Podcast Ep #101: First Principles: An Introduction to Agile Lawyering 101

A new year and a new number on my podcast episodes feels like the perfect time to slow down for a moment and get back to some foundational questions. Not so much what tools should we be using to power our law practice, but how do we want this law practice to be working in the first place?
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This episode kicks off a reboot of The Agile Attorney Podcast with a return to first principles. Why so many legal professionals feel pressure, internal and external, to do more and more work. Why that so often leads to overwhelm and burnout, and how you can start to prevent that overwhelm by focusing on what it really means to be agile in a world that keeps demanding more.

As always, my goal today is for the core ideas in this episode to be useful to you, no matter what kind of practice you have or what tools you use. If you'd like, you can stay tuned at the end for a short GreenLine bonus segment where I'll talk about how GreenLine supports the concepts I'm discussing today.

You're listening to The Agile Attorney Podcast, powered by GreenLine. I'm John Grant, and it is my mission to help legal professionals of all kinds build practices that are profitable, sustainable, and scalable for themselves and the communities they serve. Ready to become a more Agile Attorney? Let's go.

Hey everyone, and welcome to this reboot of The Agile Attorney Podcast. I'm treating today's episode and the next several episodes as something of an Agile Attorney 101 course, trying to give you a fresh take on the core concepts, the methods, and the tools that I've been using for well over a decade to improve the flow of work inside law practices and to improve the lives of the people who work in those practices.

We're in such interesting times as I record and release this series. I spent a big chunk of my early legal ops career trying to convince lawyers to adopt new ways of working, both from a technology and a process/business model perspective. And now, all of a sudden, we're three years into this generative AI era, and in some ways, we almost have the opposite problem. From my perspective, we kind of have too many lawyers who seem to be willing to say, "Chuck it" on various parts of their practices and turn them over nearly whole hog to our sort of new AI overlords, whatever.

And the perils of that chuck it approach are the things that keep turning up in the legal news headlines, right? We know about them. But I'm old enough now. I've got this growing patch of gray on my temples, and I've personally seen many waves of disruptive innovation, right? From the PC or cable television or cell phone revolutions to the internet and streaming and smartphone revolutions.

And we're obviously now solidly in the middle of an AI revolution where there are some amazing things happening and even maybe more amazing things being promised, some of which will come true and some of which will turn out to be hype.

One thing I know for certain that every single one of those revolutions have in common is that the people and businesses who made the most of them did not just focus on the tech. The tech can be amazing. It can be a force multiplier, but not for people who adopt it based on just what it can do instead of focusing on what they need it to do. I've always said that true organizational improvement comes from a three-part focus on people, processes, and tools, roughly in that order. And nothing about our latest flavor of technology innovation changes those fundamentals.

So while I will certainly incorporate discussions around tools in this series, I'm going to mainly focus on the people and systems part because you're not getting those from the technology and marketing companies that are trying to get all of us to buy their latest next great thing. So I really want to start this series by naming the things that tend to cause legal professionals to seek me out and get help from this process and operations work I do in the first place.

Because there's something of a tension there. Almost every lawyer I work with or even just talk with is getting pulled in a couple of different directions at the same time. They're under these twin pressures or maybe twin desires that they feel like they can never fully resolve with one another. So, let me describe them and let's see if you recognize yourself anywhere in this.

On the one hand, legal professionals of all kinds, like people almost everywhere, are under significant pressure to do more work. And that pressure comes from a lot of places. A lot of it is intrinsic. It's aspirational. It comes from this genuine desire to help as many people as possible or a desire to become more financially successful. I think we all have a desire to do good work and to be seen as competent, reliable, someone others can count on. Maybe it's a desire to please bosses or mentors, partners, coworkers, certainly clients.

