Podcast Ep #100.2: Managing Capacity by Making Work Visible: Agile Lessons for Law Firms with Dimitri Ponomareff [Bonus]

John: There's a particular kind of project that just grinds people down, whether they're on a technology team or working in a law practice. The scope keeps changing, the deadlines keep slipping, and everyone involved feels like they're being dragged along by something outside of their control.

My guest today is my GreenLine co-founder, Dimitri Ponomareff, an Agile coach turned software entrepreneur. Early in his career, Dimitri was dropped into one of those massive slow-motion train wrecks of a project. Overloaded e-commerce and ERP implementation that had all the markings of a classic death march project.

And in the middle of that chaos, he stumbled into something that ultimately changed his entire approach to work: making everything visible. In this case, it was sticky notes, painter's tape, and a wall full of this shared reality instead of scattered assumptions.

And that shift didn't just rescue a failing project, it opened the door to decades of helping teams get out of overwhelm by seeing their work differently. And it's the same shift that underpins the work he and I are doing now at GreenLine. We're bringing visual clarity and flow to legal teams who feel like they're drowning in work.

In today's episode, you'll hear Dimitri's origin story, the lessons he carried forward from those early Agile experiments, and how they translate directly into the way modern law practices can operate with more calm, more confidence, and far more control.

You're listening to The Agile Attorney Podcast, powered by GreenLine, the Agile workflow platform built specifically for legal teams. 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.

All right, everyone, welcome back. This week, I am really excited to bring on for the first time, which is hard for me to believe because my guest today and I have had so many deep conversations about Agile and Kanban and its application in the legal profession over the years. I'm excited for you to all listen in on one of these conversations for the first time.

I'm pleased to introduce Dimitri Ponomareff. And Dimitri is one of my co-founders in this technology thing that you hear me talk about every so often, GreenLine Legal. So Dimitri, welcome to the podcast.

Dimitri: Thank you, John. Glad to be here.

John: Dimitri has got, I think, a really fascinating story of you've been working in sort of the Agile world and systems thinking and Lean and all of these process improvement, project management methodologies for a long time. How did you get started in all this?

Dimitri: I didn't really realize it really, I was just helping teams and suddenly they asked me, is there a better way? And obviously there's always a better way. I started just visualizing things using stickies on a wall and it just started to make sense to work in a more visual way and to start collaborating also in front of something that held all the information you needed to know on a daily basis. So like most in Agile, stickies and painter's tape were my tools and obviously a wall or windows, I found were fantastic to write with markers.

John: Totally. Yes, yes. So, it's I don't know if you ever listened to the episode I did with our other co-founder, Jeff, but we sort of waxed poetic about the sticky note board and the magnet boards and the various sort of physical iterations of his stuff.

But were you using this sort of sua sponte or did you actually learn because, you know, Agile was in the ether in the early 2000s around anything having to do with technology, or certainly Scrum was, right? And people still conflate Scrum and Agile, and I'm not sure the differences are important, but how did you first become aware of these emerging methodologies? Because I think they are sort of still emerging.

Dimitri: For me, I was in the very early days, so I was probably a year in when it all got started and I just picked up a book called Scrum and it had these funny colors on the front and it played with your psychology because the color names were not the color. Anyways, it was a fun cover book. Remember? Like it said blue, but the word was yellow. It was just the cover made me go, this is interesting. And…

John: Oh, I'd forgotten about that. The whole purpose is to point out that we process visual information more quickly than we process textual information, right?

Dimitri: Correct. And you see that's the thing is that it started just with a book cover, and I still have the book. It's completely trashed, but the idea is that I picked up the book and I felt it was interesting and I knew no one from the community or anything. It was just a book.

And I had just been asked from my company to relocate to the US and take over an entire e-commerce department in the middle of what now we call these death march projects where they’re so huge, they're going to take years and you know there's going to be bodies left on the side of the road at the end of the project because it's these never-ending projects and it was an ERP implementation and…

John: Yeah.

