Dennis Kennedy is an award-winning leader in applying the Internet and technology to law practice. A published...
Tom Mighell has been at the front lines of technology development since joining Cowles & Thompson, P.C....
As Southwest Airlines learned the hard way, failing to replace your old technology can really come back to bite you in the butt. The guys discuss some of the myriad issues related to outdated tech, from global down to personal levels, and then bring the topic home to lawyers to explain how to stay on top of your firm’s technology maintenance and replacement planning.
Later, Dennis and Tom, talk through the recent LastPass debacles and what you should do when a tool you’ve relied on is no longer meeting your needs.
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 sponsor Embroker.
A Segment: How Will Your Outdated Technology Hurt You?
B Segment: Leaving LastPass
Intro: Web 2.0, Innovation, Trend, Collaboration, Software, Metadata… Got the world turning as fast as it can, here 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 331 of the Kennedy-Mighell Report. I’m Dennis Kennedy in Ann Arbor.
Tom Mighell: And I’m Tom Mighell in Dallas.
Dennis Kennedy: In our last episode, we continued our annual practice of sharing our technology resolutions for the new year. I’m off to a great start, but it’s how you finish the year that really matters. In this episode, we consider the recent stories of organizations that seem to have their own annual technology resolution of not updating or replacing old technology and how that can sooner or later bite them in the butt. It’s okay to say, but on the podcast, right Tom? 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 when it doesn’t make much sense to put off until tomorrow technology spending that you should be making today. In this second segment, we’re going to talk about password managers and why apparently the tools that make us safer sometimes don’t do that. 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 that this podcast is over.
But first up, what’s going on with all the stories we’re seeing about old and outdated software and technology and the problems it’s causing for just the average person? First, I thought the Southwest Airlines meltdown was bad enough, but then the FAA said, hold my beer when it shut down operations of all airlines. And the reasons for both of those issues, all within the just two or three weeks since we’re recording this, seemed to revolve around old technology. We thought there was a lesson in there for lawyers and technology somewhere. So, Dennis, what did you learn from these recent stories?
Dennis Kennedy: Well, first of all, I have yet another reason not to fly. But I think the big surprise really is that we haven’t seen even more of this, especially given the current cybersecurity threat environment where people are really preying on the systems that are old and not updated. And then the systems that run our critical infrastructure, as we see, can be really old and use programming languages like COBOL and things that you can’t find people to do them or update them anymore.
So it’s surprising that they kind of clustered right here together. But I think that I’m not totally surprised that it’s happening and we might see even more of it and remind me of how I think time we both love our friend Adrian Linares’ stories of going into law firms and finding ancient computers still running DOS it’s one of my favorite things that she does and lets us know about.
Tom Mighell: Well, and for those people who may have seen some of this in the news but may not have seen all of it, let’s catch everybody up real quick. So first issue was around Southwest Airlines. I’m sure it was hard to avoid that on the news, but what may have not gotten through in some of the reporting that you saw was that Southwest’s major problems, there were a couple of problems, but the major problem was that its old scheduling software basically collapsed under the weight of a winter storm.
Is that because the storm was playing havoc, that scheduling software just didn’t really work? And it came to light during this whole thing that not the current CEO, but a past CEO made a conscious decision to forego necessary technology upgrades in favor of maximizing shareholder return because can you guess what he said? Can you guess? Our tech has been working okay for 20 years. That’s a great statement that we’ll all remember that. And then a couple of weeks later, came the outage with the FAA.
The FAA has something called NOTAM or I’m not sure how you say it. N-O-T-A-M which stands for Notice to Air Mission Software which is something pilots have to review before every flight, which, by the way, the system was created 75 years ago. I hope that doesn’t mean that it’s all that old, but it was created that long ago. It had a database file malfunction, and that brought down the whole everything that wasn’t just Southwest that was grounding all flights in the United States. And then, interestingly, Canada’s version of NOTAM, whatever, it also failed a day or two later, but that was because of what they called a hardware failure.
