Community IT Innovators Nonprofit Technology Topics
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Community IT Innovators Nonprofit Technology Topics
Nonprofit IT Migration from Google Workspace to Microsoft 365 with Steve Longenecker
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Carolyn Woodard talks with Steve Longenecker, Director of IT Consulting at Community IT, about a client's decision to migrate from Google Workspace to Microsoft 365, and what a real nonprofit migration project looks like once years of technical debt have piled up.
The client's story is a familiar one: a lean two-person IT team supporting 300 information workers, years of default settings, and undocumented shared folders that quietly became a governance risk. Steve walks through why this organization is moving to Microsoft, from their existing use of Outlook and Windows devices to the stronger admin and device management tools Microsoft 365 provides, and why he keeps coming back to a moving-house metaphor: sometimes you need to declutter before you pack.
This episode covers:
- Why Google Workspace's low barrier to entry can turn into years of undocumented shared folders, oversized mailboxes, and unclear file ownership if no one is minding governance.
- The real differences in how Google and Microsoft handle IT administration.
- Why this client, already using Outlook and Windows devices, is moving to Microsoft 365 for stronger device management and identity tools.
- The moving-house metaphor: purging old email and cleaning up 2,200 shared folders before migration so the new home isn't just as cluttered as the old one.
- Why leadership buy-in, often from a newly hired executive, is what finally gets a years-overdue technology migration off the ground.
Resources Mentioned:
- Google Workspace vs. Microsoft 365 – Community IT Innovators – https://communityit.com/google-workspace-vs-microsoft-office-365/
- Migrating Within Google to Use Shared Drives – Community IT Innovators – https://communityit.com/migrating-within-google-to-use-shared-drives/
- Securing Google Workspace for Nonprofits – Community IT Innovators – https://communityit.com/webinar-securing-google-workspace-for-nonprofits/
- Managing Google Workspace and Office 365 Together – Community IT Innovators – https://communityit.com/managing-google-workspace-and-office-365-together/
- Growing Your Nonprofit With Google Workspace – Community IT Innovators – https://communityit.com/webinar-growing-your-nonprofit-with-google-workspace/
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Thanks for listening.
Welcome to the Community IT Innovators Technology Topics podcast. I'm Carolyn Woodard, your host, and I'm excited today to be talking with Steve Longenecker. Steve, would you like to introduce yourself?
Steve LongeneckerI will be glad to introduce myself. As the director of IT consulting, uh my role is uh I'm I provide leadership on the IT business management team and on the projects team. So I'm really lucky to work with a lot of really great professionals on both of those teams. And so I get to be involved in a lot of uh projects and the consulting that leads up to the projects.
Carolyn WoodardAnd I think today we wanted to talk about a migration that a client is doing and some insights that you had on that. And they're moving from Google to Microsoft.
Steve LongeneckerYeah, well, what I can share is the the planning and thought that's going into the decision that is not even fully finalized yet, but the the full intention is to move from from Google to Microsoft and and and the why of that is yeah, it's kind of an interesting story. This is one client's experience.
Steve LongeneckerWe came to them through participating in an assessment that we did for them. And uh they brought um they wanted the assessment because um a new um COO was hired. And I think he recognized that there was a lot of uh technical debt in the organization and needed help identifying like maybe how bad it was, and also like, you know, maybe some triage thoughts on what the most critical things were to address and maybe prioritizing them. Um, and also um,
Steve LongeneckerYou know, coming in as a not necessarily as a technical person, as a COO, you're you're at a higher level, you're looking at it from the 10,000-foot view, but getting some senses of what the risks of being like like we are now are, what um what uh it might cost to get out of that out of the position that we're in, um, and and sort of some of the things that that one needs if you need to make a case to your your C-suite colleagues, and I guess ultimately to the you know, the person who makes the the chief executive who makes the final decisions, like, you know, we need to do this, um, even though it's gonna cost us a lot of money or whatever. So yeah,
Steve LongeneckerThey had a lot of stuff, a lot of issues. They had been underinvesting um for a long time. I think, you know, you've talked a lot about how Google Workspace has, as its advantage, like a very low bar to entry, right? Like you can set up Google Workspace as a non-technical person. And because there are uh fewer switches to look at um and uh you know, and the defaults are you know usually acceptable and work well enough that you know you can you can have a working uh email and file system pretty quickly.
