Michael Kraft is Founder, General Counsel, and Chief Executive Officer of Kraft Kennedy, which provides IT services...
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....
| Published: | October 31, 2025 |
| Podcast: | Kennedy-Mighell Report |
| Category: | Career , Legal Technology , Practice Management |
When teaching technology, empathy and patience are key to helping the learner engage and understand tech’s necessary role in legal practice. Dennis and Tom talk with Michael Kraft about his many years in IT service to legal professionals. They discuss practical methods for encouraging tech competence, favorite tools for collaboration, recent legal tech trends, AI, and much more. Michael also shares insights into his fascinating career path in legal technology, with an early start founding Kraft Kennedy in 1988—a business that has grown into a trusted IT solutions provider in the legal industry and beyond.
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.
Show Notes:
Special thanks to our sponsors Draftable and GreenFiling.
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 403 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, Tom and I talked with legal tech educator April Dawson at North Carolina Central University. As part of our fresh voices on legal tech interview series, be sure to give it a listen and hear April’s Fresh takes on AI legal education and more. In this episode, we have another very special guest in our Fresh Voices on legal Tech series in Fresh Voices. We want to showcase different and compelling perspectives on legal tech and much more. Tom, what’s all on our agenda for this episode?
Tom Mighell:
Well, Dennis, in this edition of the Kennedy Mighell report, we are thrilled to continue our fresh voices on legal tech interview series with an ever fresh guest, Michael Kraft founder and CEO of Kraft Kennedy, a multidisciplinary technology and management consulting firm that’s widely recognized as the top IT consulting firm on the legal market. We want our Fresh Voice series to not only introduce you to terrific leaders in the legal tech space, but also provide you with their perspective on the things you want to be paying attention to right now. 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 be this podcast is over. But first up, we are so pleased to welcome Michael Kraft to our Fresh Voices series. Michael, welcome to the Kennedy MA Report.
Michael Kraft:
Well, thank you very, very much. I appreciate being here, known Dennis forever, and this is a real treat. Thank you for inviting me.
Tom Mighell:
Before we get started, tell our audience a little bit more about you. What do you do at Kraft Kennedy? What’s your role, what our audience should know just to get started.
Michael Kraft:
Well, I was a co-founder. I used to practice law and I have absolutely no background in technology, although I was around during the time when there was A-M-T-S-T and Eck and all of those cool machines, but I understood, at least I understood how to pronounce word processing. It wasn’t anything I ever used. I was a litigator, so I was much more interested in what were the issues in a particular case in 1988 we started Kraft Kennedy, Pete Kennedy being the engineer, he had been with IBM and we were fortunate enough to be a partner of IBM, so it said Kraft Kennedy with IBM on the business card. So nobody cared that it was two guys. It was quite remarkable actually.
Dennis Kennedy:
So Michael, first of all, it is so awesome for us to have you as a guest on a podcast and although it’s been fun and I’ve been flattered over the years, when people ask you if I’m the Kennedy in Kraft Kennedy, you’ve clarified that’s not the case. I like to start out by saying that it’s not always easy to talk with or teach lawyers about technology. So sometimes I do, as you know, get frustrated with how difficult it still is to explain technology old and new and its benefits to those in the legal profession. I like the way that you are able to talk about these topics as in your every man, I’m not really techie approach, but could you talk more about your own approach to communicating with lawyers and others in the legal profession about technology and what you found that works well for you? Because obviously something has worked really well for you over the years.
Michael Kraft:
I’ve often thought that the combination of my lack of understanding and Pete’s depth of understanding was really what differentiated us from others. I needed to ask the questions that most lawyers would ask and I needed an answer in English, not jargon. So to answer your question, Dennis, I think empathy is probably at the corner of all of this because I am our clients. I am that group of people that look at these, particularly in the early days, look at these boxes as magic and not really understanding what they would do. And now of course we started in 1988, so things have changed a great deal since then, but I am still well behind other than recognize I use certain tools. I don’t necessarily, I’m not capable of telling you how they work. I’m appreciative that they do and when they don’t, I would like to know why, but I want to know why in English, not jargon. My analogy would be asking a lawyer to explain something and all the lawyer does is talk in statutes or some esoteric area that you had to be fluent in legalese in order to understand doesn’t do anybody any good. The key to anything in my view is the speaker must be the person who’s responsible for being understood, not the listener. So that’s the way I think about this and fortunately I have a lot of patient people at Kraft Kennedy who patiently explains stuff to me. That’s really it to be frank.