Dimitri: Correct. And they're very serious, right? They have their rules, they have their titles and me, I was always the redheaded stepchild because I was the web guy, right, doing all the e-commerce and they kind of didn't pay attention to me. So I read the book and I started printing out sections to my teams and I said, hey, and they were all movie buffs, right? And they loved the movie Reservoir Dogs. So each lead of the team was Mr. Blue…
John: The colors.

Dimitri: And again, I stuck to the colors, right? And of course, we had the conversation around, well, who wants to be Mr. Pink? It was hilarious, but what it did is we combined a fun concept of Mr. Blue and Mr. Pink and Mr. Green are going to take these teams and do something with it.

​​​​​​​And everything was experimentation, which is the premise of this Agile thing as a whole is it's about conducting experimentation that are sometime as short as a day or a couple of weeks or a quarter sometimes because it's a longer thing. But what happened is, I started printing these concept and exercises and we would talk about it as a team and John, we had fun.
We actually built something, we survived the death march, we actually survived it.

John: Right.

Dimitri: But we survived it in a way and this is a true story. Every single lead of these teams became extremely successful in their careers after holding director and VP position and CIO position later because we learned so much together. We just picked ideas from a book and we applied it.

We had zero attrition during our project, which was not true of the other team, because we collaborated well and we actually showed up every morning for these darn daily stand-up, these things that you do in Agile that at first sound strange, but when you do them and you build that momentum or consistency, these routines are very helpful.

John: Well, and it's interesting. So by the time this airs, I will have had another episode with Tim Lennon go live. And one of the things that Tim and I talked about, even the concept of the stand-up, right? And I think part of why you and I get along so well around all this is I feel like I'm peeling back the curtain for lawyers who don't really pay that much attention to the Agile world writ large.

In a lot of ways, I think I'm the window into it. Agile in technology is in this weird nebulous place right now where a lot of people are pushing back against the notion of Agile. But I think you and I would agree that they're not pushing back against the things that work in Agile, it's that there's this sort of management layer that has taken and tried to create a world where you are doing Agile as opposed to being Agile. And they've made Agile very prescriptive, and it's that prescriptive nature that people are pushing back against.

And I think one of the things that you and I just totally align on is there's no one way to do any of these things and what matters is that we're having the conversation and that it's working together. And so the thing that Tim brought up is like, yes, stand-ups are really useful, but they're not useful as someone says, okay, new rule, everyone has to be in this room at 9 o'clock every morning and we're going to go from 9 to 9:15 and these are the very rigid things we're going to say as we do this, and then we're all going to walk out and go about our day.

And people will inevitably come out of that meeting saying, oh, well, that was a waste of my time. That doesn't feel useful at all. But that's not what you did. You've kind of built this ground up approach of like, oh, this like syncing up every day feels good and so we'll keep doing it.

Dimitri: Yeah. And you see, without going too deep into where Agile is today, in the technology world, you're right. There's been some sort of evolution, but what's fascinating is very early, like 15 years ago, I actually got out of IT and started applying this in other areas. And these other areas could care less about hearing the word Agile, which is fascinating because to tell you the truth, John, you see them online all the time. Oh, Agile is dead or Agile is… It's not that it's dead, it’s that when something becomes so part of your day-to-day, you forget that it even exists because doing daily stand-up is now something that people might not even connect back to Agile. It's just something that feels right to do.

John: Yes, although it's one of the things that a lot of my law firm clients struggle with, right? They don't necessarily feel like they can find the time. And my recommendation to them is, hey, let's try one a week. Let's try two a week. It doesn't have to be daily at first. Let's see how it feels. Let's ease into it, right? This idea of safe to fail experiments or whatever else and we can kind of just go from there.

Dimitri: And I'm sure we're going to talk about lawyers specifically, but just know like when we talk about like teams and team dynamics, I like using personality tests to kind of get a map of the team and stuff. Let me be clear, lawyers are not like developers.

John: No. Yes and no, right? I mean, I don't know. Without going too deep, right? There are human things that are just human and then there are tendencies of experts, I think, that emerge regardless of what the area of expertise is. And then there's just some things that lawyers are weird in lawyer ways and developers are weird in developer ways and that is also can be true. So there's lots of different places.

But let's go back. So from that experience, you and I will accelerate the timeline a little bit, but you started working with more teams. Was that more as an employee or as a coach or consultant?