Steve LongeneckerNow there's some, you know, we've talked about the gotchas, like maybe out of the box, the default might be people are just using their my what I call their My Drive and maybe sharing folders with each other, which is not the same thing as using what call what Google has introduced a while ago now. I mean, we've talked about this before the the Shared Drives and how much of a superior solution for an organization that wants to have good governance and good ownership of their intellectual property and all that Shared Drives are.
Steve LongeneckerSo you can definitely you can definitely set it up with the defaults and think you've got a thing that's going okay here.
Steve LongeneckerBut like if you know you if there's no one to offer some of that counsel ever, you can like, you know, seven years later have a kind of a hodgepodge of no one knows where the files are. Um, there's been no policies, no governance. So mailboxes might be ginormous. We we had you and I did the webinar about security risks with Google Workspace. So offboarding procedures might be out of line. There's all these things that can go wrong.
Steve LongeneckerAnd this client, you know, was doing a lot of those things and uh was, you know, also in the hole a little bit because they only had two people, sort of their IT department was two people. But still, we're talking about like 300 people that are classic information workers. And like, you know, they were still living in that someone set this up once upon a time, you know, and we never really did anything more than that, you know. And so everything's everything that's had happened since is kind of a historical accident of one sort or another. And so yeah.
Carolyn WoodardYou and I have talked about kind of the different philosophies of Google Workspace and Microsoft, where Google Workspace is so consumer-oriented, like you said, a person can set it up, and it doesn't ever require you to really have an administrator. Like you can, someone can take on that role, but it's not baked into how Google Workspace works necessarily.
Steve LongeneckerI mean, I think that's what we're stating. Certainly, yeah.
Carolyn WoodardMicrosoft have an admin, like, can you even operate it?
Steve LongeneckerWell, I mean, there is always an administrator in Google Workspace as well, but it's certainly the case that Microsoft fundamentally views like IT as um the organization's prerogative and ownership and there and and expects there to be a lot of a heavy hand, if you will, from IT administration, um, and builds all sorts of tools to make that heavy hand possible. So, you know, the
Steve LongeneckerThe classic example of that is, you know, if if an executive director says, hey, we're having a personnel issue with this person, and we need, I need access to that person's mailbox, but I don't want that person to know that I have access to their mailbox. And um, but it's important. The lawyers want me to get that so that we can monitor their email without them knowing for now. And uh, you know, that's a that's always like a a request that, you know, no one likes that request. I'm sure that the person making the request doesn't really particularly like making it, but like whatever.
Steve LongeneckerThe point is that that that as their outsourced IT department, that's one of our roles is to provide that to meet the request when it's made. And frankly, everybody knows when they, you know, sign up to work somewhere that that's sort of part of the social contract of employment, or it's literally the it's literally the contract of employment.
Carolyn WoodardYeah, it's in your acceptable use policy, usually.
Steve LongeneckerSo anyway, we can do that in Microsoft. You actually can't do it in Google, which is like just it's just kind of interesting. Like you just can't do it. You can definitely get in as an administrator, get into someone's email, but not without them knowing. You basically have to re - either they have to make you a delegate, which is obviously you have to request it, or you have to reset their password. And which case they're gonna be like, what happened there? You know, now maybe you could, you know,
Carolyn WoodardYeah, interesting. How deceptive, you are going to be
Steve LongeneckerSo it's different. It's different. But but I was what I want to say is that you do need to have an administrator. Like someone needs to create the user account. Like if you order someone, if you if if someone new is hired, someone has to have that super admin role to log in and create the new account.
Steve LongeneckerBut it's true that it kind of like can be a little bit of a fix-it and forget it thing once you have the things. Yeah, once you have like the initial email domain name established and the mail flow is flowing, you know, uh your users can access Google Docs, they can access Google Drive, they can access Google Meet, they can access, you know, Gmail, yeah, um, and they can do all of those things, and you don't really have to pay attention to it. And so if as a and so they can get out of control.
