MJFChat: The Evolution of Windows from an IT Pro’s Viewpoint

We’re doing a twice-monthly interview show on Petri.com that is dedicated to covering topics of interest to our tech-professional audience. We have branded this show “MJFChat.”

In my role as Petri’s Community Magnate, I will be interviewing a variety of IT-savvy technology folks. Some of these will be Petri contributors; some will be tech-company employees; some will be IT pros. We will be tackling various subject areas in the form of 30-minute audio interviews. I will be asking the questions, the bulk of which we’re hoping will come from you, our Petri.com community of readers.

Readers can submit questions via Twitter, Instagram, Facebook and/or LinkedIn using the #AskMJF hashtag. Once the interviews are completed, we will post the audio and associated transcript in the forums for readers to digest at their leisure. (By the way, did you know MJFChats are now available in podcast form? Go here for MJF Chat on Spotify; here for Apple Podcasts on iTunes; and here for Google Play.)

Our latest MJFChat, recorded on November 23, is all about the evolution of Windows from an IT Pro perspective. My special guest is Tim Warner, a Microsoft Most Valuable Professional (MVP) and Pluralsight Staff Author.

Tim has a lot of history with Windows — ranging from its security mechanisms, to the management tools that surround it. He has a lot to share around the Windows-as-a-service paradigm; Microsoft’s morphing role in the open source community; how and why Windows pros need to be thinking about Azure and lots more.

If you know someone you’d like to see interviewed on the MJFChat show, including yourself, just Tweet to me or drop me a line. (Let me know why you think this person would be an awesome guest and what topics you’d like to see covered.) We’ll take things from there….


Mary Jo Foley (00:01):
Hi, you’re listening to Petri.com’s MJF Chat show. I am Mary Jo Foley, AKA your Petri.com community magnate. And I am here to interview tech industry experts about various topics that you, our readers and listeners want to know about. Today’s MJF Chat is going to be all about the evolution of Microsoft Windows from the IT Pro perspective. And my special guest for this chat is the perfect person to talk about this Tim Warner, who is a Microsoft MVP and also a Pluralsight staff author. Hi Tim, and thank you so much for doing the chat today with me.

Tim Warner (00:43):
Hi, Mary Jo. You’re most welcome, and it’s an honor to be here. Thank you.

Mary Jo Foley (00:47):
Great. Well, when you came to me originally with the idea for this chat, which I loved, we talked about diving into some of the big picture Windows trends that have had a big impact on IT Pros over the years. But since this chat is only 30 minutes, we can’t get into everything that happened over that time. In fact, when we’re talking about how far back does this go? Windows 1.0, just turned 35 earlier this month. So there’s a lot of history here.

Tim Warner (01:18):
That’s for sure.

Mary Jo Foley (01:18):
Right? But there is still plenty we can talk about from an IT Pro perspective. And some of the topics I was hoping you and I could chat about include things like the move by Microsoft from open by default to closed/secure by default, proprietary to open source and what that means for IT Pros. Operating system as a service, of course we can’t not talk about that. And then the whole evolution in general of management services, like Endpoint Manager and autopilot MDM. So there’s lots of fodder here. I’d say let’s start with the concept of open by default, moving to closed or secure by default. So I’m curious how this change in Windows default security posture has happened. And what do you think it means to IT Pros?

Tim Warner (02:12):
Well, to answer the last part first, I think that this evolution matters to IT Pros because if a business has a breach or an extended outage, this is not only going to be a resume generating event for the IT Pro, him or herself, but potentially a catastrophe for the business. Because most businesses are extended in some way or another across the internet. So thinking back to when I joined the industry, it was in the Windows NT 4.0 Days, Microsoft was moving their protocol stack from really just land only like NAT buoy into NetBIOS over TCP, and then ultimately a native TCP stack, I think that was in Windows XP. I think Microsoft just saw the writing the wall sooner rather than later, and realized they needed to start really thinking of securing server systems as well as client end point systems. And I think particularly that sea change in my experience as an IT Pro really started kicking in with Windows XP and Server 2003, specifically, like I said, the movement to a true TCP/IP stack that actually included, I guess, some BSD Unix components, which caused Microsoft some legal issues at that time.

Mary Jo Foley (03:31):
I remember that.

Tim Warner (03:33):
The movement from a flat management space, the NT domain to a DNS-based LDAP directory, that was a big deal at the time in Windows 2000. Then there’s of course the Windows Firewall or whatever it was originally called, being inbox with server and client. And then, originally I remember it was anti-spyware was the thing and then antivirus. And then it’s anti-malware. I remember particularly I was a fan of GIANT anti-malware or anti-spyware. And when Microsoft purchased that company, they used it as the engine of what is now the Windows Defender client product.

