COVID-19 Resources for Lawyers
Featured Guest
Ben Schorr

Ben M. Schorr is a senior technical writer at Microsoft. He is the author of several books and articles...

Your Hosts
Sharon D. Nelson

Sharon D. Nelson, Esq. is president of the digital forensics, managed information technology and cybersecurity firm Sensei Enterprises. Ms....

Jim Calloway

Director of the Oklahoma Bar Association’s Management Assistance Program, Jim Calloway is a recognized speaker on legal technology issues,...

Episode Notes

After the disaster that was Windows 8, many lawyers are hesitant to upgrade to Windows 10. But for those of you with Microsoft operating systems, the change is likely inevitable. Furthermore, Windows 10 has a free upgrade for a year! So what do lawyers need to know about the new OS? Are rumors of high bandwidth use and computer sharing true?

In this episode of The Digital Edge, Sharon Nelson and Jim Calloway interview technologist and Microsoft expert Ben Schorr about the price, benefits, and downfalls of Windows 10 and what lawyers specifically need to know.

Topics Include:

  • What happened to Windows 9
  • The start menu and live tiles on desktops without touch screens
  • Microsoft Edge versus Internet Explorer
  • The quality of Cortana
  • Rumors of peer-to-peer networks and bandwidth use
  • New and existing hardware and software compatibility
  • Whether lawyers should download the operating system and when
  • How much Windows 10 costs

Ben Schorr is a technologist and chief executive officer for Roland Schorr & Tower, a professional consulting firm headquartered in Flagstaff, Arizona. He is also the author of several books and articles on technology including “The Lawyer’s Guide to Microsoft Outlook”, “The Lawyer’s Guide to Microsoft Word” and “OneNote in One Hour”. Ben has been a Microsoft MVP for more than 18 years and involved with management and technology for more than 25.

Special thanks to our sponsors, ServeNow and CloudMask.


Advertiser: Welcome to The Digital Edge with Sharon Nelson and Jim Calloway. Your hosts, both legal technologists, authors and lecturers, invite industry professionals to discuss a new topic related to lawyers and technology. You’re listening to Legal Talk Network.


Sharon D. Nelson: Welcome to the 92nd edition of The Digital Edge, lawyers and technology. We’re glad to have you with us. I’m Sharon Nelson, president of Sensei Enterprises.


Jim Calloway: And I’m Jim Calloway, director of the Oklahoma Bar Association’s Management Assistance program. Today, our topic is Windows 10: What Lawyers Need to Know.


Sharon D. Nelson: Before we get started, we’d like to thank our sponsors. CloudMask offers cost-effective and efficient data encryption for law firms. Whether large or small, in Google Apps, Office 365 and other Cloud solutions. Sign up now for your 60 day free account at We also thank Serve-Now, a nationwide network of trusted, prescreened process servers. Work with the most professional process servers who have experience with high volume serves, embrace technology, and understand the litigation process. Visit to learn more.


Jim Calloway: We are happy to welcome, once again, our good friend Ben Schorr. Ben Schorr is a technologist and chief executive officer for Roland Schorr & Tower, a professional consulting firm headquartered in Flagstaff, Arizona with offices in Hawaii and Oregon. He is also the author of several books and articles on technology. His books include, “The Lawyer’s Guide to Microsoft Outlook”, “The Lawyer’s Guide to Microsoft Word” and “OneNote in One Hour”. He’s been a Microsoft MVP for more than 18 years and involved with management and technology for more than 25.In his small free time, he’s an ironman triathelete and a high school football coach. Thanks for joining us today, Ben.


Ben Schorr: Thanks Jim, it’s always great to be back with you guys.


Sharon D. Nelson: Ben, I know you know because we’re friends, that I am numbers-challenged. But I know you don’t count 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, but Microsoft does. So what the heck happened to Windows 9?


Ben Schorr: Well, that’s a pretty good question and a common one. There’s a lot of answers to that question, most of them I think were just jokes and not really the truth. But the best answer I’ve gotten for that question so far from the guys at Microsoft has been that it was a marketing decision and that they wanted to show that Windows 10 was a pretty significant departure from Windows 8. So what they did is they skipped Windows 9 in an effort to communicate that this isn’t just a minor update for Windows 8, but really a complete departure and that hopefully people give it a chance.


