By Oguh Reinreb, Evil Consultant

NOTE: Today’s post was written by Hugo’s evil twin Oguh. The views, information, or opinions expressed in this guest post are solely those of the evil twin involved and do not necessarily represent those of Hugo Bernier.


Everybody can migrate SharePoint to Office 365, right?

All you need is a credit card to create an Office 365 tenant and an old SharePoint instance and you can get started migrating your files!

But if you’re looking for job protection — or if you’re offering professional services — you probably don’t want the migration to happen too fast.

Why would you want the migration to complete quickly when you can just let it drag longer than it should?

This article will give you pro tips to guarantee your migration from SharePoint to Office 365 will fail.

This list is a compilation of pearls of wisdom that I have learned over the years with dealing with people who know better.

Follow this list and you’ll be able to bleed your employer/client of all their money and not deliver anything of value. And if you do deliver something, it’ll be completely useless.

You can always blame Microsoft if it doesn’t work.

What do we mean by failing?

The best way to fail is to avoid establishing any kind of success metrics. If people don’t know how to measure your success, they’ll never know you failed.

But to make sure you fail real good, let’s establish some failure criteria:

  • Costs overruns and delays: a study by Deloitte (I think it was Deloitte, but who cares, 82% of statistics are made up on the spot — who will check?) found that the common practice of awarding a contract to the lowest bidder usually results in project delays and spending over budget. In fact, the average cost is equivalent to 5 times higher than the price of the highest bidder. Now that’s something to strive for!
  • Poor user adoption: if you improve your user’s lives and made them more productive, they’ll keep on expecting more from you. Make sure that the migration you did is so bad that your users won’t want to use SharePoint and that they’ll find alternate ways to store documents and collaborate. That’s what email is for anyways.
  • Lost files and metadata: If your old SharePoint library had 1,000 files, just make sure that you migrate 1,000 files over. That’s enough QA. Nobody needs metadata.

Don’t involve your users

Ugh. Talking to users is such a waste. of. time.

Why should you spend your valuable web-surfing time at work to interview your users and find out what their pain points are? That’s like saying "please whine some more".

Just because your users spend all their time doing their daily job doesn’t mean that they understand what they need better than you. I mean, they don’t know anything about IT, probably less about SharePoint, so how can they possibly add value?

Remember: you know better

The worst part about interviewing your users and asking them for their pain points is that it would give you something to measure your success with. Users might actually expect you to deliver everything they ask for.

My advice: don’t talk to users. You do you. They’ll just have to adapt.

And don’t even think about nominating so-called "Champions". They’re the worst. "Champions" (read with air quotes) might think of things that you didn’t think of and identify gaps, just because they know sooooo much about how they need to do their jobs. They might even help change other users’ opinion by talking to their peers (and then everybody will expect you to deliver stuff).

If someone insists that you need to identify "Champions" in the organization, get the Executives to name people that don’t really know anything — don’t let them name people who will actually use the system.

And whatever you do, if a group of people approaches you and they want to be early testers on your migration, steer clear of them! I’ve seen it too many times before: they may find issues before everybody else gets to use the system (and then you’ll be expected to fix the issues !).

Even worse: "keeners" (that’s what I call them) might generate excitement in the organization. The may get other groups (who would otherwise leave you alone) to get jealous, to get excited about features they have been whining about for a long time, and demand to be early adopters.

Don’t communicate

This is just common sense. If you tell people that a new version of SharePoint is coming, they’ll just get worried about the coming changes and they’ll make your life miserable.

Remember that your users have jobs to do. They have probably worked really hard to learn the last version of SharePoint (they change everything between versions, don’t they?) and if you tell them about the upcoming SharePoint migration, they’ll fight you.

Even worse if you tell them about moving to the cloud! Remember: users don’t know anything about the cloud, and they probably have concerns over safety and security. If you tell them in advance what’s coming, you’re probably going to have to explain to them why the cloud is better, blah, blah, blah.

Let the rumours fester. If you let users guess what’s happening, they’ll make up stuff and may not even have to deliver anything because they’ll fight the migration before you even get started!

