46. Embracing the Beautiful Mess: How Organizations Actually Work with John Cutler

Summary

Podcast Summary: At Work with The Ready

Episode 46: Embracing the Beautiful Mess: How Organizations Actually Work with John Cutler
Hosts: Sam Spurlin and Rodney Evans
Guest: John Cutler
Date: April 6, 2026

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Overview

In this episode, Sam Spurlin sits down with John Cutler, Head of Product Work and author of the acclaimed “Beautiful Mess” newsletter. The conversation explores what really happens inside organizations—the inherent messiness of human-centered workplaces, how change happens (or doesn’t), and finding meaning in the “mundanity” of everyday work. John reflects on his career-long fascination with organizational patterns, complexity, sense-making, and why striving for clarity too quickly can be a trap. The episode also dives into John’s current work at DOT Work, lessons from tool-building, and explores how leaders shape—intentionally or not—the conditions for real (and lasting) change.

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Key Discussion Points & Insights

1. Career Threads & Origins

Timestamps: [02:58]–[07:11]

• Early Jobs:
  John and Sam share colorful stories about unusual first jobs, connecting them to skill development and early insights about work (“I learned a lot right there that you have to be detail oriented...But I ultimately didn’t know if anyone ever read this stuff.” — John, [01:22]).

• The Ongoing Thread:
  John describes being obsessively curious about “how people work together, show up together, how organizations work, the fun of being on teams.” He traces this back to formative experiences in music, observing group dynamics, and a habit of questioning the status quo (“I tend to be kind of a sponge in organizations for picking up on...elements of the zeitgeist,” [03:10]).

• Pattern Recognition (and Its Traps):
  Recognizing patterns doesn’t equal being able to change them. There’s a difference between observation and impact, which led John to focus on sharing insights through writing rather than always being the face of change ([05:24]).

2. Empathy, Power, and the Limits of Agency

Timestamps: [07:11]–[10:21]

• Empathy Origin:
  John zeros in on “when power in an organization is wielded in a hurtful way,” which informs his trigger words and approach to writing (“I instantly zero in on that,” [07:24]).

• Local vs. Global Change:
  “There’s more locally that we can control and less globally that we can control.” You can have outsized influence on small teams (30–50 people) but little sway over the total company. Most people are shaped more by their company than they shape it ([09:00]).

• Finding Pride in the Local:
  Despite this, moments of levity, joy, and flow on a small scale are worth cherishing (“There is potential to have moments of levity and joy and flow on that kind of local level that you always look back on and be really proud that you were able to shape that local environment.” — John, [10:00])

3. Organizational Ephemerality & the ‘Gold Rush Town’ Metaphor

Timestamps: [10:33]–[17:25]

• Organizations as Temporary Entities:
  Most organizations are neither monolithic nor permanent—more like “gold rush towns” or “mutineer ships” than centuries-old institutions ([11:20]).

  “Your average company is at best like a mutineership or something. It’s like pirate ships are way better organized than your average company. We’re talking about fairly ephemeral institutions of temporary pacts between people...” — John [11:45]

• Clinging to Legacy:
  Many companies act as if every organization should become a Venice or New York—a thriving institution for centuries. But it’s often healthier to accept that value can come in short, meaningful bursts ([15:25]).

• Cherishing the Moment:
  The work becomes about finding meaning in the present and not expecting organizational love or permanence.

4. Finding Meaning in Mundanity & Shaping Experience

Timestamps: [17:25]–[21:32]

• The Mundane as Opportunity:
  Sam discusses the potential to imbue mundane routines with meaning, regardless of an organization’s grand goals.

  “There’s generally a lot of opportunity to instill the mundane that we deal with in our organizations with a lot more meaning and value and really quality of attention...” — Sam [17:25]

• Leaders as Game Designers:
  John explores how leaders, consciously or not, design the “game” teams play—not just through incentives but by shaping the work environment and experience ([18:08]).

  “You are the head game designer...you have the ability to make intentional decisions...that are going to impact the dynamics of what it’s like to work here.” — John [18:30]

• Discomfort with Design:
  Many leaders shy away from this responsibility or fear being manipulative, but can’t escape their influence.

5. Interactions, Agency, and Systemic Forces

Timestamps: [21:32]–[25:06]

• Interaction is Real:
  Focusing on the quality of workplace interactions grounds system thinking and gives individuals a sense of agency, even amid environmental constraints ([21:32]).

  “We are shaping our environments, our environments are shaping us. We can choose how we show up. We do have agency...Yet it’s undeniable that certain environments exhibit enough of a force...” — John [22:30]

• Naming Patterns and Tensions:
  John highlights the value of “naming to tame” organizational challenges and shifting the mindset from “tension = someone did something wrong” to “tension = opportunity” ([25:06]).