Jim Calloway: Well, Ben, on behalf of those of us who are still comfortably sitting with Windows 7, did Windows finally return the start button back?


Ben Schorr: Jim, in fact, they kind of did. One of the biggest complaints – probably the biggest complaints – about Windows 8 was that the touch screen start screen and the start screen was the replacement for the start menu for Windows 8. That was the screen that contained all the tiles. That was an okay experience on a tablet device. The reality is that most people and especially most lawyers still do the majority of their Windows computing on a computer with a keyboard a mouse, a desktop or a laptop, typically. And the tiles just really weren’t a good experience on a non touch device. So with that lesson learned and properly chastised, they went back to the drawing board a little bit and what they’ve given us in Windows 10 is a start menu that looks a lot more like the Windows 7 start menu. In fact, when you click the start button, and you do have the start button right there on the taskbar where you’re used to seeing in Windows 7. Then what you get now is a column that looks very much like the old Windows 7. It’s a little more stylized which shows you your most frequently used apps. It’s got buttons that you can click to show all programs like you used to with Windows 7. There’s also links right there where you can get into Windows Explorer and you can get into Control Panel and Settings. Also where you can hit “power.” That was one of the other things about Windows 8’s initial release that they hid is how do you restart or logout? Well that’s right on the start menu where it used to be where you can click power and you can reboot or shut down. And then what they’ve also done is they’ve sort of given us a little bit of the Windows 8 experience and right next to that, you have a very narrow pane, although you can make it as wide as you like, that does contain some live tiles. Even people who didn’t like the full screen of tiles tended to think that the live tiles were kind of nice. So for example, the weather app that shows you the current temp and what the next three days re going to look like. That’s a nice feature. So they did retain some of the better features of the tiles, but they did it in a much smaller format and they retained or brought back some of the features of the Windows 7 start menu that people liked. And it’s also much more configurable, so now when you click that button, rather than getting a full screen that’s a little bit disorientating, you just get a little box that pops out. For example, on my machine, there’s not even a quarter of one of my monitors, which is a lot more familiar to folks who like the start menu.


Sharon Nelson: So are they really sending Internet Explorer to boot hill and replacing it with Microsoft Edge?


Ben Schorr: No, that’s a common misconception, and I’ve even seen some of the tech journalists say Microsoft Edge is the replacement for Internet Explorer. Maybe it is eventually, but it’s not any time soon. Internet Explorer 11 is still with us. It’s a little harder to find in Windows 10, it’s been sort of deprecated. And by deprecated, I just mean it’s hidden a little bit. But you still have Internet Explorer if you need it. Microsoft Edge is another browser, not a replacement. And Microsoft Edge is – for those who don’t know – Microsoft’s sort of bare-bones browser. People have criticized Microsoft for years for not really taking Internet Explorer to Jenny Craig and slimming it down because it tends to be pretty slow and bloated in some cases. Microsoft Edge is then recreating a browser from the ground up, and it’s a little bit more like other third party browsers that people are fond of like Chrome in that it’s quite fast. It has, however, a lot of functionality stripped out of it, but honestly, that’s functionality most people don’t use very often anyway. So I’m not sure how important it is that that functionality’s not there in Edge. But Edge is not really a replacement for Internet Explorer, at least not in the immediate future. It’s just a new, fast, experience for browsing.


Jim Calloway: Well, Ben, as far as I’m concerned, any time they bury Internet Explorer, it’s a good thing.


Sharon Nelson: Yeah, ditto to that.


Jim Calloway: But today, personal assistants are all the rage with Siri and Google Now. But they’re mostly limited to mobile devices and Windows 10 includes Cortana on the desktop computer. Have you experimented with that much and what’s that experience like?


