Windows 10 migration and management strategies

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  • Mary Jo Foley
    Mary Jo Foley

    Our next MJFChat, scheduled for Monday October 28, is between me and Aaron Suzuki, the Founder and CEO of SmartDeploy. The subject of our chat is Windows 10 migration and management strategies.

    What questions do you have for Aaron about provisioning, disk imaging and migration from Windows 7 to 10? No question is too big or too trivial. I’ll be chatting with him on October 28, and will ask some of your best questions directly to him. Just add your questions below and maybe you’ll be mentioned during our next audio chat.

    Brad Sams
    Brad Sams

    You can find an audio replay of the interview, here.

    Mary Jo Foley: 00:01 Hi, you’re listening to the MJFChat show. I am Mary Jo Foley, AKA your community magnet. I’m here to interview tech industry experts about various topics that you, our readers and listeners want to know about. Today’s MJFChat is going to be all about Windows 10 migration and management strategies. And my guest today is Aaron Suzuki, who is the founder and CEO of smart deploy. Hi Aaron. Thanks for coming to the chat. How are you?

    Aaron Suzuki: 00:37 Hello. Great to be here. I’m doing well. Doing very well.

    Mary Jo Foley: 00:41 Good. I wanted to talk to you now when we’re about three months out before the end of Windows 7 end of free support because I think this is high time for people who either are maybe in the midst of migrating from seven to some other operating system, possibly windows 10 possibly not, or some people who have not yet started and are kind of freaking out at this point thinking, uh oh is it too late? But yeah, and for those who haven’t heard, I don’t know how you haven’t at this point, January 14th, 2020 is the date after which Microsoft will no longer provide any more security updates for Windows & unless a company agrees to buy them either through extended support updates or in some other way. So that that means as you told me, Aaron in an email exchange we had, wWndows 10 is basically a strategic inflection point for it pros who manage the enterprise desktop.

    Aaron Suzuki: 01:44 Yeah. Tt’s not, it’s not unfair to say that. I think for a number of reasons. And you know the interesting thing is the date is January X for end of end of Windows 7 but is it really that is definitely the date today come November, will it be come December? Will it be? So, you know, this is something we saw with Windows XP and that carried on for a long, long time and much longer of course than Microsoft would like it to when it’s because customers were very unprepared or rather they were so entrenched that it was really unfair to kind of do that to them.

    And it put a lot of Microsoft business and reputation at risk. So I think this notion, the discussion, and I think you really teed it up well of saying, Hey, you can buy more support like planting that seed now, like, yes, there is this hard stop in January, but we’re going to keep making stuff and you can pay for that and it will cost you dearly because we don’t want you on that, but we’re not going to leave you hanging.

    Aaron Suzuki: 02:50 That’s sort of a new narrative, right? Compared to where we were all the now years ago when we migrated from XP. The idea of the fact that this is more, a more strategic time is in that wave. When we got into, you know, what I would consider this more modern versions of Windows 7, 8, 8 and 10, you know, there’s all kinds of new approaches. But, It’s worth rewinding back to that sort of XP migration time frame to look at what has happened. I mean a lot’s happened.

    Mary Jo Foley: 03:34 It’s true. That’s true. I know there’s so many other things that happen between then and now and it’s not fair. Like you’re implying to think it’s going to unroll the same way it did with XP, right?

    Aaron Suzuki: 03:49 That’s right. That’s exactly right. So we have to consider, you know, kind of the whats, whys and hows and there are, there are new ways to do this job and it kind of goes back to the really fundamental aspect of deployment, operating system deployment, operating system migration, which is an imaging question.

    Mary Jo Foley: 04:13 Exactly.

    Aaron Suzuki: 04:14 And that’s something that we do a lot of and as part of this landscape of PC management, which is, you know, sort of been grossly neglected. You know, there was just this great wave of products for a number of years and then everything came to a screeching halt because everyone focused on RMM and they focused on, you know, all of these other scenarios and then the cloud happened and, and so there was a lot of, not distraction, but I think just maybe the desktop, the PC stopped looking quite so shiny and it wasn’t the place that growth was happening was the perception. And validated by the market truthfully. But, you know, there are still half a billion or so of us that all use Windows PCs and we rely on them to get our work done.

