When Tom and I started the Fresh Voices series on The Kennedy-Mighell Report podcast, we had a pretty simple idea.

A lot of the most interesting work in legal tech seemed to be coming from people who were newer to the field, earlier in their careers, or just not as widely known yet as they probably ought to be. We wanted to make room for those people. More than that, we wanted to introduce the next generation of legal tech and then, as much as possible, get out of their way.

That was the idea behind Fresh Voices. We were not looking for novelty for novelty’s sake. We were not trying to identify whoever happened to be getting the most attention that month. And we were definitely not trying to create one more little arena for personal branding. What interested us were conversations with people doing serious work, thinking clearly, building useful things, asking good questions, and giving us a better sense of where legal tech and legal innovation might actually be headed.

Three years in, that instinct feels even more right than it did at the beginning.

Part of the reason is that the series gave us something more valuable than we expected: a broader and more grounded perspective on AI in law and legal tech generally than we could have gotten from any one lane, institution, or business model. We heard from builders, teachers, practitioners, access-to-justice leaders, strategists, and experimenters. We heard from people working inside institutions and people working at the edges of them. Just as important to both Tom and me, we heard from global voices as well. We did not want a series that treated legal tech as though it stopped at the water’s edge. Some of the most useful perspectives came from hearing how similar issues were being approached in different countries, different legal systems, and different professional cultures.

Somewhere along the way, Fresh Voices became more than a way to introduce interesting newer people. It became one of the ways we made sense of what was actually happening in legal tech, especially at a time when AI conversations can turn into hype, anxiety, or vendor copy with impressive speed.

That mattered to us.

What We Learned from Our Fresh Voices Guests

One of the nicest surprises of the series is that Tom and I did not just get to meet interesting people. We learned a lot from them. A few lessons came up again and again.

  1. The people doing the most interesting work usually are not spending much time trying to look interesting. A lot of our guests were not performing expertise. They were not polishing a persona or delivering neat, conference-ready talking points. They were doing the work, learning from it, and talking about it with a level of honesty that was hard to miss. After a while, that became one of the clearest signals for us.
  2. In legal tech, practical experience usually beats abstraction. The conversations that stayed with us were often the ones grounded in implementation, adoption, workflow, training, trust, and the stubborn realities of how legal work actually gets done. Big ideas are useful. We like big ideas. But the people who could connect those ideas to actual use were usually the ones we found ourselves thinking about later.
  3. Curiosity turns out to matter more than most people think. Many of our guests were willing to experiment, willing to question assumptions, and willing to learn in public. In a field changing this quickly, that is not a side virtue. It is close to a core competency. You can feel the difference between someone who is still genuinely curious and someone who has settled for talking points. Often, the most significant barrier to innovation isn’t the technology, but the institutional fatigue that replaces curiosity with compliance.
  4. The best conversations about AI in law rarely stay confined to AI. Again and again, our guests brought the discussion back to people, institutions, incentives, and outcomes. Clients. Lawyers. Judges. Students. Court users. Communities. The most valuable conversations were not the ones most impressed by tools. They were the ones most attentive to what people were trying to do, where technology might help, where it might complicate things, and what the tradeoffs would look like in real life.
  5. Career paths turned out to be one of the hidden stars of the series. From the beginning, Tom and I found ourselves especially drawn to the stories our guests told about how they got where they are. It turned out our listeners felt the same way. Those parts of the interviews consistently got some of the best feedback. I think that is because they made legal tech feel less abstract and more human. They also made clear that there is no single path into this field and that some of the most interesting careers are the ones very few people even know exist yet.
  6. Great guests often turned out to be great scouts. One of the pleasures of the series was how often our guests suggested future guests for us. They knew who was doing thoughtful work. They knew who had an interesting story. They knew who was building something worth paying attention to. After a while, the series started to feel a little self-generating in the best possible way.
  7. Newer voices often notice things the rest of us have learned to step around. Sometimes they ask a better question. Sometimes they pick up on a pattern earlier. Sometimes they are simply closer to an emerging reality than the settled conventional wisdom is. That was one of the most rewarding parts of the series for us. It reminded us that if you want to understand where a field is going, it helps to listen to people who are still encountering it with fresh eyes.

Taken together, those lessons deepened something we suspected when we started Fresh Voices and believe even more strongly now: important people in legal tech do not always arrive with a spotlight already on them. Quite often they are just out there doing thoughtful, practical, ambitious work before the rest of the field has fully noticed.

That is exactly why we wanted to talk with them.