Dimitri: Now that I was in the US, I realized that the best thing to do in the US is open your own company and start living the American dream of building something, right?

John: And we should say in the US from Canada, which is where you grew up.

Dimitri: Correct, correct, correct. Anyways, it's very easy to launch a business in the US. My point is is that I've been my own company for long, long time. And as soon as I did my next contract because the first one I described to you was, I was an employee. After that, I've been a coach or contractor for all these years. I went straight into state government.

And in state government, I didn't hit lawyers, I hit financial planners that refused to take no for an answer. They saw the benefits on the development team and the data warehouse team and they're like, why are you guys standing up in the morning? Why are you happy? Why do you have pictures of your kids everywhere? It was an agency for early childhood education. But the point is that our room was fun.

We actually stood up in the morning and talked to each other, and we actually felt like we were building great stuff. And the financial planners were like, Dimitri, this is not good for us. You don't understand. We liked being able to blame IT for everything and now we can't because you guys are actually doing good things. So you need to help us look good now. And I'm like, I don't know if I can do this. And it was early on in Agile where it was all about software, right?
John: Yeah, we didn't know if it would work outside of it.

Dimitri: And because they wouldn't take no for an answer, I was game and we were building a grant management system and we literally put the grant documents on the walls. Our cards were actually the grant themselves and we started visualizing what a grant management process would look like and the team was fascinating because for them, again, could care less about the method or anything.

They just felt that now in the morning, they would stand up in front of a wall, they would have a place to congregate and talk and have that freedom to say, I've got a problem or I need help. And as soon as I survived the government, which was actually super fun, and I've done many governments after, I hit my first legal team in a massive insurance company and again, same story.

They just, they said, we want it and that's where my experience with legal started, which was a long time ago and it blew my mind because I was scared. Because lawyers, well, first of all, I've only dealt with lawyers for not good reasons. And…

John:  Right. There is that. Yes.

Dimitri: There's that. But they were fascinating. They loved process. Agile for me as a coach is about structure and discipline. And I had very little difficulty implementing structure and discipline with lawyers because they had already a lot of information that was very well documented, but they had no way to share it and to visualize it, which is what we did, to make it stick and more importantly, improve which was fascinating.

John: So that's fascinating because I think there's so many things I can unpack about lawyers, right? We do love our process and we love our sort of rules and our structure, but one of the things that I think can be true is we can build so much structure in something that it actually becomes unstable or not really usable because it's like, oh my gosh, we're having to do all this. It's a courtyard that's nothing but columns and no open space, right?

You're constantly bumping into something. And you know, this is going to get into a quasi plug for GreenLine, which we're allowed to do. It's my podcast. But one of the things that I've really loved in the conversations that you and I have, and Jeff has helped with as well, is we have to take all of these good intentions around rules and policies and procedures, but we have to turn them into ways of working that are usable and actionable and sustainable and ultimately comfortable for the people that are doing the work.

Dimitri: Yeah. And John, I think you and I have had many conversations about this because one of the things that the law firms we've worked together on fell in love with was creating very precise tasks. And when I built that feature, I thought, you put a few tasks in there, you check them off, you're done. No, this turned into an entire system of task and checklist that there were so many of them, but I understood the need.

But for me, I never expected to see so many checklists and then the use of it being so precise in terms of, well, Dimitri, we don't want the checklist to appear until this point of the process. And I'm like, my gosh, I was just thinking of giving you little tasks and you turned it into a checklist management system that works and I think it boils down to naming, it's silly, but it boils down to naming conventions often to make this work, right?

John: Sure. The other things that you and I have talked so much about in terms of GreenLine and these tools we’re building together is I think the status quo with a lot of Matter management systems, law firm management systems is they're very, very checklist heavy.

But they bring the checklist forward in these very robotic, clumsy ways where it's like, okay, you've defined that these are all the things that need to happen and then the robot, the software says, great, I'm going to make all these things show up at once and assign one person and we're going to give dates to them and we're not going to give any consideration to how many other things that person has on their plate, what other things are due on that day.