Tom Mighell:
So let’s expand out on that a little bit and talk about technology competence for lawyers. We have rules out there now that all the states, most of the states have adopted in some form of fashion, this duty of technology competence. Haven’t seen one officially charge anybody with it or find anybody in violation of the rule, although I’m starting to see more calls for it now that we have lawyers who are relying on artificially generated case law without paying attention to whether it’s hallucinated or not. But from your perspective, I think that lawyers who aren’t technologically oriented want to understand at least how does it work and why does it work. But what do you feel like a technologically competent lawyer needs to know today? What do they need to know about technology in order to properly serve their clients, especially if we’re talking more large firm and corporate law department setting?
Michael Kraft:
I have a very simplistic approach to all of this. My thought is they need to get their thoughts into something that can be shared and as such it can be reviewed and as such can be edited and it needs to be in a reasonable form so that there can be discussion, reuse and a whole host of other things that now are available. IEI can send it to people, I can get information from people, I can look at it outside of the office, I can look at it wherever I am. Back in the days when I was practicing, it was just at the advent, I’m very old. It was just at the advent of Lexus and there were firms that had that, but the firm I worked for, it was a carbon paper firm. So imagine that you had changes to a particular document and you had four or five carbon papers. You were really hard pressed not to go too far over a page because it meant that they had to type everything. Again, today’s world editing is now part and parcel of what lawyers do, and that is clearly the advent of the technology as it is, et cetera.
Dennis Kennedy:
So I always like to mention the first time we ever talked is because you’ve reached out to me and you had this really enthusiastic discussion about a tool called Dolphin Search, which was probably considered, it was a patterned recognition program in eDiscovery, probably considered in the AI category, and you understood the implications of that in ways that I think were profound and went on at Kraft Kennedy to do some work along those lines. So from your vantage point where you sit now and what you’ve seen happening out there, to me it’s some of the higher or highest levels of technology in the profession. What are the areas in legal profession could be technology might not be that need the most attention right now, and how do we actually get the lawyers and I think even more so all of the other legal professionals to pay the attention that’s needed to those things?
Michael Kraft:
This takes me in multiple directions, but it’s interesting you bring up Dolphin search. I really, really liked that product. It was created by a university professor by the name of Herb Roy Blatt. Herb happened to be a triple threat. He was a professor of biology, linguistics and computer science, and the Navy came to him saying, could he possibly create something that would emulate the sounding capability of dolphins to show you how far an object was, wasn’t what the object might have been, and that’s what Dolphin search was. As a result of the interest, I became pretty good friends with Herb and you both may be interested to know that he’s back and he’s got a new company called Eth that’s rely a TH, and what that’s charged with is to take as much hallucination out of AI as possible. I saw a demo of it the other day.
It’s quite interesting. He’s using vectors and giving back percentages of what they find as to reliability. If you haven’t seen it, it’s very worthwhile. And of course talking to Herb is always worthwhile. So there’s the dolphin search stuff. I’ve always been interested in that, which will help the practitioner truncate the effort and get to a better solution faster. We were early in on the document management groups back in the days when there was a documented administrator. People didn’t even know about that and a couple of others that never really surfaced, but for instance, extended name, which is part of the World Docs group, it was so exciting because I think it was a nine character capability of naming an extended name, put it out to 15 or 16 characters and we thought, wow, this is the greatest thing ever.
