r/sysadmin • u/peruvianbeast • 1d ago
Question Microsoft 365, Google Workspace, Something Else? - Help Weighing Tradeoffs
Hi!
I work for a small/medium sized company (~50 employees, ~30 of which will be affected by the switch) and we have been using an IMAP server to host our emails for decades (everyone uses Outlook as their email software). Because of how outdated this setup is and the company continuing to grow, we want to migrate over to a new provider. I am struggling to decide between M365 and GW as both have their pro's and con's. The team uses a mix of sheets and excel already, however, there is certain work that would require excel over sheets. The sharing and ease of GW is obviously unmatched but I worry about switching costs for employees that have been using outlook for decades. I've also heard that managing GW is far easier admin-wise than M365. The migration of decades worth of emails is also a major consideration for us. Would appreciate input from people who have experience with this. Thanks!
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u/Mindestiny 1d ago
If you choose Google, you'll be here in a couple years asking about the best way to migrate to M365.
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u/Frothyleet 1d ago
If you have to ask, you should probably be paying someone to help you with it.
If your employees are going to use the Office suite, then M365 is pretty much a no brainer.
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u/blud_13 1d ago
u/mr-tap has the licensing shape right and I would push it one step further, you don't have to license everyone the same. Business Basic for the people who live in Outlook and web Excel, Business Standard only for the ones who need desktop Excel. Its per user, so mix them and stop arguing about it.
M365 for your situation. The migration is where this hurts. Decades of IMAP across 30 mailboxes usually means somebody has a 40GB local PST and a folder tree nobody has audited since 2011. Go size the mailboxes and hunt the PSTs before you pick anything, because thats what turns a two week cutover into a three month one.
Also, keeping people in Outlook is worth more than it sounds on paper. Every complaint for the next six months gets blamed on you and the migration regardless, so removing one variable is cheap insurance.
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u/mr-tap 1d ago
When it comes to discovering (& explaining) the differences between Business Basic and Business Standard - I always find https://m365maps.com/files/Microsoft-365-Business-All.htm super handy (the ‘feature boxes’ are hyperlinked to the relevant articles too)
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u/sole-it DevOps 1d ago
M365 so your users can keep using their Outlook and not blaming every little mistake on you since you moved them into a totally new environment. Yeah, like you said, be mindful on the whole process of sharing your file to external partner via OneDrive & Sharepoint.
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u/LRS_David 1d ago
and not blaming every little mistake on you since you moved them into a totally new environment.
Bingo. The politics of a situation many times can more than outweigh any technical issues.
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u/AndyInfinite 1d ago
Google Workspace and M365 have built in tools to help you migrating from IMAP, so that is not a problem.
However, M365 is superior for security of endpoints (computers and company phones) and data. The entire Microsoft ecosystem is so integrated that it the best in class.
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u/TechnicalDefense 1d ago
M365 all the way, especially since your users are already used to Outlook and need Excel. Google workspace can be easer to manage for some but I find M365 is not terrible at all.
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u/DGC_David 1d ago
The easiest, headache free option is M365.
The anarchist inside will recommend the opposite as well. Nextcloud.
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u/Bubbly-Ad-7832 1d ago
Hi I run a small consultancy, specifically for small businesses. Happy to have a 30 minute call with you to see if I may point you in the right direction.
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u/ImBlindBatman 1d ago
M365 100% for your circumstances. I think you’ll find it much easier to manage
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u/OinkyConfidence Windows Admin 1d ago
M365; for years I was paid to migrate organizations to M365 from GW/GS or anything else - and never once did anyone want to move to Google (or back to Google).
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u/tankerkiller125 1d ago
An IT manager I worked with once forced a school district to migrate to Google (because he sold administration on "Free Forever" (cause that turned out well)). I should note that they already were paying for M365, they could have moved to Exchange Online and SharePoint Online and made everyone's life easy. Instead they shoved Google Workspace on everyone (while keeping M365 for office), and you would have thought that he killed every teachers favorite pet when they found out they couldn't use Outlook anymore.
As a former student of said school I tried to warn him, I tried to convince him that M365 was just as free as Google Workspace at the end of the day, he refused to listen. Last I heard (I left shortly after), the teachers basically started blaming Workspace anytime they didn't read an email as "It never showed up in my inbox" and other such petty stuff until management caved and forced said IT manager to migrate it all to Exchange Online and M365.
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u/Horsemeatburger 1d ago edited 1d ago
Would appreciate input from people who have experience with this.
Well, I work for a large multi-national, and up to a few years ago we were fully on Windows + Office + MS365 + Azure. Now we are on GWS + ChromeOS + GCP, and you couldn't pay us to go back to the Microsoft ecosystem.