  “These are things that are going on that we may want to, like, make some different decisions about...If you are able to get beyond it, then...a lot of open space, a lot of freedom of movement...” — Sam [25:55]

6. The Beautiful Mess Philosophy & Chasing Clarity

Timestamps: [28:07]–[30:54]

• Newsletter Name:
  “Beautiful Mess” reflects the idea that workplace messiness is not inherently bad—it’s often a source of creativity and connection ([28:07]).

• Caution Against Rushing to Clarity:
  The urge for organizational clarity can force premature convergence, stifling deeper sense-making and innovation.

  “If I could wave a magic wand, I would help people get real and just extend the amount of tension that their conversation could hold.” — John [29:30]

• Friendly to Hard Problems:
  John invokes Kat Hicks’ research: Rather than “chasing the complex out” of our organizations, we should make environments friendlier to tackling hard problems together ([30:29]).

7. Ashby’s Law & Organizational Variety

Timestamps: [30:54]–[34:46]

• Embracing Complexity:
  Organizations need internal variety and complexity to respond to an unpredictable world—avoid over-standardizing everything for “consistency’s sake” ([31:19]).

• Premature Scaling:
  Rolling out practices everywhere rarely works and is often motivated by misplaced notions of fairness or equality rather than actual need ([32:27]).

  “Everyone says they want to connect the dots, but they don’t really want to connect the dots. They want to see the dots that are connected to what they care about...” — John [33:17]

• Limits of Information:
  Even with perfect information (e.g., via AI), people are often paralyzed or uninterested in answers that don’t directly affect them.

8. DOT Work & Tool Design Learnings

Timestamps: [35:32]–[44:07]

• Origins of DOT Work:
  Born from previous work on AgileCraft (later Jira Align), John describes the realization that most “rollup” tools fail to help leaders truly sense-make—they’re about translation, not understanding ([35:48]).

• Graph Thinking:
  The product explores how organizations can visualize work and relationships as interconnected graphs, not just hierarchical trees.

• Flexible Approaches:
  Different orgs vary in how explicit and intentional they are with their operating systems; DOT Work aims to provide flexibility and not force rigid definitions ([41:09]).

• Balance of Legibility and Process Aversion:
  Tools must provide helpful structure without robbing local context or building process for process sake.

9. Career Reflection, Hyper-Generalism, and Personal Branding

Timestamps: [44:12]–[48:52]

• Career Arcs:
  John admits he hasn’t mapped out a long-term narrative, but tries to remain aware of “what’s giving me joy” and lets interests and serendipity shape his path ([44:43]).

  “The hypergeneralists are probably more valuable than ever. But they also have the hardest time to explain how their hypergeneralism helps...” — John [45:42]

• The Struggle of Boxes:
  Specializing (“picking a lane”) makes you easier to market; but John values the flexibility to explore both actionable and philosophical topics (“I don’t even know what you’re about the last year, John.” — anonymous feedback, [47:19]).

10. Final Reflections: Packaging Complexity

Timestamps: [48:52]–[50:20]

• Trojan Horses and Narrative Covers:
  Packaging ideas simply or accessibly can be a “Trojan horse” for deeper thinking (“You can shoot for both...and you can design it with flexibility in mind,” [49:24]).

• No Easy Answers:
  The episode wraps with the recognition that finding meaning at work—and finding your story—are open-ended, ongoing journeys for individuals and organizations alike.

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Notable Quotes & Memorable Moments

• On local vs. systemic change:
  “Globally, companies will have far more impact on you than you could ever have on the companies. Locally, we can shape our environments and our environments shape us.” — John ([10:05])

• On the myth of organizational permanence:
  “We talk about companies like they’re this solid entity or institution and it’s really not the military.” — John ([12:00])

• On leadership and designability of work:
  “You are the head game designer...you have the ability to make intentional decisions, whether you like it or not, that are going to impact the dynamics of what it’s like to work here.” — John ([18:30])

• On systems, agency, and reality:
  “Interactions are real...we are shaping our environments, our environments are shaping us.” — John ([22:30])

• On organizational learning and sense-making:
  “Instead of trying to chase all the complex out of our work, why don’t we make our environments more friendly to doing the hard work that we need to do?” — John citing Kat Hicks ([30:29])

• On scaling and fairness:
  “If we’re going to do something in one place, we have to do it everywhere...it’s sometimes grounded in this idea of justice and equality...but that good impulse sometimes leads to operational challenges.” — Sam ([32:27])

• On career and identity:
  “It is a good time for generalists. So having to kind of weave those stories together seems like the puzzle of the day.” — John ([45:53])

