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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 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.
As Director of IT Consulting, Steve Longenecker divides his time at Community IT primarily between managing the company’s Projects Team and consulting with clients on IT planning. Steve brings a deep background in IT support and strategic IT management experience to his work with clients. His thoughtful and empathetic demeanor helps non-technical nonprofit leaders manage their IT projects and understand the Community IT partnership approach.
Steve also specializes in Information Architecture and migrations, implementations, file-sharing platforms, collaboration tools, and Google Workspace support. His knowledge of nonprofit budgeting and management styles make him an invaluable partner in technology projects.
Steve is MCSE certified. He has a B.A. in Biology from Earlham College in Richmond, IN and a Masters in the Art of Teaching from Tufts University in Massachusetts. He is a regular contributor to the Tech Topics podcast at Community IT, drawing on his decades of experience interacting with clients on complex projects and IT management challenges. This conversation on how to prep your file permissions for AI tools is on many clients’ minds and he was happy to share his experiences.
Carolyn Woodard is currently head of Marketing and Outreach at Community IT Innovators. She has served many roles at Community IT, from client to project manager to marketing. With over twenty years of experience in the nonprofit world, including as a nonprofit technology project manager and Director of IT at both large and small organizations, Carolyn knows the frustrations and delights of working with technology professionals, accidental techies, executives, and staff to deliver your organization’s mission and keep your IT infrastructure operating. She has a master’s degree in Nonprofit Management from Johns Hopkins University and received her undergraduate degree in English Literature from Williams College.
She was glad to have this conversation with Steve Longenecker on Nonprofit IT Migration from Google Workspace to Microsoft 365
Community IT has been serving nonprofits exclusively for twenty-five years. We offer Managed IT support services for nonprofits that want to outsource all or part of their IT support and hosted services. For a fixed monthly fee, we provide unlimited remote and on-site help desk support, proactive network management, and ongoing IT planning from a dedicated team of experts in nonprofit-focused IT. Our clients benefit from our IT Business Managers team who will work with you to plan your IT investments and technology roadmap if you don’t have an in-house IT Director.
Being 100% employee-owned is important to us and our clients. It is an important aspect of our culture as a business serving nonprofits exclusively for 25 years.
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Carolyn Woodard: 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 Longenecker: I will be glad to introduce myself. As the Director of IT Consulting, my role is to 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 projects and the consulting that leads up to the projects.
Carolyn Woodard: And 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 Longenecker: Yeah, well, what I can share is the planning and thought that’s going into the decision, which isn’t even fully finalized yet. But the full intention is to move from Google to Microsoft, and the why of that is… it’s kind of an interesting story. This is one client’s experience.
We came to them through participating in an assessment that we did for them. They wanted the assessment because a new COO was hired, and I think he recognized that there was a lot of technical debt in the organization. He needed help identifying how bad it was, and also some triage thoughts on what the most critical things were to address, and prioritizing them.
Coming in not necessarily as a technical person, as a COO you’re at a higher level, looking at it from the 10,000-foot view. But you get some sense of what the risks of being like we are now are, what it might cost to get out of the position we’re in, and some of the things you need if you have to make a case to your C-suite colleagues, and ultimately to the chief executive who makes the final decisions: we need to do this, even though it’s going to cost us a lot of money. So yeah…
Steve Longenecker: They had a lot of stuff, a lot of issues. They had been underinvesting for a long time. I think you’ve talked a lot about how Google Workspace has, as its advantage, a very low bar to entry. You can set up Google Workspace as a non-technical person, because there are fewer switches to look at, and the defaults are usually acceptable and work well enough that you can have a working email and file system pretty quickly.
Now, there are some gotchas we’ve talked about. Out of the box, the default might be people are just using what I call their My Drive, and maybe sharing folders with each other, which is not the same thing as using what Google introduced a while ago: Shared Drives. We’ve talked about this before, how much of a superior solution Shared Drives are for an organization that wants good governance and good ownership of its intellectual property.
So you can definitely set it up with the defaults and think you’ve got a thing that’s going okay here.
But if there’s no one to offer that counsel, ever, you can, seven years later, have a kind of hodgepodge where no one knows where the files are. There have been no policies, no governance. Mailboxes might be ginormous. You and I did the webinar about security risks with Google Workspace, so offboarding procedures might be out of line. There are all these things that can go wrong.
And this client was doing a lot of those things, and they were also in the hole a bit because their IT department was only two people. But we’re talking about 300 people who are classic information workers. They were still living in that someone set this up once upon a time, and no one ever really did anything more than that. So everything that’s happened since is kind of a historical accident of one sort or another.
Carolyn Woodard: You 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 someone can take on that role, but it’s not baked into how Google Workspace works necessarily.
Steve Longenecker: I mean, I think that’s what we’re stating. Certainly, yeah.
