Kennedy-Mighell Report

Home Tech vs Work Tech: Managing the Intersection

The technology lawyers use at home can differ greatly from that at work, especially in medium or large law firms. This can result in two separate technology worlds that are at best difficult to manage. Many lawyers have multiple smart phones, calendars, computer operating systems, or even versions of Microsoft Office. For some, commingling systems can be the answer, but this can cause security and organization issues. So how can we effectively bridge the gap between our dichotomous technology lives?

In this episode of The Kennedy-Mighell Report, Dennis Kennedy and Tom Mighell discuss managing multiple tech personalities, how to bridge the gap (or not), and ways lawyers can organize their technology. Tom mentions how iPads and other popular home devices mean people have better personal hardware. Because of this, we might need more workarounds including bring your own device (BYOD) policies at law firms, but we need to be aware of the risks and benefits. Dennis talks about the three tech crossover scenarios: totally synced, partially synced, and independent systems. Dennis and Tom then discuss how partially synced lawyers can effectively organize their tech to reduce chaos in areas like passwords, contacts, calendars, and website bookmarks.

In the second half of the podcast, Dennis and Tom talk about Twitter’s move away from reverse-chronological order. They talk about feed relevance, events playing out in real time, and whether they’re happy with Facebook and Amazon’s algorithm. As always, stay tuned for Parting Shots, that one tip, website, or observation you can use the second the podcast ends.

Special thanks to our sponsor, ServeNow.

View transcript

Kennedy-Mighell Report: Home Tech vs Work Tech: Managing the Intersection – 3/11/2016


Advertiser: 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 166 of the Kennedy-Mighell Report. I’m Dennis Kennedy in St. Louis.


Tom Mighell: And I’m Tom Mighell in Dallas.


Dennis Kennedy: In our last episode, we took a deep dive into notifications and reminders and how you might make them work better for you. As we discussed that topic, it became clear that many of us have different approaches in the home and work settings. I really hesitate to use a term like technology schizophrenia, although it might seem that way to some of you. But it does feel like we have multiple technology personalities, at least metaphorically if not clinically. Tom, what’s on our agenda for this episode?


Tom Mighell: Well Dennis, in this edition of the Kennedy-Mighell Report, we will discuss the issues and challenges in dealing with too often very different worlds of work tech and home tech. In our second segment, we’ll talk about the hubbub of rumors that Twitter is going to do away with the reverse chronological order we all know and love. And as usual, we’ll finish up with our parting shots, that one last tip, website or observation that you could start to use the second that this podcast is over. But first, let’s talk about managing what may be your multiple tech personalities. Unless you work for yourself, you probably find that the technology that is chosen at work often differs from what you would chose to use in your personal life, sometimes by a great deal. This can sometimes lead to what we think is kind of like schizophrenia and how we are forced to deal with technology. Dennis, I know we’ve talked about this topic, we’ve touched on it in the past episodes, but I think we handled it and talked about it in different ways. What made you want to dig into it for this episode?


Dennis Kennedy: I think that I run into so many people who talk about having such radically different technology at home and then at work. I know a lot of people who are Mac at home and Windows at work. You and I are both that way with Mac at home, Windows at work. We have people who have iPhones at home and maybe the Android phone or Blackberry even at work. So there’s this big separation that you find, and there are a whole bunch of examples, not just basic hardware but software services, all these other things. So maybe really focus on it because it seems like these days it’s hard enough to keep up with one technology. But if you have two sets of technology that seems to make it even harder. Also I think that because it seems these days that most people have a lot better technology at home than at work and that didn’t always used to be the case. So many people were asking me things and you realize you were crossing a line as you went between work and home and it was a common thing that I wasn’t the only one who was facing.