So there's not this sort of capacity management and coordination role in the existing tools. And that's a big part of what we're trying to build in from the ground up with GreenLine is to make sure that not only are we describing what we think the process should be, we're making sure that our team has the knowledge, the skill, the understanding, but also the time and the availability to actually execute this process.

Dimitri: Absolutely. And you see, I like that we're like talking about the power of some of these concepts like checklist and tasks because they're useful, but what you've taught me, which this is why I love working with legal firms is that you always word your tasks in the past tense. And if you could explain it to the audience, because for me, that sounded silly at first, I'm like, why? But now I'm following your direction every time.

John: Yeah, I came to this through experimentation with my clients. And what I learned is that when there is a task that is done and it's written in the past tense, there's something about the human brain that reads the language of that text and the fact that it has a check mark next to it as this sense of finality, right, that this has been accounted for.

It gets back to the thing I've talked about on the podcast and you and I obviously have talked about this a lot. These checklists aren't to-do lists, they're quality standards. And the reason to talk about what are all the things and it can be in the context of definition of ready, definition of done, or sometimes we call those entrance criteria and exit criteria, right? There's all this nomenclature.

It's funny because I will say this even of a basic shopping list or a daily to-do list. It's like, we think of it as a to-do list, but really it is a quality standard. I have not had a quality shopping run if I haven't considered all of these items that are on my list. I have not had a quality day if I haven't bought a birthday card for my nephew whose birthday is next week because that's on my to-do list, whatever it happens to be, right?

If I miss that, it will have been a low-quality day, which means I've now got to do something different tomorrow to make up for that quality failure. This mindset shift of thinking of checklists as quality standards really does, I think, improve the way you think about and the way you approach them, the way you prioritize them. I don't know, I can't unpack all of the psychology at work. I just know that it works.

Dimitri: And you see, I like how you're positioning it because it's probably a good idea that we start talking about tasks since lawyers love their tasks so much is for me, they're action. And you feel good when you felt that you actually took action on a few things today, maybe five, maybe 10, because guess what? Your matter ain't getting done today. It might take weeks, it might take months, but your tasks are getting done and you feel that you're at least moving the needle on a daily basis.

And for me, the way you positioned it is the most important. The matters in the tool that we use, they're cards. They're not tasks, they're cards. And why do I mention that? Well, because they're very visual. Cards are very visual. They flow on a board, but why is that important? Because the value is at the card level when the matter moves through the board, right? And eventually you get either paid for your services or you complete a case or win a case, right? But the value is the matter. The tasks are all these things that make the matter successful.

John: Yes, some of which are administrative, some of which are on the value chain, right, or actually creating things. And again, you and I have talked about this and I think I've mentioned it in the podcast before too, but I think there's some middle ground between matters and tasks. And I think of those as task sets, which is a group of things that should be done in a single sitting. And this is because of my insistence and even going back to the stand-up, right? One of my suggestions for my teams is to banish the words, I worked on, from your daily stand-up, right?

Because I don't want to know about your effort, I want to know about your progress. And the task sets allow you to decompose things down to that task level, but then regroup them in ways that make sure that the matter is getting either to its next high level state, right? So from pleadings to discovery or something like that, but if not to its next state, at least to its natural resting phase of like, okay, I've sent out all of my discovery requests and now there's nothing I can do because there's a 30-day response period.

And my mind is at ease for this particular matter because I can't do work on it and that allows me again, from a resources and capacity planning standpoint, it allows me to apply my resources to some other thing that is ripe for work right now.

Dimitri: And you see, it looks like, and that's why when we started the call talking about Agile and Scrum and all, it's often based on sports analogies, right? And for me, what you just described is passing the baton between a paralegal, to an attorney, and the matter stays open, but the matter keeps changing hands. And that's why I think this works so well is the collaboration is critical in a law firm.

John: And not to again, not to like get too, too deep into selling GreenLine because even though we're allowed to, it's not the most compelling radio to just talk about the product, but one of the things that I think is really effective about the way that we've been designing this is it allows a lot of those handoffs and the communication that accompanies the handoffs to exist inside of the card. And therefore you don't have to have it off to the side, either in a flyby conversation or in the bane of everyone's existence, yet another email.