Carolyn Woodard: With Microsoft, you have to have an admin, like, can you even operate it without one?
Steve Longenecker: Well, there is always an administrator in Google Workspace as well, but it’s certainly the case that Microsoft fundamentally views IT as the organization’s prerogative and ownership, and expects there to be a heavy hand, if you will, from IT administration. It builds all sorts of tools to make that heavy hand possible. So…
The classic example of that is if an executive director says, hey, we’re having a personnel issue with this person, and I need access to that person’s mailbox, but I don’t want them to know that I have access to it. The lawyers want me to get that so we can monitor their email without them knowing, for now. That’s always a request that no one likes. I’m sure the person making the request doesn’t particularly like making it either, but whatever.
The point is that as their outsourced IT department, that’s one of our roles: to meet that request when it’s made. And frankly, everybody knows when they sign up to work somewhere that this is part of the social contract of employment. Or it’s literally the contract of employment.
Carolyn Woodard: Yeah, it’s in your acceptable use policy, usually.
Steve Longenecker: So anyway, we can do that in Microsoft. You actually can’t do it in Google, which is kind of interesting, you just can’t do it. You can definitely get in as an administrator and get into someone’s email, but not without them knowing. You basically have to either have them make you a delegate, which means you have to request it, or you have to reset their password, in which case they’re going to be like, what happened there?
Carolyn Woodard: Yeah, interesting. How deceptive you’re going to be…
Steve Longenecker: So it’s different. But what I want to say is that you do need to have an administrator. Someone needs to create the user account. If someone new is hired, someone has to have that super admin role to log in and create the new account.
But it’s true that it can be a little bit of a fix it and forget it thing. Once you have the initial email domain name established and the mail flow is flowing, your users can access Google Docs, Google Drive, Google Meet, Gmail, and they can do all of those things, and you don’t really have to pay attention to it. And so they can get out of control.
It can get out of control, and you can get to a place where the debt is pretty steep, because now you don’t know where your files are. It’s all locked into the institutional knowledge of individuals. And there’s a real risk to that.
So with this particular client, we did this assessment and identified some of these concerns, and it wasn’t all about Google Workspace. To be clear, the same thing can happen on the Microsoft side of the fence. I don’t want this to be about Google being the problem.
But I do think most organizations that are in Microsoft probably have the defaults, Microsoft gives them a bit more organizational structure, so they’re less likely to be quite so laissez-faire. So anyway, this organization…
Steve Longenecker: So what’s interesting about this organization, and this is not at all our best practice, is that they use Outlook to access their Google Gmail. Some people like Outlook, and apparently a lot of people at this organization do, or maybe it’s just a historical accident. Maybe they got the Office desktop suite at nonprofit prices, and in our generation, yours and mine, everybody uses Word, everyone uses Excel.
The kids today may have all grown up on Google Docs and Google Sheets in their schools, and Word and Excel seem like kind of heavy, ungainly applications.
But (this client) uses Outlook, and it’s getting harder and harder to hook Outlook up to Gmail. Part of the reason they’re still able to do it is that they’re actually using a really old version, Outlook 2016 everywhere, I think, and connecting that to Google. Again, it’s that you just get into debt: no one’s paying attention to this.
Carolyn Woodard: I was going to ask you about that, because one of my questions was: so you’ve done the assessment, this is the recommendation, and leadership is on board with this as a way to address this technical debt, moving to Microsoft.
And I would think that one of the ongoing issues would be the capacity of an organization used to using Google to change that mindset: okay, now we’re going to use Microsoft. But if they were already using Outlook, it seems like maybe it’s a slightly lighter lift for them.
Steve Longenecker: That was definitely part of the argument.
The recommendation was moving to Microsoft, the Microsoft 365 stack, because they’re a Windows-oriented organization, and Windows is made by Microsoft. So the Windows laptop management tools in Microsoft 365 are outstanding, because Microsoft controls both ends. They can do all these deep integrations, it can integrate with Entra ID identity, and…
Microsoft is very good at building this. They may not be the best at any particular piece of the stack, but it all works together, and it’s all pretty good. The sum is greater than the parts in some ways, particularly if you’re not so small or so big that you can afford to do this best of breed thing, where you say, okay, I think the gold standard for document storage is Box, so I’m going to use Box for that. And then for identity, let’s say your position is it’s Okta, so you use Okta for that. And then this for that, and so on. You love Slack, so you’re going to use Slack. So you end up with all these different things.
I think that’s a doable approach for small, nimble organizations full of IT-savvy workers, ones so small that they don’t have to worry about the challenge of scaling this many platforms up. If it’s just the 15 of us and we’re all sharp people, we can make it work.
Carolyn Woodard: Yeah.
Steve Longenecker: Or if you’re big enough that you can have a whole IT department, or at least a segment of your IT department, just focused on Box.
