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Dennis Kennedy

Dennis Kennedy is an award-winning leader in applying the Internet and technology to law practice. A published author and...

Tom Mighell

Tom Mighell has been at the front lines of technology development since joining Cowles & Thompson, P.C. in 1990....

Episode Notes

Each year on the Kennedy-Mighell Report, Dennis and Tom enjoy taking the time to consider new personal goals focused on technology and podcasting. Legal tech is constantly evolving, and staying ahead of trends takes a concerted effort! Dennis and Tom offer their perspectives on how to approach the development of resolutions and offer tips for effective follow through. They also share their hopes for the podcast in 2020.

As always, stay tuned for the parting shots, that one tip, website, or observation 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 answers to your most burning tech questions.

Special thanks to our sponsors, ServeNow.


The Kennedy-Mighell Report

Dennis & Tom’s 2020 Resolutions



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 #252 of The Kennedy-Mighell Report. I am Dennis Kennedy in Ann Arbor.

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

We would 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 to learn more.

Dennis Kennedy: And we want to mention that the second edition of our book, ‘The Lawyer’s Guide to Collaboration Tools and Technologies’ is available on Amazon. Everyone agrees that collaboration is essential in today’s legal world, but knowing the right tools will make all the difference.

In our last episode, we had our friend Debbie Foster join us for a look back at legal technology in 2019. We aren’t big believers in predictions on this show, but we do like to share our legal technology New Year’s resolutions every year and it’s that time of year again.

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 sharing our 2020 Technology Resolutions. In our second segment we will actually be sharing our podcasts 2020 resolutions for the coming year and as usual, we’ll finish up with our parting shots; that one tip, website or observation you can start to use the second that this podcast is over.

But first up, New Year’s Technology Resolutions, a long time tradition on this podcast. I think anyone can make predictions but to be honest I’m lousy at predicting anything. I usually stay far away from it. What we don’t see a lot of are people publicly sharing their technology resolutions each year.

I like the idea of resolutions because they give you a place to get started as the New Year starts, but if you don’t happen to follow through on all of them, it’s also not the end of the world. It’s usually around this point that we revisit last year’s resolutions to see how we did, but I noticed from the script Dennis that you gave me that, that I’m looking at that you suddenly don’t like to look back at last year’s resolutions and dwell on what you didn’t accomplish.

What is up with that? I mean you, you went to Failure Camp and all this past year, isn’t reflecting on the past important?

Dennis Kennedy: Well, I think it’s good to take a quick look at the past, but I think that resolution is about looking forward and Failure Camp as you mentioned was a great thing I did at Nashville with Cat Moon and others and it’s about resilience and learning from what’s come before. So I think you can look back at your resolutions and you can kind of be happy with the things that you accomplished.

And I don’t think you need to beat yourself up for the things that you didn’t accomplish, but I think that what I’ve learned with the whole resolution things is, it’s about experimentation. So what is it that I’m experimenting with, how does that work, what lessons have I learned from that and then do I make adjustments to that, because typically the resolutions I start out with kind of evolve and change over time.

And then even they could pivot in a completely different way that makes a lot more sense. So the actual resolution starts you down a path, but where you ended up is a different path. So I don’t dwell so much on the past. I just like to look forward at this point.

I know Tom you like to kind of tally things up and kind of decide how well you did or not, but I’m like ready to move forward.

Tom Mighell: Well, no I actually — for being honest, I like to look back and see what I said I would do this past year and see if I actually did it, because I am tend not to be good in my resolutions. I hope that I do the things that I think that I’m going to do but I also don’t write them down and I don’t pay attention to them the way that you do.

So that’s part of the reason why I like looking over them last year. But this year, I’m ready to move forward. So maybe let’s talk about the approach that you use and that I sort of have adopted as well to set the resolutions for that not just this coming year, but the years that we’ve been doing this on the podcast.

Dennis Kennedy: Yeah, and I did want to mention that you — what a lot of people do is they write things down and then put it away in a drawer and so what I do is because I use this software program called OmniFocus, I surface those resolutions from time to time. So they come to my mind and they are something that I’ve worked on and I’ve sort of broken up into chunks and other things like that.


And so I guess Tom that typically we go back to the so called smart goals approach on resolution, so they need to be specific, they need to be measurable, they need to be achievable, they need to be relevant and they need to be time-based. And then if you do all of those things, you’re more likely to come up with something that makes sense.

