Podcast Ep #102: Build a Promise-Keeping Machine for Your Law Practice [Agile Lawyering Part 2]

We humans have a natural tendency to want to please other humans. It's part of what makes society work. But that inclination to please people has a hidden cost if we don't give it some reasonable guardrails. We all know that when we say yes to too many things, it leads us to a place where we are juggling more and more commitments.
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And the more time you spend juggling, the less time you spend on delivering on any one of those commitments. That ultimately leads to commitments not kept, which is another way of saying we've broken our promises, and that never feels good.

In today's episode, I'm going to teach you the first step for building a promise-keeping machine that will help give you some of those guardrails and help you avoid promising something until you're pretty darn sure you can deliver it.

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.

A quick note: The concepts I'm discussing today should be useful to you no matter what kind of law practice you're part of or what tools you use. If you'd like, stay tuned at the very end where I'll briefly discuss how my software tool, GreenLine, helps reinforce the practices from today's episode.

Welcome back, everyone. So, this episode is part of my Agile Attorney 101 series, where I'm stepping back from primarily tactics and tools and really focusing on first principles, the mindset, and the big-picture orientation that sits underneath all of the things that I talk about week in and week out on this podcast.

And if you listen to Episode 101, you'll know that I kicked off this series by reframing what I mean when I talk about agility. And capital A Agile is not a tools-first methodology, and it's definitely not about hustle or speed or chasing every new thing that comes along. At my core, I care a lot more about you all being agile than doing Agile. And being agile is something of an identity; it's a systems orientation. To me, it's about building a strong enough foundation so that you can respond intelligently to change instead of feeling like you're getting pushed around by it.

And one of the big themes from that episode is that finding stability is the key to agile responsiveness. If you want to be adaptable, you first need to have a strong base and a strong core. And in the context of a law practice, stability starts with having a realistic understanding of your capacity and being intentional about the commitments you make against that capacity.
Another idea I'll keep emphasizing is that overcommitment leads to a self-defeating spiral. In my nerdy world, we call this a self-reinforcing negative feedback loop, but here's what I mean. When we say yes to too many things, even with the best of intentions, we don't become more effective; we become less reliable.

Our ability to deliver on time becomes less predictable. The quality that we deliver becomes less consistent, and those things mean we're ultimately less helpful to the people we're trying to serve.

So, this episode is a continuation of that part of the conversation because, at the end of the day, one of my favorite ways to frame Agile is as a set of principles, practices, and tools that are designed to help you and your team make and keep credible promises. Not heroic promises, not aspirational promises, credible ones. And the Agile practice that I'm going to focus on today, making work visible, is a great first step towards building what I'm going to call a promise-keeping machine for you and your law practice.

But first, let me give you a literal ripped-from-the-headline story that illustrates why this is so important. Just last month, the Oregon Court of Appeals sanctioned an attorney with a two thousand dollar fine for AI-introduced false citations and a fabricated quote in an appellate brief.

But the AI use is not what's interesting here. In fact, if you're like most people, you probably feel like it's not really news anymore when some new report comes out of a lawyer getting in trouble for bad AI practices. It's become sort of a daily occurrence. But this particular news story, as reported in The Oregonian, helps illustrate why it happens so often.

Because the real issue comes into focus when you hear the attorney who got sanctioned's attempted defense. And in asking the court not to sanction him, the lawyer wrote the following, and I want you to listen to how familiar this might sound.

Quote, "As a busy attorney with a heavy caseload and a desire to fight for justice for all clients, there is an inherent risk of becoming overwhelmed. The temptation of relying on technology to support these well-intentioned goals is strong." End quote.

So, that's the lawyer's own language, and he's right. All of those things, I'm sure, are true. He is busy. He has a heavy caseload. He has good intentions in fighting for justice. He's overwhelmed. He's tempted to use a technology shortcut. That could be any lawyer in the world.

But, of course, we all know now that he took that shortcut, and it bit him. And the two thousand dollar fine really seems pretty mild, but we all know that the reputational hit and the damage this does to his credibility is bigger than that. And it remains to be seen whether anyone decides to file a bar complaint over it, so his headache around this probably isn't over.

I want to be really clear about something. The overwhelm he reports feeling is so real. I'm impressed that he was able to name it so clearly, albeit in retrospect, because I thinkit's a lot harder to identify when you're in the middle of it.

I talk with lawyers all the time who feel that overwhelm without really being able to name it. They live it, and they are quietly struggling under it. And a big part of it comes from that well-intentioned desire to please people, to say yes to new work, to be responsive to new requests, to fight for justice, to impress a partner, to help a colleague. That is not a character flaw. For many lawyers, it's core to their identity and a big part of why they chose this profession in the first place.