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Timestamps of Key Segments

| Timestamp | Segment / Theme | |----------------|--------------------------------------------------------| | 02:58–07:11 | Origins and "the thread" in John's career | | 09:00–10:21 | Limits of agency: Local vs. global change | | 10:33–17:25 | Organizational ephemerality & temporary pacts | | 18:08–21:32 | Leaders as “game designers” of the work environment | | 21:32–25:06 | Interactions and agency | | 28:07–30:54 | The “Beautiful Mess” philosophy | | 31:19–34:46 | Ashby’s Law and resisting over-standardization | | 35:32–44:07 | DOT Work: Lessons from tool-building | | 44:12–48:52 | Career narratives and hyper-generalism | | 48:52–50:20 | Branding, narrative, and wrapping up |

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Final Thoughts

This episode is a rich tapestry of insights into why organizations are messy, how agency exists in the local not the global, and what it means to shape work environments deliberately (or accidentally). For anyone interested in organizational design, meaningful work, or finding joy among the “beautiful mess” of teaming, this is a must-listen—and a reminder to embrace both the complexity and impermanence of the modern workplace.

Transcript

[A]

And so I do believe that it's more likely that your company will change you than change your company. But when people look back on their careers, there is potential to have moments of levity and joy and flow on that kind of local level that you always look back on and be really proud that you were able to shape that local environment.

[B]

Hello and welcome back to OrkwithReady. I'm Sam Sperlin and this week I get to talk to one of my organizational thinking idols, John Cutler. John is head of product work and writer of the excellent newsletter about all things product and organizations, the Beautiful Mess. John, very welcome to work with ready. Thanks for being here.

[A]

Yep. Thank you so much for having me.

[B]

So when I worked at the Ready, there was not a month that went by where somebody didn't throw one of your articles into Slack. And by somebody, I usually mean me. And the conversation ultimately would coalesce somewhere around, Goddamn, John is smart about this stuff. So it really is a pleasure to talk to you today. Before I pump your tires anymore, we got to do a check in question though. Check in question is a tradition around here. We do it at the beginning of every episode. So today's check in question is what was your first job and did you learn anything from it that you still use today?

[A]

When I got to college, I sort of made my own job. I had this video game company and yeah, so I got pretty weird with jobs pretty quick in terms of I was a rickshaw driver in New York City, which was fun driving the rickshaws. But before then I was with a group of musicians and people that I knew from, from growing up. And we would work these sort of weird graveyard shift jobs doing PowerPoint for investment banks. And that was. I learned a lot right there that you have to be detail oriented. Like there'd be like two point font for some things. But that ultimately I didn't know if anyone ever read this stuff. So that was the lesson there.

[B]

Nice for me. I don't know if you can consider this a job. In second grade I convinced my mom to buy some bulk candy and I sold it to my classmates and my brothers. And I've been kind of searching for that, that high ever since. Turns out when you don't have to buy your supply, your margins are incredible and so far have not been able to find that again someday. Oh right, we're checked in. We're going to spend some time talking about DOT work, about organizations in general, kind of some of some origin story stuff that I've now become very Curious about, as you named like five different things that you did in your 20s. Uh, so let's start with a. A kind of a general question. What's the thread that you've been continuously pulling throughout your career?

[A]

Yeah, I've been thinking about that a lot lately because sometimes I can't figure it out myself to do this.

[B]

But it is one of those things. It's more in a retrospect than a. A prospective way, I would imagine.

[A]

Yeah, it's interesting because I think that there's this weird thread around how people work together, show up together, how organizations work, the fun of being on teams. I mean, certainly that was something from a music background. It always felt great to be with a group of creative people and feel that spark. That was something that was always really exciting for me. I think there's also that I was always been the person asking, why? Why are we doing it that way? Or could it be better? And also probably one thread is I tend to be kind of a sponge in organizations for picking up on, not the fringe perspectives at least, but there's elements of the zeitgeist in particular companies that I often pick up on. And I'm always pulling on that thread of, you know, why is that happening? Why does that exist? Right. What's going to happen? And so I don't know. It's not something I've ever put a lot of thought into. And a lot of my writing has just been exploring ideas that were coming to me over time. And so I don't know if it was super well thought out. A lot of folks have a thing, you know, there's. That's their thing. Our thing is some framework or thing is something. I guess I've been just an amateur student of organizational design for all these years, and that's maybe the common thread.

[B]

Were there any formative experiences early on that kind of kicked you in the direction that you've been traveling now? Like where you started to see what was going on in the Zeitgeist or picking up what's going on in an organization. When did you notice you were good at that?