But then there's this other layer of pressure that I think is a little bit more fear-based, more worry-driven, largely extrinsic. It manifests with thoughts like, "I don't want to let down the people who are counting on me," maybe parents, spouses, kids, other support systems. Maybe it's, "I need to hit my numbers or else there's going to be consequences." And those might be billable targets, revenue goals, utilization expectations. Maybe you've got, like so many of us, student debt or other financial commitments, mortgages, childcare, tuition, family obligations, that all depend on you being able to make a good living doing legal work

So when people say that they're feeling this pressure to do more, I recognize that pressure is real. It is not imaginary. It's not irrational, and it's not a personal failing. And yet, on the other hand, one of the defining features of a life in the law right now seems to be overwhelm. And when people turn to me and my work for help, I hear the same things over and over again. I feel like I'm on the hamster wheel. I'm running hard all the time, but I rarely feel like I'm making actual progress. Maybe I feel scattered across too many things. I'm juggling so many balls that I'm worried I'm going to drop one.

Or maybe worse, I've already dropped one and it fell through the cracks without me noticing. It could be I feel like I'm always working from one emergency to the next, and I prioritize everything based on who's yelling the loudest or who's bugging me the most. Everything feels urgent. I often hear people say that they feel like they never have the time or the energy to work on their practice instead of in it. They feel like they're always fighting fires. Therefore, they never have time to do fire prevention.

And, you know, of course, the thing that stands out to me is all these feelings are coming from smart, hard-working, dedicated people, right? It's not a lack of commitment. It's not laziness. It's people who care very deeply and who are trying very hard, but they still feel like they're falling behind. And of course, we all know that sense of overwhelm doesn't stay neatly contained inside of our work life. It has a way of leaking out into everything else.

And I think that overemphasis on professional work, especially when that work never really feels done, tends to crowd out other parts of our lives. And lawyers as a group are notorious for this. We all know we have higher than average rates of substance abuse, higher than average rates of depression and anxiety. We have higher than average rates of divorce and strained relationships.

I'm not going to go too far down that rabbit hole, but I do want to name it because what I hear again and again is something like this: I don't think of myself as someone who makes bad choices. I don't think of myself as reckless or as irresponsible or checked out. I've got values. I have goals. I want a full and meaningful life. I just don't know how to have this career in the law and also have the rest of my life because the legal part of my life is so demanding. It never really seems to let go.

So that's why I'm starting here before Agile as a methodology, before tools or frameworks. I feel like if we don't name this tension honestly, then everything else just becomes sort of another coping mechanism, another way to try to do more or faster with less. And that is not what this is about.

Agile, or at least the way that I teach it and the way I'm going to talk about it in this series, is not about getting more output from already overloaded people. It's not about doing more with less. It's not about squeezing maximum leverage out of people or resources or technology. And it's definitely not about chasing the latest tips or hacks to make some small part of your practice better in the hope that that improvement will somehow provide you with systemic relief. That approach almost always backfires.

What this is about and what everything else in this series will be building toward is finding a way to do meaningful work at a sustainable pace, to create balance, flow, and agency in how work moves through you, through your team, and through your organization. And I think an Agile approach is a great way to do that.

So what do I mean by Agile? I want to start with what you already know about agility. Even without knowing anything about a particular discipline or tool set called Agile, almost all of us resonate with the idea of being agile in our law practice and in our lives. To be agile means being nimble. It means being light on your feet. It means doing your work with a certain sense of flow.

It means navigating obstacles skillfully, not by pretending they aren't there and not by crashing through them, but by adjusting and adapting and responding intelligently to what's actually in front of you. To be agile means being responsive to changing circumstances. And that means having enough clarity of vision and purpose that you can adapt your strategies and your activities as conditions change without losing sight of what you're actually trying to accomplish.

And I think that idea, right? Agility is nimbleness, responsiveness, and flow tends to land for people pretty immediately because it's not theoretical. It's something you feel when it's present, and it's something you deeply miss when it's not there. I think it's also important to say a few things about what agility is not. It's not the same thing as speed for speed's sake. It's not about being rushed.

