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In this Podcast, Migrating from Dropbox to OneDrive, we discuss…

4:50Box to OneDrive Migration podcast
5:40What all is moving out of Dropbox to OneDrive
5:45Microsoft FastTrack 
9:00Workflow for data migrations. Reference the Ultimate Guide for Microsoft 365 Migrations
12:05New Dropbox functionalities
15:55Platform vs purpose built applications podcast
18:26On-Prem to Microsoft 365 migration service
18:30Jive to Microsoft 365 migration service

Contact Us page for inquiries about migrating


Danny Ryan: It’s Tuesday, June 18th, and in today’s podcast, I sit down with Tommy, and we talk about migrating from Dropbox to Microsoft 365. We cover some of the tools, some of the decisions that need to be made, and an overall strategy of how to do this. Enjoy! 


Welcome to the Work Together Better podcast. This is your host, Danny Ryan. I’m here with cohost Tommy Ryan. How are you doing, Tommy? 


Tommy Ryan: Wonderful. Spectacular. 


Danny Ryan: Good. 


Tommy Ryan: Would you like some more adjectives? 


Danny Ryan: Sure, or should I say, my other bald prince brother. 


Tommy Ryan: You’re going to have to explain that. 


Danny Ryan: Yes, I’m going to have to explain that. Yesterday, I learned that the original form of Ryan was Mulryan, which, one of the translations from Irish means “bald prince,” which I think is so appropriate for the two bald brothers. 


Tommy Ryan: Not “bald fresh prince.” 


Danny Ryan: No, it’s “bald prince,” which we’ll take. I think it’s kind of cool. That’s just fine with me. Today our subject is continuing on with migrating from different platforms to Microsoft 365. Today our focus is going to be on another one of the file platforms, or one of the ones that came originally and was very purpose-built, which was Dropbox. And Dropbox, we’ve got a long history with. 


Tommy Ryan: We do. 


Danny Ryan: That’s probably a good place for us to start here. Originally it was one of those products that just worked, and had a million and one integrations, and just seemed to be the dominating product that was out there, one that you could use both internally and externally, and security seemed to be very well done. We used it pretty often here at ThreeWill. 


Tommy Ryan: We were coming right off of Groove, I think, and trying to find another way to share information. 


Danny Ryan: Yeah. 


Tommy Ryan: Groove was that natural way to work with documents and it pushed it down to the file system, so you kind of worked with documents as though they were documents that were local to your hard drive, and that’s, I think, the beauty of what Dropbox brought as a product. It just worked. It was simple, and it had enough security and controls to make you feel comfortable that your files were being taken care of. 


Danny Ryan: It was just so tightly integrated into File Explorer or Finder on the Mac. It was just really a well-built, purpose-built type of product. In fact, we’re talking here about migrating and moving off of different platforms into Microsoft 365; this is one of those that we still continue to use to this day, even though we use OneDrive quite aggressively, and use SharePoint and OneDrive and all the Microsoft products, we to this day still use Dropbox. For us, and it might be a reason that larger organizations do this, but it’s been primarily for security reasons, just for us to know that the content is secured. Our primary concern, because we’re a lot of very technical folks that might have elevated access to different parts of our Microsoft 365 tenant, we just didn’t want anybody running into information about salaries or stuff like that and messing stuff up with that. 


Tommy Ryan: Yeah, and because of the simplicity of administrating your Dropbox account for a corporate account, it allowed us to have a very small set of people that could have exposure to that kind of sensitive information. Like you said, when it’s in Microsoft 365, that’s across the entire organization. We’ve got multiple people that have different levels of permissions, and we’re moving files around. A lot of times, there’s a little bit of a concern of, “Are we going to put this in the wrong place, where it gets surfaced and searched, and all of a sudden people are stumbling across information?” That’s not good to have out in the open. 


Danny Ryan: This is one of those that was in line with Box and some of the more purpose-built types of applications, in this case for file sharing and keeping secure file purposes, so when we talk about doing the migration, I think here we’re primarily talking about those files moving over, and we’re talking about file content. We’re talking, typically, about security or permission. We’re talking about folder structure and maybe some of the metadata with regards to the files moving over as far as what’s coming and moving over out of Dropbox and into Microsoft 365. 