And now then of course comes perfect solution which had to change its name to soft solution because Word perfect got angry and that got sold to Word perfect where they meshed it into GroupWise and the next thing you know is that got bought by Novell and Novell decided that the coolest thing going was the operating system didn’t understand that the desktop would be Reger Gates understood that and along comes Microsoft who just blows everybody out of the water. My sense is that products that allow lawyers to take care of their practice more efficiently and pervasively so that they can respond to their clients, those are the things that really seem to stick. Now having said that, I’ve been on a tear to say to lawyers, okay, you buy all this stuff, maybe you should start thinking about fixed fee because, but that’s a whole other discussion. I hope I’ve answered your question.
Tom Mighell:
Different set of discussions there that maybe we’ll have later on. I do want to talk, I want to take a slight right turn and talk about collaboration. We like to talk about collaboration a lot on this podcast and I always am interested to understand what our guest’s favorite ways of collaborating are, and usually for me it’s selfish. It’s selfish because I want people to tell me about new tools they’re using that maybe I could go out and take a look at as well. I’ll limit it if we’re talking technology to talk about the use of SharePoint and teams and the explosion and collaboration in that regard, but don’t necessarily have to limit it to that. What are you seeing as far as what are the best ways that you find to collaborate, whether it’s with your clients, with coworkers, with other groups? I know that you’ve long been a pioneer in those Microsoft collaboration spaces, but you can take it in whatever direction you want to.
Michael Kraft:
Well, we’re a big team shop and we’re becoming an even bigger copilot shop. In fact, every week we have an internal meeting to discuss those new things that copilot introduces and it is quite exciting. For instance, copilot is offering a skills matrix, and if you think about the idea of having a list of skills for individuals in an organization, what that does from my point of view, is it truncates that email that goes out, has anybody done this? Is anybody good at that? Which really annoys everybody. So if copilot can deliver skill sets and you have multiple offices with a myriad of professionals and you can find that professional without that email or find, I remember there was, I’m not going to mention the company, but a major entertainment organization. Somebody was saying, oh, we’re going to deal with Disney, who’s done this work with Disney?
And it went through, there were four different divisions of the law department. It was huge and it was a problem. How are you going to find that out? Well, in the copilot teams world and the skillset, it’s fantastic. Boom, there it is. The other thing is it offers bots and therefore, I was thinking as soon as I saw this, I said, well, you remember how everybody’s doing intranets and they didn’t know what to do with them. They thought they were really cool and we’re going to share information, but what happened? They put menus on it for the local things. But imagine that the bot now is your view into the policy manual. So anybody can ask, I’ve been here for X number of years, what are my vacation days? Or what is this and what is that? I’m very excited about this kind of technology because it gives you a quick, reliable answer and I don’t have to bother people.
Tom Mighell:
Copilot just added a helpful feature that I wish they wouldn’t turn on by default because I created a new team for one of our clients last week and it automatically created an agent and said, hi, I’m your agent. I’ll be doing regular status reports in this channel from now on. I’m like, I don’t want you in this channel to do that. We’re going to do that in a different way. So I love it. I love that it did that, but I also hate that it did it because it didn’t ask it told, and so anyway, yeah, there’s some amazing things coming from Microsoft. We have a lot more questions with Michael Kraft at Kraft Kennedy, but we need to take a break for a quick word from our sponsors
Dennis Kennedy:
And we are back with Michael Kraft at Kraft Kennedy. We found in the Fresh Voices series that we love to hear about our guest career paths and our audience does as well. You have a great career story that’s still going and you keep threatening to go into standup comedy as well, which I think is an interesting career path for you. Would you talk about your career and the kinds of things that you’ve done to get you into your current role and focus?