And this is where I can be a little picky sometimes with language because I often hear people say that they want to make their law practice more efficient. But I'm hesitant to use the word efficiency because in the wrong context, efficiency tends to drift towards corner cutting. And that leads to quality problems, which leads to rework, which is decidedly not efficient.

What I care about a lot more is productivity, not in the sense of just doing more work, but in the true sense of the word, actually producing things, making progress, delivering outcomes, finishing work. And agility supports that kind of productivity, not by pushing people harder, but by creating the conditions where work can move with less friction and less waste.

And this is where Capital A Agile can help. So first off, Capital A Agile is a thing, which is not necessarily well-known in the legal industry. And it's called Agile because it aspires to inspire exactly those lowercase a agile qualities in its practitioners.

So without going into a deep history of the methodology, you should know that Agile grew out of some very specific needs in the software and technology industry, particularly around how projects got managed and how products got built. And the old ways just weren't working. Projects were late, they were over budget, often misaligned with what customers actually needed, and sometimes obsolete by the time they actually got delivered.

So Capital A Agile was developed to help teams and organizations refocus on flow and balance and value. It emphasizes short, iterative delivery cycles paired with short but frequent feedback loops. So teams can assess progress, learn quickly, and adjust course before things go too far off the rails.

And, you know, when we talk about innovation in the technology world, we usually think about tools, apps, platforms, devices. I did it in the intro today. But people who really know about innovation will tell you that the single biggest improvement over the past 25 years has actually been a process innovation. And that innovation is the Agile movement itself. And if you listen to episode 100 of this podcast, you'll recall that bringing those kinds of process innovations from the knowledge work-centric world of software into the knowledge work-centric world of legal has been core to my mission for 15 plus years now.

I think another important thing to know is that Agile didn't come out of nowhere. It shares a lot of DNA with methodologies that are much older than it is, primarily, there are a lot of concepts from Lean or Lean manufacturing. And that's a tool set that initially emerged in post-World War II Japan, primarily at Toyota.

But over the past 50 plus years has completely overhauled the way that physical things get made. I kind of think of it like if the Industrial Revolution was version one of manufacturing and Henry Ford's assembly line was version two, then Lean was an incredibly successful version three. And it didn't stay confined to manufacturing. It has significantly influenced telecommunications, transportation, healthcare, and a whole host of other industries.

And there's a bunch of other related concepts too. There's Six Sigma, total quality management, just in time, theory of constraints. They all fall loosely under this umbrella of what we'd call systems thinking approaches to work. And I mentioned them not because you need to remember all the jargon, but to make the point that this is a rich, mature set of ideas. These are methodologies that have revolutionized a lot of industries. But they've only barely scratched the surface in legal.

In fact, I think it's safe to say that the legal industry as a whole, particularly with its emphasis on time tracking and hierarchical management, is kind of still stuck in an older version of the manufacturing revolution, and it's not even the latest version, it's more like version two, Henry Ford's version from like 100 years ago. But of course, again, with all this new tool and technology excitement, I think that's starting to change, although maybe not all of it in the right direction.

And that's because, and I think this is important to hit on before we go any further, this thing shows up everywhere once you start looking for it, which is the deeply human tendency to want quick fixes, right? Silver bullets, magic wands, that one thing that is going to finally make everything feel manageable again.

And when you're under pressure, when you're overwhelmed, when it feels like there's more coming at you than you can possibly keep up with, of course your brain goes to looking for relief, anything that promises to make things easier, anything that promises to give you back control or even just a break. And like I've said, that impulse doesn't come from weakness or laziness. It is very, very human.

But it's also heavily reinforced by the culture we work in, both inside and outside the legal profession. We've got this constant cultural bias towards a sense of urgency, or we're told to have a bias towards action, or to do more with less. And if I'm being honest, a lot of the time what that really translates to is just do more. Period. Do more. And when we're getting those messages, it's easy for us to feel like a failure if we're not responding, if we're not keeping up.