Best strategy: hope that your users enter a deep coma until your migration is done. When they wake up, dump the new platform on them and let them fend to themselves.

If you’re a consultant and you were brought in to migrate, try to can keep the rest of the IT department in the dark. It is fun to watch them squirm and think that they’re going to get laid off.

And they’re always trying to show off with all the stuff they know about their legacy systems and why you shouldn’t do this and that. Yecch!!!

Probably the best way to make your life easy is to never explain to users about the benefits of moving to the cloud and using Office 365. Don’t tell them what’s in it for them. Because they’ll expect stuff from you!

Don’t waste your time on a content audit

Why would you take the time to list all the sites, subsites, document libraries and file shares that you’ll have to migrate when a cursory glance at the data will give you enough to make up an estimate?

Trust me, if you do an audit, people will expect you to make educated decisions about what content needs to move. Or even worse, they might expect you to consult them to find out what you should move.

Status Quo is good

Copy and paste. Don’t think!

Don’t start going through the content and try to identify duplicates, or content that you should migrate. Don’t look at permissions and folder structure. That would be using your brain, and we don’t want that.

So what if your users have eleventy layers of folders and sub-folders, that’s their problem.

And if you move from a file share to SharePoint and change the folder structure, your users might whine that you lost "implicit metadata" (i.e.: metadata that is implied by where a document resides in a file structure). You would have to take extra time to apply metadata to documents, and that sounds like too much work.

Just copy and paste the documents the exact same way they are at the source. Don’t start spring cleaning — you can always clean next time you migrate.

Estimates are for losers

Estimates are hard. Like "work" hard.

Why would you take the time to analyze the data thoroughly to estimate what the effort will be to migrate the content when all you have to do is give an estimate that your boss/client/stakeholders will be happy with? Go ahead, underestimate.

Most cloud migrations take 6 to 9 months to be done right, but if you tell your bosses that, they won’t like it and they’ll demand smaller estimates. It is better to give them an estimate that they want to hear (like 1 month or 3 weeks).

Once they signed off on starting the migration, it’s not like they can do anything if you take longer, right?

You know as well as I do that they won’t stop asking you for shorter and shorter estimates until you tell them what they want to hear. Why go through the trouble when you can just skip to the estimate they want.

For extra bonus points, once you gave them a short estimate that you have no hope of meeting, try to rush the migration to keep deliver to that ridiculous timeline you committed to. The best part about that approach is that nothing will be done right, and you may spend the next several months or year (usually more than your most pessimistic estimate) fixing all the issues.

You could try to give them a reasonable estimate based on actual calculations, and ask your stakeholders to give you enough time to perform a few test migrations so that you can improve your estimates, but that sounds like too much like adulting.

Oh, and whatever you do: don’t keep a master risk list or, if you’re using Agile, a risk registry.

If you tell people about the risks, you’ll need to have uncomfortable discussions about why you think something may impede your migration.

They might even expect you to create a mitigation plan to prevent risks from happening, or contingency plans to do if the risk actually happens. Sounds like more work to me!

Best thing to do: cover you’re a* and mention the issue once, casually, whenever you have a chance. The less formal the better. For example, tell your boss when he’s late for a meeting. Don’t offer a constructive way to solve the issue, just complain*.

That way, if something goes wrong, you can always say "I told you so!".

Gap analysis shmanalysis

Gap analyses are so overrated!

Who needs to look at the differences between the old version of SharePoint and the new version.

For example, if you found out that your old sandbox solutions are no longer supported, or that your mission-critical application built on Access Services won’t work anymore, people are going to expect you to find an alternative solution.

Don’t waste your time with migration tools

Why would you use a migration tool when you can just drag and drop the documents from the old SharePoint to the new SharePoint Online?

Arrgh! Those annoyingly demanding users are going to complain that all the documents’ Last Modified date and Author have changed.

And you better hope they don’t notice that you lost their version history either!

I guess you can always look at Microsoft’s free SharePoint Migration Tools, which handles migrating sites and file shares. But how good can it be when it is free?

