Podcast Ep #100: Why Agile Lawyering Matters & The Journey to 100 Episodes

Every so often in a career, you hit one of those milestones that kind of causes you to look backwards and forwards at the same time. And this episode is one of those moments for me. So, instead of my usual advice and tactics around Agile and legal practice, today I'm taking a little bit of a step back to talk about the bigger picture, how I got to this milestone, why I've stayed committed to this work, and what's happening in my world that will shape where this podcast goes next.
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You're listening to The Agile Attorney Podcast, powered by Agile Attorney Consulting and GreenLine. I'm John Grant, and it is my mission to help legal professionals of all kinds, including myself, build practices that are profitable, sustainable, and scalable for themselves and the communities they serve. And you all are part of my community. So, ready to become a more Agile Attorney? Let's go.

Hey everyone, welcome back. And welcome to episode 100 of The Agile Attorney Podcast. It's a little crazy to have hit this milestone, and I wanted to spend a little bit of time talking about what it means to me to have gotten here and why I've been able to stick with it for as long as I have.

My production team tells me that fewer than 7% of all podcasts ever get to episode 100. So, there's a lot of podcasts in the world, so that's still a large number, but I think that puts me in relatively rare company.

So, I've released weekly for going on two years now. I've had a few little cheats in there where I've rerun some episodes where I appeared on other people's podcasts, but for the most part, I'm putting new stuff out into the world week after week, and I do it because it's important to me in a lot of different ways. And I spend a lot of time on this podcast talking about the what and the how of building a more Agile legal practice. Today, I'm going to talk a little more about the why for me, right? Why this work matters to me.

And you know, I don't think anyone gets to a milestone like this without kind of three high level drivers, right? Perspiration, inspiration, and determination, if I'm going to be a little cute about it. But the perspiration part, it's real, right? I've spent a lot of hours on this. I'm often recording these episodes sometime between like 5:30 and 7:30 in the morning. That's the time of day that my house is relatively quiet and I'm not tied up with other commitments. For those of you who have suggested that I should turn this into a video podcast, one of the main reasons why it isn't is that I have zero interest in being camera ready at that hour. Maybe someday my workflow will change, but I don't think that's going to happen anytime soon.

As far as inspiration, you know, there's a lot of sources, but the big one, frankly, is the great feedback I get from all of you. I really love hearing from people who tell me how an episode has changed the way they think about their practice or has given them permission to maybe slow down and dive a little deeper, be more intentional about something in their law practice.

I also love hearing when something I've said has inspired people to try something new or innovative. Those are all the things that I'm going for. And with all of the competition for your time and attention, I appreciate that you let me be part of your world and that you give me such great feedback about how it impacts you.

I definitely want to thank my wife, Katie, not just for tolerating those early morning recordings, but for her love and support on this whole Agile Attorney journey I've been on for well over a decade now. She works from home too, and she's had to tiptoe around probably more than she should have to while I'm recording these things, including right now.

She also was my first window into Agile practices. She's in the software world as a usability and user experience expert, and while I was in law school, she was working on technology teams that were adopting Agile and Scrum. And so, she's the one who first introduced me to the concepts and the language in our sort of household vocabulary, not that we like do it as a household, but you know what I mean. And actually, sometimes we do do it as a household, it just isn't like a regular part of who we are.

For the fact that I have this podcast at all, I owe a huge debt of gratitude to Melissa Shanahan, host of The Law Firm Owner Podcast. She gave me not only the inspiration, but also sort of the concrete information to help me envision what a podcast could do for my mission and for my business. She was gracious enough to pull back the curtain on her own workflows and kind of share what it takes to release a weekly show.

She also connected me to that fantastic team at Digital Freedom Productions I always talk about, and they keep me on track with calendars and deadlines, feedback, just general guidance about what's working and what's not with this show. So, Melissa, thank you, and thank you to the DFP team.

In terms of my inspiration for the larger Agile Attorney mission, I've talked about it a little bit, but I'll just kind of reiterate. It goes all the way back to my sort of first real job out of college, which was at a company called Photodisc. That later merged into what is now known as Getty Images, and all those years were really formative for me.