Michael Kraft:
Sure. I graduated law school in 1969. I’m very old and I went to work for the New York State Attorney General’s office and I was in the Bureau of Consumer Frauds. It was really a very interesting opportunity because it allowed me to operate in terms of helping the consumer public, but also I learned to litigate. So that was really a beginning. I was there for a number of years and then I went to a law firm where I was a litigator and we handled a significant amount of international matters because the person I reported to would go over to Europe and bring back these matters. It was really exciting. It was a very small firm, but the matters that he brought back had large firm people defending the other side or we were defending and it was against some of the bigger organizations. It was extremely interesting in that because we were small, we didn’t have a lot of the tools that the majors had, so we didn’t have Lexus and as crazy as this seems today, there was a photocopy machine in the room where the secretaries sat.
There weren’t a lot of secretaries, three or four. It was a small firm. They still used carbon paper because there was an economic reaction by the managing partner, and that was always interesting to me. I wasn’t happy litigating because basically you’re out trying to kill people. A friend of mine from law school had started a financial printing company and I wound up going to work there and I became a salesman and that was an incredible education because now all of a sudden I’m seeing all of the corporate documents that people are putting together and I’m there at the printer. You may or may not know this stuff would get edited through all hours of the night and get filed at the SEC, and I had an incredible opportunity not only to be there and watch how things evolved in terms of document creation, but I had a close friend from a firm who we were doing a deal with and he needed to file in Washington and he said, I need somebody to help me and go with me.
I went and there we were in Washington at the SEC and I’m watching the thing get filed. It was terrific. I’d never had that experience. I wasn’t a corporate guy. Anyway, so fast forward, I was at another financial printing company. The bottom fell out October 19th. The company I was with filed bankruptcy and they decided that they would renege on my contract, which were allowed to do in bankruptcy. I was sitting there very anxious, as you can appreciate kids in private school, they had just built a new house. So I called Kennedy and asked if he was going to take the early out from IBM, and he said, why? And I said, well, we could do this, this, and this. He says, no, Michael, it’s networks, it’s computers. Not a clue what he was talking about. Three months later we started this organization and IBM allowed us to be an agent and they loaned us a substantial amount of money to start. So there we were, and I got to go to the educational offerings of IBM. Now that was beyond amazing because they had an extraordinary number of seminars and we were right there in the new IBM headquarters on 57th and Madison. It was remarkable. Anyway, and that’s how it started.
Tom Mighell:
We talk to a lot of our fresh voices guests about AI and we’re always interested in learning about is kind of what your perspectives are on the future of AI or where you think it’s going. So let’s talk primarily about legal operations and what do you see? Is there any role that you see AI playing in legal operations in the next five or more years, or we talk about it in terms of litigation and access to justice in other areas, but I haven’t heard a lot of talk about how it might benefit legal operations. Do you have any thoughts in that area?
Michael Kraft:
I’m very interested in this legal ops idea, but the question I have is AI as a tool allows one to expand a universe that you would not otherwise easily appreciate. It gives you what ifs. So just like anything else, the challenges that exist in legal ops will be benefited by an array of questions and answers that come from this technology. Dennis and I talk about this often on our calls, and of course you all know that Dennis is deeply into this and I’m always appreciative of the education that I get, but he’s teaching a course or courses in law school about this, and I’ve had the benefit of talking with a number of his students. So just like any other technology that goes deep and broad, I don’t know of anything that has been as big a game changer as this or the practitioner or actually any worker. But here’s what I do see, forget about legal ops. I think there’s going to be a lot of lawyers that are not going to be working. I think this is a major challenge, not just lawyers, but it’s going to change the employment arena so that less people are going to be needed in the same way we’re going to have an opportunity to retrain and or find new initiatives, both legal ops and legal period, and while it’s going to be painful, it’s also going to be very exciting.