I mean, what incentive can Microsoft possibly have to spend time and money building a decent tool to migrate to Office 365?

My advice: don’t even look at the tools. If someone tells you about the free SharePoint Migration Tools, you can always use the age-old IT consultant trick. Just say the following words:

I’ve heard that [INSERT PRODUCT NAME HERE] is slow and buggy

No one will ever argue with you. If you say it is slow and buggy, it must mean that you used it and nobody will ever doubt your IT knowledge ever again.

Don’t waste time researching the various tools available. Don’t look at how well they support their products or how they take time to educate their users to migrate successfully.

Don’t evaluate whether the tools support scripting or automation. That way, no one will expect you to test your migrations and save them to a script that you can re-run without introducing issues.

Nah. If you have to use migration tools, pick the first one you heard of without worrying about why it is better than any other tool. It’s not like you’re spending your money, right?

If the tool doesn’t work, you can always blame the tool.

Users love surprises

If you tell your users that you are going to migrate their stuff, they will pester you with questions.

It is better to hope that you never have to talk to your users, and just migrate stuff without telling them.

They can’t stop what they don’t know about, amiright?

If you start telling people what you’re doing, I can promise you that a lot of the managers and directors of employees who may be affected by your migration will start asking you hard stuff. Like "how much time do you need from my staff to help?". They may even ask you to schedule meetings in advance!

Pro tip: Users don’t have anything better to do. When you finally realize that you need their help, just expect them to drop everything. They’ll be excited at the opportunity to take on additional duties to help you.

Don’t schedule maintenance windows… that’s what lunch breaks are for!

If you’re pretty sure that nothing is going to go wrong, don’t even bother telling people when you’re migrating stuff. I mean, everything should go perfectly, so why worry users?

If they lose something important that they were working on, we have a backup, right?

Uh, I never really checked that the backups actually work.

Just wait until people are away from their desks (lunchtime or late Friday afternoon is a great time to do this), that way you can hope that if you have to reboot a server or if you affect the network or server performance, users won’t notice it.

Training is for babies

We’ve discussed this before: anything that you can do to avoid telling your users what’s coming will reduce the risk of them asking more questions and demanding answers.

The best training strategy is: throw them in the deep end and expect them to swim.

Don’t waste money and time on training people. That’s time you can’t be Facebooking or Instagramming.

Sure, Microsoft has tons of customizable training materials available for free, but how good can it be, really? I mean: it’s free.

Let users figure it out on their own. They’re all technical experts, right?

Users are stupid.

Start with the assumption that users are stupid.

Also: feel free to make decisions to disable functionality because people won’t understand it. Don’t reward users who are more technologically savvy. Instead, assume that if you give your users too many options, they will spend so much brain power trying to understand that they will probably lose basic motor functions and be unable to maintain bladder control.

I always admire it when a manager or a director says "oh, our users will never understand that". They understand how you and they are intellectually superior to everyone else and don’t even give users the opportunity to learn.

For example, don’t give people access to Microsoft Teams, because they are too stupid to understand how to use chat applications.

Don’t let people post profile pictures, because they’ll instantly post pictures of their private parts. Instead of revising your "IT Acceptable Usage Policy", just disable those functions immediately.

And don’t get me started about letting people use emoticons and comments in sites. So unprofessional! Better to spend all your efforts finding ways to disable those features, otherwise every single one of those previously professional people will suddenly lose all sense of proper conduct.

It’s a wonder that they never thought of doing this with email? I mean, e-mail was invented in 1971 and we let people send emails to "All employees" and external email addresses and it hasn’t occurred to them that they could send inappropriate emails before? Stupid people.

I know that the workplace landscape is changing and that some statistics (somewhere, can’t be bothered to check) say that over the next 3 years, 48% of the working population will reach retirement age. It means that the new wave of people entering the workforce will be used to new modern tools, but what do they know — they’re young.

Keep your antiquated old views

You started using SharePoint back in 2001. How much can it have changed?

Don’t waste time learning new features that Office 365 offers. True SharePoint gurus stick to the OG functionality.