And I just want to reiterate, it is not a failure, right? This is the world we're in, but you are not failing by having these human responses to these pressures. Especially when you layer on top of that, the fact that we're living in this moment of incredibly fast technological change, especially right now with AI, and that pressure is getting amplified even further.

Now, partly, that's because technology and marketing companies are very, very good into tapping into your feelings of inadequacy. Their job is to sell solutions, and one of the most effective ways to do that is to first try to amplify the pain.

In fact, you may not know this, but there are entire marketing playbooks built around identifying a pain point, agitating that pain point, and then presenting a product or service as the thing that will finally make that pain go away. It's literally called PAS for Pain Agitate Solution. And when you're already stretched thin, you're already worried about falling behind, already feeling that fear of missing out, those messages tend to land.

In fact, if there's a version four of the Industrial Revolution, I don't think it's AI. I think it is the refinement and weaponization of attention hacking. The badges, the notifications, the nudges, the gamification, all of it is designed to keep you reacting, clicking, responding, and often buying. And these businesses aren't creating products anymore that respond to demand. They're trying to induce demand.

So we're now in this world where unless we take affirmative steps to protect our time and attention, our time and attention are going to get pulled in directions we didn't choose towards goals that we didn't consciously set and in service of priorities that aren't actually ours.

And this is where Agile, at least the way I think about it, really starts to matter in a deeper way. Because being agile isn't about chasing change, it's about being stable enough to respond intelligently to change. It's not about hacks or shortcuts or cool tools that promise relief without requiring any real rethinking. It's about stepping back and looking at your work and your practice as a system.

And when you're looking at systems, systems thinking asks a very different set of questions. Not what should I be doing next, but what am I already committed to and what do I need to honor those commitments? Not what is that shiny new tool capable of, but what do I actually need something to help me accomplish? Not how do I go faster, but how do I create enough clarity and balance that speed becomes a useful byproduct instead of a risk?

A big part of becoming more “agile,” both lowercase A and capital A, is learning how to design your environment and your systems instead of constantly reacting to stimulus. It's an act and a tool set that focuses on curation. It encourages you to curate your goals, to curate your commitments, to curate the tools you use to meet those goals and commitments. And at the end of the day, you're trying to set things up so that your finite time and attention are supporting your larger purpose, not just being consumed by the loudest input in the room.

And that idea, designing for agency instead of surrendering to urgency, is I think what's going to lead us into the next part of this conversation because once you start looking at work as part of a system, something else becomes very, very clear very quickly. Busyness, especially the busyness that pushes us into overwhelm, doesn't actually make you more productive. In fact, it tends to do the opposite.

And I'm going to go back for a second and I'm going to reiterate what I mean when I say productive because this is where things often get confused, especially in the legal perfection. When I talk about productivity, I am not talking about effort. I'm not talking about hours worked. I'm not even talking about hours billed, even though hours are still the thing that many of us are measured by. But hours are the measure of effort. They are not a measure of outcomes. They're not a measure of value delivered, at least as perceived by your customer. And they're not even a very good measure of progress.

And so again, when I talk about productivity, I'm talking about outcomes, about deliverables, or at least tangible visible progress towards an outcome. And that means actually finishing things, delivering work, fulfilling commitments. And here's the paradox around busyness as compared to productivity. The more work we take on at once, meaning the more promises we make, the more commitments we stack up, the less productive we become overall.

And again, it's not because we're lazy, it's not because we don't care, we're not trying hard, or because we're quote inefficient. It's because our time and attention are finite. And as the number of commitments increases, more and more of that finite capacity gets consumed just keeping track of everything. Tracking progress, remembering what we did last time, context switching, checking in, following up, worrying about what might be slipping. All of that effort feels necessary, but none of it is actually moving the valuable work forward.

