400! Celebrating the Kennedy-Mighell Report’s Quadricentennial

Episode Notes

Transcript

Announcer:

Web 2.0 innovation 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 400 of the Kennedy Mighell Report. I’m Dennis Kennedy in Ann Arbor, and I’m Tom Mighell in Dallas. In our last episode, Tom and I returned to our second brain projects and the role that AI will play in them as we pivot them into some new iterations. I’ve been recommending the episode to anyone who wants to learn about some practical and personal ways to think about using ai. In this episode, we hit another podcast Mighellstone. This is episode number 400 of the Kennedy Mighell Report podcast. The term for 400th anniversary is either a quarter centenary or a Quadra centennial. Tom, I’ll let you choose the one you like best. I know the one I like best. Unfortunately, there is no widely recognized traditional material gemstone or precious metal like gold or diamond officially associated with this Mighellstone. 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 celebrating our 400th anniversary, which will officially call, we will officially call our Quadra centennial. I decided I liked, I guess, the noun version of that better than the whatever the Quadra century, whatever form of word that is. Quadra centennial sounds more formal with a special guest who is well known to our listeners and was the first name to come to mind for Dennis and me when we discuss this episode. Debbie Foster of Affinity Consulting and longtime friend of the podcast. Debbie, welcome to the podcast.

Debbie Foster:

I am so happy to be here.

Tom Mighell:

Alright, so we’re going to finish up as usual with our parting shots, that one tip website or observation, you can start using the second that this podcast is over. But first up episode 400 for such a huge Milestone. We thought we’d indulge ourselves a bit and make this a very meta discussion. Podcasters talking about podcasting, this podcast in particular, and we’re going to do it kind of scrooge style looking things over at various points in time. We’re going to do it past, present, and future. So Debbie, we’re going to let you kind of take things in whatever direction you want, but let’s start with segment number one, which we will call podcast past.

Debbie Foster:

Awesome. Well, thank you for having me. I feel like you called me the moderator earlier, but I feel like I’m actually the host for this episode.

Dennis Kennedy:

That’s good.

Debbie Foster:

Fair?

Dennis Kennedy:

Yes.

Debbie Foster:

Okay, so my first question is off script. What was the date of your first podcast episode?

Tom Mighell:

Holy crap. Really seriously.

Dennis Kennedy:

I believe it was in February or March, 2006 because we were trying to get an episode in before we did a presentation about podcasting at a tech show that year. I

Tom Mighell:

Think that’s a brilliant guest, Dennis. I was going to also say 2006, but I do not have a recollection of 19 years ago and the exact date and time to do that, but we’re

Dennis Kennedy:

Both getting older. That’s one of the answers. Thank you, Dennis,

Tom Mighell:

For pointing out

Dennis Kennedy:

Podcasting

Tom Mighell:

That we are older.

Dennis Kennedy:

Yes.

Debbie Foster:

No, but seriously, 19 years of a podcast. That’s bananas. We’re going to talk more about that later. So first question, I mean second question, that was actually the first question, but what sparked the idea for the Kennedy Mighell report? How’d you decide that Dennis’s name got to go first before Tom’s name? How did that happen and did you have any idea that you would be doing this 19 years later? Dennis, I’m going to throw that to you first.

Dennis Kennedy:

Well, yeah, it’d be interesting to compare our story. So I think my recollection is that three things kind of came together, and I say the big driver was that Tom and I were task tasked with speaking at a tech show about podcasting and with the idea of how people listen to podcasts. And Tom especially thought that it wasn’t a good move for us. It wasn’t a good look to talk about listening to podcasts and be speakers on if we didn’t have our own. So we decided we needed to do one. So that was one driver. And then Tom and I were doing a column together on Abba’s law practice today, which had kind of hit sort of an end point where it made sense to explore podcasts. And then Tom, this will test your memory too, about the same time, I think we were doing the Between Lawyers blog and we decided to try a podcast there, which has sort of been lost in history. So I think all three things came to together and we just decided that a podcasting was something we had to do. What do you think, Tom?

Tom Mighell:

I mean, I wouldn’t add anything to that other than to say that to me it felt a lot like how I felt when I started my blog, which was I kind of wanted to get out there and do something others weren’t doing, that lawyers weren’t getting involved in. And I was always wanting to push into new technology areas and try them out. But a podcast at least at the time, and well, gosh, 20 years later, I feel the same way is not something that I just want to automatically do on my own. I mean the work involved, and we can talk about this more, the work that was involved initially in doing the podcast was not something anybody would want to do by themselves. And the people who did that and had their own podcast, bless them, taking that on. But it just made sense to do it with somebody else because we could divide and conquer and do different types of work. And then to answer your very last question, which was I never had any sense at all that it would become influential or popular or any of those things. And I still don’t because I still think that we’re two friends having a good conversation about the things that we love to talk about. And if it’s helpful to other people, then that’s fantastic. We love it. But I’ve always been sort of amazed that anybody else listens to us to begin with.

Dennis Kennedy:

And I would say to answer the other question is it’s the order of the name’s purely alphabetical. That’s how we did it. And I would say that, and that’s

Tom Mighell:

Dennis’s version of that story.

Dennis Kennedy:

Yes, we did a lot of testing. It is pretty much how it came out

Tom Mighell:

From a syllabic standpoint. Kennedy Mighell flows better than Mighell Kennedy, so it just makes sense.

Dennis Kennedy:

It is pretty straightforward. Then I would say that Tom’s right, the idea with the podcast is that we were just going to do it as if it were the two of us recording a conversation that we had. If it had an audience, if it found an audience that was great. We had an idea that it would be a show from the beginning, which I think is a lot of times when people have podcasts that don’t last very long, they don’t have this notion of it being a show. So there’s one sentence and then I would say that it is Tom in me. Of course it’s going to be influential in legal technology.

Debbie Foster:

I agree. I agree. I love your podcast. As you know, I listen to every single episode, but speaking of the episodes, what’s cringey about the old ones? Have you gone back and listened to some of the early ones and what makes you say, oh my goodness, I can’t believe we did that. I can’t believe we said that.