Mary Jo Foley (04:12):
Oh, wow. I totally forgot that’s how they got that technology, yep, okay.

Tim Warner (04:18):
And then to take it one step further Vista, I know it’s been panned because I guess it was rushed and there hardware driver catch-up issues, but the end user access control the idea of running as a lower privileged user and then elevating access when needed that certainly was a big deal. Although it created headaches for IT Pros, why? Because in doing something different, if it ain’t broke, don’t fix it. Of course this was broke, it did need fixing.

Mary Jo Foley (04:48):
Yeah. Yep. What about on the Azure side, do you think IT Pros need to be cognizant of what Microsoft is doing around identity and security on Azure and in terms of how it will affect them at the client and server level.

Tim Warner (05:05):
Thanks for bringing that point up. Yes, cause I really want to evangelize to those IT Pros who are thinking well, we’re thinking of Azure eventually, but not now. I’ve got too many plates spinning locally. Maybe it’s later. Now I would suggest you look into it now. Why? Because more and more of these Microsoft engineering teams are putting their innovation first in Azure and then for SQL server would be a good example, the innovation in Azure SQL database first. And then if a feature becomes popular enough, maybe it’ll be back ported to SQL server local. So, you know, the innovation is happening in the cloud, all of the threat intelligence and the AI ML intelligence. I mean IT Admins regardless of where their servers are, can benefit from these things. So they definitely should be looking at Azure right now.

Mary Jo Foley (05:59):
Okay. That’s good. Good advice. Let’s talk about Open Source, the favorite topic of all of us in the press and analysts. You know, Microsoft’s undergone a huge transformation over the past couple of decades from Open Source foe to Open Source champion. So I’m curious how you think this impacts IT Pros in particular and Windows. That’s a big topic, but dig in wherever you want there.

Tim Warner (06:25):
It really is. And you know, I’m actually gonna turn the question back to you Mary Jo, because I have been so curious to pin down when that sea change happened, where Microsoft began looking at competitors like Amazon, let’s say instead of ignoring that they exist looking at them as potential partners or at least recognizing and providing paths from Amazon. Did that happen with Satya Nadella or do you think it happened before?

Mary Jo Foley (06:54):
Yeah, that is an interesting point. And I talk about this a lot in my own work about Microsoft kind of flipping things on their head and no longer looking at everybody as the enemy and instead looking at potential ways to befriend and at least partner with people, they call their coopetitors, right? So people even like Salesforce and Amazon and Google, it’s not just us versus them anymore. And I think that did start to change in earnest when Satya came in as CEO a few years ago. But, just in general, I feel like the whole change they’ve done around Open Source has been interesting because it felt like their own employees and their customers were telling them, we need you to maybe not befriend Open Source, but at least accept its existence. And the fact that we use it internally and they have done that now, which I find super interesting.

Tim Warner (07:51):
It reminds me of something that Jeffrey Snover has said from time to time when he tells the story of PowerShell. Some colleagues were saying, what part of Windows don’t you understand Jeffrey? So I’d like to credit him in there somewhere with that evolution. Gosh, yeah, this is a big subject. I mean, if you go a bit to kind of tie over from the previous subject on security. There’s the movement as I said, from the proprietary protocols to native TCP and the BSD Unix pieces in there. Embracing competitors as partners, there’s the embrace and purchase of GitHub.

Mary Jo Foley (08:31):

Tim Warner (08:31):
Microsoft probably was planning that purchase a lot earlier than was announced because as you know, more and more engineering teams began putting their code in, GitHub and open sourcing it to the world. The MS Docs organization and the fact that the majority of the MS docs are open source in GitHub.

Tim Warner (08:51):
I mean, it’s an industry trend at the end of the day. How do I think this affects the IT Professional? I think on one hand, it serves as a disruption, again because of that human nature factor of a if it ain’t broke, don’t fix it. Don’t mess with me. I feel as secure as I can be now, don’t bump me out of this, who moved my cheese, to reference that business. But on the other hand with mode 2, as Gartner calls it. IT in a dev ops orientation and faster software delivery, this forces the IT Professional into a more collaborative stream. And I’ve always seen collaboration and open source as being hand in hand. So again, it just seems like Microsoft doing a pretty good job of keeping with industry trends over time. And, you know, I imagine that we’ll see a Microsoft Linux distribution before too long.