[A]

Well, it's either good or bad at it. I don't know if paying all sorts of attention to it all the time is good for one's mental health. Exactly. But it's interesting because I think that's a good thing for people to take away. It's very much as strengths become weaknesses in these settings. So I was always kind of that person. Let's say I was working with a founder and they Had a great startup. I was always the person wondering, is there a here here? And what are we doing to think about that?

[B]

I can imagine not every founder is loving that line of questioning.

[A]

Yeah, well, exactly. That's the type of thing. But it is funny because I would be the one who's sort of noticing that the coherence checking in companies are doing that. And so I guess that's when I started to notice that maybe I was good at also seeing the patterns and understanding and maybe describing the patterns to people. One major trap in companies is thinking, because you can see or understand or think you can understand the patterns. That means you can do anything about it. The two things are actually separate. And so, you know, trying to transition to thinking about, like, well, okay, you can, you can sense these things that are going on. So what. And what now has definitely been an adventure. But yeah, I was always kind of good at picking those things up. Sometimes it flames out, and sometimes it works out really, really well. Like, it's, it can be polarizing for the folks around you, and sometimes you also become the face of change in companies. And that's never a great place to be in from like a career standpoint. But over the years, I think I've been able to harness it a bit better and figuring out where it's valuable or not. And one thing I've noticed too, it's all about finding your way. It's helpful to other people. So sometimes one's role doesn't necessarily need to be to change through your own actions. Like, if my writing or other things impact people in a positive way, you don't always need to be the face of change or pushing it forward yourself. One thing that helps is I'm. I know I'm not alone. You know, I'll be on calls with people who were nerding out about this stuff, and people are like, oh, my God, this is like therapy. This is like, it's great to know that other people out there pick up on the same things and believe in the same things and are encouraged by the same things and find joy in the same things. And so I think that that's, that's also a good reminder.

[B]

Yeah, I've always really admired the empathy that you bring to the way that you write about this. And I think we're just getting a glimpse bit there as well. Where, where does that come from for you? Kind of that, that empathy that you bring to this.

[A]

You know, like when power in an organization is wielded in, in, in a hurtful way to People, I instantly zero in on that, you know, so if it's like a person of power who's generalizing people and maybe putting people in a box or, you know, Justing for what happens, I'm. I like zero in on that in two seconds. I've done like, fun little things over the years, like, what's your trigger word? You know, and some people are like, oh, the is my trigger word. Or keep it simple is my trigger word. We just need to embrace continuous improvement. Oh, if we could. If we could just make the work visible or something. Yeah, but then we all have our butts. Like. Well, we do all have our butts, but in the sense that, like, we all have our things. Like, oh, but we. Did we do enough research or. But you haven't thought about the different perspectives of the people in the company. And so over time, I've sort of tried to really lean into thinking about my own justs and then thinking about what you can do in a particular sense. That's the can, you know, like, how can we hold things constant enough to make progress here together? One has to develop kind of like a healthy habit internally for how to navigate these situations. Because it can be pretty difficult, I think.

[B]

Yeah. As you've gotten more experienced in your career, which I guess as you've gotten older, do you feel like there are more places to intervene in organizations or actually fewer, that there's actually less that we really have control over?

[A]

Yeah. It's funny because I think there's more locally that we can control and less globally that we can control.

[B]

So locally, like on the individual or team level or small or.

[A]

I wrote a post recently where I was like, you know, minimally viable trust boundary that you have. And it's not 150 people. It's like 30 people or 50 or something. It's like you can do a lot more with 30 and 50 people, especially if you are a formal manager and you've been bestowed with some sort of structural elements of the company than you think at that scale.

[B]

Yeah.

[A]

And then there's a lot less at the global scale of a particular company that even VPs can control or like, even. Even folks like that can. There's a certain inertia at the most global levels of the company that is just very, very difficult to impact. And so I do believe that it's more likely that your company will change you than change your company. But when people look back on their careers, there is potential to have moments of levity and joy and flow on that kind of local level that you always look back on and be really proud that you were able to shape that local environment. So globally companies will have far more impact on you than you could ever have on the companies locally. We can shape our environments and our environments shape us. And so that's, that's tend to be. As I've gotten older, I believe that more and more.

[B]

Yeah. And. And I'm guessing that you're, that you're also saying that we. The combination of a bunch of different locales does not necessarily equal the globe. The global is. Is kind of what you're saying.