Tommy Ryan: Yeah, it’s one of the subtler ones. We thought it was interesting when we were looking at what’s supported by FastTrack and not seeing Dropbox there was interesting, when they do have Box. It might be due to, there’s less complexity there. There’s less to work through to do a migration. The tooling out there is well-supported to get that over there, so it becomes less of a technical feat to accomplish it, to more of “How do you organize around? Where’s this going to go?” 


 I’ve got OneDrive, I’ve got TeamSides, I’ve got Microsoft Teams, I’ve got Communication Sides. Where does this content reside and how do I do the analytics around that content to understand what’s valuable to leave behind, what’s more appropriate to archive, and figure out how to maximize the impact of that content, where we’re not diluting it by bringing everything over and plopping it over in one place, but we’re putting it in the appropriate place and only bringing over what is necessary. 


Danny Ryan: Just like when you’re moving to a new house, you do some of that cleaning up, and you say, “Do I really need to keep this or not?” You end up coming up with a strategy around both where does it need to go to from a security standpoint and from how it needs to be shared within the organization, to deciding what can be archived and won’t be edited in the future and just needs to be archived somewhere. 


Tommy Ryan: Yeah. That might seem simple, but I find that that can be the most challenging part of the effort, is, “Where do we draw the line?” We can go look at containers that have content and say that we want to move this over there. Well, looking through that container of content, maybe you have some files that have been changed in the last couple of months, but maybe you have files that have been there for five or six years. Do you bring everything over, or do you just bring over the more recent content that has collaboration? Do you know, is this a reference file that people just read and never update? Can we get the views that have been made on this document? If you know this document’s never been touched, viewed, or edited in the past ten years, is that a document you need to have within your repository, or is it time to archive that type of content? 


Danny Ryan: The other thing, you mentioned this a little bit earlier, which, this is a great candidate for using migration tools. When we started looking through what’s out there, we saw that a number of our partners were open to using the tooling that’s appropriate for our clients. We saw SkySync, we saw Quest,, I know another one that’s out there. There are other, I’m sure ShareGate, I didn’t run into them right away, but I’m sure that’s one of the types of migrations that they can do as well. 


 Doing this right reminds me of what the conversation that I had with Kirk about migrations, which is that the important piece of these migrations is communication, communication, communication. It’s really about planning this out and making sure that you’re moving somebody’s content, and you’re communicating about where it’s going to be moved to, giving them choices as to how it gets moved, letting them know it’s going to move on this day, and then reporting back. Again, internally you really want to make sure that people, people are spending a lot of time developing this content. You want to make sure that they feel in control of it and that your systems that you’re putting in place are reliable, and that they won’t show up one day and all of a sudden something’s moved without them knowing it, how vital that is. Even just talking about files, you really need to nail the communication piece of it and have a good communication plan. 


Tommy Ryan: Hearing you talk about that, another dimension to that communication is getting people excited about the move, not just the logistical parts of it, but why are we making this move in the first place? What are the benefits and what are going to be the ways you can collaborate in the future that you couldn’t do in the past? What pain points are being addressed as part of the migration? Some of it, also, has financial aspects. We’re saving the company a million dollars a year by this consolidation. Not only are we saving that money, but we’ve got better ways to collaborate. We have a more seamless, integrated experience because we don’t have two or three products for file management. We have one product, and so you learn how to do it. That applies to every aspect of your collaboration throughout the company. 


Danny Ryan: A couple of other things before we wrap up here. We were looking and we could see how, within Microsoft Teams, within that experience, that you could add Dropbox, and just having it as another place where you’re storing files. Not a whole lot of additional integration, as far as being able to start a conversation about a specific document, but a way of just helping you to stay in the team’s environment. Along the lines of what you’re saying right now, once you’ve got the content moved over, you do have things where you’re accessing it via teams and you can do a lot more with it than if it’s just a file in your file system and you’re just getting the latest version of it. There’s a lot more within the Microsoft experience that, once it’s been moved over, you can do with those files. 


Tommy Ryan: We said earlier, it just works with Dropbox, where the file sync technology was very solid. I think that played well to the success of Dropbox. It just worked. It was simple. You’re always kind of toying around in a purpose-built, singular-focus type of software, versus a broader vision for what you’re doing. We saw that with Dropbox, where now they’re going with the new user interface that has kind of that single pane of glass, similar to what Teams has, to be able to manage and collaborate with that content in the context of teams or one-on-one conversation. 