Tom Mighell: So I’m going to take somewhat of an issue with you during this episode – not too much – but I really want to try to figure out what are we really talking about here in terms of different tech at home than at work. Because to me, I think of myself as an exception because I work for a small company. So my home tech works with my work tech, it’s just the way it is. You’re right, I use some different things at home than I use at work and we might talk about some strategies for how you might do that. But I think that this problem is especially a big deal where for our listeners, this is probably a bigger deal than people who don’t listen to this podcast. But if you really care about the technology that you use, then I think you’re right. You are likely to have better tech at home than you have at work. I would say that there are many people who have poor or no technology at home because they rely on whatever they get at work. I also say that to the extent that iPads have kind of gone through the roof in the past couple of years and what people have is what automatically gives them better tech than what they have at work. If the tech is better at home, I think there’s two reasons for that. The first reason is that work refuses to upgrade. We’re not going to upgrade because there’s no need to do that, we’re perfectly fine with what we have. Or maybe a slightly related version where work doesn’t refuse to upgrade, it’s just unbearably slow at upgrading and does it much longer after you or others have moved on to better and newer technologies. I think those are some of the reasons why we might see your home technology being different from work technology, but I guess I’ll come back and say it. What are we really talking here besides my work computer? I have a laptop; my home computer, I have that. When we talk about everything else – and I guess to the certain extent your phone is going to be one. But what else are we talking about here?


Dennis Kennedy: There’s a hardware element and I think it comes down to if you can argue whether it’s better tech at home, but it has to be newer tech. So for me, newer versions of software just across the board. Newer because you tend to be on a faster update cycle across the board. So what I see a lot of is that people are using an older version of, say, Office at work than opposed to at home. You might be using different email programs. I know a lot of people use GMail for personal and they’re using Outlook at work. There can be a lot of separation between that. Tom, I really enjoyed our experiment with Slack just ourselves for the podcast. But I don’t think you would typically see Slack being used in a lockdown work place like a law firm. So you say in each of these categories, it’s possible that I’m using a completely different set of programs or possibly newer programs at home than what I use in the office. Not a terrible thing in some ways, but it really kind of forces you to think separately about each of the domains that you’re in. So does that help, laying out my thinking on this?


Tom Mighell: Well, it helps, but I’ll push back on that. I agree with you on the hardware issue, there’s not much I could talk about with hardware. With software, I agree wholeheartedly about Office. I like to have the most recent version of Office. I think there are some real challenges with using different versions of Office. I use the most recent version of Office because I took the time and I spent my own money to get my own Office 365 subscription for personal use. So I use that software for work as well and everybody else in my company is on Office 2013, which I would imagine most law firms are on. And maybe if they’re not on Office 2010, they’re somewhere in between the two. But I will say that every time I get a document and I save it again, I get the message you are saving it into the newest format. And for the most part, that doesn’t make a huge difference, but I would imagine there are some times where you have formatting issues or you have features and spreadsheets with formulas or other more complicated spreadsheets that could be lost because you are saving it in a different version. I would argue that with email, there are ways to deal with that. We have GMail because it’s a convenient way of getting our email. But I can get my GMail through my Outlook just as easily as I can on Exchange email too. So I think that the reason why we have technology different at home rather than having it as it is at the office is simply because it is different and very few of us are likely to have it. Exchange servers at home for email or other things that are singular to an office environment and so to a certain extent there are a lot of things that have to be set.


Dennis Kennedy: I think you’re right and that gives it the notion of work arounds. There are ways to bring things closer together that make this work. So I think there’s hardware, there’s software, there’s the internet services that we talked about like GMail, Slack and other things like that that you may not be able to use at work depending on the office you’re in. The other thing is what I’ll loosely call data or information. So personally I use things like Evernote. I use Omnifocus as a task manager. Like I said, Dropbox, other things like that where they’re just things that you do routinely. I might use iCloud or Google Photos. Different things like that that I’m just used to using personally. So I would suspect for a lot of people if you look at your computer and the most commonly used programs and services on your work computer and your home computer, they’re going to be different. I think the emphasis is going to be different and that becomes part of this and then that gets into the whole notion of siloing. Either by policy or by the technology where you say I would like to have all my to do’s in one place. I’d like to use Evernote in the same way, I’d like to move things back and forth between work and home. My situation a Mastercard is probably different to other people in how a secure environment I work in and how separate those things have to be. So that emphasizes this notion for me. But I think anybody listening, if you just look at your computers and say at home and work and say what are the main programs you use and what you do with them, I think you’re going to find that the emphasize is going to be significantly different.