But the court did not accept that explanation as an excuse, and rightly so, because this isn't really a story about misusing artificial intelligence. And it's not even a story about a single bad decision made under pressure. What this really is, is a cautionary tale about overcommitment, about what happens when we allow ourselves to make more promises than our actual capacity can support.

When a law practice or the people within it become overloaded, the failure doesn't usually show up all at once. The temperature rises gradually, which makes it easy to miss that it's happening. Deadlines feel a little tighter, judgment gets a little sloppier, the margin for error shrinks, and eventually, people's brains start looking for shortcuts, not because they're unethical or incapable or lazy, but because the system they're operating within has become unsustainable.

Even right now, I bet there is at least part of your brain sitting here thinking, even with all that, I would never submit a brief with AI hallucinations to a court. And I think that, too. We don't tend to see ourselves as the kind of people who make those kinds of mistakes. But that is another manifestation of the optimism bias I talked about last week.

The unfortunate truth is that overwhelm changes how our brains work. The stress and the chaos delude us into believing we can justify behaviors in that moment of overwhelm that we would never defend in the abstract. And then when that happens, of course, the consequences don't just fall on the lawyer. They fall on the client. They fall on the lawyer's credibility, their firm or organization's credibility. And in a way, they erode society's trust in the justice system overall.

So, this is the pattern I want you to notice. Nobody sets out to get themselves overloaded or overburdened. It's one of those paths that is paved with good intentions. But if you want to avoid the bad outcomes that are the inevitable result of overwhelm, and court sanctions are just one possible bad outcome, then you need to do two things.

First, you need to learn how to recognize and name the early warning signs of overwhelm in yourself and in your colleagues. It may feel like admitting defeat or pointing out weakness in the moment, but truly, it is a sign of strength and of maturity to pop the bubble of delusion before it gets too big. And I'll admit, this is way easier said than done, but it will pay huge dividends over the long-term viability and sustainable of your particular legal practice and of your overall life and career in the law if you figure out how to do it.

Number two, and I'll talk about this for the rest of this episode and beyond, you need to learn how to build and maintain systems that help protect you and your team from becoming overloaded in the first place. We need to design practices and adopt tools to protect your finite capacity, to regulate and to manage work in a way that reduces the risk of overwhelm. Because the triggering events for a bad outcome don't happen in the moment when a shortcut gets taken and, say, an erroneous brief gets filed.

In a way, this particular lawyer's sanction looks a lot like a quality control problem. You've probably already wondered, why didn't he review the brief one more time? Why didn't he look at things more closely before he filed it with the court? Why didn't he catch those errors?

Of course, that makes sense in hindsight, but it ignores the realities of overwhelm. That attorney was already struggling to keep his head above water. In the moment, I'm sure it felt like a small victory to find the time, even with the AI shortcut, to get that brief filed in the first place. It is completely unrealistic and not really fair to blame him for not finding even more time to do another round of quality control before he filed it.

But we can fault him, and I think we have to fault any law practice, for allowing and accepting the conditions that led to the overwhelm in the first place. And those conditions happen well upstream of the actual error or the lapse in judgment. They happen when the commitments get made without a clear, honest reckoning with capacity.

So now, let me tell you about how that reckoning with capacity worked in practice for one attorney, my friend and colleague, Amanda. So Amanda is one of my co-founders in the Commons Law Center, the nonprofit modest means law firm here in Oregon. And Amanda is a force of nature. She is smart, she cares deeply about access to justice, and she's willing to put in the work to improve outcomes for her clients and her community as a whole.

And for a long time at the Commons, she was both the executive director of the organization and one of the lead attorneys on its cases. But she also has a life, and several years ago, that life included starting a family. When her first baby arrived, I was able to step in on a part-time basis as an interim executive director and eventually fulfilled something of a case manager role as well. We had some staff attorneys by then who were doing the day-to-day legal work.

And in order for me to get my arms around everything that was going on at the Commons, the cases, the fundraising, all the back office stuff, I started putting the work up on a Kanban board, a very low-tech one, sticky notes on a wall in Amanda's office. And when Amanda came back, she, of course, noticed that I'd made some pretty dramatic changes to her office decor, but she was intrigued.

And I explained to her how the board worked, what the columns meant, and how I was using it to track the work and the commitments the organization had already made. And she got it immediately. As I said, Amanda is an achiever. So she was very diligent about writing her tasks and commitments on sticky notes and putting them up on the board. And then also about moving those tasks across the board, especially into the done column, which became incredibly gratifying for her. It was a tangible marker of progress, this sort of visual representation of promises kept.

But she also started to notice something else. New commitments were stacking up on the left side of the board faster than finished work was showing up on the right. And some of those sticky notes started hanging around longer than she expected, and more than a few of them got a little stale. Actually, some of them would literally fall off the board when the HVAC kicked in, which I jokingly referred to as the Autumn of Kanban.