But at the size this client is, and most of Community IT’s clients are, it’s really helpful to have one platform, one stack.
We do have plenty of clients who straddle that, but they try to have a clear demarcation. Maybe they’re on Windows, so they have Microsoft for identity, Windows device management, and maybe the Office desktop suite, and then they keep all their information in Google if that’s where they came from: Google Docs, Google Drive, Gmail. That’s a possible straddle, and we have plenty of clients who do that.
We have plenty of clients that are just in Google, but then they’re not really getting the device management. If they’re on Macs, Microsoft won’t help much with that anyway. So maybe they have a third-party Mac management platform, or maybe they’re small enough that they don’t need one, and Community IT can provide that. We have Addigy as our platform.
Carolyn Woodard: I was going to say, make sure we mention that we can do Macs.
Steve Longenecker: Yeah, we’ll put our little brand in there. If you’re one of our clients, we can help you with that.
Carolyn Woodard: But a lot of MSPs are like, no, you’re on your own with Macs.
Steve Longenecker: Of course, yeah.
Carolyn Woodard: And Google too. There are a lot of MSPs that are like, we don’t do that.
Steve Longenecker: We don’t do Google.
Carolyn Woodard: So we do Google, I’m saying.
Steve Longenecker: We do Google, and we do the Macs, and we help people who want to straddle. Those are all good choices.
This particular client, as big as they were, with as much debt as they had, said: look, we’re already using Word, we’re already using Outlook, maybe we can make this work. And we’re going to really benefit from having all of our Windows computers managed by Intune, which is the device management part of Microsoft 365.
I’d say once you start talking about ease of administration, they’re big enough that some of the enterprise-y features of Microsoft identity are attractive, along with some of the security features Microsoft builds out. Google has a lot of these things too, but you often end up having to go to a pretty high tier to get them. Whereas Microsoft’s baseline, what they call Microsoft 365 Business Premium, has a lot of that built in.
Now, this client, I think, is too big for Microsoft 365 Business Premium, because that’s a 300-user limit. But even so, they looked at the Microsoft stack and said this is going to be the right thing for us.
Where we’ve been stumbling so far, and actually the decision hasn’t been fully made yet, is that we’re going back and talking with them about needing to do some cleanup in Google ahead of time, because of the scale they’re operating at, and because their IT department is still relatively small. Hopefully they hire on that. But we can’t always do that sort of thing with Community IT migrations.
If a client is small enough, we can really provide almost white glove service: let’s look at your folders and your drive and figure out where things should go. But…
Can we do that for 300 people? That’s a lot. So the COO has said, look, we’ve got to get rid of some of this old mail, because it’s bogging us down, and in a migration we’d just be pulling over 20-year-old email. He said, I need to be the bad guy and say that after email reaches a certain age, it needs to be purged, we need to delete it. That will help.
And then on the file side, there are something like 2,200 folders shared with different people. Again, the scale of that: where do all these folders go? So the decision is we’re going to clean this up in Google, and then…
I always like to go back to the metaphor, with migrations I’m often using moving (as a metaphor), like physically moving from one home to another. I use that a lot, and…
In some ways this COO is looking at the state of their current house, the clutter and confusion of it, not knowing where anything is or whether half the stuff is needed, and he’s made the decision: we need to move.
Because moving is going to force us to look at things and say, we don’t need this, we do need this, and we’re going to pack and be organized in the new home.
Carolyn Woodard: Yeah.
Steve Longenecker: Although in some ways, Gmail allows you to have really large mailboxes. That’s just not something Google makes a fuss over. It could be their engineering is different, or they’re just a lot more generous with space in general. Nonprofits get 100 terabytes of space across their Workspace tenant, and Microsoft is much more like two terabytes of SharePoint space.
Now, that’s just SharePoint, so it’s not apples to apples, but mailboxes are usually 100 gigabytes max, and Google isn’t that way. So if they’re going to move to Microsoft… I’m speculating about what the COO is thinking, but I’d imagine he’s thinking, no, I’m going to view that 100-gigabyte mailbox limit as a feature of Microsoft, because I don’t want my staff dragging around 400 gigabytes of email from the last 30 years. I want us to clean this up. And if I can use the fact that we’re moving as the hammer, the excuse for this, then that’s actually a good thing.
But back to that metaphor: sometimes you actually need to make some amount of organization and improvement in your situation before you move, because it’s too much. You’ve got to clear stuff out.
Another thing this client needs to do, we just said this would be so much better if they did it before the migration: they have a lot of old, clunky computers. Let’s replace those.
Carolyn Woodard: Yeah.
Steve Longenecker: Let’s replace those.
Carolyn Woodard: That’s also part of that debt, that attitude toward technology. And you can see, especially as we’ve been talking about this and you’ve told me about this migration, how it’s not just this client, it’s nonprofits in general: it piles up. There are certain things in place that allow the technical debt to pile up. Well, we’ve got all this storage, why should I archive my emails from seven years ago?
