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"We'll Deal With It When the Time Comes" — The SharePoint Strategy That Always Backfires

24.03.26 03:44 AM Comment(s) By Boitumelo

Every IT leader has said some version of this at some point. You're managing a full pipeline, your team is stretched, the system is still working fine, and the deadline feels like it's far enough away to worry about later. So you shelve it.

Until it's not later anymore. Until it's now. And by then, the timeline that would have been comfortable has become a crisis.

We see this pattern repeatedly with SharePoint migrations. And with the July 14, 2026 end of support for SharePoint Server 2016 and 2019 fast approaching — along with an April 2 deadline for classic workflows and Add-Ins — the gap between "we'll get to it" and "we're out of time" is closing faster than most organisations realise.

Why Migrations Take Longer Than Anyone Expects

Here's something that surprises people who haven't been through a full SharePoint migration: the actual moving of data is often not the hardest part.

Before you migrate a single document, you need to know what you have. That means auditing every site collection, every document library, every custom permission level, every workflow, every Add-In, every integration that touches SharePoint. In environments that have been running for five or ten years, that audit alone can take weeks.

Then comes the conversation about what to bring across, what to rebuild, and what to retire. Classic SharePoint Designer workflows won't survive the migration to SharePoint Online as-is. They need to be rebuilt in Power Automate. Add-Ins built on the retiring framework need to be redesigned using modern solutions. InfoPath forms need to be replaced.

None of that is technically impossible. All of it takes time.

"Migrations can take 6 to 18 months depending on complexity. A last-minute migration is a recipe for budget overruns, data loss, and business disruption."


The Two Deadlines Running in Parallel

One of the things that catches organisations off-guard is that there are effectively two separate timelines to manage, not one.

  • April 2, 2026: SharePoint Add-Ins and classic SharePoint 2013 workflows retire. Any business process built on these frameworks stops working. This isn't a 'soft' retirement with a grace period — it's a hard cutoff.
  • July 14, 2026: SharePoint Server 2016 and 2019 lose all support. Security patches stop. Bug fixes stop. Vendor-assisted support stops.

If you're planning a migration and only thinking about July, you may already be behind. If your environment has classic workflows or Add-In dependencies, April is the real pressure point.

What a Late Start Actually Costs You

Let's talk about what happens when organisations start their migration planning in Q1 2026 instead of now. A few things tend to happen:

  • The migration gets compressed. Work that should take six months gets squeezed into three. Corners get cut. Testing is abbreviated. Change management gets dropped entirely because there isn't time.
  • Business disruption goes up. A rushed migration means more unexpected issues, more downtime, more user confusion, and more IT firefighting during the transition.
  • Cost increases. Emergency timelines require more resources. What would have been a measured, well-planned project becomes an expensive sprint.
  • Post-migration problems linger. Without proper testing and user adoption planning, teams end up with a technically completed migration and practically no adoption. You've moved the files but nobody knows how to work in the new environment.

What a Well-Planned Migration Actually Looks Like

A properly planned SharePoint migration isn't just a technical exercise. It has several distinct phases, and each one has genuine business value:

  • Environment assessment: Understanding exactly what you have — content, customisations, permissions, integrations, and ROT (redundant, obsolete, and trivial) content that doesn't need to move at all.
  • Workflow and Add-In inventory: Cataloguing every automated process and identifying what needs to be rebuilt in modern tools like Power Automate and Power Apps.
  • Migration path decision: Choosing between SharePoint Online, SharePoint Subscription Edition, or a hybrid approach based on your compliance requirements and cloud strategy.
  • Phased execution: Running pilot migrations, validating, then executing in phases with proper testing at each stage.
  • Change management and adoption: Making sure your users understand what's changed, why it changed, and how to work effectively in the new environment.

Start that process now and you have time to do each of those things properly. Start it in January 2026 and you're making hard choices under pressure.

The Honest Conversation Your Team Needs to Have

If your organisation is still on SharePoint Server 2016 or 2019, there's a conversation that needs to happen — and it shouldn't be between the IT team and the calendar. It needs to involve business leaders, finance, compliance, and operations, because this decision affects everyone.

The questions are straightforward:

  • How much of our business depends on SharePoint working reliably?
  • What happens to our compliance posture if we're running unsupported software?
  • What's the real cost of disruption if something breaks post-July 2026 with no Microsoft support?
  • What would a controlled, planned migration cost compared to a reactive one?

Those aren't questions IT can answer alone. And the longer they stay in the IT queue without executive visibility, the more limited your options become.

At GTconsult, we help organisations answer these questions before the pressure builds. An environment assessment gives you the real numbers — what you have, what it'll take to move it, what the sensible timeline looks like.

Boitumelo

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