Photodisc and Getty were one of the great disruptive innovation stories of the late 90s and early 2000s. And you know, Getty doesn't quite have the name recognition of like Amazon or Netflix, but those were kind of our peers back in the day, and we were doing true B2B e-commerce before most people even knew that was a thing.

We weren't just taking payment over the internet, but we were actually delivering our product that way. And this is back in the dial up modem days, so we were pretty early. We really were one of the first companies in the world to figure that out.

Working there and being part of those teams gave me a front row seat to what innovation looks like. And I learned what it means to be really customer focused and work on solving the problems as they express them, not as we assume that they are. I learned about being willing to break the status quo when the status quo isn't serving customers very well, and even if that means disrupting your existing business.

I learned about product thinking long before I had a language for it, and I really learned the value of collaboration and leadership, not just within a team, but across disciplines. So, at Photodisc and then Getty, I sat in product, I sat in tech support, I sat in sales, I sat in marketing, and I sat in legal, and they all had to work together in ways that I think were ahead of their time.

We also had this amazing culture of iteration and innovation, experimentation. We were always tweaking things, launching something, watching how customers responded, and then adjusting. And looking back, this was before even the official Agile manifesto. And I think a lot of the things that we were doing, I now think of as sort of proto-Agile. We were doing some team practices, pair programming was a big one, things that weren't really formally labeled as Agile yet, but definitely carried the DNA of what would become Agile a few years later.

And then I also had this really unusual sort of before and after experience. So, when I left for law school, left Getty in the early 2000s, they hadn't really formally adopted Agile methodologies, but when I came back as in-house counsel in 2007-2008, Getty had gone capital A, Agile. They had trained their teams, adopted Scrum at scale, they had changed their communication rhythms, their meeting cadences, and kind of really reset how the product and delivery organizations worked.

And I just remember noticing when I was back sort of inside those walls, how much of a difference it all made. The product got out the door faster, the communication was calmer, it was clearer, there were sort of less arguments, the teams were more aligned. And really there's kind of like less chaos, less contention overall. Not to say it's perfect, right? Nothing ever is, but it was noticeably, noticeably better.

And I like distinctly remember having this sort of question, this spark of what I do today, hit me in, you know, sitting at my desk inside of the legal department of Getty, where I was like, you know, this works so well in technology, I wonder if there's something in this Agile thing that can work for legal.
You know, like I said, it was very much a question at the time. I had no idea whether it would work. I obviously thought it probably could work, but I knew nothing about how to actually do it.

And it's interesting today, so many years later, after doing this work and seeing the results with team after team, I can say with absolute certainty that the answer is yes, Agile practices work in legal. And you know, they solve problems that are kind of almost historically thought of as just something we need to accept as part of the work we do as lawyers. And I think I'm proving that a lot of those assumptions don't have to be true.

In terms of determination, parts of that are a little more personal. I've mentioned before that I am a fourth generation lawyer. The success of my great-grandfather and sort of earlier generations of lawyers created this kind of cultural gravitational pull towards the profession inside of my family. I had almost this very real lens into the lives of lawyers and lawyer culture without really knowing that's what it was. And that includes obviously the benefits and the successes, but also a lot of the struggles.

And frankly, I don't think I've said this out loud on the podcast before, but I say it privately to people, which is, I've seen how this profession can turn people into miserable bastards. And you know, it's not to say that the members of my family are bastards, although I'm going to talk about one who might have been here in a minute. I say that with love, right? I have seen people in my family have great successes, but also kind of get broken down, get overwhelmed, and have problems in their personal lives in large part, I think, because of the pressures of their law practices.

And the main example is my stepfather, technically my ex-stepfather, and he's a guy who it was part of his identity to project the image of a successful lawyer. And he had some places where he deserved it. He had some big wins. He carried some of the major follow-up litigation in the Erin Brockovich cases, not the ones with Tom Girardi, although I do think he consulted with the now infamous Tom Girardi on some things.

But despite those successes, behind the scenes, he struggled mightily with the business side of his law practice. It was always feast or famine. He had this tendency to take all of these burdens on himself and kind of not share the load of the shortcomings and concerns. He had this deep reluctance to ask for help or to accept help even.