Steve LongeneckerIt can get out of control. And you can you can get to a place where um the debt is pretty steep because like, well, now we don't know, you know uh where where our files are, you know, it's all like locked into uh the um institutional knowledge of the individuals. Yeah. And and that's there's a a risk to that.
Steve LongeneckerSo this particular client, they you know, we did this assessment, we identified some of these concerns, and it wasn't all about Google Workspace. And it is oh, and to be clear, the same thing can happen with Micro ...on the Microsoft side of the fence, right? I I don't want to this is not about Google being the problem. Um
Steve LongeneckerBut I do think I do think that that um most organizations that are in Microsoft probably um have the the the defaults to Microsoft give them a little bit more um organizational structure that are more likely to have not be quite so um uh laissez faire. So anyway, this organization. Yeah, yeah.
Steve LongeneckerSo this organization uh the they they what's interesting, and this is not at all our best practice, but they use Outlook to access their Google Gmail. So some people like Outlook. Apparently uh a lot of people at this organization do like Outlook, or it's just become again, maybe it's a historical accident. You know, maybe they got the um the office desktop suite at you know at nonprofit prices, and everyone has, you know, in our generation, yours and mine, everybody uses Word, everyone uses Excel.
Steve LongeneckerI mean, you know, the kids today they may have all grew up on Google Docs and Google Sheets in their schools, and and Word and Excel seem like kind of heavy, yeah, ungainly applications. Yeah.
Steve LongeneckerBut uh they use so they use Outlook, and it's like it's it's like getting harder and harder to hook um Outlook up. Part of the reason they have out that they're continuing to be able to do it is that they're actually using a really old version of Outlook because, you know, again, it's like you just get into debt, you know, no one's paying attention to this. So they have a very an old version, I think Outlook 2016 everywhere, and they're connecting to Google.
Carolyn WoodardI was gonna ask you about that because I one of my questions was like, so you've done the assessment and this is the recommendation. And the leadership is on board with this as a way to deal with this, address this technical debt is to move to Microsoft.
Carolyn WoodardAnd I would think that one of the ongoing issues would be the capacity of that organization who is used to using Google to kind of change that mindset and start, okay, now we're going to use Microsoft. But if they were all use already using Outlook, then it seems like maybe a slightly lighter of stuff they do.
Steve LongeneckerThat was definitely part of the argument.
Steve LongeneckerAnd I should that there, we did the recommendation was that moving to Microsoft, the Microsoft 365 stack, which you know, they're when they use Windows, they're a Windows-oriented organization. Windows is made by Microsoft. So the the Windows laptop management tools that are in Microsoft 365 are outstanding because the Microsoft controls both ends. So they can do all these deep integrations. They can it can integrate with you know Entra ID's identity. Um, and and and
Steve LongeneckerMicrosoft is very good at like building this. Like, we may not be the best at any particular piece of our stack, but like it all works together and it's all pretty good. And what you and the and the sum is greater than the wholes in some ways, particularly if you're not either so small or so big that you can afford to like do this best of breed thing where you might say, okay, I don't think I think the very, very best gold standard for document storage is Box say. So I'm gonna use Box for that, yeah. And then I think, you know, identity, the very best identity I'm gonna decide. And I'm not even sure, I'm not necessarily saying this is true, but let's just say that your position is it's Okta. Okay, so you use Okta for that, and then you decide you're gonna use, you know, this for that, and this so forth. Oh, you love you love Skype, not Skype, what am I talking of? Uh what's the what's the thing the team Slack? You love Slack, so you're gonna use Slack, you know. So you have all these different things. Um that's that's like
Steve LongeneckerI think that's a doable approach for for small nimble organizations that are full of a lot of IT savvy workers that they're just so small that they don't that they don't have to worry about this that the challenge of scaling this many platforms up. Well, if it's just you know the 15 of us and we're all like sharp people, we can make it work, you know.
Carolyn WoodardYeah.
Steve LongeneckerOr if you have a big enough, you're so big that you can have a whole IT department just focused on Box, you know, not a whole IT department, but like part of your a segment of your IT department is just focused on Box. Yeah. Yeah.