So if I say that my goal for this year is to become a keynote speaker for example, probably I’m not going to accomplish that in the year but if I say that that’s within that general notion I want to be hired for three keynote speeches within — by June 30th of next year, then I’m more likely to accomplish that, because it’s specific, it’s something I can measure, it’s done in a set time period.

And that gets me toward that bigger sort of nebulous goal and the examples are always when people say they want to lose weight, well that that typically does not get it done or to stop smoking. So when you go more specific than to do that. So I don’t know Tom, maybe I will throw this to you since we have notes there.

But I have used a three-part approach in the past which I think you’ve said you like, do you want to talk maybe a little bit about that approach.

Tom Mighell: Yeah, no, I do like the approach that you’ve taken. I think it’s pretty straightforward and I like that it’s kind of a three-part approach that focuses on technology from different angles. The first one, first approach is, is there a technology pain point that I’d like to alleviate or remove, is there something in my life that I want to fix in terms of technology.

Second, is there a new technology, a new skill, more advanced use of technology that I’d like to learn and then third, is there something that I can do with technology to advance my career, accomplish more, improve processes or better as lawyers and enhance client service?

I like all of those, I will confess that this year when it comes to the approach to my three resolutions we’re going to talk about, I really only looked at two of them, because to be real honest, I don’t have a lot of pain points this year. I sat down and I’ve thought about it and I’m like you know the pain points that I’ve got are pretty straightforward and so I don’t have much to alleviate this year.

So I’m really going to focus on those second learning and an advancement of career and of work and moving forward in those types of things. Dennis, what about you?

Dennis Kennedy: Well, I tend to agree with you on the pain point, if I can use that term, because I do feel like I’m in pretty good shape. I just feel like I think it’s sort of scattered in technology and probably not as simple and together as I was like, so let me start with my resolution number one which goes to that point, which is I just want to revamp retool and really rationalize my technology stack.

So what I want to do is to say hey, what are all the things that I’m doing and what other technology I use and this seems like a good time to kind of step back and decide what makes sense, and where there’s duplication and where I can do things more smoothly, and so I think that’s cutting back.

So Tom, as I mentioned before the show I did my end-of-the-year personal off-site and so one of the things that I worked on was this resolution number one, about my technology stack and I actually feel I’ve made some progress and in putting it together.

And so the way to think about this is that it’s definitely going to be a simplification. I did a little bit of jobs to be done to say okay. So what are the things that I do? Well I write, I research, I keep notes, I have business processes, other things to do and then figure out what tools do I use and what tools do, don’t I want to use.

So my approach to this is going to be I’m going to allow myself to do some more research until the — till February 1st then I’m going to do some implementation and look at some metrics by the 1st of March and then I’m going to take a look at all of that on July 1st to see how it’s going and then on December 1st, I’m going to assess it and to see how much or how little I’ve accomplished in and whether it was a worthwhile resolution in process to go through.

So that’s number one for me, this sort of revamping, retooling and rationalizing the technology stack.


Tom Mighell: Well my first one, my first resolution is and I think I mentioned this last year feels for me sort of like the weight loss resolution is for many of us, sort of a perennial resolution that we never get around to actually doing and I remember looking — I actually did look back at our script and our outline for last year’s resolution show, and I put this here and in parentheses I put really, really, really for real this time and then it of course it didn’t happen this year and that is, I have been far too long in re-launching the official re-launch of my blog and what’s going to happen this year just to give you an update. I was hoping to re-launch it in January. I’m a little bit behind, I’m getting a new logo done for the blog and that probably isn’t going to happen.

Well, I’m hoping to get that done in January. So I may still be looking at a January launch, but it may bleed over into February. And then what I really want to do is, I don’t think that the resolution isn’t so much, the re-launch of the blog, it’s in — I’m going to be taking a slightly different approach than I did in the blog before. It’s not really going to be just about legal technology, it’s really going to be about technology in general and I think to be successful what I’d really like to look at is doing more of the hub-and-spoke approach, but with different types of social tools like YouTube, like Instagram, like more visual media in order to talk about technology. And that’s what I plan to start experimenting with. I don’t have deadlines like Dennis does, but I plan to look at using these tools to point people back to the blog or to have a separate source that people can go to if they want to learn this information.