Tom Mighell: My problem is that because of the nature of the company I work for, my experience is not different. I use pretty much what I use at home what I use also at work. So there’s two to me. I agree with you on the idea of workarounds and I’ll think about two ways to approach the workaround. The first is the more formal way. I guess it probably didn’t start as a formal way but it’s grown into a formal way and that is the whole BYOD movement. Instead of dealing with tech schizophrenia by having your own stuff at home, bring your own stuff to work and see if you can use it there. We’re starting to see more blending in the workplace nowadays. We’re seeing offices incorporating Mac and Windows. I know that TECHSHOW has got a session on Macs and Windows in the same office. And not everybody likes BYOD. There’s a lot of our friends who will say there are downsides to letting your employees bring their own technology in. Security is a main issue, company information on personal devices of course is something you would want to control or avoid entirely. But the downside to not having a BYOD policy is that workers are going to be forced to stick with either incredibly slow or no upgrade at work. So the challenge I see that firms have is that if they don’t want personal devices and don’t like BYOD, my personal opinion is they need to be more forward thinking and responsive to employee technology means. Now we can all laugh and say haha, that’s not going to happen. Then for me, that other workaround is you talk about using Evernote and Omnifocus. I use Evernote too, I don’t use it for work. I prefer – actually my team uses OneNote and that tends to be a better note taking tool for my team. But I use that at home as well. But I guess my question to you is – I’m guessing, and this is part of my ignorance of what some companies allow and some companies don’t allow – my guess is that other employers wouldn’t allow downloading of the Evernote client to your desktop but can you still get to the Evernote desktop through a web interface too or do they block those as well?


Dennis Kennedy: Well I think that both things can happen. So one is you may find that you have to get significant approvals and have an application loaded. So you have to go through an approval process and that could be a deterrent. The other thing is you may find that in certain cases that you can’t upload files – maybe some other things like that. So it depends obviously on the firm, sometimes the industry, other things like that where there may be some issues on those cases; so those things do come up. I guess Tom when I think about this, I sort of divide this into three common scenarios. One is which I call totally synched or almost totally synched where you have essentially almost the same thing at home and at work. I think you showed that you fall into that camp.


Tom Mighell: Pretty close, not exactly.


Dennis Kennedy: That can happen I think in smaller firms where you say even if you have a Mac, you might have a virtual desktop or run a program like Parallels and other virtual desktop type of programs. Sync up GMail or other things from Outlook so everything’s pulling from multiple places and showing up in Outlook for you. So let’s just call it synced and then also your data is available at home and work in the same way. You see some of the issues with that on the security side as you alluded to as how secure is the home computer compared to the work computer. Second category I would say whether some overlap and some syncing. So this is the middle ground that may be helpful in a lot of ways but also may give you not the best of either world and then something that I’m probably closer to and probably the lawyers at bigger firms would be and probably most corporate lawyers as well where you have either independent systems or parallel systems. For me those three categories are a useful way to think about approaches and how you might deal with the issues you may run into. Tom, is that a fair assessment?


Tom Mighell: I think it is and I  think that as you get down to that last category your options become a little more limited and you’ve got to make decisions about how you’re going to manage things whereas if you’ve got the ability to either have some overlap and syncing then you have a few more options at your disposal for being able to use certain types of tools. I think there are pros and cons for each approach. What are some of the advantages and disadvantages that you see to those approaches?


Dennis Kennedy: I think that the synced approach, the advantage is that wherever you are whatever you’re using, you’re going to have access to  everything in pretty much the same way. So that I think is a big benefit of that approach. I think it’s sort of hard to do especially with what we talked about before. If you have an aging work computer versus newer stuff at home, your experience is going  to be different. If you have a computer with a drive on it versus one that doesn’t, the performance is just immensely different these days. In some ways, for me, having the independent or parallel approach is that even though there are drawbacks, you can do whatever it is that I’m forced with what I have at work but I can do whatever I want at home. So in some ways that lets me be more creative and do more things with my technology at home. And the middle ground I think is where there’s opportunity. The synced and the parallel approaches to me are pretty straightforward. I think what might be interesting for us to look at is whether there’s some overlap or potential of overlap. Because that’s where I think probably most people fall in and that’s probably where you can help yourself the most by thinking through some of these issues.