So no telling if that was just a glitch or a wild coincidence or not, but there’s just too many things that we’re seeing with old technology. And for me, the theme is very apparent, which is I really don’t know how Southwest fits into my theory. But government agencies I mean, government agencies to me are a big target because they’re going to be systems running on those old platforms like you mentioned. They’re going to be things that have been in place for a long time. And because governments don’t always have the most robust technology budgets, they’re going to be the ones to fail, which, frankly, is a little bit terrifying when we consider some of the things that these systems control.
Dennis Kennedy: Well, we don’t get a lot of transparency, right? So you go like, there’s this hardware failure. What does that mean? Somebody kicked the plug out of the outlet. It’s really hard to know what’s happening and then my favorite thing in all of this is I love when people use the word “unacceptable”. So it was unacceptable, right? That what Southwest was doing and the FAA and Department of Transportation were definitely going to make sure that something was going to be done because that was unacceptable.
And then shortly after it’s unacceptable what happened at the FAA, which sort of means like, maybe they’ll do something, maybe they won’t, who knows? But I think you’re right. And then I think these things that happen do have the sort of aging software explanation, but they’re also symptomatic. They show symptoms of cyberattack. And I would lean that the actual explanation is the aging systems, but there are certainly symptoms if you’re diagnosing cyberattacks do or something you would want to rule out and make sure that we’re protecting against. So I don’t know Tom, maybe that’s just repeating what you said, but I don’t know if you have other thoughts on what might be going on there.
Tom Mighell: I haven’t seen anything to suggest that any of the recent troubles were caused by cyberattacks. But I also think that what I mentioned about the fact that government agencies tend to have the oldest technology, they are the biggest targets for cyberattacks. I mean, frankly, I’m terrified what a bad person could do to our water systems worldwide. I mean, I keep hearing about what bad shape our networks are and how easy it would be to literally cut off water to the entire country just by hitting a few major water systems. And I’ve got to believe that that’s an issue. I think that that’s a huge risk. But it comes down to this. The cyberattack really comes down to the same issues, right?
It comes down to attacking software that has vulnerabilities or hardware that has vulnerabilities. It’s attacking systems that have not been maintained or replaced according to a schedule. So I think that’s really what we’re talking about. Whatever the cause happens to be, whether it’s something that fails or whether it’s more vulnerable to attack, the cause is still going to be the same.
Dennis Kennedy: So Stewart Brand, I know, is working on a book about maintenance. And in our sort of connected systems-based world, I sort of feel that maybe maintenance is the key issue of our time, especially preventive maintenance. I mean, look at bridges, roads, other infrastructure, what we do around our houses, everything out there, and it’s replacing things and sometimes updating them can be expensive. It can certainly be disruptive. And so, you do come back to that point where you say, like, what is it that I really need to fix this year and spend the money on and what can I push off for another year?
We sort of seen it with laptops used to get replaced on maybe a three-year basis. Now, it’s probably easily four, could be five. Who wants to incur the cost. As you said Tom, the technology has basically worked for a long time, we haven’t run into anything, so why spend stuff on something that you can’t see the benefit of? And the maintenance only brings us back to where we were. And its sort of like we know that the roof on our house is old and it has a 15-year-life, and we’re at year 14, so maybe we can eke another few years out of it and then we wonder why the roof leaks when we have a big rainstorm.
So I think it comes down to that, the cost piece of it, and just not where you don’t see like, oh, I’m getting this cool new thing as a result of the money I’m spending. I’m just sort of bringing something I have back to way so it runs well. So I think that’s one thing and then I think the other thing that we see here is that probably, and I would say in the government, when you change administrations, that they just don’t know what they have and who maintains it or who can fix it, especially these days if somebody leaves.
Tom Mighell: I think maintenance is important, but it’s not just maintenance. It’s also knowing when the maintenance is no longer going to cut it, when you’ve got to replace it. And I think that saying, well, this computer has lasted for a good five or seven years. It can last a couple more. It’s not the same as your trusty car, you know. My boss was telling me he’s got a car that has 175,000 miles on it and it is a 21-year-old model that he is still driving around. But I’m less worried about the power grid going down if his car has a problem then I am — so it’s being smart about the technology that you need to replace and realizing that what is the risk if something does go down?