Tom Mighell:

So I will make a confession that says that I can never, ever listen to anything that I ever do, ever. I’ve never watched myself on a video. I never listen to myself. Everything that I hear myself in is cringey to me automatically. So I’ve never gone back to listen to anything unless I had, I needed to pull some content out of it. There have been times where I’ve wanted to hear things and I’ve gone back and listened to it. To be honest, the only thing that was cringey to me was the fact that we, and by I mean Dennis was having to edit this himself and that I think the production values were not what I would’ve preferred. I am truly, again, amazed at the podcasters who can put on a show, and these days it’s easier, the technology’s better these days. But back then the technology was, and Dennis, how long did it take you to edit that first episode? It was like a full day to just get through 30 minutes of conversation or something.

Dennis Kennedy:

It is, Quadra centennial is really good. It took four times as long as the amount, the number of minutes in the show.

Tom Mighell:

Exactly. So of the things that made make me think, I wish I didn’t have to do that again. I’ve always been in debt to Dennis for taking that on because it was just a thankless job and I’m glad he did it, but I’m glad we’re also not doing it anymore.

Dennis Kennedy:

And the flip side of that is that Tom, even though I was doing editing and stuff, Tom was actually getting the podcast out, which was putting on a site called Lipson and doing all these other things, which is no easy task. I was glad to be editing rather than do that. And then as you said that once we found our way to Legal Talk Network, that that just made all the difference in the world because the professionalism just went way up. It’s hard when you’re starting your own podcast and you’re saying, do I want to buy a nice microphone? Do I want to do all these things? Or do we want to see whether we just even have anything here that will even work? So I don’t have a lot that I think back on that would make me cringe. I mean, there’s that where you’d say we made some predictions about how lawyers were actually going to adopt certain technologies that haven’t worked out. But I will say the one thing that, and this does go back to the early episodes that make me cringe out time. I feel that the intro music is like original intro music and it does make me cringe. We’ve

Tom Mighell:

Never changed the

Dennis Kennedy:

Music. We just have to update that at some point.

Tom Mighell:

Well, at one point in time it’s been like, what is it? A year or two ago, you came to me and you said, here I’ve had AI generate these three or four different new theme songs. And I’m like, I’m great with all of them. And then we never did anything more with it. So yes, that falls under Podcast Futures. We need to get it changed because if you listen to the beginning, does it still say Web 2.0? It does because that’s one of the first things on it. And Web 2.0 has only been not been a thing now for how many years? 19 years. Totally. Take it back. I take it back, I wouldn’t know it because I don’t listen to the episodes, but yeah. Okay. There’s the biggest cringe right there is that Web 2.0. We’re on the cutting edge of Web 2.0.

Debbie Foster:

I’ll tell you what’s really funny is when I listen to you guys on my phone, I listen to my podcast app and it is at 1.3, and then occasionally I’m at my desk and I get my notification from Dennis that the new edition of the podcast is out. And I’m like, oh, I’ll just click on it and I’ll listen to it on my computer. And then it’s like the slowest version of the intro and I’m like, why does this sound so ridiculous? It’s because my computer defaults to normal speed

Tom Mighell:

To normal speed.

Debbie Foster:

So for those of you who are not listening at 1.2 or 1.3, this is an easy show to listen to at 1.2 or 1.3

Tom Mighell:

And do yourself a favor and listen to the music at that speed too. So get to it quicker

Dennis Kennedy:

Using music at 2.0. No, you’re right. Because when I listen to podcasts at the increased speeds and then I hear somebody, I say like, oh my God, did somebody have a stroke? No,

Debbie Foster:

Seriously, it’s crazy. Okay. How did you get your on air dynamic? Did it happen naturally? Did you already decide that Dennis was a good guy, Tom was a bad guy, not that’re suggest minute suggesting that that’s your on air dynamic or anything like that. But how did you decide that?

Tom Mighell:

Dennis, you start on this one. I want to follow this up

Dennis Kennedy:

At the end. Oh wow. I think we just sort of had personas, but they’re pretty close to who we are. And that was always the idea. Like I said, the original idea was that Tom and I never got to talk to each other about technology. So we said if we do this podcast in every two weeks, we’ll be able to talk about technology. And we realized it had an audience, so it had to be some kind of show and we would have a little bit of honor dynamic, but it needed to be close to who we are. And so I think it tends to be like I’m more futuristic and more kind of out there, a little bit more irreverent in Tom’s sort, the voice of reason and that sort of thing that he’s really good at. Although one of my favorite aspects of the podcast ever was when we went through this period where our B segment, we did Tom’s rant and then Tom just would go off on whatever

Tom Mighell:

Technology that was the golden age of the podcast right there.

Dennis Kennedy:

Those were the days. So that’s how we developed it. So it’s pretty close to who we are. And sometimes with legal talking now, they would say you guys should mix it up more. You always agree and stuff. And so we sometimes try to, and we’ve done it at different times, just try to take different points of view. We end up in similar places, but we don’t always agree different times, we don’t agree on different things. We kind of play off the Apple and Android thing as we did in the last episode. And then like I said, this is a show we’re professionals. We do disagree from time to time and sometimes right before a show we’re disagreeing. And when we count it in 3, 2, 1, we’re pros and we go,

Tom Mighell:

Well, let’s be clear. We disagree a lot offline, off mic. There’s a lot of disagreement about not anything important. But what’s so strange to me is that even when we don’t talk about it ahead of time, our agreements during the podcast and I’m sorry, legal Talk Network, this is how it is. Our agreements are totally organic. We don’t plan it ahead of time. We come to the same conclusions and it’s infuriating to find that he thinks the same thing as I do because I would like it to be different. And that’s part of why sometimes, and I still am thinking bad guy, am I the bad guy here? But I want to be provocative because I want to make it more than just me too and Dennis too and all of that. Not that I don’t like that he agrees with me, but I think it’s less interesting when we don’t have those conversations. So that’s why when we do our end of the year stuff, I like the fact that we are forced to take opposing sides and now I have to come up with the counter argument to it even though I don’t believe in it at all. But I think that’s part of what makes it fun,

Debbie Foster:

And that’s why I call you the bad guy because you have to always win in that end of year episode that I’m almost always a guest on. So you’re the bad guy, let’s

Tom Mighell:

Be clear. I don’t have to win. I just do win. See, what is the deal?