[A]

Yeah, right. And also the globe. Even thinking of it as a global thing, it's. It's not a global thing. It's not. Forget the. Is it, is it Ralph Stacy or I mean something like that had the as if trap. And that's when you view an organization as if it were something, you know. So you say the organization and then in your mental model is like it's

[B]

an organization a hundred thousand people. And maybe even when it's 100 people like this, they go back to that

[A]

thing of 100 people. Yeah. Every, every person in that company had a job before, they had a job after. They're a member of a craft community, they're a member of their local community. There's people coming in and out. And I try to. It's funny, forget the community I was in, but someone made a great point. Like your average company is at best like a mutineership or something. It's like pirate ships are way better organized than your average company. Like we're talking about fairly ephemeral institutions of like temporary pacts between people to achieve some kind of mutually beneficial outcome somewhat. And so it literally is the difference between like, I mean when you read the history of pirate ships, they're way better organized than your average company in terms of what happens and what can the cap and do and, and how does it supposed to benefit people. Your average company is almost like a mutineer ship. It's almost like hey matey's, like who wants to maybe just go out and get over the ocean with us together and maybe plunder or something like that. It's pretty, it's pretty ephemeral. And so I think that's an important. We talk about companies like they're this solid entity or institution and it's really not the military. And the US military is an institution that's like centuries of an institution and even that changes. Sports teams are institutions in some. Right. Like culturally embedded within their Cities and things and. But like your average company here today, gone tomorrow. We used to be great. Now we print money and we're an insurance company and you know, it's like, I don't know. So that's, that's my take on it.

[B]

No, totally. Well, and I'm sitting here thinking about that ephemerality kind of comment and trying to decide if it is aligned with this other thing that I think goes on inside a lot of organizations, which is this general sense of just inscrutability or this feeling of organizations as even being somehow like basically that they were not created by humans and there's nothing you can really do to understand what is happening and they are just doing things to you and you just kind of got to survive. Pairing that with the ephemerality thing that you just said, are those similar ideas or we talking about something different?

[A]

But I think that that's an interesting point because let's say that there is something with centuries of history that accumulated inertia that exists in there. You're interacting with that company or that institution. And what I find very interesting there is inertia is a thing. There's. It's slower change. The, the cultural inertia that exists in that particular setting is definitely there. I think the point I'm trying to make is that for your average 20 year old company or 10, or you know, the company that used to be amazing 30 years ago but now is pretty much on life support, it's much more akin to a gold rush town. I use the analogies of like cities.

[B]

Yeah.

[A]

So think about the difference between the city of like. So Venice or Girona or a place like that, like sort of a thriving megapolis. But, but there's a lot of ephemerality like people coming in and out, very dynamic environment. But you've got the place like Venice and, and you see how for centuries those trading posts were those particular things. My point is, is that like a lot of companies resemble more like a gold rush town. Right.

[B]

No longer anymore.

[A]

It used to be there and it. Or not. And it's kind of been. There's an element of it being kind of astroturfed and doing those things. And then other companies though are even of both. It's like maybe how maybe some of the challenges like a Detroit has been experiencing right where it's like it is a very thriving place, but structurally many things have changed and you could get this sense that it might not be. It's in. It's in its quest to find a way to prosper still. And I just trying to give that perspective to people when they think of the company as like, we call it like an institution. It's, it's much more, you know, your average small company, your average small startup is much more like literally the, the covered wagons going across the prairies to maybe find a gold rush town than it is like a Washington, Washington D.C. or New York.

[B]

Sure.

[A]

Or something.

[B]

Yeah. And I think there's a, often a baked in assumption that every organization, and to continue the metaphor, every town should strive to be a Venice or a Girona or whatever.

[A]

Right.

[B]

Is it okay that we have organizations that basically are kind of like bright bursts of short amount of time where a lot of value is created and then they go away? Should we let go of this idea that every organization needs to be around for 150 years?

[A]

Well, I think so, because that's how, whether you like it or not, that's how people start acting in those particular organizations. Right. Like all this talk about, I mean, every founder says at least when they accept venture capital money, this can be a generational company because that's the storyline they need to say. Surprising. They're also the same ones that jump ship exactly four years after their company's been acquired and going off and do the exact same thing again. Right. So apparently the generational company thing wasn't, you know, there's very, very, very, very few generational companies to be able to do it. But I think that that's that interaction between people who care about organizations and care about community. An observation is that it is this polarity of both being in the moment, in these incredibly interesting collaborative situations with other humans doing cool things and then understanding that the company, as if it's an entity, will not love you back. And so how do you cherish the moments that you're spending with people doing cool work? And then how do you embrace that which you'll remember for your whole life against the ephemerality of that exact situation? You know, so I think that that's the, that's the challenge of going to work. That's the challenge of being involved. And so I think it's an interesting one. I mean, I'm curious for you all at the ready, where you get together so many people who are passionate about it. And when you were there, like you get people who are so passionate about it, how do people even embrace the ephemerality of that? It's a tough one. Maybe a discussion for another day.