Dennis Kennedy:
So let me follow up on that challenge and opportunity. I actually see me, Michael, I’m really intrigued by the opportunities and so I think both for the legal profession and the actual delivery of legal services. So I loved what you’re talking about, about the skills finder. Those are the types of AI uses that I think are really fantastic and underappreciated. But as you look out there and kind of in what you see from, again, from your vantage point with what people are actually doing with ai, especially in large firms, I mean there’s a ton of talk out there, but what do you see that people in those firms actually feel is working what they’re enthusiastic about and where does it feel like there’s actual action and outcomes and not just talk,
Michael Kraft:
I can’t give you specifics, but there are any number of vectors that people jump on to excavate new or broader thoughts within the arena they are focused on, and in that regard, if they use it in an appropriate way, the expansion of their worlds are going to be geometric. In my view. The ones that get in trouble are the ones that try to find the definitive answer. And therein, I think is the Achilles heel because no matter what you do in whatever iteration of AI you choose to partake in, I think you have to vet it. You must go in and make sure that what it’s telling you is actual. There was an article that we put together recently and my CIO said, so here’s the take on this and we did it and blah, blah, blah. He said, but Michael, go make sure that the references are true.
Now that admonition is very, very important because it’s only as good as the truth of what it is you are thinking about now on that level. But the expansion of thinking the what if world, Dennis, that’s what you thrive in. And in fact, I’ve had significant conversations with a couple of Dennis’s students, one particular who is really an eyeopener in terms of how he sees the world and what he’s been able to do with the variety of tools that he’s learned about in that class alone. Anyway, a long-winded way of saying be careful, go deep, use it and play with it because it’s one of the more exciting things that I’ve experienced.
Tom Mighell:
All right. We’ve still got more questions for Michael Kraft at Kraft Kennedy, but we need to take another quick break for a word from our sponsors.
Dennis Kennedy:
And now let’s get back to the Kennedy bio report. I’m Dennis Kennedy.
Tom Mighell:
And I’m Tom Mile, and we are joined by our special guest, Michael Kraft at Kraft Kennedy. We’ve got time for just a few more questions.
Dennis Kennedy:
So you talked about some of my students who you’ve been gracious to talk to and then to help out. But how would you, I mean, think back on your career path and the opportunities that are out there in law, but not necessarily in a practice of law. How would you encourage today’s law students and new lawyers to find career paths in legal tech and other non-traditional careers, especially ai?
Michael Kraft:
I would say that go as deep as you possibly can. Learning the good, the bad, the ugly about the technology. Appreciate what the technology was designed to do. Does it do that or is it hype? What other products are out there trying to do the same thing and how do they measure up to whatever product you’re focused on? And one of the things I’m thinking about is the matter management world where historically my experience has been a particular lawyer has decided on a matter management approach and then decided that, oh, this is very cool. I’m going to productize it and therefore sell it. And that’s why we have so many matter management products out there. The more important thing is being able to take a step back, understand what it does, as if I were starting this today, I would want to have a deep dive into what particular technologies help in facilitating my ability to get the job done, save time and service a client base, but I want to know why.
I don’t want to just pontificate that this is terrific or this is great, or that is because there’s always the next thing that comes along. I mean for somebody ask me, well, which document management package should I use? Well, hold on, let’s find out what you do. Let’s find out what your focus is. And it’s the same thing with any technology. So if you can dive deeper, understand the need of the individual, and then come to terms with what product does what you don’t even have to talk about, which is better or worse, it doesn’t matter what fills their need is everybody has a different way of approaching things.
Tom Mighell:
Alright, our last question is the question that I like to call the best advice question and you get the choice of which way you want to answer this, either. What’s the best advice that you’ve been given yourself around legal technology or what advice would you like to leave our listeners with before we go about legal technology? Either way, you can answer one or both.
Michael Kraft:
I guess the bottom line from my point of view is stay skeptical, ask questions. It’s a wonderful opportunity to use a variety of tool sets, but understand they are tool sets. It’s you that is really the focal point. You are the thinking organism. You are the one that’s supposed to take the lead. You’re supposed to be that person that helps the client and or others to navigate and you can’t relinquish that responsibility to any technology. It won’t work, my view.
Tom Mighell:
Alright, we want to thank Michael Kraft, founder and CEO of Kraft Kennedy for being our guest on the podcast. Michael, tell us where people can learn more about you, where they can reach out to contact you if they want to do that.