 They’re creating this layer that’s on top of this, to be able to do tasking, to provide a team context, and collaboration and leveraging things like Slack, to build some of those conversations, so it’s interesting that Dropbox can kind of stay in that lane of, “We’re just going to be the best file sync technology that’s simple and easy.” They’re trying to be the front door, and I think everybody wants to be that front door into the content, because people can make that switch easier if they just have, “Well, that’s just a dumb file repository, I’m going to save some money and consolidate and get rid of these licenses and just go put it in OneDrive or SharePoint.” I think they’re trying to invest in their future and that’s interesting that they’re making that move, and how that will play out for them, if it plays out well or maybe complicates things for their users. 


Danny Ryan: It feels a bit like, when we’re looking at the experience of Dropbox within teams, they’re almost relegated to an experience. It’s just sort of there. It’s just another file source that’s out there. Everybody wants to be the front door. We’ve gone through a lot of these different platforms, and it’s interesting to see how they’re sort of organizing themselves. 


 Somewhere there’s the social piece of this, like Workplace by Facebook, and Slack, and then we’re seeing some of these that are just the file component of this, like Box and Dropbox. They’re all trying to build additional types of things into the experience that they have, and they want to play against the big boys. I’m almost classifying, then we have the big ones that are really competing head-to-head, which for me would be Google, SalesForce, and Microsoft. They have a lot of the overlapping entire experience, and there’s tremendous amounts of overlap there. It’s interesting to see how this has sort of organized itself into different types of apps. For us, I think where it’s interesting is trying to understand where people need help, what types of things people need help with in addition to the basic stuff. A company like ThreeWill can come in and really provide a lot of help and value to them when they’re looking at making some of these moves. 


Tommy Ryan: I think a lot of that comes from, you just don’t migrate things that often, so kind of knowing what are the pitfalls and what are the best practices around communication and organizing around an effort so you don’t stumble upon that in a project. You’ve got to do it right the first time, because you’re only going to have kind of one chance at doing it. 


Danny Ryan: We’ve done a blog post or a podcast in the past about this, in fact, I’m fairly certain it’s a podcast, which is best of bread versus all-in-one platforms, and there’s benefits to either one. Anything else you want to cover before we wrap up here? 


Tommy Ryan: No, I think that covers the main points. The simplicity of Dropbox makes it more of a file migration effort if you’re trying to pull into the fold what you have in Dropbox. There’s integration, but anytime you have that integration, it’s less than the optimal experience. We saw the integration with Dropbox and Teams, and you can navigate through that file structure, but you can’t search it. I think the more you can bring under one platform, the simpler the user experience is. You’re always going to have one-off situations that make sense and it just works, and you’re going to leave it alone. You just have to figure out, is there enough pain to bring it into the fold, or do you leave it as it is today and just use the integration? 


Danny Ryan: As we come to wrapping up these different platform migrations, part of the reason for doing this is, for the larger clients that we work with, is coming up, again, if it’s important about the communication and how these projects are run, is to be a provider that can help with migrating off of multiple platforms and into one. If they’re looking at moving, at a certain point in time, from one or two or three of these different platforms over to Microsoft 365, how we can help with coordination and the communication around doing those types of migrations. I think it’s come up with us, where we’ve seen some of our clients, where we can see some benefit for us helping. 


 It’s just not from a technical, it’s also from a, “How do we plan this out, coordinate this, and put the right communication plan in place?” So as we’re wrapping this up, we’re getting to the point where we’re saying if you’re looking to migrate from any platform over to Microsoft 365, we’d love to be able to talk to you about doing that. It’s not just from that technical standpoint, but from more of a planning, coordination, what’s the right strategy for you to do this? We’d love to have those types of conversations with you. We’ve been doing a lot of on-prem to Microsoft 365, of people that want to make that move. We’ve been doing a lot of migrations from a product called Jive Software to Microsoft 365. We’re just stepping out and looking at other platforms that people need help with. I appreciate everybody listening to this. Thanks for doing this, Tommy. 


Tommy Ryan: Sure thing. 


Danny Ryan: Thanks for listening, and have a wonderful day. Bye-bye! 



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