WonderLaura @iwmentor – Laura Rogers

I started my SharePoint admin career 20 years ago, and if there’s one thing that hasn’t changed since then, it’s this: SharePoint migration planning is where projects succeed or fail — long before anyone opens a migration tool.

I did a Power Hour this week about this, and I want to walk through what I covered, because I think a lot of you are either mid-migration right now or about to be. The video is at the bottom.

🚧 Why SharePoint Migration Planning Gets Skipped — And Why That Fails

Here’s the thing — the technology is rarely the biggest challenge in a SharePoint migration. What trips people up is what you’re migrating and how ready it is, which is exactly why SharePoint migration planning has to come first.

I’ve seen these five problems sink projects over and over:

1. Unknown content. You can’t plan a migration if you don’t know how much content exists or where it lives.
2. Excessive permissions. Crazy, granular permission structures that nobody’s cleaned up in years.
3. Stale content. Files nobody’s touched in a decade, still sitting there, still “needing” to be migrated.
4. Poor information architecture. Content that got dumped into folders with zero planning, now multiplied a hundred times over.
5. Unclear ownership. This one’s the killer. I’ve watched migration projects stall for years because nobody could say who actually owned a set of files.

That last one deserves its own paragraph. If nobody owns the content, nobody can tell you what’s important, what’s junk, or what’s safe to leave behind.

Here’s what’s imperative: Leadership buy-in. You need someone with authority willing to say “you’re going to spend time on this, and we’re migrating by this date.” Without that, people just never get around to it — and then they’re upset when their files are gone. I’ve seen it happen too many times to count, and it’s always a SharePoint migration planning gap at the root of it.

✅ Your SharePoint Migration Readiness Checklist

Before you move a single file, start with this list high-level list. Every one of these belongs in your SharePoint migration planning process:

• Inventory your content. Put it in a spreadsheet. Know what you’re dealing with.
• Identify site owners and business owners for each set of data, such as top level folders or departments.
• Decide what not to migrate. Set a cutoff date — maybe you only bring over anything modified in the last five years. Not everything needs to make the trip.
• Review permissions and sharing practices. Ask whether what exists today is actually what you want going forward, or if it’s time to rethink it.
• Determine your version history requirements. You get to decide how far back those versions go.
• Identify stale and duplicate content. Copilot is actually shaping up to be pretty good at this once your content lands in SharePoint.
• Design your target information architecture. This is huge, and I mean it — spend real time here. The nightmare I see most often is someone taking an entire file share, folders 20 levels deep, and dumping it into a single document library. Don’t ever do that. Think about your top-level folders as candidate SharePoint sites, and lean on metadata instead of endless nested folders.
• Plan user communication and training so nobody’s caught off guard.
• Decide whether folder structures should be modernized as part of the move, not left exactly as-is out of habit.

Here is the PDF of the presentation that I shared in the video:

🛠️ After SharePoint Migration Planning: Picking Your Tool

Once you’ve done your SharePoint migration planning, then it’s time to pick a tool — and this is where SPMT and ShareGate diverge in ways worth understanding before you commit.

The SharePoint Migration Tool (SPMT) is Microsoft’s free option. No license required, and it’s genuinely simple — point-and-click UI, PowerShell for automation if you want it, and three destinations: SharePoint, OneDrive, and Teams (and yes, Teams files are really just SharePoint under the hood).

SPMT handles files, folders, lists, permissions, version history, metadata, and even some basic SharePoint Designer and 2010 out-of-the-box workflows converted into Power Automate — though I’ll be honest, if your workflows have a lot of branching or actions that don’t have a Power Automate equivalent, it’s not going to do a great job.

What SPMT won’t touch: Teams chats, messages, email, custom Visual Studio workflows, InfoPath forms (those need to be rebuilt as Power Apps), custom code, and complex permission structures. It’s also strictly a one-way, on-prem-to-cloud tool — no tenant-to-tenant migrations.