For example, when you create a new Team Site or Communication Site in SharePoint Online, it creates a new Site Collection. Talk about overkill! They’re called "Sites", not "Site Collections" for a reason!

Microsoft could just create one giant site collection with all your sites in one place.

If a feature didn’t work well in a previous version of SharePoint, don’t waste time to see if it has improved; just dismiss it completely and never go back to it. That feature is dead to me.

I mean, really, all that the SharePoint team has done since then is make it look uglier. So much whitespace!

If you wrote a book or a blog article even remotely related to SharePoint 10 years ago, you are absolutely absolved from having to learn anything new. Just hold on to those views, just like you’ve been holding on to your BlackBerry because let’s face it, it’s better.

Also, grey areas are for sissies. You need to have an unwavering opinion about every topic, and it needs to be absolutely black or white. No wiggle room to account for the customer’s unique needs.

For example, folders are bad. Period. Immediately dismiss the opinion of anyone who says otherwise. Don’t even waste time to think about whether there are acceptable scenarios where folders should be used.

I once worked with someone who refused to learn this new "SharePoint" thing we were implementing at her work (even though her new role was "SharePoint Administrator"). When I asked her why she didn’t want to learn it, she said: "because I’m retiring in 5 years and I want things to stay the same". Be more like that: don’t learn anything new.

More wisdom

Here are more pearls of wisdom I have learned from people.

Waste valuable time trying to rename

When you had your old SharePoint on premises, you had full control over your SharePoint’s domain name and server name. You could call it sharepointy_mc_sharepoint_face if you wanted to.

When you switch to Office 365, your new SharePoint domain will be

That will confuse everyone. People won’t be able to handle it. There will be desks flipped over and people will set things on fire.

The best thing to do is to spend all your energy to find a creative way to rewrite your SharePoint online URL to something that won’t confuse users.

Never mind that Microsoft doesn’t support this, they just don’t know any better.

Rebrand SharePoint completely

Office 365 and SharePoint support the use of themes and some limited organization profile colours.

Again, Microsoft doesn’t know any better and hasn’t spent any time researching how to optimize content for legibility, accessible contrast, etc.

If you don’t completely rebrand your SharePoint site so that it meets your corporate designs, your users will not understand that SharePoint is a tool for work.

If they aren’t constantly reminded of what company they work for with a giant logo occupying the top 1/3 of the screen, they may even forget who they work for.

Best advice: do everything you can to rebrand SharePoint to meet your corporate design.

Microsoft says that you shouldn’t change the master pages or inject CSS in the page because (read this next part in a whiny/mocking voice) "they reserve the right to change the page structure at any time".

So what, for example, if you change the master page to suit your designs and it blocks you from receiving any new features/fixes Microsoft releases? It’s not like they release new features, and updates twice a week, right?

I mean, can Microsoft really have this whole release thing down so that they technically have the ability to do multiple releases a day? I don’t think so!

Don’t worry about what’s supported. Do what feels right.

Spend time disabling features you don’t understand

If you don’t understand a feature that Microsoft offers, and they don’t provide you with a way to disable it, spend as much energy and resources as possible to disable that feature, regardless of the impact.

For example, if you don’t understand the benefits of using the News feature in SharePoint, you should stop every single team from using it.

Even if you have practically unlimited storage space in Office 365, don’t let users create groups. God forbid they create a collaboration space where they can do their work.

I mean, people are going to stop doing all their work and spend their entire days creating team sites and groups and put bad content in there, and then they’ll leave it there.

No, instead of spending time trying to create a proper governance process, and quotas and other easy solutions to help prevent issues, disable those functions completely.

Don’t use all the tools at your disposal

Don’t even look at the tools and features that are included in your Office 365 subscription. That would require you to spend time understanding what they do and — sigh — explain to people how to use them.

For example, don’t use the built-in voice, video, and whiteboard features of Microsoft Teams that integrate natively into pretty much everything. Instead, insist on using another third-party video conferencing tool that you have to pay extra for without understanding what the gaps are. (Remember, say it is slow and buggy).