And by pushing the information and the status and the communication into the card, I think we turn down the temperature on the law, right? It allows us to have these handoffs without basically saying, hey, hey, take the baton right now. It's a more fluid way of working.
Dimitri: And you see, without going because you and I tend to go into feature development every chance we get.

John: I know. Yes, we do.

Dimitri: But what's fascinating about not relying on email is me, no matter which industry you're on, I never want to have anything outside of the card because the card helps me save time. If attachments, comments, task, everything is in the card, I don't have to look for stuff.

Now, why am I mentioning this? It’s because you and I are now talking about a ship log. And that's the beauty of working with you is that we're calling it the ship log right now, but we don't know what it's going to look like at the end, but we've noticed that lawyers like taking notes. And right now they're able to do it two or three different ways, but you and I have a gut feel that there's probably a better way to make it easier on the entry, but also easier on tracking what's really going on with the case.

And I think that's the beauty of me, a technologist, working with two lawyers is that you keep pushing the boundaries to me on things that I'm like, why would you need this? But it makes total sense and I think the features that come out of it are really positioned to say, well, that's how a lawyer works and we're able to really make, I think, richness in the interface for them to say, that's exactly how I work.

John: Yeah, well, and I'll push you and we're diving into features. So I do it knowing that there's some risk in doing this. But one of the concepts out of Agile and the Kanban method in general is this notion of a blocker, right? And a blocker is when you can't make progress on the work you hope to make progress on for some reason and you call it blocked. And what I've learned, partly from working with you becauseunlike you, most of my experience in Agile actually comes from working with lawyers.

I have touches with the technology world, but I haven't been as deep in technology teams as you know, most people in the Agile community. And one of the things that always kind of confused me is that technology teams tend to see blockers as almost an emergency, something that needs to be dealt with right away. And my lawyer brain is like, what are you talking about? Like you file it with the court and it's blocked. You can't do anything, but you also can't do anything about the fact that it's blocked, right? The court's going to do what the court does.

And so I want to be able to, on the card, visually know that yeah, this is out with the court without it throwing off emergency signals that says you should do something about it. And so one of the things that we've done in GreenLine is create the ability to have different blocker types. And I've rolled this out with a couple of users already. They love it because we have a blocker type that is literally out with court. We have a blocker type that is client homework, which is a little different, right?

Because we do have influence over client homework. We may not have control, but the interval at which we try to get it unblocked is maybe going to be different based on what that blocker type is.

Dimitri: And you see what's fascinating is me because I work with various industries and obviously when I build the software, I use our platform to build our software, right, is I haven't changed yet. My blockers are red, they are urgent, and they are bad.

John: Right. Yes.

Dimitri: But my team is now talking about it and we're saying, well, could we soften our blockers? And I'm like, yeah, we could create one for legal when legal blocks us, right?
John: Right.

Dimitri: And those are the examples I put immediately for us is like legal vendors external, right? But you really opened my eyes and you see, we started talking about the importance of words, right? So the way we describe things, right? And now we're talking about colors.

And the second you said, but Dimitri, maybe the blockers are not all red. I'm like, what do you mean they're not all red? Now that I see blockers that are purple and orange and it's interesting. To your point, it softens the impact of the blocker and it right away puts your brain at peace and say, well, it's an orange one. It's one that we were expecting to have. And I was not, me and my world, I was not expecting a blocker to be something, yeah, it happens.

John: Yeah, it's things you can live with, right? Inconvenient truths or whatever. Yeah.

Dimitri: And you see when we go back to the Agile methods, right? The reason it's so negative for me and my world is that in Scrum, is you have to remove them immediately. Like today, you can't. Something’s blocked you. In fact, that's one of the thing in the daily stand-up, if you're blocked, you have to say it and you have to remove it, right?

But in Kanban, what's fascinating is we actually practice avoidance. And I want to make sure your audience hears that. When we block in this other technique, we actually say, listen, it's block. Go find something else to do unless you can really unblock it, right? And that's the thing. If it's an external block, then all you can do is say, we're blocked. What are you going to do? Sit around and do nothing all day? No, you're going to avoid that card and you're going to go pick another one and find a way to continue flowing your work. It's less negative, but it's avoidance. And avoidance is an interesting term.