Debbie Foster:

Why can’t get that into their head. Just making my point. I am the winner. Okay. Early episodes or guests that changed how you think about legal technology or the profession, who were they? What are some memorable moments from the past?

Dennis Kennedy:

Well, I think that some of the early episodes started to raise themes that we developed over time. So collaboration, technology, jobs to be done theory, some things that really continued throughout the show and the whole notion that technology has to solve a problem and we’re less interested in the details and the thing that lawyers always do, we’re trying to find the best product, like the best, what the heck are you talking about? What do you want to get done? Then I think the guests, there’ve been some really good ones, but I wanted to just go to the thing we’ve been trying for the last two years, Tom, the fresh voices. I mean that’s just been so great. And so the guests on there have been great and we’ve learned a lot and introduced some of them to new audiences. So that’s good. So I have a little bit of recency bias because I think the last two fresh voices with Bridget Carr and Bridget McCormick have been great.

And I think our last episode where we talked about how we were not exactly calling our second brain project, which we’ve been working on for years, a failure, but an experiment that we were pivoting to because with the things we’ve learned and how we’re going to use AI in it, and I think that’s really instructive that episode for people who are thinking about personal ways to use ai. So basically it’s all been good. Like I said, there’s some things that definitely have dated, but I think one of our approaches is try to talk about topics in a way that doesn’t date very quickly.

Tom Mighell:

Well, the only thing I would change is I want to answer the question that was asked, and it was which early episodes or guests changed how we think about it? Because if you remember Dennis, in the early episodes, we didn’t have any guests in the early episodes and they kept wanting us to have guests in the early episodes and not me wasn’t interested in having necessarily, so there were none. So to answer your question, Debbie, there were no early guests that changed how I think about technology. I will say though, with the recency bias that Dennis talks about, the new guests that we have totally are changing the way I’m thinking about technology. I mean, I think it’s so important and I’m glad that we’re having these voices, whether they’re fresh or not, they are influential people in legal tech and I love having them.

I love that they’re getting out and talking about these things. But as for the things that we talked about, we always talk about what we want to talk about. We’ve always tended to talk about certain tech topics before others are talking about it. We tend to be a little bit ahead of where certain people are. So my thinking really has remained largely constant on this. There are amazing ways that lawyers can use technology to improve their practice, and they are consistently slow to come to that realization themselves. So that’s kind of how I’ve been thinking about legal technology in the profession, and that really hasn’t changed tremendously. AI has maybe changed it a little bit over the past year or two, but it’s been pretty solid the whole time.

Debbie Foster:

It’s funny because obviously I saw these questions ahead of time and I was thinking, I wonder what they’re going to say about the early episodes or guests, but as you say that we didn’t have guests. I’m pretty sure that I was one of the, maybe even the first guest on the show, because I remember the debate about we don’t have guests on our show, so I don’t know if it’s true or not. I’m just going to go ahead and claim the first guest of the Kennedy Mighell report, even if it isn’t true.

Dennis Kennedy:

No, you’re not allowed to claim that because, so the original idea was we didn’t want to have guests that at the very beginning was that we would bring people on as co-hosts,

Tom Mighell:

The third host

Dennis Kennedy:

As the third host. And so Adriana Ez was on, Alison Joes was on a couple of times you were on

Debbie Foster:

All, I can’t remember if

Dennis Kennedy:

We had others. And then we’d have the occasional guest where sometimes somebody reached out to us or we reached out to somebody.

Tom Mighell:

There was a book, we brought the jobs to be done guy in, and we interviewed him and that was terrific and fantastic.

Dennis Kennedy:

Oh yeah. And your friend at Microsoft, I don’t know whether she’s still there, but at the beginning of COVID, talked about what was happening with Microsoft Teams.

Tom Mighell:

That was

Dennis Kennedy:

Fantastic.

Tom Mighell:

We’ve had some amazing guests just not soon enough.

Debbie Foster:

Yeah. Okay. I’m going to ask you the last question of this segment talking about podcasts pasts, and I’m going to go down to, since everybody has a podcast now, and also everyone who doesn’t, even though everyone already does, is thinking about having a podcast. What do you wish you would’ve known about podcasting when you started that you’ve learned over the last 19 years?

Dennis Kennedy:

I wish I would’ve known at the very beginning the value of being on a network like Legal Dog Network to handle all the production side of things and distribution side of things. So you can just be talent. So that’s one thing, but that’s sort like an easy thing to say. You’re right, it still surprised me now where people are announcing that they have this new podcast, it’s some big deal thing. And then you know that I would say most podcasts, if they do half a dozen episodes, they’re lucky. That’s

Tom Mighell:

Their season. That’s a season of a podcast. Yes. It’s

Dennis Kennedy:

Like all that happens with them. And so I think that what we kind of knew intuitively at the beginning that I always come back to when anybody asks me about podcasting is it has to be a show. And so it has to have things like segments, it has to have breaks, you have to have continuing features. People have to have certain types of personalities, but it’s a show and I think people go like, oh, we’re just going to interview people and it’s hard to interview people. And so I think that you have to think through it as a show. And I think the most interesting thing that we’ve done, and probably other than Tom and I’s own chemistry, it kind of led to the longevity of this, is that we changed things around a lot like our B segment, we do new things, we try different things.