And coming in as the COO, you’re going to think, those are liabilities, and that’s a risk. So…
I guess I was going to ask a bit more about, well, that’s on the client, right? It’s on the executives to prepare the staff to see why we’re making this move, why now.
A good thing about it, if you think about the moving house metaphor, is sometimes we have to move by the end of the month.
Steve Longenecker: Right.
Carolyn Woodard: And 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.
But if you come into this situation with some time to plan, and you think, let’s not bring everything from the garage storage, let’s take some of that to the dump or have a yard sale first to get rid of it before we move, and you’ve got time to plan that, it goes a lot better, I think.
Steve Longenecker: Yeah.
Carolyn Woodard: The hasty move.
Steve Longenecker: Yes. Well, I think the way this is going to play out, perhaps, is we’ll create these Shared Drives and say, 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, we’ll just move it to your Microsoft OneDrive, which is the Microsoft equivalent of Google’s My Drive, but then it won’t be shared. And that will create, at least initially, not an insurmountable amount of confusion. But if you want this to be smooth, let’s get this ready.
It’s kind of like parents going to the kids and saying, okay, here are the three cardboard boxes. If your stuff isn’t in these boxes, you might not know where it is when we get to the new place, and you might not have it for weeks while we unpack. So if you want to make sure the stuff you value is available to you, put it in these boxes. Metaphorically, that’s kind of how I think this may go.
So I think the files are the sticking point, and the computers too, but that’s just kind of a classic thing when you’re underfunded, or not even underfunded, when you just make choices, you make choices.
Carolyn Woodard: Yeah. Well, I want to end on the note that clearly talking to you, you have so much experience, and our team does too. I’ve talked to Robin about migrations, and we have a lot of experience helping client executives think through and be organized about it: what do we have staff do first, what makes sense for them to do here, what’s going to make sense for them to do in the new house?
It can seem like an overwhelming project, and I think that’s another reason it doesn’t get done for years and years. It’s this big change management effort, it’s going to take a lot of focus, priority, funding, pain, even if eventually you’re going to save time, effort, and budget on a new stack that works better. It’s a big project.
So 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 Longenecker: Yeah. We can definitely help a lot with the technical process and understanding the technical process, and we do that. I think that’s very important to successful migrations.
But at the end of the day, that pain part is absolutely real. And like you said, and you’re correct, that comes from the client. Someone needs to say, no, this is important, and we’re doing this. I can’t make that calculation for them.
But this COO is committed to it. I was saying to Nura, who has been working with the client most closely, that I kind of admire the COO for saying: you hired me to come in here and make this place better, and that’s what we’re doing. If when I try to do that it falls apart because people don’t listen or won’t do it, or it turns out you don’t want to do what I say, well then let’s find that out, because maybe you shouldn’t have hired me, and maybe I shouldn’t have come. This is what I’m here for. I’m here to do this.
Carolyn Woodard: Yeah.
Steve Longenecker: And if we’re not going to do it, if you just wanted someone to come in and keep the same old, same old, well, that’s obviously headed toward disaster. And I don’t want to be that person anyway.
Carolyn Woodard: That’s a choice, yeah.
Steve Longenecker: Yeah. So I kind of like it.
Carolyn Woodard: That’s interesting to hear, because it sounds very intentional and deliberate, and that can be a hard role to have.
I definitely have friends who’ve gone through this, working at a community college, where every time there’s a new provost, there’s a new migration, a new system, we’ve got to do the thing. And it doesn’t ever feel like it’s because they did an evaluation and this would be the best thing to move to. It’s more like, I want to make my mark, or this is what I used at my old place, so that’s what we’re going to use here.
So I like this story, it has that intentional feel. Our assessments and evaluations are so thorough, going through all the risks, all the technology debt, all the things that are barriers holding you back from being able to do your mission. If you’ve got old computers and nobody can find anything in 2,000 shared files in Google, that’s keeping you from doing the work you want to be doing at the organization. So I like that too.
Steve Longenecker: Yeah.
Carolyn Woodard: Well, Steve, thank you so much for sharing this story with us today, and your experience with migrations. I really appreciate your time.
Steve Longenecker: Oh, thank you, Carolyn. I’ll let you know how it unfolds. We’ll see.
Carolyn Woodard: I was going to say, yeah, let’s check back in after you’ve had a year to get it under your belt, and see how it’s going.
Steve Longenecker: Yeah. Okay. All right.
As advocates for using technology to work smarter, we’re practicing what we recommend. This transcript was drafted with the assistance of AI, and is not a verbatim transcript. The content was edited for clarity, and was reviewed, edited, and finalized by a human editor to ensure accuracy and relevance.
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