    Mary Jo Foley: 05:02 That’s true.

    Aaron Suzuki: 05:02 So how does IT get this job done when, you know, it was the old way of doing it, sort of sector based and you get your, the exact make and model that you’re going to get 5,000 of from the manufacturer and you say, yeah, we’ll test this one, this looks good. Okay, we’ll keep a couple to build our image around and then we’ll take shipments and you know, you decide whether you’re going to have your MSP or your reseller image them and hand them to you kind of pre imaged or if you’re going to do them yourself. And you know, there’s sort of all of these questions about the way.

    Mary Jo Foley: 05:40 You brought up to me when we were first talking about doing this chat, you said, you know, a lot of these IT pros, they’re still in the stone ages when it comes to imaging, right?

    Mary Jo Foley: 05:49 Like they still think about it in the old ways, but there’s so many new variables, new tools, new approaches. And it’s not just the old way of here’s how you image it or have your OEM image it or have a reseller image it. Now you yourself can take much more of a hands on approach if you want. And it’s not so painful. Right?

    Aaron Suzuki: 06:10 That’s exactly right. And I think, I think that’s unfortunate because I think the innovations stalled there. There wasn’t this opportunity for IT people to look at it and say, Oh yeah, there are these new ways I’m gonna try it this before. I’m gonna try it that way. For a while there was so much pain, it was almost like a PTSD kind of moment I think. And the reason that we know installed that badly is that our support team talks to customers and their image names are still Dell Opta Plex 70 70 or Lenovo ThinkPad T 4 70 so we know that hardware based sector based imaging is still what a lot of people are doing, which is, you know, kind of it’s, it’s, it’s like that old blanket that is tattered and torn to pieces and you know, stains that won’t come out.

    Aaron Suzuki: 07:06 But it’s soft and you know, and it just gives you this comfort and there are warmer blankets and they’re, you know, easier to clean blankets. But boy that, that’s just my safe place. I feel like that’s, that’s so much of what’s going on and with good reason because these problems that you run into are incredibly time consuming and people don’t have time for that. IT teams, have all these demands and you’ve got to do more and automate everything. And why is this a problem? You know, there’s a lot of pressures. So you know, if you’re going to make a bet on something, it’s not going to be a bet that you’re going to risk, you know, investing, you know, lots of time in supporting one device. Like people don’t have time for that. So, so that’s, that’s where I think it’s worth it. You know, again, a strategic inflection point, you’ve been, you’ve been, you know, kind of waiting along in the trenches and continuing to have your, you know, T four 70 image and it works great for your T for seventies and maybe you will or won’t move to another manufacturer or model, but you’ve just accepted that I’ve got to create a new image for a new device.

    Aaron Suzuki: 08:15 Just take a second and look at what’s out there, right? There’s new image standards. You can use virtual machines to help in this process. There are all kinds of ways to go about this. You can start using more cloud services to reach remote workers and address BYO. And all these other things that are happening, but we’re still sort of hanging on to that old blanket that’s comfortable to us. So one thing a key consideration here is drivers.

    Mary Jo Foley: 08:51 Right? I was actually going to ask you about drivers actually. Let’s talk about non-sexy parts of this process, right? But ones that trip everyone up and driver management is one.

    Aaron Suzuki: 09:04 This is the crux, the very crux. So windows works and we know it works and it has its soft spots and deficiencies. And we know that you know, I am a believer that windows is kind of a miracle because there really aren’t many other organizations that have successfully gotten an operating system to run on so many different kinds of hardware.

    Aaron Suzuki: 09:26 And you might argue now very, very recent announcements. Maybe this is changing maybe or they’re going to have different versions of windows for different kinds of hardware. Okay. Maybe, maybe, but we’ve heard that story before too. We’re still in a place where we rely on windows to do work and IT does its job to help people do more work. And in the process, the expectations, IT has to do less work. How? Well there are all of these trade offs that happen in the job of migration, deployment, imaging and part of that is an inevitable process of preparing the image with a process called Sysprep and you can only Sysprep so many times. So how do you circumvent that? You create an image that has no memory or you create a reference computer that has no memory and better what better platform than a virtual machine.