We’re now doing interviews, we never did it before. We do games, we incorporate ai, we just try a bunch of stuff and we say in the context of the show, you’re going to get a topic, you’re going to get something a little bit offbeat and the B topic that’s interesting to Tom and me and might be interesting to you, and you’re going to end with the parting shots and it just has that structure and you sort of know what I’m going to be, and you know what time’s going to be, and it just becomes the show that you like to go back to. And that I don’t think a lot of people who are jumping into podcasting really realize,

Tom Mighell:

I’m going to disagree with Dennis in one respect. And I’m going to say I don’t think interviews are hard. I think that coming up with the questions can be challenging, but the formula that we have for fresh voices tends to be, we kind of want to know what our guests think about the same topic. So it’s not like we’re asking them new questions every time. And so I guess if I said, what did I wish I’d known about podcasting that I’d learned through experiences, I wish I knew how easy it was to prepare for a guest. I would’ve pushed for guests much sooner because those are some of my favorite episodes now, because I don’t have to worry about preparing ahead of time, and I do have to prepare. It’s just I can sit back and let them do the driving, which the guests are happy to do, they’re happy to take off with that. And to me, that makes it just so much more of a pleasurable experience to me.

Dennis Kennedy:

Well, Tom, can I point out that there’s this great thing, I’ve learned that a lot of times what you think is really easy is your superpower. And I think for most people the interviewing is very difficult and they’re not comfortable with it. But I think that one of our things, which I think really works now is it’s difficult to do a two person on one guest interview.

Tom Mighell:

Totally agree with that.

Dennis Kennedy:

And so the fact that we can do that and it seems easy shows that that’s the 19 years of doing this, that coming into play.

Tom Mighell:

Totally agree. I don’t know. That’s my superpower. I just happen to feel differently about it. Alright, with that, we’re done with the past. It’s time to move to the present, but before that, we need to take a quick break for a message from our sponsors

Dennis Kennedy:

And we are back. Debbie, let’s move to podcast present.

Debbie Foster:

All right. So how has the podcast specifically influenced your career trajectories, Dennis, from practice to MSU and now retirement? Congratulations by the way, and Tom for you, the evolution of your practice.

Tom Mighell:

I’m about to say some things that Dennis doesn’t like me to admit publicly on the podcast, which is I’m not involved in legal technology. And so to be honest, the podcast hasn’t really influenced my trajectory at all. I’ve actually moved continuously away from legal tech and I hate it. I don’t like it because that puts pressure on me to feel like I know what I’m talking about on the podcast. But when we started, I was the head of legal technology at my law firm and that’s all I was doing. I was living, breathing at work, and I was living, breathing it in my personal life, blogging and podcasting and doing all those things. And I was all in on legal technology. I left the firm, went to work for an eDiscovery company, which was still legal technology, so I was still there, but literally get laid off within a year and a half when they decided they couldn’t do the kind of work that we were hired to do in the first place. I’ve been in information governance, which I love dearly, and it is law adjacent, but it’s not legal technology. And so I think that it has helped shape my ability to do work in this area, but it really hasn’t affected it as much, nearly as much as it has with Dennis.

Dennis Kennedy:

Yeah, I mean this is an interesting question because I think that it is had a lot of impact in the same way I’d say my website blog, other things in creating the career that I have, but I’ve never mapped it specifically onto what my job was. So what my main job was. So did at MSU would they have said, oh, we listened to your podcast and we knew we had to hire you. I don’t think that’s the case, but I think that what it did was it allowed both Tom and I to talk about things that were really interesting to us and where the directions we were headed. And then as we shaped that it sort of shaped what people thought we were doing and had an impact on the career side. And I would say now retirement as well. And when we get to podcast future, I think this is an ongoing question we’ve had for a number of years of what does the podcast mean? What is the audience? What do we offer to the legal tech audience? How are we going to shift that? And as I said, I think the Fresh Voices series has kind of really helped us with I think what’s going to be a bridge from what we’re doing now to probably what we end up doing in the future. But that’s a great experiment and that we haven’t started yet.

Debbie Foster:

So walk us through how you prepare for your episodes. What does that look like and how has it evolved?

Tom Mighell:

So Dennis, the process really starts with you, although I’m going to talk about that in a minute, but since it starts with you, why don’t you start, and I’ll take it from where I pick it up.

Dennis Kennedy:

So the main division of work we have is that I come up with the topics

Tom Mighell:

Unless I have something I want to talk about,

Dennis Kennedy:

Which is not as often as Dennis comes up with the topics through, there’s once or twice in the last year.

Debbie Foster:

You’re like Guy, bad guy. I’m just saying.

Dennis Kennedy:

So then I say, Tom, you want to talk about this? And then he says, yeah, great, let’s do it. And then I say, then I do the script and I send the script to Tom. Tom looks at it, he might have some input or not. And then we’re set. And then we come into the podcast itself and then we have different approaches. So I do my own prep, which kind of happens as I’m doing the script. I know the things that I want to talk about and I put it into the script. Script is a very loose term. It barely qualifies as an outline. I mean it’s a set of talking points. And then time does a lot more preparation frankly than I do. And as time has gone on, I kind of improvise a bit more, which sometimes you can tell. And that’s pretty much how we do it. And then we have the time that we connect on Zoom to record, and then we talk about almost everything other than the podcast for a while till we’re ready to record. And then if we have some questions or about directions we might go or things we want to cover, we talk about that. And then we hit the record and go.

Tom Mighell:

So really talking about it from my angle is I tend to rely on Dennis for the ideas because he’s out there and he knows what’s interesting and he’s always, I think coming up with the things that I also want to talk about. But I’m more, and I’ve always been more on the consumer side of legal technology than on the legal side of legal technology. And so I’d rather start from the legal perspective more often than my perspective, which is why I don’t come up with ideas that often. I get the script from Dennis, I edit a bit here and there, I insert the language I want to use, I then send it back to Dennis, then I prepare my end, and Dennis is right. I tend to prepare a little bit more and the amount of time that I need to prepare is directly related to the comfort level I have with the topic.

And when I know the topic, I can prepare a night ahead of time, but if I need more time, I need that time. So there is always a little bit of stress involved when I may not get the script in the time that I need to be prepared for all of that. That’s one reason why I like our Fresh Voices series because the amount of preparation I have to do is a little bit different. I do research on the guests. I go out and find out what the internet has to say about them. I will tell you that AI has changed a lot of my preparation now. It makes it easier for me to find stuff. I have a prompt written that says, here’s my guest, tell me all this stuff about them. And it immediately brings back a report on the speaker, on the guests that I’m going to talk to. And that’s why some of my questions change because it helps me suggest some of the things I want to talk to with them. So I feel like my preparation has gotten a little bit more straightforward these days. But yeah, I think that’s the process.