If we’re just talking purely from a legal standpoint and lawyers with their technology, what will happen to you if that equipment fails? How will you be affected by that? And that’s got to be part of the risk decision that you make. To your point that people don’t know what they have, most of our lawyers in the country are solo lawyers. They’re not going to remember what they have. And they were the ones who were supposed to maintain it in the first place. So I think that a lot of this discussion goes to those lawyers who are in a position where they’re having to maintain or replace information themselves if they are working at big firms, and they should have those who are already thinking about this, who already have scheduled, who already are maintaining it. But as lawyers, that’s not part of our lawyer job description. And that’s why we want to talk about it here.
Dennis Kennedy: Well, we saw the pandemic accelerate. The pandemic accelerates some of this movement away. But the evolution of technology also causes some of these things to kind of creep up on you. And you may be going along and then decide that, like, oh, we did that once before, and I know it starts somewhere, and you find out it’s on a floppy disk or something that you actually can’t use anymore, or you can’t access it because of the old version of something, and you can’t do that.
I think there are a number of areas of concerns and how this can happen, but I think that we do really need to start looking at this because these examples show I mean, the fact is there are no planes flying one morning, right? It’s like having no electricity one morning or you’re going to your office and you can’t do any work because nothing is running. The risks are fairly significant in these cases and you add cybersecurity risks on top of that. And I think most people are kind of comfortable saying, if it’s not broken, I don’t need to fix it. And I don’t think that many people are like me who absolutely hates, I hate technology and software that’s not updated, but I always feel like I’m in the minority on that. So, Tom, I would say that the good news for our listeners is I think that we have an approach and plan to help them out with this. But first but first…
Tom Mighell: Let’s take a quick break for a message from our sponsors.
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Dennis Kennedy: And we are back. Tom, not to put too fine a point on it, but the basic approach and plan is in the new version — actually, it’s in the old version of our Collaboration Tools book, isn’t it?
Tom Mighell: Well, of a sort it is. I mean, our book is talking about understanding the collaboration tools you have, not necessarily all the tools you have, all the hardware. I mean, we don’t really talk about things in terms of understanding what you have from an entire technology portfolio. We’re more talking about collaboration. But I think the same principle applies, which is understand what you have and understand kind of what the schedule should be for those items? What should you be doing? When and how should it be maintenance? Should it be replacement and have that documented? I think that there’s more to it, but tome that’s kind of where it starts. Right, Dennis?
Dennis Kennedy: Yeah, to me it’s like audit it, map it, then I think, importantly, figure out what’s missing and then you start to look at what’s critical of importance to you and then where are the risks at, and then kind of do it on a portfolio basis. You’re probably not going to upgrade every single thing you have in one year, so you’re going to have to set priorities. But to me, it’s sort of like figure out where the risks are, where you get the return on your investment in the upgrades and replacement and maintenance, and then do the cost benefit thing to say, okay, so here’s the sequence, here’s some staging on that. And that’s the approach that I really like and just say, like, hey, everybody else does it on this schedule. Figure out what makes sense to you because what you rely on and what’s critical for you is probably going to be different than what it is for somebody else that you’re talking to.
Tom Mighell: Well, I think that looking at risk on return on investment and that sort of thing is necessary if you can’t afford to keep your technology updated or if you have to put it on a multi-year schedule. And keep in mind, we’re not talking here about keeping bleeding edge technology in place. This is not about having the best and finest all the time. Obviously, if you can afford it and you want it, then you do you. But I would say this is not what we’re talking about. It’s a matter of, like we said, creating a technology inventory both software and hardware, and then setting up a repair or replacement schedule for everything.
For software, I think that we tend to recommend updating it when new versions come out. I think that the only software that I can think of that people pause on is new versions of Windows because there are sometimes some bugs to iron out. But most types of software that we have these days are more incremental, smaller versions that are easy to update, and there’s no reason not to update these things. I think we’re long past the time where you need to wait a few releases to update it.