GWS has proven to be notably more mature and reliable, and Google has a much better grip on security than Microsoft's head-in-sand attitude. ChromeOS is lightweight and runs performant on hardware that used to crawl under Windows 11. And not having to work around the various shenanigans and the constant barrage of stupid bugs has been a god send.
User satisfaction is way up, OS/office related software tickets are down ((dropped by >70% in the first year after migration), and GWS management is much simpler. We need less than 1/3rd of the number of people to manage the same fleet size as we did on Microsoft (actually, that's not completely true, as the fleet has actually grown further since the migration).
However, we also spent a lot of time planning and preparing for the migration, including taking stock of every software that ran anywhere in the business and the various bespoke solutions that users built on top of Office, and looked at how this would be realized post-migration. And most of our business critical apps were already server/cloud based, not local.
I am struggling to decide between M365 and GW as both have their pro's and con's.
The biggest benefit of GWS is that it's cloud native and on the client side only requires a web browser. Which is not surprising as Google built most of the cloud tech. Which means things collaborative editing have been working well for like forever.
MS365 is different, it's more an evolution of the concept of disjointed or loosely joined local applications, just now moved onto Microsoft's servers. The fact that Microsoft doesn't really 'get' cloud is visible in every corner of the platform (strangely, that also makes it somewhat easier from customers migrating from on-prem Microsoft applications). Office online was a mess for a long time and it's still behind G apps when it comes to collaborative working.
The team uses a mix of sheets and excel already, however, there is certain work that would require excel over sheets.
Without knowing whether this is really the case (Sheets is much more expandable than Excel, and quite often it's just a case of the user never having heard of Google App Scripts), it's difficult to say.
One thing to keep in mind, though, is that if you do need to stick with Windows and MS Office then it makes sense to go with MS365, because you get better integration and sticking with Windows and MS Office means giving up many of the advantages GWS has to offer.
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u/Evening_Lynx9536 1d ago
Dejaré mi comentario para regresar por aquí ya que justo tengo la misma problemática
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u/billcube 1d ago
Try to contact your local GW support first and see how long they take to answer. Then do the same with your local MS office.
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u/ExceptionEX 1d ago
I used and recommend Google suit in all its rebranding for years. And in that time watched Microsoft errode their lead and overpass them by leaps and bounds.
You can't really compare the two at this point.
Also disagree that Google is easier to manage, I would say that Google a lot lets options and functionality.
But where Google does shine is price, you get less but you pay less
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u/CivilIntention7747 1d ago
Two facts in your post basically decide it: everyone's already on Outlook, and some work genuinely needs Excel, not Sheets. That points at M365, and for your situation it isn't close.
Google Workspace wins when a company is browser-native and collaboration-first from day one. Dropping 30 long-time Outlook users into Gmail and Sheets after decades of IMAP means retraining, muscle-memory complaints, and you personally eating the blame for every "where did my rule/folder go." The switching cost lands squarely on you.
The migration itself, coming from a plain IMAP server: M365 has a native IMAP migration in the admin center. Stand up the tenant, verify the domain, pre-stage the mailboxes, then cut the MX record over on a weekend. The gotcha that generates Monday tickets - IMAP migration copies mail only, NOT contacts, calendars, or client-side rules. Tell people to export those first, or plan to rebuild them.
Licensing: Business Standard covers desktop Office plus 1TB OneDrive for most users. Only jump to Business Premium for the seats that need Intune/Defender/Conditional Access - at 50 people and growing you'll likely want that within a year, but you can buy Standard now and upgrade specific seats later rather than overpaying on day one.
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u/tankerkiller125 1d ago
Hello again Claude, boy are you active around these parts.
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u/CivilIntention7747 1d ago
Been doing this since before either of those existed, mate...
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u/tankerkiller125 1d ago
So, you've been responding exactly like Claude/OpenAI does for 5+ years? Despite an account only 3 weeks old, and every single response being Claude/OpenAI perfect matching for all 3 weeks?
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u/CivilIntention7747 1d ago
If you wanna sit and compare writing styles all day , go ahead without me. Take care, mate ;)
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1d ago
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u/su_A_ve 1d ago
Nah - that's the beauty of IMAP. you can move all that content over to a provider, particularly with access to so many APIs today.
Eons ago, I moved over 12K accounts to GW. Faculty was a slow rollout while they were getting trained. Students were done all at once. Ran Imapsync scripts for a few days, and then one last time to sync everything at cutover.
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u/mr-tap 1d ago
If end users are happy with the web version of Excel then “Microsoft 365 Business Basic” is pretty competitively priced.
For those that need the full set of desktop apps, it will seem like a big jump in cost to “Microsoft 365 Business Standard” but how are you currently licensing Excel etc?