Mary Jo Foley (09:47):
Oh, good. I’m going to ask you about that in a minute, because that’s something that’s become like a hot topic lately on Twitter, especially. But before I ask you about that, Windows Subsystem for Linux and how Microsoft’s baked that right into Windows 10, do you see this as a big kind of game changer for the IT Pro community? Because I know there are a lot of IT Pros and devs who are really jazzed about it, but I’m just trying to get a gauge of like how big a deal is it really that they’ve got a whole Linux kernel right inside of Windows 10 now.

Tim Warner (10:20):
Personally, I think it’s fantastic because at one point in my career, I worked at a research organization at Vanderbilt U and half the people were committed to Windows and half were committed to Linux. And the Linux people had to do Windows for some work. So as a manager, I’m helping them with dual boot issues and that’s never fun for anybody. So in that sense for shops that do have a Linux focus, whether they’re developers or administrators, definitely a win. The fact that Azure being such a huge focus for Microsoft and one of its big value propositions is that you can run non.net applications. You’ve got first-class support for Java Node and Python. And if you are an open source developer, you’ve got that available to you, just a terminal session away on Windows. So you can kind of enjoy the best of both worlds. And I also like the fact that WSL is kind of tucked away. It’s not in your face. So if an IT administrator and their group doesn’t need it, don’t worry about it.

Mary Jo Foley (11:29):
Yep, right. Just because it’s, there doesn’t mean you have to use it. Right. It’s there.

Mary Jo Foley (11:37):
Let’s talk about Linux though. Cause you touched on this and this has become like a big point of controversy. What isn’t a point of controversy on Twitter? Microsoft lately has been making some, has been submitting Linux kernel changes involving Hyper-V, it’s a hypervisor back to the Linux community or trying to get that incorporated into the Linux kernel. So this is setting off a whole wave of people saying, do you think Microsoft’s going to do their own, you know, Microsoft Linux or whatever, or at least, I had one guy say, at least they’re going to just change the underpinnings of Azure so that it’s Linux-based and not Windows based. And I’m like, Oh, that seems like a really big thing to me. Like, that’s not just like, Oh, let’s take Windows out and put Linux in. Right. So I’m curious what you make of what they’re doing here. I mean, there’s even, we just found out recently there’s even a Microsoft Linux distribution called CBL Mariner, which is Common Base Linux Mariner. And this is something they use internally at Microsoft, but it’s setting off this whole wave of speculation, like is Microsoft going to try to become a Linux vendor in its own right? What do you think?

Tim Warner (12:54):
Well, first of all, thanks for that heads up on Mariner. I’m going to track that down as soon as we get off this conversation. I mean, due to operational security, I know Microsoft, isn’t going to tell it, well then again, they have given a lot of details about what’s running in their Azure data centers, that Project Phoenix or the open source, all that. Best as I understand in a non NDA context, those physical hosts are running some highly specialized version of Server Core. Again, to kind of stitch together our previous subjects and bring that into now, back in the security context, think about Windows Desktop Server to Windows Core and then Windows Core to Nano Server and that stripping away reducing of the attack surface. It would, on one hand, you’d think it’s almost trivial for them to go from a really stripped down Server Core, kernel to a Linux one. But yeah, I can’t imagine with the footprint that Microsoft has and the partnerships that they already have. I don’t know, if switching the kernel outright, that seems like it would be too big of a lift.

Mary Jo Foley (14:03):
I agree.

Tim Warner (14:03):
More reasonable to me is as you say, this magic that Microsoft is already doing, being able to in a Hyper-V context run virtual machines that use the Linux kernel. In addition to VMs that use the Windows kernel on the same box. That seems more doable.

Mary Jo Foley (14:20):
Agree. I think that must be what they’re doing. I can’t imagine like a wholesale rip and replace going on inside of Azure. I just, I don’t see why or how that would make any sense at this point

Tim Warner (14:33):
But, on the other hand there’s historically, and I know, you know, this more than anybody of a vociferous group of open source people who are just vigorously anti Microsoft. And I know that there’s been some, I wouldn’t call it a diaspora, but a number of customers when Microsoft bought GitHub, were like, we’re going to GitLab. We’re going anywhere that Microsoft isn’t. And I don’t know. I mean, am I biased? I’ve been a Microsoft specialist for over 20 years, but if I saw something that was untoured for instance, I don’t think I’d be a Microsoft specialist anymore. So for whatever that’s worth.

Mary Jo Foley (15:09):
Yeah, exactly, exactly. That’s why you’re an MVP. Like you guys are supposed to have your hand on the pulse, but also remain unbiased contrary to what some people think.