For hardware, I would think that the hardware is going to be well, although outdated software unpatched is one of the biggest weaknesses for getting attacked by a hacker or some type of cyberperson. But hardware, I think, is where you need to really kind of create your schedule, which is, how do I need to maintain this and when should I think about replacing it?
And Dennis mentioned, I think the ideal lifespan of a computer is three years, but people have been going from five to even up to eight years if you have proper maintenance on it and if you’re regularly cleaning it, if you’re replacing aging components when it’s necessary, whether that’s a computer or whether it’s other hardware, you can probably extend the life and say, okay, this year I’m going to replace this. I’m going to replace this every three years, I’m going to replace this every four years. I have a schedule and a plan for it.
If you don’t have a maintenance schedule that’s part of that, and you don’t keep up the maintenance, your five-year plan may turn into a three-year-plan, and it may mean that you have to replace it much sooner. So be thoughtful about that and decide it doesn’t have to, albeit once. I think that if you plot out the hardware that you’ve got and kind of make decisions about how often you can base on the budget that you have, I think it can turn out to be fairly reasonable, I would say.
Dennis Kennedy: Well, I would say the other thing on hardware that still surprises me is that as firms push the number of years out, then you have really unhappy employees because they have crappy hardware that’s worn out, I mean it’s no fun to say, like, I’m working at a premier law firm and I have a keyboard that some of the letters are worn off, or that I have to make sure I press a certain key the right way or it doesn’t register those kinds of things. And I think you tend to see a little bit more of that. The other thing that I like to do in more and more things these days is kind of figure out what my desired end state is and to work back from that to say, like, if I had this to where I wanted it.
I avoided this sort of obsolescence issue. What would things look like at the end state, and then what are the phases that get me there in the best way and kind of work back from that? If you say, I see that we definitely have big problems, then I think that most of the time, slow and steady is going to win this race. If you’re setting your priorities well, except that there are going to be some things where you potentially guess wrong and you’re going to wish that you went a lot faster. And then I think the big news in all of this, and this again, is in our book, and it was made clear throughout this pandemic is that the cloud gives you a lot of benefits.
And one benefit is that your software stays up to date, and that’s a huge benefit, and that’s something where you’d say, hey, part of what I’m doing maybe is not this updating thing, but part of my strategy is to move things into the cloud and into cloud platforms. Tom, I know we want to wrap up here and I think there are things, it’s like a plan and schedule and all that, but in this area, there’s this phrase I came across called technology debt. And in this context, I liked it and this is my approach to it. So I’m not sure I’m using the term exactly correctly, but I think of when you own a house and you say, my roof is getting old, my furnace is getting old, and you see it with your car as well. So your friend with the car, I’m sure it does this, where you say, I know I have to budget a certain amount because these things are going to become due and you can build up this sort of technology debt because the spending is going to come and I think that part of what you want to do is to say, if I need to do this, what’s the cost going to be because if it does accelerate, I’m going to be experiencing those costs. And I sort of like that debt notion as a way to think about this idea as well.
Tom Mighell: Well, the way I like to think about it is a little bit like a credit card, which is when you cut corners or when you underspend to maintain your equipment like Southwest, when you choose investors or shareholders over technology, it’s like making a minimum payment on your credit card. You are saving money now, but that debt overtime is just going to increase and increase in balloon and ultimately, it’ll take you over. So, yeah, I think that’s an appropriate way to describe this. And then finally, we’ll just wrap up real quick by saying again, there are not many topics we cover that would not fall under that duty of technology competence that we talk about so often, which is, do you, as lawyers, have some duty or obligation to understand what the timeline is, what the lifespan is of the technology that you have?
If you are prevented from providing services to your clients because your technology is old or outdated or needs to be replaced or repaired because you did not adequately plan for it, then there arguably are some issues around that duty of technology competence. So, again, this is one area where we think having that knowledge, having an understanding of how your software and hardware needs to be maintained, repaired, replaced, what have you, is going to help you better be able to serve your clients down the road. All right, 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’m Tom Mighell.