    Aaron Suzuki: 10:22 And we’re constantly reminded that the whole universe is not aware of the power of virtualization and the whole universe is not sprinting to keep pace with the industry. A lot of IT people are in a battle for survival, right? In no inconsequential way. These are people who are just putting out fires and trying to prevent fires and get people working and keep people working. So to take that time to get ahead and evaluate this can can take some effort, but the virtual machine can preempt a lot of problems because it has so few drivers going back to this driver discussion, right?

    It doesn’t take as much. It doesn’t have all the bells and whistles, especially with a laptop or some of these modern devices. Moreover, these devices are starting to converge. Right? So look at your phone. You’ve got how many cameras now? The front facing camera, multiple back facing cameras and a GPS sensor and all of this stuff.

    Aaron Suzuki: 11:25 Well that’s all in our PCs now too. So we have, you know, a million Bluetooth things and all the specialties that do all this stuff. How do you get all that to go well, all those things take drivers. And so those have to be added at the right time and the right way or it doesn’t work so great.

    Mary Jo Foley: 11:46 We’re even seeing Microsoft in that same dilemma, right? With Windows 10 of these feature updates because every time they, the feature update, there are blockers for certain PCs that can’t take it. Inevitably their drivers, I mean is like whenever it’s the block I’m like, did you check your drivers? Because that is probably what it is.

    Aaron Suzuki: 12:04 You are speaking truth, this is the truth of it. And so, so that’s the other part of this whole Windows 10 consideration and discussion is this is not going to be, it is not exactly what it appears on the surface in terms of the promise of Windows 10 being this is the last windows operating system that we’re gonna make.

    Aaron Suzuki: 12:28 It’s the last one is the operating system you’re going to buy. It’s all windows 10 from here forward. That is not exactly how it is. It’s a lot more like, it’s always been that and so you have to keep pace with this as an IT person and how are you going to do that? It again goes back to having a very flexible starting point and realizing that your updates strategy might be re-imaging every so often, right?

    That might be part of this. And so part of this strategic inflection point of getting to Windows 10 or using Windows 10 if you’ve already started down this road as an opportunity to pivot into this other motive of Windows delivery in a sense is looking at it and saying all of our assumptions about the way this is going to work or may or may not be true.

    Aaron Suzuki: 13:22 And now that we know how this is going to work, let’s look at the way we’re doing it and ask ourselves if we can do it better and more efficiently. And it may mean insourcing versus outsourcing among other things.

    Mary Jo Foley: 13:37 Do you think it’s oversimplifying to think about management strategies on Windows 10 the way that many IT pros think about Windows 10 and office. And by that I mean the idea is touch the minimal number of times that you can a single desktop when you’re updating it. So does that apply for management along with something like office?

    Aaron Suzuki: 14:00 Yes, I think it does. And, and again, the question is how, so, you know, Office 365 is set up in such a way that that’s a possibility and how do you do more kind of self-service delegation to the end user button manage with policy so they don’t get themselves in trouble.

    Aaron Suzuki: 1421 And how do you capitalize on, you know, sort of better informed end users and workers coming into the workforce, kind of more adept digital natives, who are going to do that. But also with the sophistication of attacks going on and all these other things prevent them from getting themselves in trouble. Right? So there are good tools and you know, we make such tools and, and you know, Microsoft’s improving their tools.

    There’s a lot of good options around to be, to do that where some, some pieces of the picture are required. They’re mandatory, they get pushed down by policy. Some of them are self-service. I can go to the app store and choose these things and install them. Some of them are kind of IT hands off. There’s a category of capabilities that you can do on your own right there, there becomes too a very, very important compliance question in all of this, right?

    Aaron Suzuki: 15:18 That, that is increasingly inescapable. Now only the EU stuff. Um, but our own stuff, uh, here in North America and in regions beyond, and it varies by industry. You’ve got, you know, sort of in North America, the HIPAA stuff and the financial services industry has their own set of requirements.

