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Episode Notes

Haunted by the negative impact of some of their past decisions, Microsoft has decided to refocus their efforts on cloud-based technology. In this episode of the Kennedy-Mighell Report, hosts Dennis Kennedy and Tom Mighell discuss the reorganization of Microsoft and the implications of their shift in focus. They also share tips for unsubscribing from pesky emails and what makes a newsletter worth receiving. As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Special thanks to our sponsors, ServeNow and TextExpander.


The Kennedy-Mighell Report

How Microsoft’s Changes could Affect Windows and other Products



Intro: Web 2.0, Innovation, Trend, Collaboration, Software, Metadata… Got the world turning as fast as it can, hear how technology can help, legally speaking with two of the top legal technology experts, authors and lawyers, Dennis Kennedy and Tom Mighell. Welcome to The Kennedy-Mighell Report here on the Legal Talk Network.


Dennis Kennedy: And welcome to Episode #211 of The Kennedy-Mighell Report. I am Dennis Kennedy in Ann Arbor, Michigan in my first podcast from our new home.

Tom Mighell: And I am Tom Mighell still in Dallas. Before we get started, we would like to thank our sponsors.

Thanks to TextExpander for sponsoring our show. Communicate Smarter with TextExpander. Gather, Perfect, and Share Your Knowledge. Recall your best words instantly and repeatedly. Learn more at  HYPERLINK “”

Dennis Kennedy: And we would also like to thank ServeNow, 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  HYPERLINK “” to learn more.

In our last episode we discussed the practical aspects around the latest Facebook privacy brouhaha and the latest round of people, a lot of them friends of ours saying that they will once again quit Facebook and that they really do mean at this time. Although most of our friends, Tom, still seem to be posting merely way on Facebook as of this recording.

Tom Mighell: I know one person who erased their Facebook account.

Dennis Kennedy: We also mentioned that the second edition of our book, The Lawyer’s Guide to Collaboration Tools and Technologies is now available in the ABA online bookstore. Congratulations to us, Tom, on getting that one done. And in this episode of the podcast however we were both intrigued by some recent announcements at Microsoft that some are heralding as the end of Windows. We want to discuss whether that’s a big deal, a little deal or no deal at all. Tom, what’s all on our agenda for this episode?

Tom Mighell: Well, Dennis, in this edition of The Kennedy-Mighell Report, we will indeed be discussing the new reorganization at Microsoft and how people are interpreting the changes in connection with Windows itself. In our second segment, we’re going to talk about some practical approaches to unsubscribing to all those email newsletters and updates we seem to be getting in our Inbox, and as usual, we’ll finish up with our parting shots. That one tip website or observation that you can start to use the second this podcast is over.

But, first up, Windows, Windows and Microsoft. On March 29th Microsoft announced a major reorganization although they’ve been doing that a lot lately in the past couple of years, but a major reorganization that actually has some consequences, as far as we’re concerned, we’re going to talk about this in more detail in a minute but basically they’re splitting Windows across the company including, the cloud and Artificial Intelligence team as well as establishing or maybe renaming a new team that they’re calling experiences and devices.

Clearly the Windows that we have come to know and not necessarily love, is about to change, and Dennis, I know there is nothing that you enjoy more than reading stories that start about the death of a technology. How excited were you to read about this one?

Dennis Kennedy: I really do love the death of technology stories. It’s kind of my hobby, and actually it was the topic of one of our very first podcasts and this one does seem important as we move forward, and so, I listened to a number of podcasts about this and a great post on April 2nd by Ben Thompson on the blog Stratechery about this, and I’m just fascinated by this reorganization, believe it or not, because I can’t believe those words, it just came out of my mouth having been in the corporate setting for a while. But, I like Ben’s approach of saying that Windows is no longer the standalone unit, it’s being incorporated to other aspects of Microsoft and it seems like the focus is really on the cloud and the productivity apps or as we would think of it — might think of it as Azure and Office 365 might be a good way to think about it, and that sort of tells us something about the future and a different way of thinking in Microsoft.

Tom Mighell: I think as I mentioned a minute ago that what they’ve done is that they have split Windows across, including it within the cloud and Artificial Intelligence team which like you mentioned is more closely aligned with the Azure Group, which frankly is probably a good idea because that’s – it probably was meant to be there to begin with, but it’s also being part of this new group that used to be called Windows and Devices, now it’s called Experiences and Devices, and it’s going to explicitly include Windows, Office and Surface, the surface line of computers.