Debbie Foster:

So you guys talk about, and even integrating in the Fresh Voices, you talk about so many things, cutting edge stuff, but you also know that you have an audience of lawyers who aren’t necessarily tech savvy. And how do you balance those two things? How do you talk about the things that lawyers absolutely need to know about all while understanding that it might just not even be something that is within their reach right now because of where they are on the technology path?

Tom Mighell:

When we talk about topics that might be new to lawyers, I will say that a lot of times they’re either new to me as well or they’re things that I just don’t have a lot of knowledge about. We did an episode a while back on quantum computing and what lawyer knows about quantum compute or needs to know or care about any of that. So I’m approaching it from my perspective as someone who doesn’t know anything about it either. I don’t know about it. And so I want to understand how it’s important to lawyers and what lawyers should know about it. Now, to be aware of it, I say this on all of our Fresh Voices series, I feel like we are the Statler and Waldorf, if anybody remembers the Muppets who stand out there and complain about the lack of technology competence out there. But that’s how I frame all of these discussions. What do lawyers need to know about this topic in order to be technologically competent, even if they’re not using quantum computing with their clients, what might they need to know about it to be conversant with a client or talk about it? It’s about taking the small steps to not being an expert, but just being aware of it. So for me, it’s about finding the practical advice on the cutting edge information that would make it more approachable for lawyers.

Dennis Kennedy:

And I think that’s always been the challenge. And what’s fun about this is that we can take the newest topics and we pride ourselves in being the first podcast to talk about topics, which is, I will confess from time to time, it is weird to see people on podcasts talking about things that we did three months earlier as if they were the first ones to talk about it, but occupational hazard in podcasting. So the idea is if there is this technology that lawyers have to deal with it and they can’t know every detail and they can’t know the best and every detail is, but they need to advise clients who are dealing with these technologies, they need to help people who are using these technologies. And so there are fundamental ways to understand these things. And so in a way, we’re trying to educate people, but I think it’s become a challenge that after this many years, if you’re still talking about the same things or you’re explaining cloud computing, it’s tough.

And I think that that has become a bigger challenge for me over the years. Part of the reason I’m retiring from the main things that I’m doing is because I’m not sure I’m the right, that’s the audience for me anymore. I feel like I am going backwards and it’s too basic and it’s not challenging to me, and I potentially want to find a different audience. And when Tom talks about the work he’s doing, the work I’m doing, I think that we’ll have some conversations in the future about where the podcast is going. I really like what it’s doing. It’s a fantastic creative outlet that I don’t want to give up. But the audience, when you’re saying lawyers just don’t get this or they’re really slow, I am not sure that’s the audience that I want anymore and I’m happy to confess that.

Debbie Foster:

Interesting. So I’m going to ask you one last question in this podcast present series because I want to make sure we get some good time to talk about what you just said about what’s happening in the future. But let’s finish this segment up by talking about some specific examples of listeners who have transformed their practice based on your episodes. And I know that that’s happened because I’ve been for sure with Tom and maybe with Dennis too, when people have come up to you specifically at a tech show and said, Tom Mighell from the Kennedy Mighell report, you guys are recognizable and you absolutely have made an impact. So what’s your favorite story about that?

Dennis Kennedy:

I mean, recently I just had a number of people come up and say, your podcasts on AI and the way you’re thinking about it, I’ve really changed my approach and I’m not as afraid of AI as I once was, and I’m trying these things because it seems really accessible. And I think that to me is the real feedback I like to get where somebody said, I thought this a really difficult topic and it’s actually pretty easy and I’m trying it and because you made it feel like it was something that I could do. So I think those are examples. But I would say the thing that I like is when people say, I heard your podcast and I decided to start a podcast. I heard your podcast and I decided to write a blog or do something because that to me is the impact that I like to have. Can we do something that lets you know that you can kind of find an outlet for your own creativity, that you have a story to tell, and this could be the medium for, and you give it a try? And those are the things that I really like.

Tom Mighell:

And I think we’ve started a few podcasts. I know at least a couple people who’ve mentioned that they started podcasts because of this. I would say that my perception is much simpler in this, which is, you’re right, Debbie, the number of times where people have come up at legal technology conferences who have said, you’re Tom Mighell, Kennedy Mighell report, to me, that’s all I need to know to know that it’s had an impact. Because if we’re just having and giving average advice and people aren’t paying attention, then they’re going to walk on by, they’re not going to say anything, they’re saying something because it’s had an impact. I am happy to hear all of that because I have become memorable in that regard. We have become memorable in that regard, and I think that’s important.

Dennis Kennedy:

And one of the tests, Tom, of course, is that they pronounce your name correctly, so we know they actually are listening

Tom Mighell:

To, which is an amazing bonus. So yes, the more people I can get to pronounce his name, the more successful this podcast becomes. Alright, we’re moving on to podcast future, but before that, we still need to take another break for our message from our sponsors. And now let’s get back to the Kennedy Mighell report. I’m Tom Mighell, and I’m Dennis

Dennis Kennedy:

Kennedy, and we’re with Debbie Foster. Debbie, let’s wrap up with podcast Future. And I don’t care what Tom says, this podcast is so much fun. It can go on as long as you want it to. No disagreeing Tom. I don’t disagree.

Debbie Foster:

No disagreeing. Okay, so this is going to be my favorite part I already know. What about the future of the podcast, Dennis, you have retired and both of you, your careers have changed over the time that you’ve been hosting this podcast. How will the show’s focus or approach change in the future?