In Lean terms, it's just waste. You may think of it in other ways. It may be coordination costs, administrative overhead, tracking expense. Whatever label you put on it, it's the same phenomenon. Capacity that could be applied to actually doing the work is instead being consumed by managing the fact that there's too much work on your plate at once.

Now, I'm going to say something I've said already, but I think this is important. This tendency to overcommit is not a personal failure. It's not a character flaw. It's not a discipline problem. It is quite literally the predictable result of how human brains are wired.

One of the biggest drivers here is a literal human cognitive bias known as the optimism bias. And the short form of it is that we humans are innately optimistic about how long things will take to get done, which means we consistently underestimate the amount of time we'll need to do that thing.

We're also innately optimistic about how much personal bandwidth we have, which means we will always overestimate how much work we can handle. And when those two things collide, that something's going to be easier than it is and that we have more bandwidth than we have, then you wind up with things that lead to overcommitment.

Another manifestation of this is we tend to assume that future me will have more time, more energy, more clarity than present me does. But that's never really the case. And when you layer that optimism bias on top of all of these pressures we talked about, right? Aspirational pressures, fear-based pressures, urgency culture, and attention hacking, you wind up getting this perfect storm for overwhelm. And we all see it, right? You get these people and teams that are permanently operating at or beyond capacity, even though no one ever sat down and consciously decided that was a good idea.

And it's why I sometimes say that one of the core purposes of these Agile practices I'm so fond of is to help you and your team build some guardrails that help prevent this overwhelm from happening. Think of it as something of a scaffolding that protects us from our own lesser instincts. Not because we're bad, but because we're human.

And Agile, when done well, creates sort of external and systemic structures that help us slow down just enough to see what we're actually committing to. It helps us make invisible assumptions visible. It helps us notice when we're trading short-term relief for longer-term chaos. And it helps us design systems that make it easier to keep our commitments credible to ourselves, to our teams, and to the people we serve.

I'm going to say that again. One of the biggest benefits of an Agile approach to working is that it makes your commitments credible. It gets you into position where you can make promises and keep them. And getting to that place, yes, there are practices that can help. There are processes, there are tools that can help. But as much as anything, it's about mindset.

And so before I get into specific Agile practices over the next several episodes, I want to leave you today with a small set of ideas, not tactics, not tools, just ideas. Maybe they're aphorisms, or you can think of them as mantras if that feels useful. But I think these are things you can return to when you feel that pressure rising, when the overwhelm is starting to creep in, or when everything feels urgent or behind.

And I'm going to slow down and I'm going to say them very carefully. I'll probably repeat them. And I want you to just notice how they land. How do they feel to you? You don't have to agree with all of them, but if even one of these resonates, I think it can become the first layer of that scaffolding, a little bit of protection that helps you move towards a more Agile way of working and thinking about work and living a balanced life in the law.

So, here we go. Stop starting and start finishing. Stop starting and start finishing. Before you take on a new commitment, before you say yes to another piece of work, take a pause. Look around for any unfinished work you already have, any commitment you've already made, anything you've started but haven't yet delivered, and then finish at least one of those things first. When you do that, two important things happen.

First, you fulfill a promise. Maybe it's a promise to a client, maybe to a colleague, a boss, maybe it's a promise to yourself. But whatever it is, delivering on a promise always feels good. We like to keep our promises.

The second thing it does is it frees up capacity, real capacity, not just time on your calendar, although that's important, but also mental and emotional and cognitive space. Because when you finish something, you create room, room to think, room to weigh options, room to make your next commitment with more clarity and more confidence. Stop starting and start finishing.
Start less to finish more. Start less to finish more. And I think you already know this is true, even if it's hard to live by. When you have too many things going on at once, it becomes harder and harder to do any one of them well, or sometimes just to do them at all. And you might think of yourself as a good multitasker. Most lawyers do.