Ben Schorr: I have, and actually I was a little skeptical when I first heard they were going to put Cortana on the desktop. But I am a Cortana user on my mobile phone and I do like Cortana there, so I figured I’ll give Cortana a fair shot on the desktop. And I’ll tell you, I’m really impressed. It’s not Jarvis from Iron Man yet, but it’s getting close. The other day, I walked into my office and from across the room, I said, “Hey, Cortana,” and my computer woke up. It wasn’t off, it was just idling; and I said, “What time does Staples open?” And Cortana did a few seconds of searching and came back and said to me – and keep in mind, I’m still 6 feet away from my computer, I haven’t even gotten to my keyboard yet – and Cortana comes back and says, “Your local Staples isn’t open yet, but it opens at 9 AM.” And on the screen it displayed a little clean map of how to get to the local Staples, which I already knew. But what a nifty feature to be able to just come all the way across the room and say, “Hey, Cortana,” and ask it a question like that and have it give me the answer. Not a page of search results, but it’s the actual answer. It also lets you do some really interesting things. So, for example, one thing I can do is say, “Hey, Cortana, what’s on my schedule for tomorrow?” And it pops up a little page and it says, “I see five things on your calendar tomorrow,” and it shows me a list of what’s going on. I can have it reschedule things for me. I’ve occasionally told Cortana if I have a meeting that’s canceled, “Hey, Cortana, cancel my 3 o’clock,” and she takes it off my calendar. You can use it to send emails. You can use it for interesting searches, you can ask how the weather is or what the weather’s going to be tomorrow and not even in your local location. I have gone off to speak at conferences and said, “Hey, Cortana, what’s the weather going to be next week in Tulsa, Oklahoma?” And sure enough, there it is. So it’s pretty nifty. Of course, like all voice recognition technology, it does depend on you having a relatively quiet environment. It’s fortunate that I work in a fairly private room here, and other than my dog, I don’t have other co workers chatting or arguing or listening to music and things like that. So I’m in a situation that’s fairly ideal for Cortana. If you work in a cubicle farm, you may not find it to be quite as good of an experience. But I’m actually pretty impressed with what they’re doing with Cortana on the desktop as well as on mobile.


Sharon Nelson: So what servers does all that run through and is the information stored?


Ben Schorr: So Cortana uses Bing as its backend, it’s Microsoft search engine. And I’m not intimately familiar with where all of the details are stored. Most of it I believe is synchronized to your Microsoft Live account, which is the same thing that synchronizes OneDrive and uses your Microsoft account. As you may know with Windows 10, just like with Windows 8, when you sign in on multiple devices using the same Microsoft account, some number of your settings and file actually synchronize between the two devices. So I believe they’re using the same Microsoft Live account to store the data and settings that you have for Cortana across multiple devices. A lot of the things are just searches against Bing, especially things like weather. Now my calendar is in my Microsoft Exchange server, and Cortana actually just interfaces with Outlook on my local device to look that up, so it doesn’t have that access to anywhere in the server other than Microsoft Exchange server in Office 365.


Sharon Nelson: Okay, that’s a lot clearer. Are there other advantages over Windows 7 or 8 that 10 offers people? And can I make the second part of that question, should lawyers upgrade and if so, when?


Ben Schorr: Windows 10, in my experience, is generally a little bit faster. That’s been one of their mandates. Windows 8 was faster than Windows 7, usually. Not always, but usually, on the same hardware. And Windows 10 is designed to be tighter and faster on the same hardware than even Windows 8 was. So one of the advantages, you should get a little bit of a performance improvement with Windows 10, generally. Your mileage my vary, of course. Windows 10 is a little bit more secure than Windows 8 was because they’re always learning and closing various vulnerabilities. And of course, Windows 10 is going to have longer support than Windows 7 or 8. Windows 7 support goes out of support I believe in 2020. Windows 8 would be a couple of years after that, so Windows 10 should run to at least 2025 before it goes out of support. So you’re going to have those advantages. Plus, of course, the new feature with the new start menu. There’s a new file manager that replaces Windows Explorer. It’s a little bit evolutionary with the new File Manager, but it’s pretty nifty. It has a real emphasis on recently accessed files and folders, which is kind of nice. I do a lot of scanning and then I go to get those scans and I either upload them somewhere or I send an email with a scanned attachment. It used to be that I’d have to scan the file into my local harddrive and then I’d have to go open that location and then attach the file. But now, when I click File Explorer right after I’ve scanned a document, it recognizes that a new document is in my system somewhere and it gives me basically a link directly to that document, which saves me a lot of time in tracking those documents down and attaching them. It’s just one example of where the new File Explorer is a definite improvement of Windows 8. A lot of other little nice things, there is a notifications capability in Windows 10 that didn’t exist in the previous operating systems. It’s sort of modeled after what you’re used to in mobile phones where you get a notification when there’s an email or an appointment or a reminder of some sort. It’s okay, personally i don’t find it that useful because most of my notifications come from Outlook, so it’s a little bit redundant. But some people will probably like the new notifications capability.