ShareGate Migrate is the tool I’ve personally used in nearly every migration I’ve been part of for about eight years now. It’s a paid, third-party product, but it earns that price tag: tenant-to-tenant migration, Teams channel chat history, cross-platform sources like Google Workspace, Box, Dropbox, and Exchange Online, advanced permissions, metadata remapping, and — my favorite feature — the ability to restructure as you migrate. That means promoting old subsites into top-level sites (something Microsoft’s been steering everyone away from for years now) without losing version history or who-modified-what along the way.

If you’re doing a simple, contained file migration, SPMT can absolutely get the job done. If you’re dealing with complexity — multiple tenants, Teams data, messy permissions, or a full architecture overhaul — that’s where ShareGate earns its keep.

💡 The Real Takeaway on SharePoint Migration Planning

Here’s what I want you to walk away with: your migration tool decision comes after your planning, not before. Do the readiness work first. Get leadership buy-in. Understand your content. Then, you’ll have a better understanding of which tool will work best for your migration.

Twenty years in, and I’m still geeking out 🤓 over clean information architecture and a migration that goes smoothly. Some things really don’t change.

Here’s the full video about preparing for your migration, common problems, a high level checklist, and demonstrations of both SPMT and ShareGate.

🎥 What I Actually Showed in the Demos

I didn’t just talk about these tools — I ran real migrations for you, so let me walk through what you’ll see if you watch the full episode.

SPMT in action

I showed you around the SharePoint Migration Tool and — scanning content, viewing migrations in progress, and starting a new migration either from a single site or from a CSV file that defines all your source and destination pairs.

For my live demo, I migrated a set of demo folders into a brand-new site. I created a new library on the fly, turned on permission preservation and automatic user mapping, and set a cutoff date to filter out anything too old.

Once the migration finished, I pulled up the report — 76 total items, 34 filtered out by my date cutoff — and then went to the new site to confirm everything landed with the original modified dates intact.

ShareGate in action

I connected two tenants side by side and spent some real time in the Plan tab, because I want you to see the reporting you get before you touch a single file — permissions matrix, permission inheritance, site collection reports, checked-out documents, a full teams list, and an unused site report.

Then I ran three different scenarios:

• Restructuring subsites into top-level sites. I took three old subsites and promoted them to top-level sites, picked a Communication site template for one of them, assigned new owners and URLs, and showed how ShareGate won’t delete the original subsite until the promotion completes successfully. One of mine actually hit an error, which turned out to be a great teaching moment — nothing gets cleaned up until it’s fixed.
• Importing content from a file share. I walked through the deeper options here: preserving authors and timestamps, choosing whether to keep custom permissions, flattening folder hierarchy (something SPMT just doesn’t offer), limiting how many versions come along, filtering by date range, and excluding certain file types. I also showed metadata mapping and saved my settings as a template I can reuse next time.
• The permissions matrix report, where I drilled into broken inheritance and flagged spots where individuals had direct permissions instead of group-based access — a great cleanup list whether or not you’re migrating anything at all.

SPMT Demo

• Tool overview & starting a migration: 12:58
• Setting migration options (permissions, user mapping, date cutoff): 16:41
• Migration complete & reviewing the report: 18:10
• Confirming results in the new site: 18:52
• What SPMT won’t do: 20:04

ShareGate Demo

• Demo intro & tenant connections: 22:51
• Plan tab & reporting options: 23:24
• Restructuring subsites into top-level sites: 27:52
• Importing content from a file share (flatten hierarchy, metadata mapping, templates): 31:38
• Permissions matrix report walkthrough: 37:37

Resources

Here are several helpful links related to these technologies:

• Migrate to Microsoft 365 – Migrate to Microsoft 365 | Microsoft Learn 
• Migrate file shares to SharePoint and OneDrive – Migrate to Microsoft 365 | Microsoft Learn 
• Microsoft 365 migration tool & software for reliable & scalable migrations | ShareGate 
• SharePoint Migration Tool for SharePoint and OneDrive – Migrate to Microsoft 365 | Microsoft Learn 
• Microsoft Teams migration tools: SPMT vs. ShareGate  
• Understanding SharePoint migration tool limitations 
• The ULTIMATE SharePoint Migration Checklist – ShareGate