[B]

Maybe. I mean, I think I am always so fascinated by the mundane aspects of everything. So the mundanity of being in an organization or being in a role and how an organization does anything, being kind of a reflection of how it does everything. I think there's generally a lot of opportunity to instill the mundane that we deal with in our organizations with a lot more meaning and value and really quality of attention that is separate from like how the organization is doing, you know, financially. Something like that.

[A]

Yeah. And I think I have that hope to, I mean, I think that's what drove me a lot for these things, which is, you know, like ideas that you're creating environments where people can thrive and, and it always seems like people give lip service to that idea. But like the intentional decisions you can make internally to be able to, to make that. And I've gotten really into game design recently and behavior design and all kinds of stuff. I've just gotten so deep into that. And you know, part of it is because it makes people uncomfortable and I like that. Like, I'll say to a leader, I was like, you are the head game designer. And they're like, oh, you mean in that kind of just crafting incentives kind of way, right? I'm like, no, no, no, no, no. Like that might be part of it. Yeah, but you're, you, you have the ability to make intentional decisions, whether you like it or not, that are going to impact the dynamics of what it's like to work here. From there, they say, you know, you'll get this thing like, oh, I, I don't want to play Big Brother here. You know, like, you know, I generally believe that if we critiques of nudging,

[B]

like behavior, judging people without their awareness

[A]

makes them very uncomfortable, you know, so like, well, I would prefer to just bring in a players and have them, you know, this kind of mix of like empowerment. But it's also, it's also absolving of any responsibility in the situation because it's, that's a particular worldview. So it's like, oh, well, no, I, I, I, I don't, you know, I'm not a process person. I'm not a thing like that. Yeah, I, I want to, to do those things. And yet, having said all that, every day they're making decisions and exhibiting behaviors which set it so no matter how much they try to resist that, they are actually sort of a human factors, behavioral design game designer, shaper of the environment they're in. There's also this intense allergy to that idea because I think it makes us feel really uncomfortable too. For leaders and so I think that that's just a funny balancing act that people have to go through.

[B]

Totally well. And I, I, when you mentioned kind of game design, I, so I like to play video games. It's, you know, one of my hobbies. And I, and I think about the games that have left the biggest impact on me. And I'm not just making a one to one comparison of a video game to an organization, but the idea of example, you know, a game called Hollow Knight and its sequel Silksong, both are games that have so many intricate details that are kind of below the level of conscious realization of the player that the designers have thought so carefully about. How do I want you to feel while you're, you're doing this? What is the aesthetic, the vibe that I want to create? And I just think about in our organizations, you know, I think generally people would equate that to like physical space. Like, there's a lot of like, decisions about physical space. We walk into a space, how does it make you feel? But I wonder how that can be even applied into things like, well, how do we, how do we meet as an organization or other processes like that. These, these moments where we have interactions with each other. You know, we, I've always said, and I'm sure I picked this up from somewhere, that the culture of an organization is basically the sum total of the quality of the interactions that happen within that organization.

[A]

Yeah.

[B]

So how can we make those interactions better? However you want to define better, it just seems like it opens up such an interesting canvas to play with that. Yeah.

[A]

And I think also for the folks who are very much the system folks like I, you, you can be a just system person as much as you can be a just individualism moment. You know, there's people like just, well, you know what Deming said, it's just the system. It's like, well, who designed the system? Well, well, that person. But, oh, but, oh, but leaders. No, they've got special responsibilities. So they are designing the system. But for everyone else, like, you know, and, and these conversations go round in circles and circles as they do with humanity in general. Like people philosophers are always debating this kind of like agency versus environment type of thing. The one thing I like about the interactions framing is that interactions are real. Like if we can take one thing in our mind, the idea that at, you know, in a company where you and I are interacting right now, we're interacting with our coworkers, we are making decisions that shape the environment. You know, I'm choosing to have this of crappy background that I have right now that I haven't been able to change. Whereas for my co workers, I could make it more inviting. I'm making decisions. I think for me, that's given me a little bit of the balance of agency over the situation. But. But understanding of the environment, this idea that we are shaping our environments, our environments are shaping us. We can choose how we show up. We do have agency in this situation. And yet it's undeniable that certain environments exhibit enough of a force that are going to shape these things back. And I found that to be very valuable with people who kind of, you know, as someone who's often been known for pointing out the system. Right. If I had gone back to do many of those things. What I tried to do my writing is I try to layer in the dynamics. But it's really, really funny because I was on with this manager that I had once and they picked up a blog post that I wrote. And the blog post was basically called, like the Wicked Slide. And it just talked like each step was not something that was like malfeasance or malpractice. It was just talked about the slide as it was going. And it was so funny because the manager said, john, I don't get it. Do people actually. I used to like your blog post, but this one. Do people actually. Do people actually like this stuff? Like, do they. Does anyone read this stuff?