Steve LongeneckerBut at the size that, you know, this other client is, and most of Community IT's clients are, you know, it really is helpful to have one platform is really nice, the stack. Yeah.
Steve LongeneckerAnd, you know, we do have plenty of clients that straddle that that, but they try to have a clear demarcation, right? That maybe Microsoft, if they're Windows, they might have Microsoft for identity, the Windows device management, and maybe the Office Desktop Suite. And then they have all the informations in in Google, if that's where they came from, right? They like Google Docs, they like Google Drive, they like the Gmail. So they keep that's a that's a possible straddle. And we have plenty of clients who do that.
Steve LongeneckerWe have plenty of clients that are just in Google, but then they're not really getting the the device management. If they're if they're in um if they're on Macs, uh Microsoft won't help them much with that anyway. So then maybe they have a third-party Mac management platform, or maybe they don't, maybe they're so they're small enough that they're just you know, as a Community IT can provide Mac. We have we have Addigy is our platform.
Carolyn WoodardI was gonna say make sure we like say that we can
Steve LongeneckerYeah, yeah. We'll put our we'll put our little brand, our our our little if yeah, you're one of our clients, we can help you with that.
Carolyn WoodardBut a lot of MSPs are like no, like you're on your with Macs.
Steve LongeneckerOf course, of course, yeah. Um
Carolyn WoodardAnd Google too. Like there are a lot of MSPs that are like, we don't yeah,
Steve LongeneckerWe don't do we don't do Google.
Carolyn WoodardSo WE do Google, I'm saying
Steve LongeneckerWe do Google . And we do the Macs, and we help people that want to straddle. And that and those are all good choices.
Steve LongeneckerThis particular client, as big as they were, as much dead as they were, they they did, they're like, look, we're already using Word, we're already using Outlook. Like maybe we can make this work, and we're gonna really benefit from having all of our Windows computers managed by Intune, which is the Microsoft part of the Microsoft 365. We're gonna you get it's
Steve LongeneckerI would just say that once you start talking about like again, administration, ease of administration, they're big enough that some of the enterprise y features of the Microsoft identity um I think are attractive. Uh some of the security features that you know Microsoft builds out, and Google has a lot of these things, but um, a lot of those things in Google you end up having to go like to a pretty high tier. Whereas I think Microsoft the sort of the baseline, what they call Microsoft 365 business premium. Um got it in it, you know.
Steve LongeneckerNow, this client I think is too big for Microsoft 365 business premium because that's a 300 user limit. But uh, but uh even so I think they're they they looked at the Microsoft stack and said this is gonna this is gonna be the right thing for us. Um but we did, you know, we're
Steve LongeneckerWhere we have been stumbling so far. And in fact, the decision I think was hasn't been made yet, but that we're we're going back and and we're um talking about this with them, is uh they might need to do a some of the cleanup in in Google now ahead of time because the the scale at which they are operating at um and the fact that they are their IT department is still relatively small. Hopefully they they hire on that. But um, you know, we need to things can't be we can't do that sort of sometimes with Community IT migrations. We can
Steve LongeneckerThere's things if the client is small enough that we can really provide um uh what's that white glove, almost white glove, you know, service. Like let's look at let's look at your folders and your in your drive and figure out, you know, where these should go, kind of a thing. It's like, well,
Steve LongeneckerCan we do that for 300 people? Like that's that's a lot, you know. So the COO has said, you know, I think we need to say, look, we gotta we've gotta get rid of some of this old, old mail. Yeah because it's it's like bogging us down and in a migration, we're just gonna be like pulling over, you know, 20-year-old email, and I am I need to be the bad guy and say, you know, after a certain after email is a certain age, you know, it it needs to be purged. We need to we need to delete it. So um that will help.
Steve LongeneckerAnd then on the on the file side, there are like 2,200 folders that are shared you know, with different people. And like again, the scale of that, like where do all these folders go? Yeah. And so to to make the decision that we're gonna clean this up in Google, and then when we then we'll
Steve LongeneckerSo I like to always go back to the metaphor when with migrations, I'm often using um moving, like physically moving from one home to another. Yeah, I use that as a metaphor a lot, and um and
Steve LongeneckerSo in some ways this this uh chief operating officer is, I think, looking at the the state of their current house, yeah, and the clutter and uh uh confusion of their current house and how he doesn't know where anything is, and he doesn't know if half the stuff is needed or not, and he's like made the decision we need to move. Yeah.