Fresh Voices Guests

2023

  • Kristen Sonday: widening access to legal help through Paladin and practical pro bono innovation.
  • Chase Hertel: offering a practical guide to where legal tech is going and how lawyers can actually make use of it.
  • Natalie Knowlton: showing how technology can expand access to justice and help legal service providers reach more people.
  • Tiffany Graves: connecting legal technology directly to the fight for access to justice.
  • Ivy Grey: helping lawyers understand tech competence in a more practical and usable way.
  • Amani Smathers: exploring why so many lawyers still find technology intimidating, confusing, or easy to avoid.
  • Nick Rishwain: helping attorneys better understand legal tech and make more effective use of it.
  • Kristin Hodgins: bringing a grounded perspective on legal tech trends and what tech adeptness can look like in real firms.
  • Flo Nicholas: reminding us that diversity in legal tech is not optional if the profession wants better outcomes.
  • Catherine Bamford: explaining what it really takes to make document automation work well.

2024

  • Carmin Ballou: linking malpractice prevention with a broader understanding of legal innovation and legal tech.
  • Quinten Steenhuis: building access-to-justice tools at Suffolk’s Legal Innovation and Technology Lab.
  • Tessa Manuello: bringing design thinking and creativity into legal practice and client solutions.
  • Emily Colbert: focusing on the trusted data foundations that make legal generative AI more useful and accurate.
  • Sarah Glassmeyer: making tech competence feel less scary and more playful for lawyers.
  • Dennis Garcia: offering an in-house perspective on AI, legal departments, and the new wave of legal tech.
  • Jack Shepherd: bringing a UK and European perspective to legal business and legal tech.
  • Jackie Schafer: one of the early AI believers, focused on what legal AI can actually do in practice.
  • Amanda Brown: working on how technology can improve outcomes for self-represented litigants.
  • Amy Conroy: helping lawyers understand the “why” behind data science in legal practice.
  • Caitlin McCabe: showing that curiosity is often the first step toward real legal tech competence.
  • Cat Moon: asking whether generative AI is finally changing lawyers’ mindset about technology.
  • Megan Ma: exploring how generative AI can help lawyers, legal systems, and the people they serve.
  • Nicole Morris: bringing a law-school perspective focused on students, new lawyers, and legal tech learning.
  • Ilona Logvinova: helping lawyers keep up with the fast-moving world of AI and practice innovation.

2025

  • Amy Brookbanks and Michael Kennedy: showing how legal operations and innovation can work together inside modern legal teams.
  • Jason Tashea: putting courts, judicial innovation, and the rule of law at the center of the legal tech conversation.
  • Peter Duffy: making the case that AI competence is quickly becoming table stakes for lawyers.
  • Nikki Shaver: helping firms make sense of a crowded legal tech market through Legaltech Hub.
  • Sarah McCormick: focusing on how practice technologies can improve service, efficiency, and client outcomes.
  • Mathew Kerbis: looking at how AI and automation are expanding alternative legal service delivery.
  • Kimberly Bennett: showing how subscription and flat-fee models can scale with the help of legal tech.
  • Bridgette Carr: keeping the conversation grounded in community, humanity, and what law is actually for.
  • Bridget McCormack: asking whether AI may finally force real lawyer tech competence.
  • Marc Lauritsen: arguing that tech competence now means lifelong learning and attention to fundamentals.
  • April Dawson: emphasizing that AI literacy is becoming essential for both lawyers and law students.
  • Michael Kraft: bringing empathy, patience, and long experience to the teaching of legal technology.
  • Mary Mack: helping sort out the differences among AI, generative AI, and agentic AI.

2026

  • Chantal McNaught: examining the persistent tension between the practice of law and the business of law.
  • Megan Morrison and Laith Quasem: offering extra-fresh perspectives on legal tech from young lawyers shaped by curiosity and adaptability.
  • Thomas Officer: arguing that legal tech competence should not depend entirely on whoever happens to be leading the firm.
  • Erika Pagano: making legal tech more approachable by explaining it in simple, relatable ways.
  • Tom Martin: bringing a builder’s perspective on legal AI, grounded in practical tools lawyers can actually use.

So here is the big thing three years of Fresh Voices taught us.

If you want to understand what is really happening in legal tech, and especially in AI in law, one vantage point is not enough. Conferences will not do it by themselves. Vendors will not do it by themselves. Law firms will not do it by themselves. Law schools will not do it by themselves. LinkedIn certainly will not do it by itself. And one country’s version of the story will not do it either.

You need a wider lens. You need a better mix of voices. You need some people who are building, some who are teaching, some who are testing, some who are questioning, and some who are still close enough to the emerging edge to notice what the rest of us are missing.

That is what this series gave us.

It gave us a way to listen across the field before the field had explained itself too neatly. It let us hear from people who were building, teaching, trying, revising, and sometimes quietly changing things before the rest of us had found a tidy label for what they were doing. That kind of attention matters, especially now.

Legal tech has no shortage of noise. AI in law certainly does not. What the profession needs, and what thoughtful people in the profession are usually trying to find, is something more dependable than noise. Something more usable than buzzwords. Something with a little human texture still left in it.

Our guests gave us a lot of that.

And that is why we are still listening. Listening scales better than hype.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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