[B]

And I was like, what a delightful conversation.

[A]

Yeah, that's really interesting. And I was like, yeah, actually some people do. I can't tell you how many or what percentage they are of the global population of people, but some people actually do. What they missed about that particular post is I was trying to discuss how they were like, there's so much bad news in this. There's so much, like, bad things happening. And I was like, well, actually, what I'm trying to communicate here is how this swirl can happen as a form of like, empowerment or opportunity. So to me, writing that post was like, huh, now we can name it to tame it a little bit, maybe. We see all these points that we could have. Although we can't intervene in the whole thing, there's like, this. You can at least intervene in such to hold a soft focus on the situation and maybe tip this thing. But as their engineering brain was like, I need to know what component of this slide you're proposing that gets fixed. And that just wasn't how I was thinking about it.

[B]

Yeah, well, I think there is. There's this interesting transition point that I've seen in a lot of the organizations that I've worked with or teams that I've worked with, where we're able to shift from talking about organizational tension as something bad, as somebody has done something wrong or like, things aren't going right, to just kind of an objective description of, like, these are things that are going on that we may want to, like, make some different decisions about. And for some teams, they can never really get over that. That hump. The idea that there might be tension in the organization is sign that somebody is doing something wrong. And we never get past that kind of negative connotation. And, and if you are able to get beyond it, then there's again, just a lot of open space, a lot of freedom of movement to try things and to make things potentially better.

[A]

It's so interesting you mentioned that because on one hand, I could argue that it's like a skill, you know, so it's, it's funny because I wrote this blog post with this guy, Tom Kerwin. Like, these are the behaviors of, like, complexity aware leaders. And we almost did it explicitly as a hack because we were playing a game with people, which is like, if we frame an article as a bunch of skills that you could learn and interview for, people will love it. And Tom was like, oh, I hate writing this. This goes against what you and I believe in, John. Like, we're talking about complexity like this, and we're couching it in terms of specific skills that you can have. We write this post, everyone loved it. You know, everyone was like, oh, these are specific skills that I can pick up to do it. The reason why I mentioned that is it does seem like there is a skill which is the ability to kind of like get out of your own head for a second and say, I'm observing this. I want to test out some perspectives on this with you all. I want to hear your perspectives. Are we observing the same thing? I want to lean into the different, the different perspectives on this in the room. Can you confirm or see, like, there is a skill involved with that that's learnable? I think the challenge then is, you know, I've met people who would say, yeah, I've got that skill. I just. My, my company and organization is not a place to practice that skill. Right, right, right. You know, it's. It's like, it's not a skill issue. And so I think that's the thing where people, the, you know, the belief that, okay, if we just upskilled everyone in some level of complexity thinking or, or careful listening or intentional nonviolent communication or any of those particular things. Suddenly it's going to up level.

[B]

The.

[A]

Org is kind of. There is the other perspective that like. Well, in fact this organization is not the type of place where it helps to say. I'm curious and I'm observing this to your point.

[B]

Yeah, yeah. I'd like to talk a little bit more about your writing and I think I probably know the answer to this question already, but I'll ask it anyway. Where does the name the Beautiful Mess come from?

[A]

Oh, I don't know. I later heard that it was an emo band or something.

[B]

Oh really?

[A]

That was.

[B]

That's my scene from back in the day. I don't. It definitely sounds like it for. For sure.

[A]

Yeah, exactly. So in retrospect, to do it. I don't know. You know, it's funny because I've been writing a lot on Medium and wrote a couple hundred posts there and I've put those away. You can find those in like Cuddle Fish or there's. I took all them off of Medium at some point because I was just mad about what Medium was. Was doing. And then I started writing this and. And yeah, I just had to pick one. I do think that there's sort of a philosophy of it that this idea of, you know, mess equals bad. And my idea is like, mess could be awesome. You know, there's this thing. And so I think that that's generally where it came from.

[B]

Yeah, well. And I think you just look at this conversation. I think in some ways it's been a beautiful mess. Like that's. That's what is great about organizations. Like, there is an interesting thing that I have to find myself pushing back against, which is the idea of like getting clarity in things all the time. I think a lot of times we talk about like, oh, in a. In a. In an ambiguous situation, like we're just trying to like get clarity. Like let sense make. And I wonder if that strive for clarity is actually at odds with kind of the Beautiful Mess mentality of existing inside an organization and also think about