And, of course, this was deeply frustrating to her. And I don't remember the exact conversation, remember that she's got a new baby at home at this point. But at some point, she said something like, "This work is killing me. There is no way I can keep up with everything I need to do to keep this organization running." And I remember responding, probably in what I imagined at the time was a wise Yoda-like tone, that's not quite right. The organization will keep running in some form or another either way. What you can't keep up with is the things you're choosing to commit to.

Now, Amanda had high hopes for this nonprofit, hopes that I shared and deeply appreciated. But the reality was that none of those hopes were going to be realized if she burned herself out in the process of trying to make them all happen.

And then, I distinctly remember this, a few weeks later, Amanda called me out of the blue. She was excited, really excited about an epiphany she'd just had. She said, "I finally get what the Kanban board is for. I thought it was just a glorified to-do list. But, John, it's so great. What it really is a “no machine.” Before I say yes to anything new, I can just look up at the wall and see everything I already need to do, and that makes it so much easier for my brain to say no to things that aren't actually that important. And I can do it without feeling so guilty about it."

Now, I've told that story a lot over the years, partly because I still get a kick out of how excited Amanda was to have a “no machine” in her life. It's not something most of us think we need right up until we realize we really need it. But lately, I've come to understand that the real reason Amanda was so excited wasn't that she enjoyed saying no. Her default instinct was still to say yes. What she really cared about was keeping her promises, delivering on the commitments she'd already made in a useful way and with quality intact.

And so, I think what the visual nature of the Kanban helped her see was that every little chunk of time she spent thinking about or working on the new things piling up on the left side of the board, she was stealing from the same finite capacity she needed to finish the work that was already in progress. In other words, the more attention she gave to new stuff, the less capacity she had to give that final push that was already close to going across the “done” line.

The board was making something visible for her that had always been true, but it had been easy to ignore. When you're already at or over capacity, every new commitment you make is effectively stealing from all the unfinished commitments you've already made. And that realization, that visual feedback loop, was the beginning of a real shift in how Amanda thought about work, commitments, and sustainability, not just for her but for the entire organization. And it wasn't because the board magically fixed everything, but it did finally force her intentions to reckon with reality.

So, let me illustrate how this works in an arena that is completely outside the world of legal practice. My guess is we've probably all had the experience of sitting on a metered freeway on-ramp at rush hour, wanting to get on that highway so we can get where we need to go, but our progress is stalled by that pesky traffic light.

And most people assume that the red light is sort of punishing them for arriving late. The people already on the freeway are being rewarded for arriving early, aren't they special? And they get to keep moving while you're just sitting there waiting. It feels inefficient, it might feel unfair, and it's easy to think if they just let me onto the freeway, I can get where I need to be on time.

But that's not what the on-ramp meter is actually doing. Because the smart folks at the transportation department have internalized an important truth. If we let everyone onto the freeway at once, if we push the freeway right up to or past its carrying capacity, the result wouldn't be faster travel for anyone; the result would be gridlock. Everybody gets stuck. Nobody gets home in time for dinner.
So, the metered on-ramp is there to
protect the system for everybody by slowing things down just a bit upstream, it creates the conditions for smoother flow once you're actually on the freeway. Yes, the cars that made it on there before you did get to their destination sooner, but so do you. That short wait at the light is a small tax to pay to make sure that once you merge, you can travel at a reasonable speed instead of creeping along in stop-and-go traffic. That's the thing that's so easy to miss. That red light you hate is actually doing you a favor, too.

So, let's connect this back to your work in a law practice. When your capacity is already full, letting in any new request, idea, or obligation, letting it merge into your system at all doesn't make you more productive. It creates congestion. Everything slows down. Quality suffers, stress goes up, and none of the commitments, old or new, get delivered as soon or as well as they could have.

So, what Amanda initially experienced as a “no machine” was really functioning a lot more like a metered on-ramp. It wasn't telling her never. It was telling her not right now. By protecting her finite capacity, literally regulating how much work was allowed into her system at once, she was actually improving outcomes for everyone involved, herself included.

The commitments she had already made moved faster towards done. She could give that work her attention without so much stress and without all the switching costs. And when she did eventually say yes to something new, she could do so with confidence that she could deliver it on time and that it wouldn't throw everything else into gridlock.

So, that's the core idea I want you to take from this analogy. Saying "not now" isn't about being unhelpful or unresponsive. It's about protecting flow so that when you do take something on, you can actually see it through to completion on time and with good quality. And the best way I know to start doing that is to make those commitments as well as all of the new things that are trying to become commitments visible.