And that even led to something of what I think of now as a shiny object syndrome. And one of the things I admire about him is that he was always really interested in using innovative technology to try to make his law practice better.

But in retrospect, I do see that now as this sort of shiny object problem where, you know, he was chasing the latest and greatest technology with the hope that it was going to save his practice, that it was going to be the magic wand. But he did that without necessarily addressing the fundamentals, the core things that were going wrong, right? He was always putting his hope in this new thing.
Maybe the biggest thing is he had this powerful impulse to try to keep up his appearances long after what I now know he became aware that the foundations of his practice were crumbling.

He wound up taking two bankruptcies over the course of his career, and his practice and his marriage survived the first one, but the second one was a problem, and it kind of came down to his inability to be honest with himself, with my mom, and kind of ultimately with anyone about what was going on with the financial and operational health of his practice, ultimately led to the breakdown of their marriage and a pretty serious stretch of personal and financial fallout.

Even after my mom divorced him, I maintained a relationship with him. I tried to check in with him at least once a month, sometimes more often. And it was so hard. He was always trying to project this attitude, this optimism, that he always was just short of getting this new big case or new big client that was going to help restore his practice to his former glory.

But I, a lot of times, I don't think those clients really existed. I think he was trying to project something to me. And unfortunately, you know, he passed away before he ever found a way out. And I'm not sure he was capable of finding a way out.

Years before he died, before he took the second bankruptcy, he actually did invite me in at one point, knowing that I work with firms like his to try to improve their practices. And we talked a lot about what I thought he might need to do in order to try to resuscitate things, salvage things, build back up from some of the problems that he was having.

And I don't know if it was pride, if it was reluctance because of the personal nature of our relationship, or just because he was so brought up in this very traditional culture of how to run a law practice, he ultimately wasn't able to accept what I had to give. And you know, it makes me sad. I don't, I don't necessarily regret it because I think I tried my best, but I have to admit, it was hard watching him continue to fail even when it was so clear to me what steps he could take to avoid it.

So, part of my determination to do this work and to share it with you all is I really hope that any lawyer, every lawyer can avoid the sort of sad outcome that my stepdad ended up with because I do think that those outcomes are avoidable.

The other part of my determination, I think, started a little over a decade ago. In fact, 2016, two pretty important things happened. So, I'd been doing some work in legal tech and innovation before that. I was running the Legal Hackers chapter for Oregon. And I think because of my visibility around that work, I was asked by the bar to co-chair its Futures Task Force. And my other co-chair was then Court of Appeals judge, now Supreme Court Justice in Oregon, Christopher Garrett, which is pretty heady company.

And I have to say, that experience around the Futures Task Force, although we initially set into it to talk about innovation, technology, things like that, the thing that kept coming up and that we wound up really tying our report to was the scope and sweep of the access to justice gap in Oregon and across the country. And it really drove home for me the ways that that gap contributes to the broader societal stress and I think ultimately the erosion of trust that is a big contributor to our current cultural and political climate.

I truly believe that if people don't have good ways to access help to enforce their legal rights, it is functionally the same as them not having those rights to begin with. And my time on the Futures Task Force really drove that home. And it really sort of drove me into a lot of choices both in terms of volunteer service and professional work. It led me to run for and get elected to the Oregon Bar Board of Governors.

And I spent my four years on the BOG really trying to champion and push for the recommendations that were made by the Futures Task Force. And I think we did a lot of important work to modernize our regulatory posture overall and improve just the way we think about the role of the bar, the role of legal services in the state. I'm really proud of that time.

Among other things, we eliminated some regulatory requirements, we changed some of the RPCs that in my opinion, increased the operational burden on lawyers and therefore the cost of delivering legal services without having a really clear benefit to clients, or at least there were other ways to achieve that benefit without the regulatory burden.

The other thing that we did is we worked with the Oregon Supreme Court and the state legislature, which was no small feat, to change the statutory mission of the bar.

And we kind of transformed it from one that was a little bit noodly, it was kind of focused on public protection. And we embedded instead of protecting the public, we embedded the statutory mission around serving the public interest. And we defined what that looks like, right? We didn't lose the public protection part because that's important, but we added an access to justice prong to the mission and really did it in a way that created some tension with the public protection part.