John: And it comes back to being more intentional about managing your team's capacity and the resources you have on your team, right? You don't want someone spinning brain cycles on something that they can't do anything about. That's where I think having that softer blocker, okay, you know, yeah, we're going to need to worry about this in a few weeks, but there's really nothing I can do right now. So I'm going to avoid that card and I'm going to go work on something else.

And we've talked about this, I talk about it on the podcast all the time, right? There's no law firm I'm aware of that is in any danger of running out of work, right? The demand for our services is much, much stronger than our supply of capacity to be able to deliver those services. And in fact, again, you and I have talked about this, I've talked about it briefly on the podcast. I used to talk about the importance of managing demand with capacity as a way to finding balance inside of a business, inside of a law practice.

But I partly through conversations with you, came to understand that you can't manage demand. You don't have control, right? I mean, you can to some extent if you've got marketing capabilities and all the rest, but the demand is out there. What you can manage is your commitments relative to your capacity. How much of that demand do you actually let into your system and when?

And again, part of what we're trying to do in GreenLine is make those commitments obvious, make those commitment points really obvious so that once you make a commitment, you now have incurred what I've started calling delivery debt, which means you owe something to somebody. And in legal, you know, in a lot of times, you owe that something to somebody whether they pay you or not, because if you've signed up for it in the court, like the system believes you're the attorney of record until you get blessed to go away, right? The court has to release you.

Dimitri: You used the word commitment and would you be okay that I also use the word expectation?

John: Yeah, I think that's right. I mean, it's levels of nuance and you know, you and I can go naval gazing really, really deep if we're not careful. I think some commitments are stronger than others. A new client that you haven't even started the work with, if you say, you know what, I think I can take your case and you come back three days later and say, you know what? I'm actually full. I can't take your case. Here's a referral.

That de-commitment is not that big a deal, right? You've a relatively soft expectation at that point. You're still going to be a bummer. They're still going to be mad at you, right? They won't like it, but you're not going to have put them in a terrible spot. Whereas the reason you have to get a judge's permission to withdraw as attorney of record in a trial is that they don't want to leave someone hanging two weeks before, a week before they've got a court date. That's bad for society.

Dimitri: My background is economics, so for me, offer and demand is my favorite topic, is what we're able to do is we're able to tell you what's the offer. The offer is how many things you complete every week. That's your offer. And what you have to realize is that your offer or capacity can be measured in a platform like the one we're using with law firms and once it's measured, you need to decide, are you going to respect it or you're going to kill yourself trying to do the opposite of what the data is telling you.

So if your offer based on your current size is I can do five things a week and I have 50 things to do, well that will take you 10 weeks, right? And that's why I was talking to you about in terms of expectation and I'm simplifying here. But the reason I want to do this is because I'm fascinated by the legal world.

You know, I was working with estate planning with you and then we did other areas, but now this one because you say you don't have a problem with customers, which I'm finding out is true, which means the demand is actually always there and now the firm has to decide, do I set expectations, right, to fulfill these commitments based on what I'm capable and be careful just like a software team, it's very costly to increase your capacity because you have to hire a developer or hire an attorney, you've got to train them.

And so to change your capacity, it takes time and it also hurts your quality sometimes when you don't do it correctly, which is why you and I try to put a lot of quality checks in these process, right? But the last piece on this is that I encountered, as you know, a new type of law firm that does pro bono work in immigration.

And my first reaction is, well, don't take as many. My answer is always, don't take as many customers. But the answer I got back was, but we can't. And I'm like, what do you mean you can't? Because these people need our help and these cases are going to keep coming in and our job is to figure out a way how to help this population. And this is a model I've never seen before where you can't even stop your demand and you still have to build a system to figure out a way how to service this demand in a certain way.

John: Yes, well, you and I have all kinds of conversations to have about that. And we're running low on time. So I'm going to pull us back up. I do want to hit something you were talking about a minute ago because one of my buzzwords is that you have to start with the honest reckoning with capacity, right? And the thing that I think these Kanban systems and that GreenLine particular is trying to do is give you a feedback loop that helps you assess your own capacity.