Dennis Kennedy:

Yeah, I got to tell you, as I was thinking this summer about retiring from Michigan State University, and I was thinking what was going to change and what I was going to let go of and what I was going to keep the podcast was the non-negotiable, but it made me think that there could be a time that it came to an end, and I hope Tom tells a story about what AI predicted that he’s going to be doing with the podcast. Really funny. So I think that the interview piece is so much fun and so useful and to bring new voices on legal tech that we find really interesting and to give them an outlet is I think something that we can really do as we get older. And that aligns with what I liked about teaching law students. Then I think that we as Tom and I start to do things and Tom talks about the consumer tech side of things that he’s interested in and other things like that.

I think we will start to drift a bit away, probably in a planned way from pure legal tech to the sort of traditional legal tech to some other things. So I don’t know that we’ll ever become an AI podcast or anything like that. We have our roots and it makes sense to honor those roots and the audience, but I think we’re going explore more where our audience wants to go or wants to see us go. But I think it was a show, and so we’re going to keep trying new things and we will see what works. And like I said, it is something I want keep doing for as long as it makes sense. I mean, this is totally one of my, I would say it’s probably my most important creative outlet right now.

Tom Mighell:

Well, I only respond to that by saying, aren’t we already an AI podcast? Because it feels like that a lot. I mean, except for our fresh voices, but our fresh voices only talk about ai. That’s not true. A lot of our fresh voices talk about ai, but that leads to the thing. I mean, I think that there is an aspect to knowing about what our readers, our listeners want, but I also think that there’s a benefit to doing what we’ve done in the past, which is letting our listeners know what they might not know about and what is coming up. And so I think that the focus will continue to be on keeping ahead of the curve slightly for listeners, keeping up with the newest and latest topics. I think that it’s going to be very interesting in the next couple of years because AI has literally stolen almost all the air from the legal technology room. And I like that we’re on the Fresh Voices series. I like that we’re talking about other legal technology topics because otherwise we are just another AI podcast. I hear all over the place, and that’s all I hear our guests. I don’t know what AI is going to do in the future, but I like that we will continue to evolve based on what we see is important and what lawyers need to know about.

Dennis Kennedy:

Well, and Debbie, I would say the other thing that I’m really interested is can we use the podcasts as our own place to experiment? So like we did with the Second Brain Project and what we’re doing with Notebook lm, can we just start to say, Hey, here’s some of the stuff we’re doing and we’re putting it out there and we’re talking about it and here’s what worked and here’s what didn’t work, and here’s what you might find. And we’ve done this for a long time and we’re willing to share what we’re doing. And if it doesn’t work, so be it. But we’ll let you know. And if you have input, that’s great, and we’ll kind of be more open about some of the things we do. And especially in the ai, there’s a zillion people who claim to know everything. And I think it’d be great to have a podcast where people say, Hey, we’re just trying stuff. We’re rolling up our sleeves, we’re trying stuff, and here’s what works. Here’s what doesn’t. We’re not claiming that we know everything. We know some, but we’re beginners. We’re the white belts in the karate class and we’re telling you what we’re seeing.

Debbie Foster:

Well, in the podcast world, you’re more than white belts because you got to be in the top 3%. 400 episodes is a lot. I actually meant to go look at the statistics for this, but we’ve hinted at this before. Many podcasts don’t make it past season one or episode 10, and you guys are at 400. Speaking of that, what about new formats technologies or interactive elements? What’s coming in the next a hundred episodes?

Tom Mighell:

That kind of leads into the question that Dennis said, which was a recent experiment that I did with ai, which was tell me where I’ll be in five years. Where do you envision me in five years, which is edging up on retirement time. So I was asking where should I be headed towards? And one of the things in there that it mentioned was that the Kennedy Mall report would be celebrating its 1000th podcast episode, which I found was sort of amazing considering that means we need to do 600 podcasts in the next five years. And I was looking back, and our cadence has been pretty regular to get to a hundred podcasts every two years. We’re doing pretty well to do 52 podcasts or around 50 podcasts a year, but it’s even less than that actually.

Dennis Kennedy:

Yeah, it’s

Tom Mighell:

Every two weeks. We hit our 100th in 2013, we hit our 200th in 2018, and now we’re hitting 400 in 2025. So I’m skeptical about, I would say that chat GPT was hallucinating its mathematical ability at that point in time. But I would say so from a standpoint of new innovations, I like the idea that we might be doing more video in our future. Dennis and I have been doing the Tom and Dennis, or Dennis and Tom take it for a spin where we’ve been demoing software. And even though it’s terrifying and I’m terrible at it, I don’t know how people can be successful in TikTok videos because I have so many takes and I still have trouble getting things right. But I like the idea, I wonder whether we do more shorter targeted episodes, whether we have little bits of information, people are consuming information. One of the things I worry about, Dennis, is this is a long podcast. Will people want to listen to the entire podcast or will they want to consume a 62nd clip on a different outlet? Not everybody’s listening to podcasts the same anymore. They might be consuming things in TikTok or on LinkedIn or in a podcast app or someplace else. So I’m wondering whether or not the technology is already changing, how people are going to consume the content, should we be broadening our reach? That’s something I want to think about too.

Dennis Kennedy:

Yeah, I think that you’re looking at the podcast audience and people are going to AI summaries that are spoken word’s kind of this really abstracting out. You say, I get an AI summary of a podcast and it’s spoken to me by an AI voice, so I don’t even hear the people in the podcast, but I get the condensed stuff that I want. Now you can finally listen to all your podcasts, Dennis, and that’s what snipped is all about. So you can grab pieces of things. So I think we’re going to think about that podcasting hasn’t developed in a way of indexing where you can go to specific places. The way that I felt it might have a long time ago, what my thinking is, and I don’t spend a lot of time thinking about this, but it’s something that is kind of front and center for me, is I feel when you look at the internet and what came of it, their podcasting, blogging, other things were this communication platforms that came out of what was the computing platform.