Tim Warner (15:21):

Mary Jo Foley (15:21):
Okay. So let’s talk about operating system as a service because this is a very contentious topic among all people engaged in having to deal with Microsoft’s feature updates to Windows 10 and Windows Server. So when Microsoft originally started talking about this more than five years ago, they actually were talking about doing two to three feature updates per year for Windows Client, and Windows Server. So right now we’re at two, roughly one major one, one minor one, per year. So I’m curious first, do you think this is working for IT Pros? And do you think we’re going to stay at two and should we?

Tim Warner (15:59):
Do I think it’s working now? No. Do I think it potentially could. Yes. Here I am flexing my MVP non-biased,

Mary Jo Foley (16:05):
No, go ahead.

Tim Warner (16:05):
Cause I’m going to say something controversial, from what I understand, Microsoft released a whole bunch of their QA staff a few years ago. So how can you do that? And then accelerate your releases. Witness what’s happened with Windows Client updates over the last couple of years. Yikes. Need I say more? Break fast, quick, fast, dev ops, rapid release. That’s awesome. But if you’re missing the QA piece, your hosed.

Mary Jo Foley (16:42):
Yeah. I mean, I think it’s funny you bring that up because I think that applies on Azure as well. Like the last few months we’ve been seeing a lot of problems with Azure and with Office 365 and it does come back to QA in the end. Like people rolling out patches without being adequately tested. Not a great idea, right?

Tim Warner (17:03):
I know. I mean, on one hand, Microsoft has made its name being a dog food and company, but they’re making mistakes that they provide solutions for themselves.

Mary Jo Foley (17:14):
I know. So what do you think they can do to fix it? Like if you were giving them advice and saying, Microsoft, this isn’t really working the way it is. I would like you to do what?

Tim Warner (17:25):
Well, two things that come off my mind, literally make a decided, concerted effort for QA. Look back if they haven’t already done a post-mortem on releasing all those QA people, look back, fix that period. You need staff. Secondly, I know that Microsoft has really come a long way over the last several years in listening to their customers, pay particular attention to IT Pros who are responsible for patch management. Really listen to them, to your cadence. Certainly no more than two years, but is the twice a year cadence working for them, even if Microsoft sorts their Q and A and if not, take their feedback to heart more, because I think they’re, I’m pretty convinced there’s some stuff falling through the cracks there, look at Windows Insiders. Don’t get me started on Windows Client and whether Microsoft has been listening to the Windows Insiders community over the last couple of years.

Mary Jo Foley (18:28):
Yeah. Fair point. And, and I think next year is going to be very interesting because we’ve kind of fallen into this cadence where we’ve had a major Windows Client update in the spring and a more minor one in the fall and the fall updates are the ones that get 30 months of support. So IT Pros have kind of felt like, okay, if you’re going to force me to do two, this is a good way because I can just adopt the fall update and kind of keep rolling. But there’s a rumor right now that next year, the major update might be in the fall and the minor one in the spring, which would kind of throw everything on its head and also throw into question the whole, you know, 18 months versus 30 months of support. So I guess stay tuned there on that one.

Tim Warner (19:17):
Yeah, for sure. In the meantime, what I hear generally speaking is config manager personnel are grateful for tools like Windows Server, Update Service and Configuration Manager, where they can gate these updates because Microsoft sometimes likes to sneak them out. I know I’ve been bitten myself, getting ready to present a class or a webinar. And all of a sudden my machine’s acting wonky. Windows Update has done some stuff in the background and I need to reboot and keep my fingers crossed.

Mary Jo Foley (19:48):
Yep, it’s happened to all of us, I think. It’s happened to me on podcasts and yeah, you’re suddenly like, eh, my machine is updating yay. So let’s talk about management services because obviously that’s another IT Pro hot button. There’s a lot going on here. Right? Microsoft’s been doing things to try to consolidate Intune and config man around this new brand they have called Endpoint Manager. There’s still a lot happening on the WSUS and SCCM integration front. I mean, what do you think IT Pros, just in very broad strokes should be paying attention to first and foremost on management services right now.

Tim Warner (20:31):
Nowadays I think of buzzwords like single pane of glass management, because the chances are good that the business is hybrid cloud potentially multi-cloud. So we’re thinking of management stuff that can stretch like that. I’m thinking of vendor neutrality, as opposed to proprietary. I’m looking at you Apple. Leverage of open source components like vulnerability scanners that can pick up vulnerabilities in open source. Cause it’s likely there. I agree that Microsoft’s done some really nice engineering with Configuration Manager and WSUS. However, I’m disappointed with this whole Endpoint business, like in Azure, for instance, Azure Security Center, the what used to be just I think a single skew, a single standard tier is now decomposed into all this Azure Defender. I’m confused and I’m supposedly an MVP who’s got my finger on the pulse.