And the first way we do that is by making the work visible and you basically say, these are all the things I've let in so far and my capacity hopefully is at least this big, and usually it's not, right, because usually there's things that are behind. But then it helps us line things up. The thing you started to get to that we don't have time to go deep on and we should maybe have a whole separate episode just around metrics. It’s tricky subject, right? Because the stereotypes about lawyers and math is often real, it's not 100% real, but it gets in there.

But what the metrics help you do, I think, is to validate or invalidate your subjective feelings about what have I learned about capacity, what have I learned about demand? And you can say, okay, great. This is what I think I'm feeling, but we can go into the data and through graphs or tables or other analysis, we can say, well, that's funny that you feel like you're not being as productive because the data show that you actually are getting more things done since you made this change than you were beforehand, right? Because our subjective experiences can be squishy.

Dimitri: And you see, you're much more elegant than me in presenting this. I would have just said, there's no more emotions, there's pure data. And that's it.

John: Yeah. Well, so it's funny. I think they both tell part of the story and I think that absent the data, I think the emotions are going to override. I mean, it's funny. My friend Melissa Shanahan loves to talk about facts not feelings. And so she'd probably be more in line with how you're thinking.

I don't think you ever get rid of the feelings. I think that the facts can influence your feelings and again, help either cement them, validate them as true or say like, you know what, that feeling you're having, you're going to have to unpack that because it's not objectively what seems to be going on. What else is at play here? We're squishy things, us humans.

Dimitri: Yeah. And like I said, everything's an experiment, right? In what I've been doing for many years. So for me, if an emotion feels a certain way, you experiment and you try to find the data to either prove or disprove the way you feel. It's just that once you have the data to back it up, I think it makes the conversation you and I when we work with law firms, yeah, we try to improve their process and make them happy and do great things for them, but what I love about it is that there's much more than just winning cases.

There's running your back office. There's keeping your firm running smoothly, which you and I sometimes talk, working on the business instead of just winning cases in court, right? And that's my point is that what I love about this is as we get to work more with these law firms, they tell us and the back office situation, I run into it in all the law firms. The people who have to work on this, their emotion says, I never have time to work on this because I'm always pulled on your cases and there's no way for me to show you that.

And then we build a back office board and suddenly all the work that's back office, not only for the first time ever is visual, people realize, you mean we want to do all this and you haven't started anything?

John: Right. Yes. It's that human cognitive bias, the optimism bias that we all run into. It reminds me, and then I want to ask you one last question before we wrap up. The very first Agile coach I had when he was talking about making the work visible, said, make the work visible. No, all the work, right? It's like, it just takes that number of things. Like we think we're doing it.

There's so many things that we're doing that we don't recognize are part of the things that are taking up our capacity and it's almost a mindfulness process to be able to identify, oh yeah, there's this thing and then there's this other thing. And like really getting them all kind of dragging them into the open so that you can see them all is something that just takes time. It's hard to do in one swoop.

Dimitri: And you see John, it's a double-edged sword, right? Because the way I've been positioning it was use the data to prove a point. But often what I've seen, especially when you know someone is new in a position or is very enthused and trying to do a lot of things, they one day go to their boss and say, I'm overwhelmed. And the trick is to say, show me what you're working on. And suddenly the list might be actually much smaller than expected.

And that's the thing, it's a double-edged sword. Sometimes your gut is correct. You have way too much, but sometimes you don't have that much, it's just you're not effective. And you have to talk to another human to say, I'm drowning here and I can't explain it. Show me what you got. And as soon as we've got these visual cards, John, we can really have conversation around, it's not that bad, but maybe we need to train you on something or maybe we need to buddy you up with someone to learn something.

John: Sure. Yeah, that's great. Okay, I'm going to ask you one final question, which is based on the work we've done together with law firms and lawyers, the work you've done independently, for someone that is looking to get started, right, to tame the overwhelm, what's a great place for them to start?

Dimitri: Wow. To tame the overwhelm. So for me, my first reaction is obviously limiting the amount of work you're taking, right? And what I mean by this is that if you want to spend more time with your kids or you want to enjoy your favorite sport or just feel like you have a life outside of work, you have to protect your time.