So, I guess that Windows and Office are the experiences and Surface is the device. I’m not sure what other devices. The problem that Microsoft has had with Windows is that while we are seeing a huge push to mobile first for everything, Windows has really struggled getting to a mobile first or mobile anything platform because Windows Mobile just wasn’t very successful and it’s not going to be successful, and they’ve pretty much signaled that they’re not really going have a play with that, and because of that decision, Windows is really no longer that dominant way that people use computers these days.

So, Android has got over 2 billion monthly active devices used, Apple has over a billion, and Microsoft has just a measly 600 million Windows 10 users, which I think is a very interesting and telling point about how Windows has kind of diminished in our thinking and in our usage over the past couple of years.

Dennis Kennedy: Look, Tom, I mean as we’re talking about this, I think it reflects a lot of our thinking in our collaboration tools book that there’s the cloud has become so important and then the productivity apps that run on the cloud that people use together.

Let’s go back and look at Windows. I mean, Windows has been with us for a long time. Windows 1.0 1985, I mean Windows 95 1995, and that’s 23 years ago almost. So, much has changed over that time, and I think one of the things you pointed out when you talked about Android and iOS and how quickly the versions of these OS has changed, I mean, the long drawn-out process of going to a new version of Windows with the updates and the fixes and that we’re all used to, it doesn’t make sense anymore in a cloud-based world, so I think that has a lot to do with it.

I’ve also always felt that the better the OS, the more transparent it becomes in the less I should really care about it, so in a way I don’t really care whether I’m on a Mac, on Windows, I’m on a tablet, Android, whatever, I don’t really care just as long as I can get done what I want to get done. So, I guess one of the things this raises time for me is the question of how much do people really focus on operating systems anymore rather than what you can actually do on any given device?

Tom Mighell: Well, so here’s where this argument doesn’t make a lot of sense to me because I think it is clear and we were talking about this before we started recording. A device needs an operating system to work. I think you’re making the argument that it doesn’t matter what operating system it is. I don’t believe that necessarily to be true and I think that Mac people would very much disagree with you that it doesn’t matter that they are working on a Mac OS as compared to a Windows OS.

I think that Windows people have a love/hate relationship with Windows but using a different interface because all the OSes have different interfaces, they all have different approaches to how you access things, and yup, they’re all primarily app-related and more people are accessing things through apps, but the fundamentals of that operating system are among all four of them; iOS, Android, Windows, Mac; they’re all very different, and here’s really where the main problem that I see is, is when you say that it really doesn’t matter, is that Windows is still important to Microsoft because their install base with business is huge, and so getting and saying that Microsoft is going to move away from the operating system or from Windows when most of this world’s business is conducted on Windows, like it or not, is just really odd to me and doesn’t make a lot of sense, and this is where I start to kind of lose traction with the Windows is dying type of argument because I think that as long as business has a hold, it’s going to be there.

Now whether it’s going to morph, whether it’s going to evolve, I think that’s a good discussion for this particular segment of the podcast, but, I’m just not convinced that you and I as tech people and people who are out there not in the business world maybe now don’t have that same issue but I think the business world is what’s keeping Windows alive like it or not.

Dennis Kennedy: Yeah, I think that and maybe it’s better to say that it’s not — the OS is not really, it doesn’t matter that much to me because I just care about what I want to get done, the fact that the operating system is stable, it really doesn’t matter to me.


I know people who say, you’re right, it’s Mac, it’s versus Windows, it’s iOS versus Android, but the fact is that what to me seems like truly operating system stuff, doesn’t matter as much as what I’m trying to accomplish in the apps. So, I don’t know, if we can debate that issue, I guess, Tom, I don’t think you and I necessarily will agree on that but you’ll come around to my point of view before too long.

Tom Mighell: We will see.

Dennis Kennedy: But I think that what’s interesting to me is in some of the stuff is the response Microsoft has had to make to, and I think the thing with Windows is Windows 7 was not a happy experience. Windows 8 not a happy experience, Windows 10 people are not happy with that. The Windows Phone —

Tom Mighell: I’m going to interrupt you for a second and say, I’m going to say that I’m going to disagree with that and say that, every other Windows release has been successful. They have Windows 95, generally a successful release. Windows Vista, is it Windows Vista that came after that? Miserable.

Dennis Kennedy: 98, no it’s 98.

Tom Mighell: Windows 7 actually was not a bad release whereas Windows 8 was a miserable failure. Windows 10 however has actually got a lot of stuff right and as releases of Windows go, I think has been pretty successful, and frankly, it’s gotten, I think frankly the way that Windows 10 has evolved has actually gotten Microsoft to the place where they can start to rely less on that as an operating system.

I think they’ve actually gotten to the point where we’re cloud first, where we’re looking at things in a different way. So, I think that — where was I headed with this argument?