Instead, spend all your efforts to try to get integrate a third-party tool.

Don’t use Advanced Threat Analysis features of Data Loss Prevention features. Insist on forcing users to use your old, unpatched VPN solution.

That way, Microsoft’s machine learning algorithms can’t identify potential threats and immediately take counter-measures to protect your information. That’s something that’s best left to a human.

Don’t worry about URL limits… or any other kinds of limits

When you’re planning your migration, don’t worry that the URL of your documents may be over 400 characters (because your old file structure is like a Russian nesting doll of folders within folders).

Your users won’t know the difference. They’ll find out that their files are missing way too late to force you to do anything about it.

Force every single person to go on your home page

When users log in to Office 365, they can choose what their landing page is going to be.

For example, their SharePoint page can get them the list of news and updated documents that are relevant to them based on their group memberships and other smart algorithms.

That means that you can’t force people to go to your home page and see what you decided was important to them.

You could configure an organizational news source and use the Set-SPOOrgNewsSite PowerShell command to help push your corporate news in the user’s news feeds where it will reach them (SharePoint Home, Team Sites, Communication Sites, Hub Sites, Microsoft Teams, Mobile App), but isn’t it better to find an unsupported way to force everyone to go to whatever page you deem important for your users?

Even better, you should force your user’s workstations to launch a browser to your mandatory home page. It’s not like you can make SharePoint become such a mission-critical tool for them that they’ll naturally want to log-in to it every day.

Remember, they don’t know any better.


I hope that I have given you enough material today to help you ensure a failed SharePoint migration to Office 365.

Remember that if you succeed, people will expect you to deliver again and again. If you’re busy working, when are you going to surf the internet and watch videos on Youtube?

If anyone accuses you of trying to fail a SharePoint migration, don’t forget that according to CMS Wire, you’re in good company: nearly 50 percent of all Enterprise Content Management programs fail just from a technology perspective. And of the 50 percent that succeeds, half of those fail to really provide value to the business.

You can hardly be blamed for failing.

What other tips do you have to help ensure your SharePoint migration to Office 365 fails? Let me know in the comments — as long as you don’t expect me to read it or anything.

Whatever you do, don’t read these articles

Avert your eyes! You might actually learn something and I’ll have written this post for nothing

5 Mistakes To Avoid When Migrating from SharePoint to Office 365. Pffft, what do they know?!
5 Common Mistakes Migrating to Office 365
Top 5 Mistakes to Avoid When Migrating to Office 365
25 Mistakes to Avoid in SharePoint or Office 365 (and How to Fix Them) — they’re actually trying to fix problems?! What’s wrong with them?!!!
The Why of ECM Failure and the How of ECM Success


Thanks, everyone for your feedback, I’ve added a section on keeping your antiquated views by popular (i.e.: more than zero) demand.


Microsoft MVP and PnP Team Member. Independent consultant. Certified SCRUM Master. SharePoint, Office 365 and Dynamics 365 are his favourite toys.


  1. Lana Moskaleva Reply

    Sehr gut, Herr Doktor. Thank you, Hugo. Great article!

  2. I wish I could change my tenant’s address to be just “”. The domain isn’t even taken! What a wasted opportunity.

    Also, we’ve had a client who was successful in renaming their tenant to their custom domain – Microsoft did support this back in the day, but probably dropped the support once they realized how many hardcoded URLs they have in their own code… That tenant was interesting to say the least.

    Anyway, cheers for an entertaining read!

    • Hugo Bernier Reply

      We could always create a UserVoice entry to let us name the domain [Tenant]

      I’m glad you enjoyed it.

  3. mikeromana Reply

    Absolutely Brilliant! Hugo please know that you make a substantial difference with your generosity and sense of humor as well 🙂 Cheers!!

    • Hugo Bernier Reply

      Thank you Mike! I was hoping it came across as humorous, not malicious. You’ve made my day!

  4. Pingback: Compilation of SharePoint to Office 365 Migration Best Practices – Tahoe Ninjas

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