Tom Mighell: For me one of the biggest examples of that is the idea of contacts. I developed the habit of not wanting to keep all of the contacts that I’ve gathered over the course of my life in my work contacts. I’ve got my work contacts there but all my personal and other contacts I prefer to keep with my personal computer with my GMail or Google Contacts or something like that. But being able to have contacts to all of those contacts are important still. I want access to all of them in the same place rather than have to go to two different places. There are a number of apps out there that are very similar to some of the email apps that will allow you to add more than one account. There’s a contact app, I know FullContact is one, there are other apps out there that you can say what types of contact accounts do you want to set up and it will combine all those for you, eliminate duplicates, show you what they’re doing on social media and do all sorts of powerful things. I think that like you said where there’s overlap like that, the opportunity there is to go and try to find the tools that allow you to work in both worlds with minimum friction while still remaining in compliance with the policies of office where you still have to keep certain things separate.


Dennis Kennedy: I think the contacts thing is a great example because when you have the separate sets of contacts, it can be tricky to get those synced up and you probably end up pretty consistently with a couple of different sets of contacts and then not having the information you want when you want it because that’s how things seem to work these days. I’d say bookmarks, other things like that to the extent you use those things can be different in different places. And then the other one I think can be really tricky for people because of policies are passwords. So a password manager is totally recommended, but if you work at a place where there’s a policy that says you can’t write down passwords or store them in a password manager, then you’re really going to feel a difference between home and work because password managers make such a huge difference. So Tom, I think that the idea I wanted to talk about is how do people deal with this? What are ways to help yourself when you find yourself in these mixed worlds? Because you do want to cross some gaps and figure out how to help yourself. I think it’s the usual technology approach which is to first admit you have a problem is to do a little technology audit. But just start to look at your home screen on your computer at work versus your home screen at home and start to think about what’s different and where do you run into little problems where you’d like to be able to do the same things in both places and that can point you to some of the opportunities you might have. I think it’s as basic as that, right Tom?


Tom Mighell: Well I think so. My best advice for this is to really find a way to make things overlap as much as possible to try to find solutions; so we’ve talked about a couple of them. If you’re using a Mac at home, I have a Mac at home I use as my desktop computer, but I installed Parallels on it to take advantage of Windows so I can use Word and Excel and Outlook and I can have access to all of my work stuff here if I wanted to. So that’s how I make that overlap. You mentioned using Omnifocus for your task manager. I think that Omnifocus is widely regarded as one of the best task managers out there. Its one limitation is that it’s Mac only. That’s why the task manager that I’ve chosen is multiplatform, so I can access it from an app on my phone, I can access it from a web app, I can access it everywhere. So I think that’s part of the challenge is that once you identify those areas where there might be some separation where you might be looking at I have to do it one way for work and one way for home is to start to think, are there tools that can bring me closer together. Generally, this also depends on the policies in your firm or your company. But generally I find that that overlap usually comes around the internet somehow, because the internet is the great equalizer in finding a tool that you can access just through a web browser in most cases is going to provide enough overlap for you to solve that problem, but not always. But that’s why you need to evaluate it and decide what are the most important things you need to look at.


Dennis Kennedy: I would say look for the places that are giving you the biggest source of stress. And when you are up against policies that seem to be put in place several years ago that don’t apply to now, I think you change policies by giving people specific examples of what is a problem, what you want to accomplish, how it would benefit a client, is it safe and simple, those sort of things. So a password manager, once you’re able to say here’s how it helps me at home, then maybe you can make the case for changing the approach at work. Then I think if you can pick a few of those – for me it’s always three of them – just pick three of them to say how can I work on this. And maybe people listening will say Tom is saying he can actually grab his GMail and pull it into Outlook. That may be news to people. So if you do some exploration, talk to an IT person, do a little research, you may find that there are ways to go back and forth. Calendaring may be another example where you keep separate calendars or maybe filter out work stuff so it’s not going into a Google calendar. But get some kind of synchronization. But I think you’re right, Tom. Ultimately what you’re looking for is called synchronization. How can I do some things in both places and make that easy and to kind of simplify things from there so I don’t have to feel that I have to do something completely different in each place.