    That becomes a part of this picture too. So it’s about thinking about, all right, how are we going to make this so that I can do all the things that the organization expects of me and do them really well without causing myself more headaches that are just gonna make my life and my users’ lives miserable. And then I get a bad review. And you know, everything is slipping and deteriorating, but it was supposed to be so much better. I mean, there’s so much to reconcile comes a really, really kind of painful problem.

    Mary Jo Foley: 16:15 So do you think we should be thinking about things? And when I say we, I mean IT pros that they, I should say they, they should be thinking this is the end of the era of things like Systems Center Config Manager and now we should just not be thinking about Group Policy and we should be thinking about automating everything, virtualizing everything or is that just can it be an add instead of an or?

    Aaron Suzuki: 16:41 I guess I would say I think it can be an and, and I moreover I think it can, it could be system centerish type tools, SmartDeployish type tools for a long time into the future. I mean part of it in the case of citizen center is you know, up to Microsoft and their discretion on the way that they take that. Yeah, we are betting on the desktop and we’ve always been bullish on the desktop.

    Aaron Suzuki: 17:05 And I think it’s even more important when you consider the way that the world is thinking about that Edge relative especially to the cloud. And you can see this on phones for example. So it is no, no secret that increasingly your service providers, whether it’s Google or , you know, whatever Facebook, they’re trying to push more of the work down to your handheld device so they don’t have to do as much in the data center.

    Those compute cycles are expensive. You’ve got all this storage right in your hand. We really have the same thing in end more on the desktop. Right. So how does become a part of the literal fabric of the future of computing? How does that get woven into the modern context? How is that managed in a way that allows it to exploit all of that capacity that is, you know, kind of an underutilized or completely unutilized.

    Aaron Suzuki: 18:10 It’s not unlike the kind of data center revolution we had with virtualization. Right? We’ve got these workloads that are very important, so we have to dedicate computers to them, but their average utilization is like 8%. Well, it sure would be nice to make more of that. We have a similar thing. I am an engineer and I use very high end CAD equipment, CAD software. I’m only using my computer 8 or 10 hours a day.

    What about the other 14 hours a day? And how does that turn into something that becomes ultra powerful to the organization but managed in a way that everyone’s still in compliance and I’m not making usability compromises, you know, and so on and so forth. So you were very, very bullish and progressive I think. And sticking with this and history has kind of proven this to be the case.

    Aaron Suzuki: 19:02 You know, we are, we’re always looking over our shoulder to see if something’s coming this way, right? Whether it’s, you know, surface pro X or um, you know, possibly a Windows 10 X kind of scenario that’s going to upend this. But I think that’s why those are out there as I think Microsoft is kind of testing the market with these different devices and operating systems in the same way to say what’s going to take here. Right? And this is their cut number three now. And it keeps going back. And I think part of the reason it keeps going back is because I like the notion of us versus them. I still consider myself an IT person and I like that you fall into that too. And maybe it’s more empathy than anything now that, that we’re all saying, no, this is a paradigm that I’m comfortable with.

    They understand I can move much, much faster on this. You know, because there’s been these waves historically where, you know, analysts, journalists and you know, no fault of yours. I don’t know necessarily where you stood in this a decade or so ago, Mary Jo, and industry itself, the, the organization’s all said Oh, PC’s dead. It’s all about the phone and then it was all about the tablet and then it’s over. You keep coming back. We keep high Tivity ultra powerful device.

    Mary Jo Foley: 20:24 Yeah. I like your focus on timing is good too because I feel like you actually co, well you didn’t coin this phrase, but you propose this phrase to me when we were talking, you said, you know what? I”t’s always never a great time to revisit your PC management strategy.” And I’m like, you know what, the whole timing thing is super interesting because you can always just keep putting this off and saying, you know, I’m going to wait to see what comes next and I’m waiting for the next wave and I’m gonna, I’m gonna wait to redo my management strategy for the desktop until I really figured out, is that desktop sticking around or what’s the desktop? Right. So what, when you say that to people, what do you mean specifically? Like is it just, you know, what, you can’t put this off forever or is there more to that?