Dennis Kennedy: I don’t know I thought I was going to ask you like so what if you ask most people, okay, so what is the thing about Windows 10, this really distinguishes it? I don’t know that anybody can point to anything other than this. It seems like most of the discussion — conversation about Windows lasts you first has been is there a Start button and how does a Start button work?

Tom Mighell: Well, I think that’s a very limited and narrow way to look at Windows. I mean, if you asked me what’s different about Windows 10, I would say that it’s more user-friendly, things are in the right place where I want them. I’ve got a Search Bar at the bottom, I can use Cortana and Cortana is built-in if I want to use it.

It’s a lot friendlier than Windows 8 which took a backwards approach that everybody wanted to use it as a tablet and that didn’t really work. So, everybody got really ticked off because Windows 8 totally got rid of the Start button and bringing it back and making it a more friendly environment, I think was a big move.

I mean, there are little bits and pieces that make it a much friendlier product than previous versions of Windows have been.

Dennis Kennedy: Well, Tom, can I ask you if – I have this feeling that where the clouds becoming the operating system anyway, are you just going to disagree with me on that? Or what do you think about that approach that ultimately the what’s happening and what we’re running is happening on whatever operating system is being used in the cloud and as we see with Chromebooks and other things, as long as you were connected to the Internet like what do we really care about the operating system on the device that we have?

Tom Mighell: I think that’s probably true, but there still has to be an operating system on the device, right? I mean, you can’t just open up and have the cloud be an operating system, you got to access it somehow. I will agree that I think that we’re headed in the direction where what we know is personal computing is definitely becoming about the cloud and about Artificial Intelligence.

And, the operating systems that we’re going to be using, starting now and ten years out, absolutely have to be built around that concept because it’s not going to change and so maybe future Windows is going to serve as the frontend to this type of computer rather than an operating system, rather than maybe a be-all end-all kind of a platform, and maybe it’s more of a frontend to it. It’s not going away, it’s just evolving.

Dennis Kennedy: Okay, so next thing I want to touch on is, is really, is whether Office 365 is a real story and I think that, Tom, one of the things you and I do agree on is that the applications that would ordinarily be considered part of Office have become really the most interesting aspect of what Microsoft is doing.

And so that’s not just Office 365, it’s Teams, it’s Skype for Business, it’s that whole suite of products. And I think that I heard a podcast with Satya Nadella, the CEO of Microsoft where he talked a lot about the notion of Microsoft needing to focus on the modern workplace.

And I just loved that concept and the way he sketched out what that might mean, and I just saw these different pieces coming together because what I care about is —


Again, I always go back to how do I do the things that I want to do? And so, when we look at the collaboration tools, collaborations built into these things and you have this different way, you have the all these ways to accomplish the work that you want, and I think there is that notion as the modern workplace changes as we work more remotely.

We use different devices, we have to — and we need different toolsets based on what we need. I think that’s the really fascinating and exciting part of where Microsoft may be going.

Tom Mighell: Oh, I totally agree and that’s where maybe we do agree in this podcast that I think the more interesting story is Office 365, but I think that that’s been a story that’s been evolving the past couple of years that I think Microsoft realized early on that Windows was not the story, that cloud and AI was, and that Office 365 was the most logical gateway to get to that point.

And I think it definitely shows the pivot that Microsoft has been slowly making over the past couple of years and that what we’re seeing with Windows is really just further evolution in that pivot that they’ve been making.

Dennis Kennedy: When I think that, Tom, for me, the pivot notion here and this is why I like Ben Thompson’s Stratechery blog post is he talks about this being a classic example of disruption, which I know everybody is tired of hearing the word. But there is a precise meaning of disruption and his analysis of this is quite interesting in classic disruption theory.

So, I think that there is a business aspect of what’s going on that’s really fascinating because there is a pivot that notion of what do you do with the longtime product as the environment changes and all of those things. And I think that this to me is if we start to think about it in the legal profession, Tom, I think that if you spend some time just kind of thinking through what’s going on here and the challenges, there may be some lessons for the legal profession out of this as well.

Tom Mighell: And I guess we will leave it right there. Before we move on to our next segment, let’s take a quick break for a message from our sponsors.


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Tom Mighell: And now let’s get back to The Kennedy-Mighell Report. I am Tom Mighell.

Dennis Kennedy: And I’m Dennis Kennedy. We’ve recently moved to Ann Arbor and as I do a whole bunch of address changes and other resets, I’ve been struck by the number of emails, newsletters and updates I get, and how that number seems to grow like, well, kudzu. I’m taking the opportunity to do some unsubscribing and pruning of email newsletters. We wanted to talk about two aspects of this process, tips for unsubscribing and also determining what email newsletters you really want to keep getting these days.