I would also include that I probably will be looking at doing a very short form podcast based on the blog, but that’s still kind of in development and probably you look for more information on that in a future episode of this podcast.

Dennis, number two.

Dennis Kennedy: So the number two relates to the career advancement and so for me that’s going to be video production. So I had this notion last year I wanted to do online courses and other things and I’ve always stayed away from video, because it seems like such — like a lot of hard work and I wasn’t really quite sure that it was a good medium for me. But every time I’ve done video I’ve really liked it.

And so what I found was the blocker on online courses was just the video production side of it. So that’s going to be my resolution number two is, to work really hard on video, learning video production. So I figured out what tools I probably need, what the medium is going to be, which I think it’s probably going to be Vimeo, but I may do both Vimeo and YouTube.

And then just figuring out a way and I also have what I think is really important is I have content ideas that I can work on to give me practice and to get some things up. So I’m looking at both online, longer, courses that are longer form content and then also really simple video tips. So it could be a minute or less, it could be two minutes or less, but I want to really try to make a strong effort in that and to really look at it as a skill to learn and a technology for me to get really conversant in and that’s video production.

Tom Mighell: And for me, it’s also learning, but it also is part of the career too, because we are finding that as our clients are moving more and more to Office 365 and as Office 365 becomes more and more powerful, we want to make sure that we have enough advice for our clients to follow on the best ways to use it. And so, one of my goals for 2020 is to learn more about particular pieces of Office 365 that I don’t know enough about right now.

And that is one Power Automate and two Power Apps. Now Power Automate, you probably — if you pay attention Office 365 you’ll know that it is formerly known as Microsoft Flow, which is Microsoft’s version of the — If This Then That or the Zapier. But it’s basically tools that can set up workflows and make apps talk to each other and work together.

But when you apply all of that to Office 365 you begin to create workflows between the applications. So you can set up processes within say SharePoint where you can have a document that you can basically set up some routine and very simple document assembly or approval processes or other things that work through SharePoint and your Outlook Email and Word documents and you can set up forms where people will complete a form and then it will get forwarded on.


You can integrate that with a signing, with a signature type technology, so documents can be signed. I’m kind of going all over the place when I talk about it, but that’s because there are so many different ways that you can run your processes through Office 365.

I kind of want to learn about how all of those work. Power Automate is really the way to do that now. But I also — I am interested in looking at Microsoft Power Apps. Now what Power Apps is, is another piece of Office 365 that actually allow you to create your own applications. You can create portals, you can create other types of applications, I’ll give you an example of what we’re doing, we are actually creating record retention schedules within Power Apps. So that once you develop your company or your firm’s record retention schedule, you can load it into an app that’s easy to put on your tablet, on your phone, on a website and it’s easy to use and update and it works just like an app. It’s really very, very simple to use or at least to create it at the beginning and but it can actually be quite powerful and complex.

So part of my goal for work and for my own personal knowledge is to really learn more about those tools in the coming year.

Dennis Kennedy: Yeah, that’s a great one Tom, and not to tip my hand too much but part of my tech stack revamp is really going to be a consolidation to Office 365 and both the tools you mentioned are super interesting and I was just reading today about something called Project Cortex that Microsoft has just rolled out as part of Office 365 that is something we might do a show on I think later next year.

Tom Mighell: Yeah Cortex is a good product that right now I think is only opened to companies and it’s in kind of in beta testing, but I think that there will come a time in the coming year when we’ll want to talk more about it because I think it’s a really interesting and potentially really good tool for lawyers to use.

Dennis Kennedy: And my last one is somewhat similar to yours, but this goes — it falls into the improving processes bucket for me and what I really want to focus on is very simple automations. So this is stuff like TextExpander, it’s like Hazel on the Mac, Automator, other tools like this, If This Then That, or I want to look at some very specific things that I do on a repetitive basis and figure out ways to automate them.

And it doesn’t have to be that big a deal. I started to do some work with this especially in TextExpander last year, and it just makes a big difference. And a lot of times you just find yourself doing the same things over and over again, and when you see that it’s a good place to automate and I think the tools have now reached this point where they’re pretty straightforward to work with and a lot of it is just kind of filling in the blanks and I think becomes a way that you can accomplish things.

So that’s the one I’m doing, and I’m also on the SMART goals thing, I’m also just making it very achievable and relevant, because I’m just saying simple automations, I’m not looking to automate my whole life, I’m just looking for simple areas where it makes sense where there’s repetition.