And obviously, there are some clear differences between traffic on a freeway and matters moving through a law practice. But here's the big one, traffic on a freeway is easy to see. In fact, it's almost impossible to miss. If you drive over a bridge and look down at a gridlocked freeway, you are going to want to avoid getting on that freeway. You may not always have a choice, but if you do have one, you'll take it.

In fact, if you're like me, you may be willing to have your journey take a little longer overall if it means you can keep moving instead of being stuck in traffic. But whether you have a choice or not, your desire to avoid that gridlock is visceral. As soon as you see the traffic, you know in your bones that you want no part of it.

Knowledge work, unfortunately, is trickier because we usually can't see it. And we might know intellectually that things are stacking up. We might feel busy, we might feel behind, but invisible things that we're tracking just in our heads or buried in long matter reports, inboxes, Excel spreadsheets, they don't hit our intuitive, instinctive neural pathways in quite the same way.

They don't trigger that same visceral, "Nope!" response that gridlock traffic does. And because we don't have that visceral response, we tend to keep letting more and more work merge into our system. We keep saying yes, we keep assuming we'll figure it out later. And by the time the overload becomes undeniable, we're already deep in the gridlock.

And that's why making work visible is such a powerful practice. Amanda's Kanban board didn't change the nature of the work she was doing, and it didn't magically give her more hours in the day. What it did was make her existing commitments impossible to ignore. It took all of those invisible promises she was carrying around in her head and dragged them out into the open where she could actually see them. And once you can see them, your brain starts behaving differently.

Just like with freeway traffic, visibility creates a feedback loop. It helps you recognize when you're approaching capacity. It helps you notice when things are starting to pile up, and it gives you the information you need to intervene earlier before you get fully gridlocked, instead of reacting later when your options are much, much worse. Basically, it lets you do something before you wind up taking shortcuts that lead to quality problems like that attorney who got sanctioned for his appellate brief.

So, that's the real power of a Kanban board, especially in the very first stages of working with one. Not so much as a productivity tool, not as a flow optimization tool, although it will be both of those things. But initially, the most powerful thing it does is make your promises visible so you can be more intentional about what commitments you make and when you make them.

Because when you can literally see the work, you can start to see risk. You can start to see overload coming, and then you can start to turn on the equivalent of those on-ramp meters, not to punish yourself or others, but to protect the system as a whole, to provide a better experience for everybody involved, including yourself.

Now, I will tell you from experience working with hundreds of legal professionals of all kinds that when you first put your work onto a Kanban board, when you first start to see all the commitments you've made and where they are in your process, the very first feeling you're going to have is going to be one of relief. You're going to love it. Your brain will say, "Oh, so this is all the work that's been stressing me out. That makes sense. I like it."

Unfortunately, that relief will be fleeting because the next thing that inevitably happens, and it usually happens pretty quickly, is your brain is going to switch over and say, "Oh my god, that's all the work I've committed to. Was I crazy? How am I ever going to dig myself out of this hole?" Starting that digging out process is what we're going to talk about next week. So, stay tuned.

So, here's how GreenLine supports the things I've talked about in today's episode. First off, it's a Kanban-based system, and it's designed to be that external brain and visualization tool that I've been talking about. Now, of course, as Amanda's story represents, you can do that with any Kanban board, including the old reliable sticky notes on a wall version, and I still love that version.

But that version doesn't work when you have a distributed team or when you want to work from home or a coffee shop or maybe even be that lawyer on the beach. So there are some advantages to a software-based tool.

And even then, there is a lot of software that uses a Kanban interface these days, including a lot of law practice management tools. But just because they're using the interface doesn't mean they're grounded in an Agile methodology. In fact, I see far too many of those other tools that are actually encouraging you to be a “yes” engine instead of providing you with a “no machine” or ultimately that promise-keeping machine.

Now my co-founders and I have very intentionally designed GreenLine to be that operating system for your and your team's promise-keeping machine. Now, I'll share more about the specific ways we do that as we get deeper into the Agile methodology in future episodes. But if you don't want to wait for all that to see how GreenLine can work for you, you can go check it out yourself right now at greenline.legal. And if you want to talk with me or one of my co-founders, be sure to click on that Book a Demo button at the top of the page.

All right, that's it for today. As always, 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 found this episode useful, please share it with a friend or a colleague, maybe someone you recognize as exhibiting some of those early warning signs of overwhelm but who may not yet be willing to admit it to themselves.

If you want to do me a favor, you can follow this podcast in Apple, Spotify, on YouTube, whatever your favorite player is. And it helps even more if you leave me a rating or review on one or more of those platforms. Doing that lets the algorithm know that it should put this kind of information in front of more of the attorneys and other legal professionals who I think can really benefit from it. I hope you do, too.

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.