Michael Kraft:
[email protected] is my email main office is in New York, but email is a great way to get ahold of me and I’m happy to chat with whomever I view the world as. I don’t have enough friends.
Dennis Kennedy:
Well, thanks so much, Mako. You were a fantastic guest. Great information advice for our listeners. It’s nice to give people a little bit of a view of what some of the things we talk about on our regular now monthly conversation that we have that’s been great over the years. There’s usually so many topics to discuss in so little time, but it’s time for our parting shots, that one tip website or observation you can use. The second this podcast ends, Michael, take it away.
Michael Kraft:
Do research. Don’t just take things on its face. Make sure prove that which you think is the good thing because oftentimes as people say, if it’s too good to be true, there’s your problem.
Tom Mighell:
My parting shot is I guess a confession and it’s pretty short and sweet. A couple of episodes ago I mentioned that I think both Dennis and I had invites for the New Comet browser by perplexity, the new artificial intelligence browser. I thought, hey, it’s pretty cool to have invites that’s making it seem like people would want to be members of the club. Well, nobody asked us for an invite, so I’m guessing that shows the level of interest people having it, but guess what? You don’t need an invite anymore. I think perplexity realized nobody wanted the invites anyway, so they’re now making it available for free. I’ve been using the perplexity browser here for now a couple of months now I think. And I think it’s really interesting. I think there are things I don’t like about it and things that I really do like about it. Having a browser that is instantly ready to do AI things for you, I think is very interesting. But I think there’s a lot of work that is left to be done there. They still have a lot more things I think they need to cover, but it’s free now. So if you want to go and download it yourself, just go to perplexity and you can download it. Dennis.
Dennis Kennedy:
Yeah, comment has been hit or miss for me, but what I really like now, and it has changed my approach to using browser and search is that I now talk in natural language and I’ll give it context and say, I’m planning a trip to Boston. Should I stay at a hotel by the airport on my last night or should I do something else? What are the, and it does that is I have to figure out how to do this or God forbid that we’re back in the legal research world where I have to do some Boolean thing. So I think it’s interesting and definitely worth a try for people who haven’t really, who’ve been reluctant to try ai. This is, you can kind of compare it to Google in some different ways, but my parting shot is something I ran into recently with a law firm, and it’s not just because I spent the number of years I did it at MasterCard, but once again, I found a law firm where I was paying a bill or paying an invoice and they said, you can pay by credit card, but you have to call and only at certain times and do this, but if you just send us a check, you save 3%.
And I’m like, okay, so where’s the checkbook? And I’m like, okay, so where are the envelopes? Where are the stamps? Where’s the checkbook? And so instead of me paying them right away on the phone call or going to the website and paying them while I’m on the phone with the lawyer, a week goes by before I get around to doing that. And once before I did it and I was like in the 60 day late period thing because exactly where I was perfectly willing to pay them the day I got it. So lawyers always say they went to law schools because they didn’t do math, but here’s some math for you. Just add 3% to the bill. It’s like no big deal. Like don’t go through this. It’s super annoying. And to me that you’ve just made it cumbersome to pay instead of what I always used to say at MasterCard, what I used to say to my students in my entrepreneurial lawyering classes, you want to make it easy for your customers to pay you. You want to eliminate all that friction.
Tom Mighell:
A hundred percent. Alright, so that wraps it up to this edition of the Kennedy Mall report. Thanks for joining us on the podcast. You can find show notes for this episode on the legal Todd Networks page for our show. You can find all of our previous podcasts along with transcripts as well on the legal Todd Network website. If you’d like to subscribe to the show. Again, you can do it on the Legal Talk Network website or in your favorite podcast app. If you want to get in touch with us or suggest a topic for an upcoming episode or have a question, you can always reach out to us on LinkedIn or remember we still have that voicemail. You can call us at (720) 441-6820. Sell 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. We wanted to remind you to share the podcast with a friend or two that really helps us out. 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.
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Kennedy-Mighell Report |
Dennis Kennedy and Tom Mighell talk the latest technology to improve services, client interactions, and workflow.