Jim Calloway: Well I’ve been hearing lots of rumors about Windows 10, so let’s give you two to three of them here to confirm or debunk. I’ve heard that Windows 10 uses a lot of bandwidth. I heard they may even be using my computer to share updates with other computers. And I know a lawyer who knows somebody who knows somebody who swears that the automatic updates upgraded him to Windows 10 without him even asking for it to be done. Any truth to any of those rumors?


Ben Schorr: As with many rumors, the answer is yes and no. Does Windows 10 use a lot of bandwidth? The answer is yes, it can, and the reason for that is Windows 10, more so than any of its predecessors, is going to be predominantly deployed by download. With Windows 8, some people upgrade to Windows 8 via download, but a lot of people who upgraded to Windows 8 upgraded by getting a DVD. Of course, most people I think got Windows 8 when they bought a new computer that came with it. With Windows 10, of course you’re still be able to buy computers that come with it. But, if you’re upgrading to Windows 10, that’s going to be almost exclusively delivered to you via download. I believe it is still possible to get a DVD of Windows 10, but that’s certainly not the way they’re trying to get you to upgrade to it. And so when you’re downloading an entire operating system, much like Apple’s done with most of their Mac OS upgrades, and you’re downloading that entire thing, that’s over 3 gigabytes in size, so that’s a fair bit of bandwidth. One of the reasons – about a few weeks before the launch date which was July 29th – they did this thing where people started to see a popup on their system tray that offered them a free upgrade to Windows 10. And if they clicked that, then what happened is Microsoft prestaged some of the bits, some or all of the bits of Windows 10 on their machine. So over the next few weeks before the July 29th launch date, people were already in the background silently downloading the Windows 10 bits so that on July 29th, Microsoft didn’t have to push down 3 hundred million copies of Windows 10 across the internet. But yes, if you upgrade to Windows 10, there’s going to be a fair bit of bandwidth involved. The other issue, of course, is that with Windows update, which Microsoft has had for a very long time, Microsoft is now going to be updating the operating system much more often and much more extensively, very likely. Again, much like what we’ve become used to with mobile phones. So those kinds of updates are going to happen much more often and those are all going to be downloads. If you’re on a relatively high speed broadband, it probably doesn’t matter. If you’re on a meter network like Verizon 3G or 4G or something where you have a bandwidth cap, or even a broadband connection with a bandwidth cap, then it may be managed quite a lot. As for the second one, are they using your computer to share updates with other computers? The answer to that is yes, they might be, and that is a configurable setting. If you go into Windows 10 settings, updates, and click on advanced options, you can choose whether or not you want your computer to share updates with other computers. Or the setting is yes, share my updates with other computers, which means it could actually be sharing it with other computers across the internet. The second option is only to share with other computers within your local network. That’s what I have turned on with mine. So if my wife or one of my other machines or co workers or somebody is on my local network and needs the Windows 10 update that my machine has, they can get that from my machine. It’s all in the background of course. But my machine is not going to be sharing Windows 10 updates with others across the internet.


Sharon Nelson: I would hope not, that doesn’t sound secure.