And if this round of AI is the beginning of the internet, then I’m really intrigued by what might be the blogging and podcasting of the AI platform. I don’t know what it is. I don’t know if I’m going to be able to see what that is, but I think there are some very young people now who might already be moving in that direction. And so that’s fascinating to me is to say, how will we do that? So it could be a whole new platform, a whole new approach that we don’t expect. Could be avatars, could be other things like that, who knows? But I think it’s more of the platforms. So a lot of people think podcasts only exists on Spotify or some other place, or that they’re four hours long or they’re like a show. And so I think it’s the changes in the podcast industry, how things are distributed, maybe even the slimming down of the distribution networks, I think will be important in podcasting. And I miss the days when anybody could just say, we want to do a podcast and put it out there and have your own little radio station. So I’ll miss those days, but I’m always looking forward to see what’s happening next. People are doing some cool things out there.

Debbie Foster:

Awesome. So two questions, two last questions. The first one is maybe a futuristic view of where does the legal profession go in the next five to 10 years as it relates to technology adoption and the changing of the legal industry? I’m curious what you all think, where are we going to be in five or 10 years, maybe five years? Where do you think we’re going to be in five?

Tom Mighell:

Let me take this first, because again, like I’d said, I feel that Dennis is closer to legal technology than where I am. And so this is where I see it right now. As of today, my opinion is it’s going to depend on where AI takes legal technology Without ai. I think that five years from now, I still think that I’m going to say almost the same thing. Lawyers are slow to adopt, they’re cautious, they’re hesitant, they’re not adopting the things they need to adopt. But my question is, will AI find a way to simplify the complexity of technology? Will it find a way to say instead of, there are so many things right now that AI has already simplified. Being able to vibe code and create your own app to do anything in just a few quick steps is not something that a lawyer could not, I mean, it’s not beyond the reach of a lawyer trying to do something like that. So I think that there are so many things that AI has already in the process of making easier or simplifying. I’m hoping that that will be a catalyst to getting lawyers to learn more about legal tech or being able to use technology in a way that’s more what we’ve been trying to aim for all these years without this slow level of adoption. I just don’t know if AI is something like AI is not there as an accelerant. I just don’t know that things change. Dennis

Dennis Kennedy:

Sort of unfortunately, my answer is that the problem is the legal system and the court system and everything around it and the legal profession is being part of that. If I were an optimist on where the legal profession was going in five years on technology adoption, I probably wouldn’t say I’m really looking forward to retiring and step away from it and do something else. So I’m bullish on certain things. So I really like what the generation, the students I talk, what they’re going to be able to do once they get a chance to do that. I love what’s happening in the access to justice space with technology, but all of it is using technology to route around lawyers and its purest and best form. And lawyers are fighting to keep the monopoly. And whether it’s AI or anything else, we have issues around state-based regulation, all sorts of things. So I am not bullish on what’s going to happen in five, 10 years for the legal profession. And that’s kind of troubling to me, given as long as I’ve spent in the legal technology world.

Debbie Foster:

I think those are both really interesting answers and there’s a lot of unknowns. But I think we also all know that even though AI is a big catalyst, like you said, Tom, the problems that we thought we were going to solve five years ago are still the same problems that we’re looking at today. And so it’s hard to not, the legal industry is very resilient when it comes to bucking back against transformation. And I think we’re going to still see that even with ai. So

Dennis Kennedy:

I just say, Debbie, one thing on that, remember during the early period of COVID when people said 2021 basically when people said, we did 10 years in 10 months, it’s amazing. And we’ve spent all the time since then trying to go backwards.

Debbie Foster:

We have and bring

Dennis Kennedy:

People back into the office and do all of that. So it’s hard to be optimistic, like said that what’s happening, the access to justice space is pretty cool. So I see a lot of potential there if the state bars and the lawyers allow them to do it.

Debbie Foster:

And I think that’s a good segue into how do you both want to grow personally and professionally through the next phase of the podcast? What’s most exciting to you about what is to come?

Dennis Kennedy:

Well, the truth be told, my favorite part of the podcast is the time that Tom and I get to talk before we actually hit the record button. So I’m looking forward to having those conversations with Tom. But I think I touched on something a little earlier where I would like to say that what I want to do in the podcast is kind of be more open with the things that we don’t do well and the things that we’re trying and to not kind of fight against this urge that I see everywhere. That you have to be experts on everything and you have to know everything in a time when it’s impossible to know everything. And so I think to have that, whether you want to call it the white belt approach, the beginner’s mind, whatever it is, to kind of bring that more into the show. And then also, I just like the idea that we found this new thing with fresh voices and it shows that there’s still more room for the podcast to grow and evolve in some different ways. And I’m looking forward to that. And then Tommy, it just allows us to be at the cutting edge, the bleeding edge, and that’s really fun.

Tom Mighell:

Well, and I don’t know that I’ve ever been hesitant to say when I’m not doing some of these things right, because I think that there are, and one of the things that I have wanted to use the podcast for, but I don’t think I’ve been quite as successful personally as I would like to be, is to use a podcast as a personal growth driver to be able to learn more. And I’ll give the second brain example. Dennis was all in and he got so much farther than I did. I got in partway and I had challenges, I had time challenges, and I had other challenges and I didn’t get as far as I wanted to. As I get closer to retirement where I will have the time to do that, I really want to use the podcast to drive what I learn about to say, here are the things that interest me.

Here are the things I want to talk to the audience about. This will help me become a better use of better technologist all the way around. But I can really see, one of the things that chat GPT might not have been right about getting to our thousandth episode, but one of the things that I think it was right is it saw me becoming more of a content creator. And once my time is freed up to do that, I’m really looking forward to getting back and learning and developing more of my own skills, my own muscles around legal technology as long as I no longer have a regular job hours to concern me or to worry about. So that’s personally what excites me about it is the ability to kind of begin again and keep the spark going even though I might be retired and closer to the old grumpy man in the assisted living facility.

Debbie Foster:

Well, congratulations on 400 episodes. This is quite an accomplishment. And like we talked about before, not very many people get here. So I appreciate you all letting me ask you all of these questions and you sharing all of that feedback and wisdom about being podcasters for 19 years,

Tom Mighell:

We are so glad that you could have been here to join us. We would not have had it any their way.

Dennis Kennedy:

Yeah, the only change we would’ve made it is we were all in person and we recorded in an ice cream shop.

