Continuing my 30-year journey in IT, this chapter marks a pivotal turning point—not just in my career, but also in the trajectory of enterprise technology as a whole. The years spanning the release of SharePoint 2016, SharePoint 2019, and the rapid expansion of Office 365 encapsulate a period of critical transformation. It was a time of technological crossroads, where organisations faced one fundamental question:

“Do we continue with an on-premises environment, embrace the cloud, or adopt a hybrid strategy?”

This era was defined by complex migration projects, the evolution of IT best practices, and strategic decisions that reshaped how organisations leveraged technology to meet their business objectives. For me, it was a period of professional growth as I helped clients navigate these profound shifts while adapting to new tools, methodologies, and business expectations.

Evolution from SharePoint 2013 to SharePoint 2019

The journey from SharePoint 2013 to SharePoint 2016 and then to SharePoint 2019 marked a significant evolution in on-premises technology. Each release brought critical enhancements, bridging the gap between traditional IT infrastructure and the emerging capabilities of the cloud.

SharePoint 2016: The Hybrid Bridge

Released in May 2016, SharePoint 2016 was built on the architecture of SharePoint 2013 but introduced powerful integrations with cloud-based Office 365 services. Its standout features included:

• Hybrid Search and Sites: Unified search experiences and seamless user access across on-premises and cloud environments via Azure Active Directory (now Microsoft Entra ID).
• Data Loss Prevention (DLP): Enhanced security with tools to identify and protect sensitive information.
• Improved OneDrive for Business Synchronisation: Strengthening collaboration and file access capabilities.

While hybrid functionality was a cornerstone of SharePoint 2016, it also offered substantial improvements for fully on-premises deployments, such as:

• Support for Larger Files: Enhanced file size limits up to 10GB.
• Optimised Performance for Large Datasets: Faster data access and better resource allocation.
• Compliance and Auditing Features: Strengthening data governance for industries with strict regulatory requirements.

The migration to SharePoint 2016 involved significant infrastructure upgrades, as organisations needed to support 64-bit environments and reassess database compatibility. This often necessitated complete reengineering of custom workflows and solutions, particularly for organisations transitioning from older versions like SharePoint 2010 or 2013.

SharePoint 2019: Bringing the Cloud On-Premises

With the release of SharePoint 2019 in October 2018, Microsoft responded to the growing demand for cloud-like functionality within on-premises environments. SharePoint 2019 introduced several transformative features, such as:

• Modern UI: A sleek, user-friendly interface inspired by SharePoint Online, aimed at improving productivity and usability.
• Enhanced Communication and Team Sites: Enabling dynamic collaboration with interfaces that closely mirrored Office 365.
• PowerApps and Power Automate Integration: Allowing users to build custom applications and automate workflows with minimal coding, connecting seamlessly with both on-premises and cloud resources.

These enhancements, alongside hybrid deployment options, made SharePoint 2019 a viable solution for organisations needing to retain control over their infrastructure while gaining access to modern collaboration tools. Hybrid features like Hybrid Search provided a bridge between environments, making it easier to manage and discover content across both on-premises and cloud systems.

However, SharePoint 2019 also had its challenges. Migrating custom-coded solutions, workflows, and legacy integrations to the Modern UI often required redevelopment. While SharePoint 2019 offered significant advancements, its on-premises nature meant it lacked the continuous update cadence of Office 365, sometimes creating feature gaps that required careful planning.

Office 365: Redefining Productivity

As SharePoint 2016 and 2019 matured, Office 365 rapidly established itself as a transformative force. Originally launched in 2011 as a rebranded version of BPOS, by 2019 Office 365 had evolved into a comprehensive ecosystem that included tools like Exchange Online, SharePoint Online, Microsoft Teams, and the Power Platform.

Key Advantages of Office 365:

1. Scalability: A subscription-based model allowed organisations to scale users and features as needed.
2. Continuous Updates: Automatic updates delivered the latest features and security enhancements without downtime.
3. Integrated Ecosystem: Tools like Teams, Power BI, and SharePoint Online created a unified environment for communication, collaboration, and analytics.
4. Operational Efficiency: Cloud infrastructure shifted costs from capital expenditure (CapEx) to operational expenditure (OpEx), reducing the burden of hardware management.

The growing adoption of Office 365 represented more than just a technological shift; it was a cultural transformation that redefined how businesses approached IT. By moving away from managing physical infrastructure, organisations could focus on strategic initiatives, leveraging tools that enabled seamless collaboration and innovation.

My Journey: Building Solutions and Embracing the Power Platform

During this pivotal period, I worked on a range of projects that highlighted the strengths and challenges of both SharePoint and Office 365. These included:

• Developing Intranets and Document Management Systems: Using SharePoint Online, I built dynamic, easily accessible environments that enhanced internal communication and streamlined collaboration.
• Exploring Power BI: Creating insightful dashboards and reports that enabled organisations to harness data for strategic decision-making.
• Diving into PowerApps and Power Automate: Designing custom applications and automating workflows that addressed unique business needs.
• Enabling Hybrid Solutions: Supporting clients with hybrid environments that leveraged Office 365’s advanced features while maintaining critical workloads on-premises.

Each project reinforced the importance of understanding the client’s unique requirements and aligning solutions with their goals. It wasn’t about following trends; it was about delivering value through tailored, effective designs.

Summary: A Transformative Turning Point

The period spanning SharePoint 2016, SharePoint 2019, and Office 365 was not just a turning point in enterprise IT but also in my career. It taught me to navigate the complexities of hybrid environments, balance the control of on-premises solutions with the agility of the cloud, and embrace new tools like the Power Platform to deliver transformative solutions.

For IT professionals and organisations alike, this era marked the beginning of a new way of thinking—one that prioritised flexibility, continuous improvement, and aligning technology with evolving business needs. The decisions made during these years laid the foundation for the digital transformation journeys that continue to shape the future of enterprise IT.