Tom Mighell: And my third one is going to be, is actually a continuation of a resolution from last year when I talked about learning more about data privacy, I’m going to slightly change the focus, but it’s really going to be on data privacy. Over the past year we’ve been working a lot with companies on getting ready for a California Consumer Privacy Act which goes into effect, we’re recording this literally on New Year’s Eve, we’re going to — it goes into effect tomorrow or at least the enforcement begins tomorrow, consumers can start requesting that their information be deleted from California companies starting on January 1st.

And so the past year it has really been about figuring out how do you get ready for it, how do you identify where all your personal information is, how do you get ready to respond to a request to have your information either found and produced or deleted. And then this year is going to be more about how, how it’s going to be enforced, how the State of California is going to enforce it, but even better I think how other states are going to respond to it.

We already have their laws that are similar coming from States like Washington, New Jersey. Nevada passed a law that’s not quite the same but a lot of different laws are being looked at and then the Federal Government keeps threatening to pass kind of a broad Nationwide Privacy Law that may or may not preempt some of these laws.


So I think privacy is going to be a huge topic this year, not just from a personal privacy perspective but in the way that companies manage your information and it’s something I’m going to be keeping on top of this year and learning about making sure that I understand how both companies needs and by companies, I mean law firms need to comply with it, but also how consumers can make sure that their rights are adequately being protected.

Dennis Kennedy: I think that’s all important. I’ve kind of stepped back a little bit from the data privacy realm and I got to admit Tom, that one of the ways I remember this acronym is I just think in terms of the California Chaos Production Act to help you keep that CCPA acronym strong.

Tom Mighell: You are not wrong.

Dennis Kennedy: So I don’t know Tom, we have time for a couple other quick ones. So for me, I like to stick with threes, but if I look at anything or if I’m looking some new area, it’s going to be either some entry into the data analytics world. I like a program called Mighty Networks and the super simple one.

I’ve recommended a service that I’ve called Scribed which is sort of a Netflix for books and I’ve called it Scribed for years I think Tom, and I was listening to couple of audio books and I realized that they refer to themselves as Scribd, so I’m going to — one of my resolutions is to learn to pronounce that correctly.

Tom Mighell: It just seems wrong, it doesn’t seem right, it seems wrong.

Dennis Kennedy: So I don’t know but it was on the audio book and then Tom, believe it or not, I’m actually thinking about doing my book recording and my book lists in Goodreads believe it or not.

Tom Mighell: Wow, that is impressive. So I don’t really have any — the only other thing that I’m doing is something I mentioned on a previous podcast, maybe a podcast episode or two ago and that is I’ve been really trying to learn more about having to use Todoist, which is my task manager.

I’ve been going through a fairly lengthy series of videos on using Todoist on the Carl Pullein I guess video channel. If you want to check back to a couple of episodes past you’ll see the link to his YouTube page has a lot of great videos on it, but I’m getting a ton out of those and learning to use it better.

It’s an incredibly powerful task manager and I — maybe Dennis, you’ve convinced me that I will indeed load my 2020 goals in there and keep an eye on them, make sure that I’m keeping up with them over the course of this year.

All right, well that does it for our 2020 goals. What does our podcast have in store for 2020? Let’s talk about that in our next segment, but before we do that, let’s take a break for a quick 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. We also wanted to create some resolutions for the show. So let me throw out a few starter ideas and Tom can react and add to the list. So, first thing I have is switching for ourselves from Slack to Microsoft Teams.

We’ve gotten a lot more interest both from ourselves and others in creating a book based on our parting shot segments over the 13 plus years of the podcasts and we’ve also been talking for a while about doing a podcasting online course. So I don’t know whether those make our resolutions Tom or are there certainly something we can discuss as resolutions?

Tom Mighell: I have one more to add and I’ll add it at the end, but I would say, I think all of those three are great resolutions for the podcast and for us. I’ve been talking with Dennis for a while, we’ve been using Slack as our communications channel for this podcast, but I just over the past year or so, I’ve become increasingly convinced that that Teams if you’re living in the Microsoft world using Teams just makes sense, because it connects everything together and we keep our scripts in Word.

I just think it makes a lot more sense to move over. I would prefer because I’m using it almost exclusively now in my job in collaborating with other consultants in my company on projects with clients that it just makes sense to use one tool rather than going back and forth between Teams and Slack.