Steve LongeneckerBecause moving is gonna force us to like look at things and say, we don't need this, we do need this, and and we're gonna pack and we're gonna say this is we're gonna be organized in the new home.
Carolyn WoodardYeah.
Steve LongeneckerUm, although in some ways, like Gmail allows you to have really large mailboxes. They just don't, they just don't, that's not something that Google makes a fuss over. It could be that their engineering is different, or it could just be they're just a lot more generous with space in general. Like, you know, nonprofits get 100 terabytes of space across their workspace tenant, and Microsoft is much more like you know, two terabytes of SharePoint space.
Steve LongeneckerNow that's just SharePoint, so it's not right apples to apples, but mailboxes are usually a hundred gigabytes max, and that's Google's not that way. So if they're gonna move to Microsoft, maybe they that's good decisions, and the COO, I think, is I am speculating about what the COO is thinking, but I would imagine the COO is thinking, no, I'm gonna view the 100 gigabyte mailbox size limit as a feature of Microsoft because I don't want my staff dragging around exactly,
Steve LongeneckerI don't want them dragging around 400 gigabytes of email from from the last 30 years. I want us to be, you know, to clean this up.
Steve LongeneckerAnd if I can use the fact that we're moving as like the the hammer for this and the excuse for this, then that's actually um a good thing. And uh, but back to that metaphor, sometimes is you do actually need to make some amount of uh organization and uh improvement in your situation before you move. Because it's it's actually too much. Like you you've you've gotta like clear stuff out or whatever. Um
Steve LongeneckerAnother thing that this client needs to do, we we just said this would be so much better if you did it before we did a migration. They have a lot of old computers, right? Like old clunky computers, and like let's replace those.
Carolyn WoodardYeah.
Steve LongeneckerYou know, let's replace those.
Carolyn WoodardThat's also part of that that debt and that attitude for the technology. And you can see how, especially the way, you know, like as we've been talking about this, and and you've told me about this migration, you can see how it's not just for this client, but for nonprofits in general, it piles up. And there are certain things in place that allow it to pile up the technical debt. And well, we've got all this storage. Why should I archive my emails from seven years ago?
Carolyn WoodardAnd coming in as the COO, you're gonna think like those are liabilities, and that is a risk. And um, you know, so I
Carolyn WoodardI guess I was gonna ask a little bit more about how I mean that's on the client, right? And on the executives to prepare the staff to see why we're making this move, why now? I mean, a good thing about it, if you also think about the moving house metaphor, is sometimes like we have to move by the end of the month.
Steve LongeneckerRight.
Carolyn WoodardAnd then you just throw everything in the van, no matter what it is, and hope that you have room to put it in the new house.
Carolyn WoodardBut if you are coming in in this situation where you have some time to plan and you think, like, let's not bring everything from the garage storage, let's take some of that to the dump or have a yard sale or something first to get rid of it before we move into our new place and you've got the time to plan that. It's goes a lot better, I think.
Steve LongeneckerYeah. Yeah.
Carolyn WoodardThe hasty move.
Steve LongeneckerYes. Yes. Well, and and so I think, yeah, what what maybe the the way this is going to be play out, perhaps, is you know, we'll create these shared drives and we'll say, hey, if you want this stuff to be available in the new space in a way that's accessible to people, it needs to be in this shared drive. If it's not, it'll just we'll just move it to your Microsoft One drive, which is the Microsoft equivalent of the of the Google My Drive, but then it won't be shared. Yeah.
Steve LongeneckerAnd and it will create, at least initially, you know, not an insurmountable amount of confusion. But like if you want it, if you want this to be smooth, yeah, then let's let's get this ready.