Ben Schorr: I’m a little skeptical about that particular setting. To me, it sounds like some of these bittorrent situations where you set up these peer to peer networks. It sounds like Microsoft is setting up a bit of a peer to peer Windows update network. I understand why they’d want to do that and I understand that there can be some benefits, but I’m not sure why I would want to have my machine participate in it, even though I do have a fairly fast internet connection. Maybe I’m being selfish in not wanting to share that, but I don’t, so I have that turned off. But luckily, it’s easy to turn off. Again, just go to the settings, updates, advanced options, and you can configure that there. And you can also tell it not to share updates with anything, even on your local network if you want to do that. And the third question about Windows 10 being installed without their knowledge or not their affirmative consent to that, that one I’m a little skeptical of. I have heard a couple of people report instances like that. I haven’t heard it very much, and my suspicion is what probably happened is that they accidentally clicked, “Yes, upgrade me to Windows 10,” because again, in the weeks leading up to the Windows 10 release, Microsoft did have a popup that was appearing saying, “Hey, do you want Windows 10?” I sort of suspect those people that think Windows 10 got installed without their permission, either they or maybe somebody else who sits at their computer occasionally may have not realizing what that meant clicked yes, so that’s my guess. I haven’t heard of any confirmed report of Windows 10 being installed without permission yet.


Sharon Nelson: Go to know, Ben. Let’s pause here for a commercial break and then we will be right back.


Advertiser: In recent years, the legal sector has come under increasing pressure to improve efficiency and client services. CloudMask enables law firms and solo attorneys to leverage free and low-cost Software as a Service, such as Gmail and Google drive, to improve efficiency and client service, while reducing cost,strengthening compliance with data privacy laws, and ensuring that legal ethical duties are met. CloudMask encryption is even certified by 26 governments around the world. Sign up now for your 60 day free account at


Looking for a process server you can trust? is a nationwide network of local, prescreened process servers. Serve-Now works with the most professional process servers in the industry, connecting your firm with process servers who embrace technology, have experience with high volume serves and understand the litigation process and rules of properly effectuating service. Find a prescreened process server today. Visit


Sharon D. Nelson: Welcome back to The Digital Edge on The Legal Talk Network. Today, our subject is Windows 10: What Lawyers Need to Know, and our guest is Ben Schorr, the CEO of Roland Schorr & Tower, a professional consulting firm headquartered in Flagstaff, Arizona, with offices in Hawaii and Oregon. Ben, do people need to buy new hardware to use Windows 10?


Ben Schorr: The answer, generally speaking, is no. Any hardware you have that supported Windows 7 or Windows 8 should work with Windows 10. I’ve heard very limited examples where things didn’t work; usually with third party peripherals. But for me, everything I’ve installed Windows 10 on right now has worked just fine, even my HP multifunction device, just worked right out of the box. And I realized I forgot to answer your question earlier about whether or not lawyers should upgrade to Windows 10 and if so, when. My answer to that question would be yes, I think they should. But the when is there’s no rush, don’t rush into it immediately. I would probably give it a few weeks or even a few months and see how things shake out and let the new updates and fixes come out. People have often said never install version 1.0, but we’re kind of in version 1.0 now, even though the beta testing was very expensive for Windows 10. I would do it but I would probably wait a little bit longer.


Sharon Nelson: Good, thanks for remembering to answer that question because I think that’s a fundamental question that a lot of listeners probably have.


Jim Calloway: Another fundamental question relating to the upgrade is if I upgrade, does all of my existing software still work on Windows? I’m pretty sure that Microsoft Office will, but have you heard any complains about Legacy software not working?


Ben Schorr: I haven’t heard very many complaints about Legacy software. So far, it seems like compatibility is very good, and unless you have something very oddball, my understanding is all the existing software is working just fine with Windows 10. Not saying you won’t trip over something that doesn’t, but it would probably have to be something pretty esoteric.


Sharon Nelson: I guess the big question now is what does the darn thing cost?


Ben Schorr: For most users, Windows 10 is actually going to be free, at least for the first year. I need to clarify on that, I think, but if you’ve got Windows 7 or Windows 8, either Home or Pro or Business, you’re going to get an update to Windows 10 for free through July 29th, 2016. If you don’t have one of those versions, obviously if you buy a new computer, it will come with Windows 10 and the prices will be sort of fumbled in there. If you have Windows 8 Enterprise, you’ll have to buy the Windows 10 Enterprise licenses, and that’s not going to be free. Now if you’re coming from Windows XP or one of the older operating systems, then Windows 10 is $199 for the Business version – which is what I recommend which I believe is called the Pro version of Windows 10 – and Windows Home is I believe $119 if you’re coming from one of those older operating systems.