I like Slack quite a bit, don’t get me wrong, it works very well. I just think that if you’re in the Microsoft world, it’s hard not to use something like Teams. So I agree. I think we need to explore that and I would prefer to do that sooner than later. Always been interested and we’ve gotten some interest both online and from, from people talking to us about a compilation of our parting shots, which I think would be a fun thing.

We need to make sure that they’re not out of date, we need to go vet them and see what we’ve gotten and how many are still actually legitimate. And then I do think that doing an online course of podcasting is an interesting thing for us to do, because I think that lots more people are talking about doing podcasts, they want to learn how to do it and I think that putting that information out there is valuable.

The last resolution is a follow-on from last year, the podcast desperately once guests Dennis and I will be working hard this year to try and identify guests and get them onto the show, because I find that the ones that where we have guests tend to be well regarded and I’m hoping that everybody who’s listening to that agrees.

Dennis Kennedy: I’m with you there on that one, Tom. We sort of just have to figure out what the shows are going to be and then match the guests to the theme we went to, there’s so many interview shows out there that I still feel we want to do something that’s a little bit different.

I guess the other thing I would like to do Tom is to do like a little bit more interactivity with our audience. I mean we’re always talking about the voicemail line which we really, really would like people to use, because that would make our life preparing the episodes easier.

But I think I — part of what I’m going to be doing this year is doing some experimentation with quizzes and surveys and so we may do some SurveyMonkey, maybe in some Google Forms type of work which is another automation tool in its own way, in connection with the podcast.

So those would be the other things I might think about, but I think that interaction piece and I can’t believe it Tom after writing two books last year that I’m actually thinking that in the very, very near future are we starting another one with you.

Tom Mighell: It’s in your blood.

Dennis Kennedy: 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 the first is a website that I became aware of, I give a hat tip to our friends at Cool Tools, because they’ve mentioned this and I took a look at it and I really, really like the possibilities here and it’s a website called The Noun Project, I’m not sure why it’s called the Noun Project, but essentially what it is, is it’s a database of Icons.

Icons that you can use for presentations, for publications, for articles, for anything that you want to use and there are somewhere between a million and two million icons listed within this database. You can use it for free, you get a Creative Commons license if you want to use it for free. You can’t edit, you can’t do anything to the icon you can just use them.

But you’ve got to give attribution under the Creative Commons license. But if you want to pay $40 a year, you get royalty free licenses for all the icons you want, you can customize any icon that you want by shape or color or size or anything like that and what’s also nice is, is that you also get apps that allow you to put them directly into, if you’re a Google user, you can put them into Google Slides and Docs.

If you’re an Adobe user, you can put them into Photoshop or InDesign or Illustrator, you can put them into Microsoft PowerPoint or Word documents and then if you’re a Mac user, you can put them into — you get an automatic app or icon adder for Mac.

So really cool, very understated website, but lots of icons. I did searches for just about anything I found and I found dozens and dozens of icons just by doing simple word searches called, we will put the link in the show notes.

Dennis Kennedy: That sounds pretty cool. So just two very quick ones, so the 2020 ABA Legal Technology Resource Center’s Women of Legal Tech list just came out and you can find that list so it with tons of great names, 20 great names of new honorees on the Law Technology Today website and blog.

And then the other thing I want to mention is what’s known as Warren Buffett’s 5/25 Rule. So Warren Buffett of course is the famous investor and he has this notion that what you should do and I try and I’m trying it this year and so this is part of my off-site, my personal off-site is, he says write down 25 things that you really want to accomplish, put them in order and then draw a circle around the top five and draw a circle around six through 25 and then X out, just cross out six to 25.


And then vowed to focus on the top five until you finish them before you move to the other ones. So it’s obviously a variation on the 80/20 Rule, but it’s kind of interesting and so that’s one of the things I’m going to experiment with this year.

Tom Mighell: And I want to add my congratulations to the 2020 Women of Legal Tech, it’s a great list please take a look and get to know them.

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 on the end of this episodes listing 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 of all of our previous podcasts with transcripts.

If you would like to get in touch with us, reach out to us on LinkedIn or remember we love voicemail. Leave us a voicemail at (720) 441-6820.

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 liked what you heard today, please rate us in Apple Podcasts, 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: January 17, 2020
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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