Dennis Kennedy: And I’m Dennis Kennedy.
Tom, I wanted to talk about password managers, which have always been one of our most important recommendations to improve your cybersecurity. Well, it turns out that they also can have their own issues, and Tom has landed a little bit on the wrong side of those issues with his current password manager. We thought it would be instructive to talk through Tom’s approach to dealing with some of the questions that he’s had to face recently. Tom, have you made your last pass at LastPass? Did you see what I did there?
Tom Mighell: I did see what you did there, and I’m not sure that it’s accurate to say that I landed on the wrong side of the issues. I don’t really think this is any different from our discussion a few episodes back on rethinking our social media strategy. I mean, it’s not different from landing on the wrong side of Twitter at some point. The real question is when a tool you’re using suddenly becomes a tool you no longer want to use, what do you do? How do you approach that? And that’s really, as Dennis said, that’s the case with LastPass.
Some of you may be familiar with what’s been going on in the news. Other commentators have talked about it. At one time, LastPass was, in my opinion, the best password manager to have, and I’m pretty sure that I said that a lot on this podcast. It was the first password manager to be available for all browsers and all operating systems. It was free, and then it was the least expensive and best working password manager. Its nearest competitor was only available for Mac and iOS, part of a walled garden, which, you know, I have some fundamental issues with, and at a much higher cost. It was a whole lot more expensive than LastPass. Fast forward a few years, and some things have changed. You probably have heard some unsettling stories from LastPass. There have been several internal data breaches at the company, and recently we learned that the threat actor that was involved in the most recent episode was able to obtain a back-up of customer password vault data. That means my data, I think, if I’m reading that right that’s what I interpreted, that contains both unencrypted data like website URLs, but also encrypted fields that include your usernames and passwords.
Now, LastPass has something called a zero knowledge architecture, which means it would be very hard, if not impossible, for this person who got it to actually break into this information, because it can only be encrypted with a key that is based on your master password. So with LastPass, you have a master password, and that’s what encrypts your passwords. And as long as your master password meets best practices, as long as you’re doing the right thing, it’s long, complex, it’s not easy to guess, it would take probably millions of years to break into your passwords, and I’m confident I’m reasonably satisfied that my data can remain safe.
I do trust that my master password is strong, but I can’t say that my trust for LastPass is the same anymore. I feel like of all the password management tools, LastPass is, to my knowledge, the only one that’s been having these types of issues. I haven’t seen them from any of the other major players. And I just don’t think that I have that level of faith anymore that you need to have with a password management company, even if in their press release, they said it will probably take a million of years. Well, that doesn’t exactly inspire confidence in your security level. And when you need to have a level of confidence with your password management company that holds the keys to your kingdom, then that’s significant. And so that was the problem with me.
And in the meantime, the other company that I mentioned was way far behind, has been making a lot of strides. It’s now on all platforms. It’s pricing is competitive for the LastPass. And so it was actually an easy decision for me to make. I looked at a couple of alternatives, and frankly, the security experts say you can’t really go wrong between any of the three of these; 1Password, BitWarden, Dashlane, those are three of the password manager tools.
They all get good reviews from the security experts. I went with 1Password. It’s only been a few days, but so far, I’m enjoying it. I compared it against those other tools and found that this was really the best tool for me. Although I will say that 1Password has one requirement that feels a little bit off to me. It gives you this thing called an emergency kit, which is a PDF file that has all the information that you need to recover your account. And I’m like, okay, what do I do with this? This is sensitive information. And they say, well, put it in your safe deposit box. I’m like, okay, that makes sense. I’ll put a copy in there and then they go, also keep a digital copy in your cloud document storage application.
And I’m like, well, that seems insecure. What happens? I’d like never to believe that my OneDrive will ever be compromised, but you can’t say that about any cloud tools. It’s possible that stuff is going to get broken into at some point in time. So I’ll be encrypting that file myself and making sure that if somebody gets it, they can’t get into it without knowing a password. I will say I’m happy with the change. I think it has been a good experience, because I had to take a look and say –
All right, what matters tome, what’s important to me in terms of my security, I looked at all the options, I weighed what was important from all of those, and I thought it was a good example for me of finding another solution when your current technology is just not working out for you. That was a long answer on my part Dennis, any comments to it?