But I think it's a healthy tension, right? And before the mission change, if there was ever a debate about a policy or some program that the bar should undertake, if there was a protectionist way of going about it, that was the way we had to go because the mission said that's what our job was, was to protect the public.

And what we now have is this really good sort of balancing thing where we have to consider public protection, but we also have to consider accessibility and access to justice overall. And I think that has created a really stronger culture of service and innovation that has benefited both the bar and the people of Oregon overall.

It was right around that time in 2016 that I was approached to join the board of a fledgling nonprofit law firm that would eventually become the Commons Law Center. And I didn't know it then, but that invitation was really going to become one of the most important through lines for my professional life. I was a founding board member, as of today, I am the last one still serving from that founding group.
Our early vision was simple but pretty ambitious, right? We wanted to find a way to sort of address these twin problems of an access to justice gap, but also unemployment or underemployment for new lawyers in the profession.

And we hoped to be able to join those two things in a way that was going to provide high quality but affordable legal services at scale to people who are in that modest means gap, right? People who make too much money to qualify for legal aid, but nowhere near enough to afford traditional representation. And that modest means population is enormous, and I think in a lot of ways, it's the true front line of the access to justice gap overall.

That work with the Commons has been a great education for me in its own right. It is sort of this real time laboratory for seeing what it actually takes to deliver legal services differently, right? Not in theory, not in committee reports, but on the ground with real clients, real problems, real deadlines, real stakes. And it has been such a joy and a privilege to watch that extraordinary group of lawyers and paralegals and law students and operations folks build something that is really both principled and practical.

And I just want to pause for a minute and say that I am so thankful to all of the people who have poured themselves into the Commons over the years from our founding leaders to the current team. I am so proud of the work they've done, and I think they've built something truly remarkable.
Among other things, I think what the Commons has taught me is that you can't solve the access to justice gap with heroics. You solve it with systems, you solve it with balance, with clarity, with manageable workloads and intentional workflows that don't just deliver the legal work, but that support the people doing that work.

We've got a really good culture of mindfulness and intentionality and making sure that the people on our teams are taking care of themselves in addition to taking care of our clients. And I think that is so critically important to the sustainability and the effectiveness of the firm overall.

And the last thing I'll talk about, and this really comes from both the changes I've seen through my bar service and the changes I've seen through the Commons, and it's this core belief that change is possible. There, I think can be a lot of frustration in legal, there's so much emphasis placed on the way we've always done things, the way things have to happen.

But you know, I've changed the ethics rules, I've changed the mission, I've changed practices, we've introduced models for serving legal needs for poor people that nobody thought were possible before, right? And we're doing it in a way that is both financially and operationally stable and sustainable. And I'm telling you, these things are possible.

So, I think that's sort of the mix of things for how I got to episode 100 of this podcast. And yes, I've put a lot of effort into it myself, but I've done it really as an investment, right? And to some extent, a labor of love, but there's also, you know, I won't deny, there is an extent to which it's an investment in my business.

I'm trying to make my own living doing this work out in the world. And as you've heard me talk about in recent episodes, and you're going to hear even more in the future, I'm working on ways for me to scale that impact as well. And so, that is why over, as I've been talking about, the next several episodes, you're going to hear me transition more and more to talking about GreenLine, my new software product, instead of just Agile Attorney Consulting.

I've been trying to figure out how to help teams implement these Agile and system thinking approaches in a way that doesn't depend entirely on my personal time and attention, right? My own finite capacity. And so, I talk about scalability in my own mission every week, and I'm going to try to do that with my own approach.

So, I will still have some private consulting clients for the foreseeable future, that's not going away. I love the work I do with those clients. They give me great feedback and energy and inspiration, frankly, in all the work that they do. But as far as new business, I'm really trying to steer teams and my own energy more and more into GreenLine.

GreenLine really came out of years of me seeing the same patterns over and over again. I would go in, start with a new team, help them get their workflow visualized, get their commitments matched to their capacity, tighten up their strategy, their quality standards, build better feedback loops, all the things I talk about in this podcast. And it would work. It always worked.

