 

Search has always been one of SharePoint’s most powerful — and most misunderstood — capabilities. Testing it properly requires intention, not hope. 

How we’d do it today: 

Modern Microsoft Search, richer signals, better analytics — and still the same need for thoughtful information architecture and testing. 

SharePoint 2007 to SharePoint 2010: Migration, Adoption, and the Human Side of SharePoint 

John Becher, Cloud Developer 

John entered the SharePoint world during a migration from SharePoint 2007 to SharePoint 2010 at the Patuxent River Naval Air Station. 

What started as technical assistance quickly evolved into something bigger: 

 – Training end users 

 – Supporting site administrators 

 – Leading sessions on how teams could actually use SharePoint effectively 

 – Responding to help desk tickets routed to the SharePoint team 

What this taught us: 

Successful SharePoint projects aren’t just about migration. They’re about adoption. If users don’t understand the “why” and the “how,” the platform never reaches its potential. 

How we’d do it today: 

Adoption strategies, champions, governance, and change management — because technology only works when people want to use it.

MOSS 2007: Casino Security Incident Tracking 

Mike Ostrander, Senior Developer 

Mike’s first major SharePoint project was an incident tracking system for a casino security department. 

Before SharePoint, incident tracking was essentially a shared notepad between officers — a risky setup in an environment where incidents are frequent, urgent, and operationally critical. 

The new system allowed: 

 – Fast creation and updates 

 – Consistent data capture 

 – Clear status tracking 

 – Metrics leadership could finally see and trust 

The result was a solution that became essential to daily operations. 

What this taught us: 

SharePoint shines when it replaces informal, manual processes with structured, transparent systems — especially in high-pressure environments. 

How we’d do it today: 

Lists, Power Apps, Power Automate, and mobile-friendly interfaces — same outcome, dramatically better experience. 

What 25 Years of SharePoint Has Taught Us 

Looking back across these projects, a few themes stand out: 

 – The tools have changed — the problems haven’t. 
Organizations still need better ways to manage content, processes, search, and collaboration. 

 – Governance matters more as power increases. 
As SharePoint became easier to extend, the need for guardrails grew right alongside it. 

 – People are always the success factor. 
Training, adoption, and clarity matter just as much as architecture. 

 – SharePoint has always been a platform. 
From Flash web parts to cloud services, teams have been building real business solutions on it for 25 years. 

From Then to Now and onto the Next Chapter 

Today’s SharePoint looks very different from its early days — cloud-native, deeply integrated with Microsoft 365, and increasingly connected to automation and AI. 

For many organizations, this anniversary also lines up with a practical reality: SharePoint Server 2016 and 2019 are approaching end of support, and migration planning is already underway across IT teams. 

For those organizations, this moment isn’t just about moving content from one version to another. It’s a chance to: 

 – Retire what no longer serves the business 

 – Modernize processes that have outgrown legacy platforms 

 – And set SharePoint up for the next decade — not just the next upgrade 

At Cloudwell, our long history with SharePoint means we’ve seen: 

  • What works 
  • What breaks 
  • And what actually delivers value over time 

 

If your SharePoint environment is heading into its next chapter — whether that’s a new project or a 2016/2019 migration — our team is always happy to help you plan what comes next.