Tom, you tend to be pretty rigorous on protecting your email Inbox, do you want to take the first pass at this topic?

Tom Mighell: Well, you know, and I am rigorous about it, which is, I don’t get a lot of content delivered to my Inbox that I proactively that I unilaterally go out and ask for. I think you and I both like the Recomendo email newsletter and there’s a couple of others that I believe. There is a new a new email newsletter on social media from Casey Newton that I think is a great round up every day of the most important stories in social media.

But other than that, we’ve had our discussion already on The Daily Me and how we consume news and how we get information, and for me newsletters in it, what I’m finding more often these days is I’m finding that I am being subscribed to email content that I did not originally subscribe myself to. They make it very simple and easy to unsubscribe and I am almost every time I unsubscribe, it says, please tell us why you’re leaving, and I have to click the button that says I never subscribed to your newsletter in the first place.


But that’s kind of annoying to me and that’s happening, there’s a big uptick, I don’t know if you or anybody else has recognized that, but in terms of getting rid of things, if you’re not going to click that Unsubscribe button, that’s the manual way, it’s a painful process depending on who is sending it. It’s not always effective.

I think in general when you get an option at the bottom that gives you a click and some of these automated mail services that offer an Unsubscribe feature with instant or safe unsubscribe, sort of these certified services on unsubscribing to something, I think they’re generally trustworthy, and they’d work for me usually when I unsubscribe from something I don’t get anything back, but it is the more time-consuming activity to do.

If you’re a Gmail user a lot of subscription or mail that you might get that is being mailed to a bunch of people, mass mailings, Gmail includes a little Unsubscribe button in there and I’ve had mixed success with that, if you click on that you can get some things that would unsubscribe, and it’s easy and quick and let Gmail do the work for you, but it’s okay.

What’s interesting is there are a number of unsubscribe services that are out there and until last year one of the most popular ones was Unroll.Me. Until it was discovered I think late last year that they were collecting information and selling it to vendors, collecting your personal information, reading your Gmail and getting all that, so I will not be recommending Unroll.Me.

The one that I will — a couple services that I will recommend, the alternative to Unroll.Me is called, it works the same as Unroll.Me and that you just turn it on and it will go and unsubscribe anything you want it to unsubscribe from, but it doesn’t collect your personal information.

If you’re interested in using a tool like SaneBox, which is available for Gmail and Outlook, and I can’t remember what the other mail services it’s available with, but it also has a feature where it rather than unsubscribe it will just put it into a black hole and you’ll never see it again, so, it’s a different kind of unsubscribing.

And then, if you’re just trying to get rid of paper mail, one of the best apps I’ve seen to do that is an app called PaperKarma, where you just take a picture of the catalog or the junk mail that you just got and PaperKarma will go to work and go and unsubscribe from that snail mail document that you have got.

So, there’s a couple of options, some are easier than others, some are more successful than others, but if you’re really looking to unsubscribe there are a number of options that are out there for you.

Dennis, what are you thinking about this?

Dennis Kennedy: Well, I want to echo what you were saying, because as we know that however many years ago the CAN-SPAM Act basically eliminated spam emails, but I do find that it does seem that people are subscribing me to newsletters that I don’t ask for. And I just think that’s a big problem because if you’re doing something where I’ve done something where you’re interpreting it to mean that I’m subscribing to your emails newsletter, it’s just such a bad customer experience, and I’m just going to form a bad opinion of you, so I do see a fair amount of that.

I also see where you maybe subscribe to one thing and then all of a sudden you’re getting multiple newsletters and then they have put the burden on you to manage, so you can unsubscribe to all. They put the burden on you to manage and you go, like, all I want is I can — when I was in St. Louis, the St. Louis Business Journal had like a headline service or a daily email and that was fine, but as I tried to unsubscribe it now I see it’s been fractionated into a number of newsletters and I got to unsubscribe to each of them.

And so, what I found is that probably three times in the last couple of years I’ve been very aggressive about getting rid of email newsletters that I don’t want and it just seems like they just keep growing and growing.

So, I’m not sure what it is but I do have that sense, Tom, that there is some kind of default to an opt-out that’s happening or else it’s a trick opt-in, which is just as bad to me —

Tom Mighell: I think that’s right.