But then I also would see how hard it could be for teams to maintain those practices without either me investing energy into it on a regular basis, but also without a tool or a tool set that actually supports those ways of working in legal.

And that's especially when they're using traditional law practice management tools. And you know, there have been some good general purpose tools that I like, but most of them frankly are geared towards the software industry, and so they don't really reflect the language and the needs of the legal world.

So, as I record this, it was just about a year ago when I first started talking with Jeff De Francisco, one of my very first consulting clients. You heard him on as a guest on the podcast. And I really value him as someone who's been willing to experiment and iterate with his own law practice. And then with my other co-founder, Dimitri Ponomareff, who is an amazing Agile thinker in his own right and has this prior experience as a technology founder.

And so, together we've created what we think is the best of both worlds, a software tool that reinforces Agile practices and Agile values around flow and balance and predictability and customer value, but it does all that squarely within the context of the legal industry. You're not going to see a bunch of software or general business lingo and concepts. This is a tool that is built for legal teams.

And it's very much a work in progress. It always will be, but I think we've built a really strong foundation, and I've already seen it be transformational for some of our early adopters. It really does help legal teams do the things that they tell me they want to do, right?

Manage their work more proactively, reduce chaos and overwhelm, improve communication among their team and even with their clients, and ultimately get them to the place where they're delivering their work predictably and to a high quality standard, but without burning themselves and their teams out.

So, that's why you're going to hear the podcast become more GreenLine focused over the next several months. The podcast itself isn't changing. I'm not changing my mission, but it is going to be more of my ideas, my experiments, and my time and frankly, my heart are going to be in GreenLine because I think I've reached this point where I think that this is the best way to scale the impact that I want to have, not one team at a time, but many teams at once, supported by a tool that embodies the principles that I've been teaching for over a decade.

I also, as I've hinted at before, am going to try to revisit the core themes of the Agile methodology as it applies to lawyers. And so, although the next two episodes are going to be labeled as bonus episodes, and that's partly so that I can get a little cute with my numbering scheme, and that way, starting in January, I can kick off with episode 101, what I'm calling the Agile Attorney 101 series.

And my plan is to do 10 straight episodes, just me, no interviews or anything, really reintroducing and in some ways reimagining the foundational concepts of this Agile approach to delivering legal work.
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You know, there's probably going to be a little repetition with some of the work I did on my earliest episodes when I started this thing a couple of years ago, but I think a lot of it is going to be updated with what I've learned over those last two years, both talking about the work and doing it. And so, think of it more as refined fundamentals geared again towards building that profitable, sustainable, and scalable law practice that I talk about every week.

If you have thoughts or questions about those core concepts, now is a great time to hit me with them because I have not started recording those episodes yet, but I will be doing so very, very soon. So, if any of the things, right? The honest reckoning with capacity, making work visible, making policies explicit, all of the things that I talk about, if you have specific questions, go ahead and hit me with them because it's a good time to get them on to the show.

All right. So with that, let me go back one more time and just say thank you to all of you, truly, for listening, for connecting with me, for sharing your thoughts, and for letting this podcast be part of your professional life. It's been incredibly gratifying work for me, and I look forward to continuing this journey with you.

If there's one thing you can do for me right now, it's help spread the word. If you have found any of my episodes useful or interesting, please consider going into Apple Podcasts or Spotify to rate and review this show. It really helps other people find it when they're looking for help with their law practices.

Another thing that helps is if you happen to follow me on LinkedIn, if you can like or comment when I post about new episodes. It somehow gets the algorithm right? And that first couple of hours after a new post seems to be really important. And of course, if you have any friends or colleagues that you think would benefit from a more Agile approach to their legal practice, please encourage them to tune in.

As always, this podcast gets production support from the fantastic team at Digital Freedom Productions, and our theme music is “Hello” by Lunareh.

And I haven't talked about that choice of song much, but I have to say, I love how happy that tune is, and it really speaks to my sort of synth pop 80s Gen X-er soul. So that's why I picked it. If you want, you can look it up on any of the streaming platforms. The whole song is on there. I encourage you to do it. Maybe throw her the few pennies that she's going to get from the stream. I think it's worth it. All right, thanks for listening, and I will catch you again next week.