    Aaron Suzuki: 21:07 No, it’s exactly that. You totally nailed it. And I chuckle because you know, lived, we’ve lived this for the last decade of, you know, Oh, it’s, you know, this is dead for this reason. It’s dead for that reason. You know, keeps dying, but we all use this. I joke, I’ve got, you know, lots of industry friends and all my buddies like, Oh you are, you’re dressing back yet. It’s like, well no, I mean we keep, we keep doing our research and not enough.

    Aaron Suzuki: 21:34 He’s like, it’s so funny, you know, everyone’s sitting around in my meetings, they’re all carrying Macs. I said, yeah, but what operating system is everyone running?

    Mary Jo Foley: 21:41 Right?

    Aaron Suzuki: 21:42 He just laughed. And so and so that’s part of this, right? You can keep putting it off, but what is the trade off? Right? The trade off is you’re calling our support team and saying, yeah, you know, 70 70 image is having this problem with your, with your solution. Okay, cool. That’s a tell right there. And it’s really just, Hey, get on. And you know, the business is growing like crazy and I think it’s because a lot of people are on board with this notion that, okay, thought it was going to die. I thought it was going to die. Again, hasn’t, we’re paying all this money to whomever to do it for us.

    Aaron Suzuki: 22:24 We know there are better tools. I was tasked with this, found it, it delivers on the promise. My brain’s exploding, you know, how do we get the rest of the way there and how do we bring other things into it? How do we use, you know, the 25 terabytes per user of cloud storage we have to to reach customers, you know, in far flung locations or you know how do we move this in alignment with the rest of the infrastructure that’s also evolving. And that’s a place where I think a lot of a lot of vendors are falling short.

    Mary Jo Foley: 22:57 Yeah. Yup. Is there, is it possible even to say, here’s the checklist I’d give it pros who are thinking about migrating when it comes to desktop management. I like to close out my chats with resources or checklists or things like that. Like kind of a call to action. You know, and I’m not sure if this is too broad a topic to do that with, but um, are there, is there anything like top three things that IT pro should think about when they’re thinking about actually taking on changing their management around desktops?

    Aaron Suzuki: 23:30 Yeah. I don’t know that there’s as much there. I mean they’re, there, there are many checklists like at a technical level, but I think the key strategic questions to ask yourself, if this is your job and there are lots of people for whom this is still your job, these are people also have probably many other jobs, right? Maybe you’re also like some database person or you have these other responsibilities, you know, manage active director or something. But you want to ask yourself, how are we going to buy devices in the future?

    Aaron Suzuki: 24:02 Do we want to, do we want to truly standardize? Is it really worth standardizing on manufacturer or manufacturer model? How often are we going to refresh? What, how is that going to play out? Where is our workforce? Is it still really highly centralized? Is it increasingly distributed? And if the answer is distributed, how are we going to reach them? Right. I think there’s a third kind of group of questions, which is how are people working? Right?

    Are they, are they continuing to require devices that are high powered, high functioning? And, and as a result of that, what is my job? Is my job just to, to kind of do, you know, be the first responder, you know, should I just have my crash kit and be ready to address problems or are we gonna try to, you know, bite the bullet and get ahead of this and put in a system that’s going to give people more tools and more ways to get at, cause they get themselves ahead to prevent fires themselves. You know, I think that that, that’s the kind of I dunno not ecosystem, it’s the Headspace maybe to get into to think about how to address this. It’s a hard environment.

    Mary Jo Foley: 25:24 Right. That’s great. Nice. Well thanks. That’s a perfect note to end this chat onI think Aaron’s, so I wanted to say thanks again for doing this fun. Really interesting. Yup. And all of you listeners to MJFChat, we’re getting ready for our next chat right now, so I’ll be posting that information on Petri and that will be your signal to send in any questions you might want to ask before we do the chat. All you have to do is go to the MJFChat area in forums on and submit your questions right there. And in the meantime, if you or someone you know might make a good guest for an MJF chat, please do not hesitate to drop me a note. My contact info is available on thanks again.

    • This reply was modified 5 months ago by Brad Sams Brad Sams.
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