Dennis Kennedy: — and possibly worse. I like the Gmail unsubscribe thing, I’ve had mixed results with that. I mean sometimes it’s available, sometimes it doesn’t seem to be available and I tend to do the thing by hand. I also will do — the other thing that can be helpful is that there are some things that you like, especially like if you’ve — you bought something, I heard there’s a company that you like to buy things from, then you get in this daily thing that sometimes they’ll do like a monthly or a weekly summary email, and that can make a big difference.


Because, if you see that you have a hundred emails and they’re all in the Gmail promotions email folder, that doesn’t seem right, but there’s certain — especially in buying products that you do like to have, the emails just not when they’re part of a hundred other ones. So, you can do some things about the frequency as well. So, a number of things out there.

I don’t know that I have comfort for the reasons that you said and also just because I don’t know exactly how the services are going to work having an unsubscribe service do it for me. So I tend to be to feel pretty manual about it, but I do like to take the time every six months or so to really go down and whack away at those email newsletters I try to pick the ones that matter to me, because I feel like I’m spending more time managing all of the ones that come in there and not have any time to read the ones that I really wanted to read.

So, now it’s time for our parting shots, that one tip website or observation, you can use the second this podcast ends, Tom, take it away.

Tom Mighell: So, my tip — and it’s actually more of a site and it’s a kind of a fun site to play with, it’s not going to be terribly helpful to you, it’s from Google, it’s a new site, it’s an experimental page called Talk to Books, and it says that you can browse passages from books using experimental Artificial Intelligence and it’s not a traditional search engine, but what it’s doing is it’s showing you how Google is teaching Artificial Intelligence about how real human conversations work.

And once it learns that it’s then arguably able to predict how one statement would follow another as a response, and so they’ve gathered about 100,000 or so books kind of as the seed that they have trained and it encourages you to ask questions and see what kinds of answers you get.

So, it’s not something that you’re really going to use in your work, but I think it’s something to see what Artificial Intelligence can do. I just typed in the question, What’s the best way to find a new job? And I got some passages from books that say, Networking can also help you identify new job opportunities, it is consistently cited as the number one way to get a new job. And the next one, Although there are many ways to find employment, two methods have proved to be the best and most effective; networking and direct contact with employers.

So, the results we get are absolutely 100% spot-on, correct with the question that’s asked. And so, I think that as an example of how Artificial Intelligence and Machine Learning are improving, this is a really cool site to look at. So it’s Google Talk to Books.

Dennis Kennedy: Of course the acid test for it will be if it can predict what our train of thought is going to be one after another.

Tom, I want to mention two things; one of course is the availability of the new edition of our collaboration tools book, but the one thing that’s kind of close to my heart these days is the Legal Technology Resource Center’s Women of Legal Tech class of 2018 was just announced today, the day of our recording. And you can see that list on the Law Technology Today website, there’s 25 new women we’ve added to the list making a total I think around 85 or 90 maybe in that range.

And so, for those people putting on conferences who can only find males for their panels, this list is going to be a great place for them because there are plenty of great people they can pick and my compliments both, to this class and the great committee that worked to put the list together and do all the work on that.

Tom Mighell: I saw a number of tweets last week about a coding conference going on in Europe and they were bemoaning the fact that out of the 90 speakers 89 of them were male speakers, so still a lot of work to do here. I think that this list is a great opportunity for us in legal tech community.

So, that wraps it up for this edition of The Kennedy-Mighell Report. Thanks for joining us on the podcast. You can find show notes for this episode at  HYPERLINK “”

If you like what you hear, please subscribe to our podcast in iTunes or on the Legal Talk Network site, where you can find archives of all of our previous podcasts.

If you would like to get in touch with us, you can find us on LinkedIn, on Twitter, and don’t forget, we have got a number for voicemail questions, that number is 720-441-6820. We love to get questions so we can talk about during our B segment of the podcast.

So, until the next podcast, I am Tom Mighell.

Dennis Kennedy: And I am Dennis Kennedy and you have been listening to The Kennedy-Mighell Report, a podcast on legal technology with an Internet focus.

If you like what you heard today, please rate us in Apple Podcast and we will see you next time for another episode of The Kennedy-Mighell Report on the Legal Talk Network.



Outro: Thanks for listening to The Kennedy-Mighell Report. Check out Dennis and Tom’s book, ‘The Lawyer’s Guide to Collaboration Tools and Technologies: Smart Ways to Work Together’ from ABA Books or Amazon, and join us every other week for another edition of The Kennedy-Mighell Report, only on the Legal Talk Network.


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Episode Details
Published: April 20, 2018
Podcast: Kennedy-Mighell Report
Category: Legal Technology
Kennedy-Mighell Report
Kennedy-Mighell Report

Dennis Kennedy and Tom Mighell talk the latest technology to improve services, client interactions, and workflow.

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