Debbie Foster:

Count me in. And it’s been a long time, but here’s the thing, now it’s time for our parting shots. That one tip website or observation that you can use the second this podcast ends and I really want to go first.

Dennis Kennedy:

Of course you can. Okay,

Debbie Foster:

So I, I’ve talked before on the podcast about one of my most favorite utilities called SaneBox. I have been a SaneBox fan for a really, really long time. And a couple of months ago we had this new policy that I can’t just go buy any technology product.

Tom Mighell:

It’s terrible, isn’t it? That’s terrible

Debbie Foster:

Policy. It’s awful. These people with the policies and the things that I’m like, so I had to go get permission to do this, but I have been getting these superhuman ai, superhuman AI ads all over everything like you should. And it said email AI helper assistant. And so a couple months ago I got the thumbs up from our CIO to try it, and I am shocked at how much I love it and how helpful it is in helping me draft email responses. And because I’ve been using it for a couple of months, the first week or two I was like, I think I’m going to cancel this thing I’ve already paid for a year, but I think I’m going to cancel it. But the more that I use it, the smarter it gets. Unlike Sandbox, which you can train sandbox, but you have to actually take the effort to say, this no longer belongs in my inbox.

Superhuman figures it out. It has gotten, I’ve just even noticed how it’s interpreted my tone and style differently as it’s watching how I’m responding to emails and suggesting this is create a meeting with this one. Or, I mean it’s, it’s been awesome to have these responses, 90% written for me before I even have read the email. I open it and it’s like I click the reply button and I’m like, that’s actually pretty perfect. So I am not a big copilot person, so I have not leaned into copilot. Some people that I’ve talked to about Superhuman have said, copilot can do that for you. And I’m like, no. I like this really cool tool called Superhuman. So superhuman.ai is my parting shot.

Tom Mighell:

Well, but Copilot can do more than just draft, right? I mean, it can also organize your email too, which is something copilot isn’t doing right now. I have been wanting to do Superhuman for a long time, and this may be what tips me over my only hesitancy is because I use sandboxes and not to warn anybody else off of it, because I’m still probably going to try it, is it is more expensive than Sandbox, right? I mean, it’s not, they’re very proud of their product because it is not a cheap thing to use. But no, you convinced me. I’m going to try it out. Maybe we can talk about the battle of the email tools on a future podcast. Dennis, I have two very quick parting shots. They’re all AI related, shocker of all shocks. The first one is, and this is also a topic for an upcoming episode, perplexity has its own web browser.

It’s called Comet. And it is a very interesting approach to a web browser and both Dennis and I have invites if you are interested. I originally thought that comment was only going to be for people who subscribe to Perplexity, but apparently that’s not the case because they’re giving us invites to give to anybody. So if you have an interest in an invite, you know how to reach out to us. We’ll talk about that more at the end of the podcast and then we will let you know our thoughts and feelings about Comet on an upcoming podcast. My other one I’m going to supplement. The last podcast we were on, I talked about an add-in that works great between Notebook LM and other generative AI tools. Here are two more add-ins that work with Notebook lm. One of them is called Web Sync. It is a full site importer for Notebook lm.

You can create it to take a website and import the whole website into Notebook lm. And then there’s another one called, it’s called the YouTube link Automator that extracts YouTube video lists and links and automates adding them to Notebook lm. So if you have a lot of videos, it helps with that full disclosure, I haven’t tried those out yet. They get decent ratings in the Chrome store that I went to go look at them at. But interesting you are starting to get into Notebook lm. I think that there are a lot of extensions out there that are going to help make the process better. Dennis,

Dennis Kennedy:

So I decided to do parting shots past, present, and future look at you. So in the past just give you a T part pay

Debbie Foster:

Special.

Dennis Kennedy:

It seems fair. It seems fair. So it could be a permanent parting shot is that Kevin Kelly who’s behind Cool Tools has a regular Sunday morning email newsletter called Recommend that has cool new stuff all the time. There’s always great stuff in there for Party Chat present. This is my advice to listeners is so many lawyers I talk to talk about how disappointed they are with AI and they’re using free versions of stuff and it just blows my mind. And so I say my part shot to you is pay the $20 a month for a AI subscription and if you already are paying $28 for one, just buy another and compare them. Your view of AI is going to change in a lot of ways and you’re going to understand it a lot more. And for the future, I just did published a white paper. It’s on the SS Rrn side, it’s also on my blog, but it’s talking about what the things I’m doing with Persona ais. And when Debbie talked about Superhuman, I actually have my AI chief of staff who, especially for routine emails, drafts the emails for me and I tell ’em what I want and he’ll put ’em together and say like, you might want to not want to say it that way. You want to be more direct or everything. So I’m using the persona approach in that way and that’s where I’m going to be doing a lot of my work going forward.

Tom Mighell:

Dennis, does your AI chief of staff have a name yet? Have you named your AI Chief of Staff? I feel like that’s coming

Dennis Kennedy:

Up. I have, yes.

Tom Mighell:

And are you going to share that with us?

Dennis Kennedy:

I will share it with you after the show.

Tom Mighell:

Okay, fair enough. I’ll wait for that. Alright, 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 to Networks page for our show. You can find all of our previous podcasts, maybe not all 400, but most of them along with transcripts on the Legal Todd Network website. If you like to get in touch with us, maybe to ask for a comment invite. You can always reach out to us on LinkedIn or you can leave us a voicemail. That number again is 7 2 0 4 4 1 6 8 2 0. So until the next podcast, I’m Tom Mighell.

Dennis Kennedy:

And I’m Janice Kennedy. And a big thank you to Debbie Foster of Affinity Consulting for being with us in our special 400th episode edition. 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 Podcasts and as always, a big thank you to the Legal Talk Network team for producing and distributing this podcast. We’ll see you next time for another episode of the Kennedy Mighell Report on the Legal Talk Network.

Announcer:

Thanks for listening to the Kennedy Mighell report. Check out Dennis and Tom’s book, the Lawyers’ Guide to Collaboration Tools and Technologies, smart Ways to Work Together from a 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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