Tom Mighell: I think you’ve completely covered it right there. For me, the idea is to not complicate things, and that’s why I like the notion of finding a way to make those things overlap as much as possible. Don’t force it. There’s something to be said about trying to bring about good change at your company in terms of technology and Dennis will be the first to tell you that having a technology committee that can discuss those types of issues and be a force for change for the lawyers who want to have better technology is a good place to start. But it’s also knowing how far to push. For some companies, the security aspects of this are really significant and need a lot of consideration before sometimes companies make a move with anything. Before we move onto our next segment, let’s take a quick break for a message from our sponsor.


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


Dennis Kennedy: And I’m Dennis Kennedy. If you have never quite understood how hashtags work on Twitter, there’s been a great lesson over the past few days with hashtag RIP Twitter. So a rumor surfaced about Twitter moving away from its classic reverse chronological order for delivering your tweets and going to an approach where tweets would be delivered on the basis of some secret algorithm that many felt would be optimized for advertisers more so than for you. I already believe that the Facebook update algorithm for me must be set on random because I can not figure out why one update appears ahead of another or why updates from several days ago keep appearing. I just like that simple, reverse chronological order. So my thought when I first heard it was oh, not you too Twitter. So there’s a lot of gnashing of teeth and proclamations that Twitter was dead to many after they heard this. So you get the rise of the RIP Twitter hashtag, which definitely got the attention of Twitter when it was trending that people thought that Twitter was going to be dead to them if they moved away from this reverse chronological order. Tom, are you in the say it ain’t so Twitter camp on this one?


Tom Mighell: I would say yes and no. The first answer is that technology changes. Things change all the time and we adapt and evolve and move on. You may disagree with me but Google Reader went away and I think we adapted just fine. The trio left and was no longer a device we could have anymore and I get along with the new device just fine. Whatever Twitter throws at us, we will evolve and move on and someone will develop a way to deal with that issue or will find a new way to consumer information if they we to. But I will say the day that Facebook decided to show me a random set of posts was a very dark day for me. I don’t check Facebook all the time, I just checked it a couple of times today. I just want to see what happened for the past few hours and with Facebook’s default feed, you’re going to see posts from all sorts of different times. More than once I think I have replied to a post that turned out to be several days old and my response was out of date. Now that’s my bad for not paying attention, but I think it’s still confusing. And what’s interesting to me is reading about this is that someone at Twitter said that reverse chronological order isn’t the most relevant experience for a user, which I think is kind of insane, frankly. One of the most popular uses of Twitter, maybe not insane but maybe just doesn’t understand the user of the product. Because to me one of the most popular uses of Twitter is to provide running commentary on something that’s happening live. Political debates, conference presentations, the Superbowl – we’re recording this just after the Superbowl and oh my gosh, all we saw were people who were commenting on that. If suddenly you see things that were out of time, it would be a really bad experience. However, I will say that if the goal is to show you what’s relevant, so if I could catch up a feed that was ordered on what’s most important to me wouldn’t be an entirely bad thing. I could quickly catch up on the stuff that I missed and I think that’s the goal is while you are out, these were the sorts of things that you missed. And I wouldn’t have to go through all the junk, because there’s a lot of junk on Twitter. So for me, I would want to have the ability to have both of these views. A view for what’s relevant, and a view for what’s recent, frankly. I’ve read that Twitter is going to give users the ability to opt out of this new format but it’s probably going to be the default. So I may be thinking about changing out of the default. I think choice, though, is generally a good thing and I hope that Twitter makes that choice easy.