Mary Jo Foley (21:26):
You know what’s not helping, this year they’ve changed the branding on so many Microsoft products, especially around their security products. I’m like, I give up, I don’t even know what’s branded what anymore.

Tim Warner (21:35):
It is absolutely nuts. Yes. All of the Endpoint stuff, what is their status now? It’s really terrible because there’s a lot of great potential in there. I mean, Intune, for instance, can handle mobile devices, iOS, Android MacOS. I mean, it really is. It’s hitting all of those points that I mentioned a moment ago, but the challenge, it seems to me for the IT Professional is understanding what exists, where, today.

Tim Warner (22:06):
What its licensing model is today. And how likely is this, are the sands going to shift over the next days, weeks months.

Mary Jo Foley (22:17):
Do you out of curiosity, look much at what they’re doing around the single pane of glass management with Azure. I know they’ve been really talking up since last Ignite, this whole idea of Azure Arc, which lets you have a single pane of glass and manage your services, your Microsoft services, even if they’re running on other clouds. So in theory, this sounds like, you know, the perfect world, the perfect storm, but I’m like, is it really working yet for anybody? And I wonder if that model somehow trickles down to on-premises too.

Tim Warner (22:54):
Yeah. My, my take on Azure Arc is that its early days for sure, but I like what they’re doing organizing in workloads. So for instance, you know, you can collect your server VMs or physical servers from your data center. Other clouds, you see two instances in Amazon for instance, and you can apply a single layer of governance from Azure onto those. And I know they’re doing that with Kubernetes and with databases as well. I think that’s great. Azure Sentinel in the security space looks to be fully, I mean, again, it’s expanding the library of connectors that it has, but it’s got connectors for AWS. And you know, if you’re using Cisco hardware or F5 or Barracuda, you can bring and aggregate, all that data into one spot. All of the, what used to be the Operations Management suite tools. Now they’re part of, I guess, Log Analytics or Azure Monitor for Logs, whatever it is this week, the idea of gathering all of your diagnostics data into one spot. Yeah. That’s a good example of Microsoft looking at the world outside of its own ecosystem. Whereas it looks like in my perspective, AWS kind of acts like Azure doesn’t exist. You know, I don’t think that’s a winning strategy personally.

Mary Jo Foley (24:14):
Yeah. It’s going to be interesting to see how that evolves. You know, the again, coopetition with AWS and Microsoft, because I feel like there’s some partnering happening with Microsoft and Google surprisingly on various fronts around browsers and even back-end services, but on AWS and Microsoft, it seems more like haters gonna hate, still is the rule of the day there.

Tim Warner (24:41):
Yeah, no question, but it appears to be one-sided. For instance, if you go and look in the Microsoft docs, they’ve got all of this great stuff on Azure for AWS professionals and Google has followed suit. They’ve opened source their docs and they’ve got Google Cloud for Azure professionals, Google Cloud for AWS. What do you see in AWS? Nothing in terms of welcoming customers, come on. I mean, you have to understand multi-cloud is becoming more the rule than the exception.

Mary Jo Foley (25:12):
Yeah. That’s true. Just like heterogeneous on-premises operations as well. Right. I mean, for awhile it was like Microsoft’s guidance and other people’s guidance was, well, if you use everything from Microsoft, it just works, right? Yeah. But that’s not how people work, right?

Tim Warner (25:29):
No, that’s how Apple is. It’s weird because professionally I’m all Windows with some Linux, but at home, my family and I just happen to be all Apple and you’re exactly right. If you’re all Apple, it all works beautifully. And that hence is the value proposition, but it’s a premium value proposition.

Mary Jo Foley (25:46):
Yeah, definitely is. Great, well, Tim, we are just about out of time here. So I just wanted to take a moment to say thank you again for sharing your perspective, your historical perspective and your projections about what might be coming and what’s next. I really appreciate it.

Tim Warner (26:02):
You’re welcome. I love talking about this stuff. Thanks Mary Jo.

Mary Jo Foley (26:06):
Great. And for everyone else listening right now or reading this transcript, I’ll be putting up more information soon on Petri about who my next guest is going to be. So once you see that you can submit questions directly on Twitter for the guest, If you’d like using the hashtag #MJFChat. And in the meantime, if you know of anyone else or even yourself who might make a good guest for one of these MJF Chats, please do not hesitate to drop me a note. Thank you very much.