[solardev]

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam).

Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on.

Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge productivity booster, between meet and groups and drive and docs and calendar and sheets and such, not to mention chrome sync and sign-in with google, etc. And federated management of all of that together in the admin interface, along with integrated legal archival and discovery. Well worth the monthly cost (what is it, like $10?). If your employees aren't worth that much every month, you shouldn't be hiring them.

It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible.

[CharlesW]

> It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible.

In what way? I’ve used both Google Workspace and Office 365 during my career. I don’t dislike Google Workspace, but Office 365 is notably more mature, capable, and complete. (I mostly use Macs, but the web apps work the same on any browser/OS.)

[lultimouomo]

Does this include Meet vs Teams? Because Teams is the absolute worst piece of technology I am forced to use regularly. And this includes WebEx!

Also, and I'll never get tired of saying it, if you have both a personal and a business-managed Microsoft account you better give up computers and be a hunter gatherer, it'll save you a world of pain.

[TheNewsIsHere]

My experience matches yours. I loved Google Workspace at a small nonprofit. But if you’re running a business that has “hardcore admin needs” on the productivity services side, MS365 beats the pants off Google Workspace all day.

Tools like GAM used to make things easier and expose just how much UI Google never bothered to write, but at least as of this year I can’t find a feature in Google Workspace that isn’t in MS365, plus you have -all- of Azure right there.

[tomjen3]

The webapps for MS works terrible on Linux and there isn't a native client (Word _native_ is pretty good for Mac).

[solardev]

Really? Surely you're joking..? I've had the complete opposite experience, and in fact have never found a piece of productivity software as horrible as Office 365. Also on a Mac...

Email: Outlook UI and hotkeys are totally different from MacOS, Windows, and Web. Rules don't really work and are impossible to debug. Search is terrible. Threading is terrible (expands the subjects of each child message, but not their bodies... whyyyy).

Calendar: How the heck do you find an event you previously declined but changed your mind on? Why does Teams and Outlook both offer a calendar, with subtly different UIs and features, and the web interface is totally different yet again? It is incredibly slow (things take multiple seconds, like loading someone else's calendar, or clicking on an event it has to take time to load in the attendees...). The "suggested times" feature is hard to find and there's no visual guide (like a week view); also it again seems different between the apps.

Teams: Oh god. This... is what they came up with? It's sooooo slow on startup. It duplicates Outlook notifications. It is hard to find the meeting you're supposed to join when you first clicked on a join link, but then it asks you to login, etc. It's so much less feature-ful than Zoom, yet so much harder to use (and uglier) than Meet. Why do the chat rooms persist not only after a meeting but get resurrected later in the week, and why do they notify you for chats in a meeting that you're not even in. The share screen sidebar is atrociously hard to see to determine which window you're trying to share. Like... literally all the basics they got wrong, and this one software has the worst UX of anything I've seen.

Excel, Word, etc.: My god, the UI has gotten even worse, the forced OneDrive integration is terrible, etc...

I grew up using Microsoft stuff until Google started popularizing their online suite. In the years since, every employer except this most recent one has used Google and while it never struck me as particularly pretty, it was pretty easy to use for the most part. I was actually kinda curious to try the Microsoft stuff again, figured they had 20 years to catch up, it's gotta be better now, right? Nope. I've never hated a stack as much as this, even as a long-time Windows user... in fact it's going to be one of my questions for employers in the future, and a big red flag.

Sorry, I know I sound pretty agitated about this. Their software griefs me on a daily basis and is the single thing I hate the most about my job. It's just SO terrible. I guess YMMV, eh? I didn't realize there were actually people out there who preferred the Microsoft stuff... of the folks I've spoked to casually, all vastly preferred Google's implementations. But that's just anecdotal.

[cosmodisk]

A lot,if not all, of what you wrote here is true and I experienced some of it both as the end user and as an admin. However what are the alternatives for a business where most users sit on Windows? Google suite is a joke for anything but simplest tasks and config is lacking. Yes, Microsoft can be cumbersome, bloated,but it has to support 5 people shops to enterprises with tens of thousands of users and config complexities.

[solardev]

I guess I've never seen a business actually use Microsoft Office effectively. The odd PowerPoint or Word doc? The standalone apps work OK alongside Google, or people just send PDFs anyway. For actual collaboration, especially real-time, Docs and Sheets and Drive and Slides are soooooo much better to work with. Even if they are less feature packed, they do the basics much better.

But that is just my experience primarily working in web teams or small biz. Maybe there are enterprise features that I've never used or even thought about.

As for admin, I've been the gsuite admin (again just for smaller companies) and found it quite powerful, but the use cases are probably different. A lot of these companies basically use the computers as dumb terminals, where the browser is the only thing that really matters. And Chrome federated management makes that pretty easy.

[cosmodisk]

I work at non tech company. A lot of( if not most) interactions with the outside world are based on Microsoft products: meetings, file exchanges, or even collaboration. Some things work great and for some you just want to shoot yourself in the head. The average knowledge of a non tech business user is very very limited when it comes to software and some people even get panic attacks when told ' just download it and run it'. That's the default mode in many businesses. The average person on HN, who can pick up new programming language,read 50 pages of docs in the evening is so much beyond the average office user, that there aren't many hopes of that gap closing any time soon.

[kcplate]

I don’t have any love for MS Office and Teams, but I have experienced literally none of the issues you mentioned other than the two calendars, but that is easily solved by just using one.

[jfim]

Outlook beats the pants out of Google calendar when it comes to reminding people of meetings.

As an IC, I used to miss meetings due to the Google calendar browser notification being so tiny and unintrusive. Contrast with the totally in your face Outlook meeting notification that can't be missed.

[solardev]

I never had a problem with this, between Slack integrations and connecting GCal to the desktop calendar app and using its notifications.

On the other hand, I seem to get 3-4 reminders about the same meetings -- even ones I'm already joining -- between Outlook and Teams.

[mekster]

Google is always about backend. They suck on the frontend (except Maps) but somehow they never want to change that habit.

[mekster]

Using services like Postmark, the concern becomes smaller.

No one should send emails that should land in a human's inbox directly off a bare random IP.

At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.

[solardev]

I believe the OP is talking about emails for their employees, like personal inboxes. Postmark is more about transactional emails, no? And even that is offloading a lot of the deliverability concerns to a specialized vendor.

> At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.

You really really should not need to be doing this yourself. I've had to fix a few of those and it's REALLY not worth anyone's time.

Getting email from Google is $6/mo, Microsoft $6/mo, Zoho $1/mo, Proton $4/mo, Fastmail $3/mo, etc.

Then it's just set it and forget. You don't have to track down quarantined messages, cross-examine a bunch of headers, check blacklists and whitelists, figure out how your SPF is propagating, blah blah blah... it's just not a wise thing to skimp on.

Do you really want your startup employees to be running into email problems while you're still trying to establish yourself as a business? At some huge corporate scale it might make sense to in-house this again (and even then it's questionable), but it's certainly not worth having a dedicated person (or generalist IT scapegoat) waste time setting this up and debugging it in a small or medium-sized business.

[simfree]

Microsoft has a hidden quarantine. Google has random delivery issues. Neither are truly set it and forget it, at some point your back asking why an email bounced back or disappeared into an undisclosed quarantine with no notification...

[paulcole]

I’ve used Gmail for work for 9 years and Gmail for personal use for 18 years and have never had to ask why an email bounced back or disappeared into an undisclosed quarantine with no notification.