Dennis Kennedy: I think choice is the key for longtime users – and I think you and I are about as long time as it gets on Twitter that the idea for me would be if I can just go back to the classic style, that’s fine. And I think the trouble is when people say this isn’t the best way because we’ve figured out this algorithm that can bring you the most relevant tweets for you. There is a tradeoff and there is a certain appeal for that. If you can say what’s best that I don’t have to sift through things in reverse chronological order that don’t make that much sense for me. I think that works if they actually get it right. I don’t see Facebook getting that right for me. I’ve been experimenting with Amazon’s recommendations and adjusting those and I’m not wowed by that at all. So I’m not sure that the tradeoff is there yet. I don’t think they do a good job of targeting ads at me so I doubt that they can get my timeline in the order that’s most relevant to me. I also think you’re right that especially at the Superbowl and stuff, when you watch stuff in real time you want that reverse chronological order to see what’s going on. I think it would be weird to say if you watch a football game nowadays and there’s a play and there’s a challenge, you kind of want to see what other people think. Were they out of bounds, whatever. It’s one way to use Twitter real time search. I just think it would be weird if there were a challenge flag thrown and you didn’t see anything on Twitter until half an hour later where there’s a tweet that says, “Can’t believe he threw the challenge flag there.” I don’t know if that’s helpful, so hopefully they don’t go in that direction. But I think, Tom, change is inevitable. There’s been a zillion changes to Facebook, there’s been a zillion changes to other things, we sort of adapt. I hope Twitter gives us the classic view, but probably some Twitter app will allow us to be able to sort the tweets in the way we want and maybe, ultimately, that’s the biggest benefit that comes out of this. Now it’s time for our parting shots, that one tip, website or observation that you can use the second this podcast ends. Tom, take it away.


Tom Mighell: So I have mentioned the Note To Self podcast on previous episodes before. Note To Self is from WNYC, it’s talking about the social aspects and dealing with technology in a human way which I think provides some fantastic advice and ways of dealing with technology on a human level. This past week, they introduced something called Info Magical, and it’s designed to attack the problem information overload. Ever want to be creative, more knowledgeable, more up to date on the news, more in touch with family and friends, more in tune with yourself, and they want you to take part in some experiments designed to help you focus and discover the magic of clear thinking and to reduce information overload in your life. There are five podcasts, they’re all about 15 minutes each to listen to, maybe a little more, some of them. They provide some interesting suggestions for changing the way that you consume information or deal with it to try to take back your life and get away from information overlap. I can’t say I want to try all of them out but I’m intrigued by them. All you need to do is head over to and you can try it out for yourself.


Dennis Kennedy: I admire the effort of those. I was a little bit underwhelmed with the actual suggestions, but I think for other people they can find some really valuable suggestions there. I just fill in the not for me category.


Tom Mighell: I did too on some of them, but I would say that for a lot of people, the small steps are good steps.


Dennis Kennedy: Right. So as listeners know, Tom and I love our Amazon Echos, and we probably love even more Amazon Prime. If the free two day shipping was not enough to make you an Amazon Prime member, it’s really interesting how they’re starting to add more benefits for Prime members. Videos, music, all the things associated with Amazon Echo. Our friend, Sabrina Pacifici at posted a link the other night to a new Amazon Prime member bvenefit which I think is 6 months free digital access to the Washington Post, and then a discount after that trial period. I went to law school at Georgetown, read the Washington Post all the time when I was in law school, and this is really appealing to me for that reason alone, especially in election year. I also think it shows you the way that Amazon is started to load up that Amazon Prime with some really interesting benefits beyond just the shipping thing which people already love.


Tom Mighell: So that wraps it up for this edition of the Kennedy-Mighell Report. Thanks for joining us on the podcast; information on how to get in touch with us, as well as links to all the topics we discussed today, is available on our show notes blog at 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 to all of our previous podcasts. If you’d like to get in touch with us, please email us at or send us a tweet. I’m @TomMighell and Dennis is @DennisKennedy. So until the next podcast, I am Tom Mighell.


Dennis Kennedy: And I’m Dennis Kennedy and you’ve been listening to the Kennedy-Mighell Report, a podcast on legal technology with an internet focus. Help us out by telling a couple of your friends and colleagues about this podcast.


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