Jim Calloway: Free from Microsoft, I’m still having trouble processing that. What’s the catch? Are they going to start charging me for it after the first year? I know they are if I download it, but what’s the future of paying for Windows?


Ben Schorr: That’s a pretty common misconception too, actually. When people heard, “Oh, it’s free for the first year,” they thought, “Oh okay, sure, I’m going to install it for free and then on July 30th, 2016, you’re going to send me a bill.” The answer to that is if you install Windows 10 during that first year, you have it and it’s free to you forever for as long as you use it. So they’re not going to start charging you after next year if you install it during that first year period. Now if you wait until after july 29th, 2016 to get your free upgrade, then your free upgrade is gone. And so that’s why I tell people you can wait, people who are eligible, which is most people who are eligible for that free upgrade to Windows 10. You don’t have to actually claim that free upgrade until next July. But once you claim it, it’s yours, and they’re not going to charge you after that for Windows 10; so you’re not going to have that situation. But if you wait too long, then you’re probably going to be looking at $199.


Jim Calloway: Don’t worry, all the lawyers will be upgrading on that very last day, Ben.


Ben Schorr: Oh yeah. I expect a lot of calls on July 28th, 2016.


Sharon Nelson: Oh, yes, you’re going to get them, I have no doubt. Well, thank you Ben for joining us today. I know that as I’ve been on the road lecturing, questions about Windows 10 come fast and furious. It’s on a lot of lawyers’ minds, so we appreciate getting your expertise and you really do know more about Microsoft 10 than anyone else I know. So it was a great pleasure to have you with us today.


Ben Schorr: Always a pleasure to be with you guys.


Sharon D. Nelson: And that does it for this edition of The Digital Edge, lawyers and technology; and remember, you can subscribe to all the editions of this podcast at, or on iTunes. And if you enjoyed our podcast, please rate us on iTunes.


Jim Calloway: Thanks for joining us. Goodbye Ms. Sharon.


Sharon D. Nelson: Happy trails, cowboy.


Advertiser: Thanks for listening to The Digital Edge, produced by the professionals at Legal Talk Network. Join Sharon Nelson and Jim Calloway for their next podcast covering the latest topic related to lawyers and technology. Subscribe to the RSS feed on or in iTunes.


The views expressed by the participants of this program are their own, and do not represent the views of, nor are they endorsed by, Legal Talk Network, its officers, directors, employees, agents, representatives, shareholders, and subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.

[End of Transcript]

Brought to You by

Notify me when there’s a new episode!

Episode Details
Published: October 12, 2015
Podcast: The Digital Edge
Category: Legal Technology
The Digital Edge
The Digital Edge

The Digital Edge, hosted by Sharon D. Nelson and Jim Calloway, covers the latest technology news, tips, and tools.

Listen & Subscribe
Recent Episodes
Supreme Court of Virginia’s Lawyers’ Wellness Initiative: A Rousing Success!

Margaret Ogden, wellness coordinator at the Supreme Court of Virginia, shares insights into new initiatives focused on attorney mental health and wellbeing.

COVID-19 is Brutal to Young Lawyers

Young lawyer Graham Bryant shares the struggles of his demographic as they cope with the hardships of the pandemic.

Best Practices for Audio and Video Evidence: Avoid Mistakes in Court!

A/V forensics expert David Notowitz discusses strategies for enhancing your presentations of audio and video evidence in court.

A Legal Podcast About Legal Podcasting

Bob Ambrogi, Joe Patrice, and Tom Mighell join Sharon and Jim to discuss their experiences in the world of legal podcasting.

Professor Richard Susskind Discusses Online Courts

Professor Richard Susskind shares insights on how the pandemic will impact the future of online legal and court services.

Risky Business: How Lawyers are Navigating Through COVID-19 and the Rocky Economy

Sharon Nelson and Jim Calloway offer guidance for weathering COVID-19 and its economic impacts on the legal profession.