Dennis Kennedy: Well, I use 1Password and I’ve been happy with it and think that you go through this sort of thing and there’s a number of things that can come up. So consolidation in the industry, somebody buys a product that you use, especially security product, you would say like, do I have the same confidence level? Do I have some concerns about that? And then you look at maybe it is the time to switch and you go through the same analysis that you did to say, well, what’s the actual risk? I think this other piece for you and me and some of our friends is there comes a point where you say probably when people ask me to recommend something, I’m going to drop a product off the list just because and kind of steer them in a different direction.
And all of those things, I think, can come up. But it is something that we see more and more often that especially with consolidations, where a company has taken over or gets new management, you start to wonder about that, but pay attention to the news and some of it, especially in the cybersecurity area, can have a big impact on you. 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 I am talking about two tools that I purchased this past week that are really great. I finally made the move. I know it’s been — how long has it been since we’ve all been working from home, but I talked a lot on this podcast about my beautiful big 49-inch monitor. But I’ve never used it as my work monitor. I’ve always used the tee tiny laptop and everybody gives me grief about it.
I finally have been able to connect it to a dock, but I have my home computer and I have my laptop, and I want to be able to be able to work on both. And that means having a keyboard and mouse that is easy to switch over to both because they’ve got to be connected to both computers in order for you to use them. So I found both. They’re both Logitech tools and I’ll put links to them in the show notes. The mouse is a Logitech MX Master 3s and then the other one is a Logi Keys, I forget the exact name, but you’ll see the link in the show notes.
What I like the most about them is they allow you to connect to three different devices and they have buttons on the bottom of the mouse and they have buttons on the keyboard, 1, 2 and 3. And you can, with Bluetooth, connect to those two, three different devices. And so it is so easy for me to switch from my work laptop to my home computer by just pressing one of the two buttons. And I don’t have to worry about disconnecting or doing anything or having two sets of keyboards or mice.
I can easily go back and forth between those computers with just the press of literally one button so highly recommended if you are going between two computers, this is a great option for you. I’ll put those links to those Logitech tools in the show notes. Dennis?
Dennis Kennedy: So I have something new that I really like too, that I just bought. And I like it so much that even though this is an audio podcast, there’s a part of me that wants to hold this up so people can see it. So it has a huge long name and but I’ll describe what it is so it’s called the Quartet Glass Desktop Computer pad, 18 inches by 6 inches. So think about that, 18 by 6. It’s whiteboard, dry erase surface. And what it is, is this small rectangular whiteboard with the glass tops, which is a glass type of whiteboard. And it’s slanted a little bit and you put it up by your monitor and it sits there nicely. And you have dry erase markers and it’s like perfectly situated, so you don’t have to use Post-it Notes or little notebooks. And you can jot notes to yourself and put them in colors. You can draw little pictures to remind you of things. And it’s one of these silly little things that it’s hard to convince somebody to say, like, you actually need one. But once I got this, I was like, I don’t know how I could have lived without this.
Tom Mighell: And 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 on the Legal Taught Network’s page for the show. If you like what you hear, please subscribe to our podcast in iTunes, on the Legal Talk Network site or within your favorite podcast app. If you’d like to get in touch with us, reach out to us on LinkedIn, on Twitter if we happen to be around.
And we might complain about that more in an upcoming episode or leave us a voicemail. Remember, we like to get voicemails for the B Segment. That number is 720-441-6820. So until the next podcast, I’m 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. If you like what you heard today, please rate us an Apple Podcast and we’ll see you next time for another episode of The Kennedy-Mighell Report on the Legal Talk Network.
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|Published:||January 27, 2023|
|Category:||Legal Technology & Data Security , News & Current Events|
Dennis Kennedy and Tom Mighell talk the latest technology to improve services, client interactions, and workflow.