And for me, the first way to protect your time is to have time blocks on your calendar, but also limit honestly the amount of work you're capable of doing until you reach that point that you're doing the work, but it lacks the passion, it lacks the quality because you're just overwhelmed. And for me, time blocking, being smart about how you manage your calendar, but also being honest and saying, listen, my track record shows that when I'm really focused, I can get you three or five things a day or a week and when I'm at that pace, we're killing it.

Like everyone's happy, just like a doctor, how much time I spend with my clients and how I talk to them and I think the feeling of overwhelm for me is being honest with what you're capable of doing, where you find that your quality starts hurting, and you know when that happens, and then you've got to block time. We're doing this recording on a Friday for a reason. I don't book anything on Fridays. So it was the perfect time to do a podcast with you.

But that's been for years I've been doing it. It's not that I don't do anything on Friday. I give myself the permission to have the space to do things that are meaningful. And for me, a podcast, I'm not going to do at 9:00 AM on a Monday.

John: No, there's way more important things. I love that. I'm going to unpack a couple of it just to reiterate because you've hit on themes that I talk about in the show. So one of the things that I heard in the way that I always phrase it is when the bathtub is overflowing, yes, you have to clear the drain, but the first thing you should do is turn off the tap. You've got to limit the amount of new things that are coming in that's causing the mess.

Number two, this calendar blocking and I've talked about that a lot too, but it's a form of making work visible, right? It's not a Kanban board. It's also a way to begin to have that honest reckoning with capacity because once you're blocking your calendar for specific things, it's forcing you to say, well, how much of my time do I want to give to this type of work or to this particular project?

And then I think the last part of it is, maybe not the last, but the last I'll talk about today, is that sort of assessment of priority, right? It's like, oh, if I want to prioritize spending time with my family, engaging in this hobby, whatever, I've got to make the time. I can't just catch the time when it comes available because it'll never come available.

We have to actually, as much as we may not want to be in the rigid world of like scheduling ourselves out, we have to at least erect a scaffolding, right? We don't have to necessarily follow it to the letter, but the bigger Tetris pieces or Lego blocks, I think it helps to sort of put in place. Is that a fair summation of what you're talking about?

Dimitri: It is. And just to make it even clearer is that I plan date nights on cards on a Kanban board. Some people might think it's not romantic, but you know what? I have date nights regularly and they're planned. So we actually don't have to say which restaurant are we going to tonight. And it's a silly example, but you know what? Planning a date night is something that actually, I think requires a little planning.

John: For my longtime listeners, you now know that Dimitri is a bigger Kanban nerd than I am. But I love the example. Let's leave it at that. Thank you so much for coming on and we'll definitely have you back.

Dimitri: Thank you so much, John.

John: Okay, so you can probably tell that Dimitri and I have a lot of fun when we get started down the Agile path. And hopefully you can also hear how passionate we both are about helping our customers find balance, manage capacity, and build the processes and tools that they need to do their best work.

And these obviously are the principles and the ideas guiding what we're building with GreenLine today. And you've probably noticed this already, but I'll name it directly. I am starting to make this podcast a little more GreenLine-centric. You heard it in the intro and you'll hear a few other subtle shifts going forward. And every week I talk about helping law practices become profitable, sustainable, and scalable. And GreenLine is the vehicle I'm using to try to scale my own expertise.

Dimitri, Jeff, and I are working hard to bake in the Agile values that have served us and so many of our clients for years. My hope is that bringing GreenLine into the conversation a bit more in this podcast will help everyone see how these Agile ideas can come to life in real tools, real workflows, and legal teams like yours.

What isn't changing is the core purpose of this podcast. I am still here to help legal professionals of all kinds do great work and find more satisfaction and contentment in their legal careers.

Next week, I'm kicking off my Agile Attorney 101 series to help you and your colleagues do exactly that. So if there's someone you know who could use a little more balance, a little more sustainability, and obviously a little more Agility in their law practice, please invite them to listen in.

If you have any thoughts, questions, or topics you'd like to hear me discuss, please don't hesitate to reach out at john.grant@greenline.legal.

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. Happy New Year and I'll catch you again next week.