But what we're really doing isn't multitasking, it's rapid switching. And the more things you're juggling, the more switching you're doing, the more of your finite time and attention goes into tracking the balls you keep throwing into the air instead of moving any one of those balls forward. You're not producing more, you're just juggling faster. So, put some of the balls down and then don't accept new ones until you've fully carried at least one of those existing commitments across the finish line. Start less to finish more.

Slow is smooth and smooth is fast. Slow is smooth and smooth is fast. Being intentional about quality, about purpose, about what done actually looks like takes time. And when we're feeling pressure, our instinct is to go faster, to push, to rush, to squeeze.

But unless you've built up the systems, the policies, the practices, and the muscle memory that allow you to get to speed without sacrificing quality, then speed for speed's sake is dangerous. At some point, it will get you in trouble. If you don't have time to do something right, what makes you think you have time to do it twice? Slow is smooth and smooth is fast.

Okay. So hopefully one of those ideas resonated with you, maybe all of them. But if any of them did, I hope it will help you take a moment of pause the next time you're feeling that pressure to say yes or to pile something else onto your already full plate. I'd consider that a win for today.

And I think it'll help get you in the right mindset because over the next several episodes of this podcast, I am going to be going deeper on specific practices and tools you can use to be more “agile” in your legal practice, both uppercase and lowercase A agile. It's not about just being more efficient, it is about being more balanced, more intentional, more reliable, more sustainable, and ultimately, of course, more productive. So I hope you'll join me and stay tuned for those episodes.

Before I officially close, I want to briefly touch on the GreenLine bonus I mentioned at the top of the show. And this is a bit of a transition for me personally and for the podcast. Somewhat unintentionally over the past year, I have found myself becoming a software company CEO. But here's the thing. GreenLine exists because of everything you've just heard in this episode.

It is born out of years of me and my co-founders working with legal teams, helping them make their work visible, match commitments to capacity, clarify policies, tighten feedback loops. And then after all of that, I keep seeing how poorly a job the existing tools for legal professionals do in terms of supporting teams and sustaining those beneficial practices.

So just to sort of give you a heads up, at the end of each episode, I'm going to include this little GreenLine bonus segment. It's optional. You can skip it if you want. The core ideas of the episode will always stand on their own. But if you're curious how these concepts can be supported intentionally by a tool that was designed specifically for this way of working in legal, then I urge you to stay tuned.

And the main thing to know about GreenLine from today is that it helps legal teams make both their commitments and their capacity visible. And knowledge work is sneaky because it doesn't take up physical space. You don't have a factory floor or a warehouse where you can see it stacking up. And you can't easily see when your assembly line for delivering knowledge work becomes overcrowded.

So GreenLine is designed to make your workflow, your commitments inside of that workflow, and your capacity for delivering work visible. That allows your brain to easily see and process the early warning signs that you might be taking on too much and then make proactive decisions about what to do about it instead of having to react and fight fires once you've already taken on too much. If you want to learn more, maybe book a demo to see GreenLine in action, you can go to greenline.legal and see how it feels to you.

All right, that is it for today. If you have any thoughts, questions, or topics you'd like to hear me discuss, please don't hesitate to reach out to me at john.grant@greenline.legal. And if you find this episode helpful, one of the best ways you can support my work is to simply share it with a colleague, with a friend, or anyone you think might benefit from a more sustainable and intentional way of practicing law.

You can also follow the show in your favorite podcast player. That way the rest of this Agile 101 episodes will show up automatically for you. And if you really want to help me out, I'd love it if you could take two minutes to just rate and review this podcast on Apple Podcasts, Spotify, or YouTube. It makes a real difference. Those ratings and reviews help the algorithms put this content in front of exactly the kinds of lawyers and legal professionals who most need it.

As always, this podcast gets production support from the fantastic team at Digital Freedom Productions, and our theme music is “Hello” by Lunareh. Thanks for listening and I will catch you again next week.