Steve LongeneckerSo it's kind of like, you know, the parents going to the kids and saying, okay, here are the three cardboard boxes. Yeah. If the stuff's not in these boxes, you might not know where it is when we get to the to the new place. And it you might not have it for weeks while we unpack, you know. So if you want to make sure that the stuff that you value is, you know, available to you, then put it in these boxes. These are the boxes for that, you know. And that that's that's uh metaphorically, again, I think that's kind of what how this may go.
Steve LongeneckerSo I think the the files are the are are the sticking point that um and the computers, but the computers are um, yeah, that's just kind of a classic when you're when you're underfunded, you or not even underfunded, when you just make choices, you make choices.
Carolyn WoodardYeah, yeah. Well, and I think I just want to end on the note that I mean, clearly talking to you, you have so much experience and our team. I've talked to you know Robin about migrations and just we have a lot of experience with helping the clients, executives think through and be organized about it. Like, well, what do we have to have staff do first? And what makes sense for them to do here? What's gonna make sense for them to do in the new house? Um we we can
Carolyn WoodardIt can seem like an overwhelming project. And I think that's another reason why it doesn't get done for years and years, right? Because it's gonna be this big change management, it's gonna take a lot of focus, a lot of priority, a lot of funding, a lot of pain. Even if eventually we're gonna save time, effort, you know, budget on this new stack that's gonna work better. It's a big project.
Carolyn WoodardSo don't despair. There are people out there who can help you when you come down to the idea that it really would make sense to migrate.
Steve LongeneckerYeah. No, we we we can definitely help a lot with the technical process and understanding the technical process. And we do do that, and it's and it's um, I think I think that's very important to successful migrations.
Steve LongeneckerBut at the end of the day, that pain part is is absolutely real. And that you said, and you're correct, that comes from the client. Like someone needs to say, no, this is important, and we're doing this, and um, you know, that calculation uh I can't make that, you know.
Steve LongeneckerBut this COO is committed to it and has said, yeah, I'm uh that you know, and and I was saying to uh Nura, who um has been working with the client most closely, um, you know, I kind of like it too though. Like I kind of admire the the COO who is saying, You hired me to come in here and like make this place better, and that's what we're doing. And if when I try to do that, it falls apart because people don't listen or people won't do it, or you know, it turns out you don't want to do what I say, well then let's find that out because maybe I'm maybe you did maybe you shouldn't have hired me and maybe I shouldn't have come. You know what I mean? Like this is this is what I'm here for. I'm here to like do this.
Carolyn WoodardYeah.
Steve LongeneckerAnd if we're not gonna do it, you know, if you just wanted someone to come in and keep the same old, same old, that's obviously, you know, this just the side of a disaster. Well, then, you know, I don't want to be that person anyway.
Carolyn WoodardThat's a choice, yeah.
Steve LongeneckerYeah, yeah. So I kind of like it.
Carolyn WoodardUm, that's interesting to hear that because I mean it just sounds very intentional and deliberate, and that can be a hard role to have,
Carolyn WoodardI definitely have friends who've gone through, like um, you know, working at a community college. And every time there's a new provost, there's a new migration, there's a new system. We got to do the thing. And it's just because they're like, I don't, it doesn't ever feel like it's because they did an evaluation and that would be the best thing to move to. It's more like, oh, I want to make my mark, or this is what I used at my old place. So that's what we're gonna use here.
Carolyn WoodardAnd so I like the story, seems to have that intentional, like we did a, I mean, our assessments and evaluations are so thorough of like going through all of the risks, all of the technology debt, all of the things that are barriers that are holding you back from being able to do your mission, right? If you've got this old, these old computers and nobody can find anything in the 2000 shared files in Google, then it's it's keeping you from doing the work that you want to be doing at the organization. So I like that too.
Steve LongeneckerYeah, yeah.
Carolyn WoodardWell, Steve, thank you so much for sharing this story with us today and your experience in the the migrations. And I really appreciate your time.
Steve LongeneckerOh, thank you, Carolyn. And we'll we'll I'll I'll let you know how it how it unfolds. We'll see.
Carolyn WoodardI was gonna say, yeah, let's check back in after you've had you know a year to to get it under their belt and and see how it's going.
Steve LongeneckerYeah. Okay. All right.