[A]

just doing great work together in that sense that, you know, avoiding the rush to premature convergence kind of. I mean, if I could wave a magic wand, you know, I would help people get real and, and just extend the amount of tension that their conversation could hold. So maybe like how hopefully they have a breakthrough to be able to do it. I mean, the thing you see so many meetings, you see other things go by where people are hinting it, wanting to work through this particular thing. And you really just want them to figure out a way to kind of push through and do that. I also see just when teams are working so many opportunities, like small breakthroughs that they can have that allow them to do that. And so I think that that's, you know, there's a researcher named Kat Hicks, and Kat Hicks written this stuff about developer experience, but Kat Hicks has this line that I love where it's like, instead of trying to chase all the complex out of our work, why don't we make our environments more friendly to doing the hard work that we need to do? And that's something that's always. That quote has rung true with me. I keep using it and post out, you know, every quarter or two, I'm weaving in that CATEX post again or conference talks because it really symbolizes to me like the, you know, this, this idea of. Yeah. Instead of trying to make all the annoying problems go away, wouldn't it be nice to be able to approach them together? Is something that.

[B]

Yeah.

[A]

Has sat with me for a while.

[B]

Well, that sounds a lot like Ashby's Law.

[A]

So.

[B]

Ashby's Law of requisite variety. You know, for a system to be stable and effectively controlled, its control mechanism must possess at least as much variety as the system it's trying to manage. If our organization, we're trying to manage the crazy complexity of the world and our market and like, what's happening outside our organization, we actually need more complexity inside our organization to be able to.

[A]

To handle that and more bounded. I mean, I think that the Ashby's Law thing is interesting because I think that, you know, good walls can make good neighbors too. You know, you can't, you can't have the hum of all the stuff happening all the time. So the idea of, like, this challenge of thinking about an organization as like, layers of boundaries where you do need interfaces between them, you do need kind of, you know, dot work. Often we, we try to help a company come up, like, the minimally viable consistency, like, what's the least number of things you need across the top and language to be able to do good work. What's fascinating though, is, you know, you say that to a company like, well, I. Why wouldn't we want everything to be consistent? Like, I don't understand. Like, it's. We need this. We need to use the same sprints or we need to use the same approach, and we're sort of talking them in or trying to talk them into the other side of that. Right. Which is like, I don't know, do you do you really need to use the same tools? Do you really. You don't need that stuff. So I think that's like pretty fertile ground for thinking about Ashley's law of requisite variety.

[B]

Totally. Well, and there's such a pattern. I've seen that pattern as well too, that if we're going to do something in one place, we have to do it everywhere. And I think sometimes it shows up as premature scaling of an idea or something that worked in one place. Like, okay, it worked here. Great. Now let's just. That word again. Just roll it out everywhere. And it never going particularly well. I think what I'm being, when I am being quite gracious to the folks who are thinking that way, I think it's sometimes grounded in this idea of depending on the thing more or less relevant. But like justice and equality, like, if we're. If one part of the organization can do it, we all have to do it. That's the only fair thing. And I think sometimes that good impulse turns up in some ways that lead to some really challenging kind of. Of operational challenges down the road.

[A]

And people want to see their dots. Like it's. We had that funny line when we're doing workshops@.org where it's like, everyone says they want to connect the dots, but they don't really want to connect the dots. Like, they want to see the dots that are connected to what they care about. That's what connect the dots means. And not to connect all the dots in your particular company. And so that interesting challenge of like, we can't take in the whole org all at once. And that's what people are going to find out about A.I. you know, it's like, okay, well, you could have walked down the hall before and probably asked those questions. Now it took a lot of work. And now you think, okay, I'm going to lower the effort. I don't need to walk down the hall anymore. You know, really, I was curious about all this. But they're going to find a point of diminishing returns. Like, oh, it's great that I could talk to sales and learn about what they're doing. I kind of did, like when they just gave me the top line summary. You know, I don't now I can ask any question I want from sales. I've given you the crystal ball. You can ask whatever you want from any part of your org. And people are still sitting there. Even in workshops. Like, we do these activities where we say, oh, crystal ball. Questions you could ask of your data. It's pretty standard analytics way to think about it. People are surprisingly paralyzed by that. You would think that they would ask all the coolest questions in the world. But when you say to people, no, no, no, I'm you, you don't have to worry about the tool. Stop talking about the tool. Just like, what questions would you ask? You know, they'll say things like, they'll always say, well, how do we compare to our competitors?

[B]

Oh my God, don't get me going on benchmarking. Yeah.

[A]

Or benchmarking, you know. No, but those are the standard things. Or like, what's the ROI of what we're working? And then I'll say, well, you know, the clearer you can describe roi, probably the more you're a telephone company. So what if I gave you the answer that would actually come out of a system about the ROI of what's going on? Oh my God, that would be terrible. You know, like, oh, and so what's really funny is we, we say we want the answers to all these questions, but we don't really necessarily want, we can't imagine what we would do with that information. So you can imagine someone armed with AI, like, oh, now I have access to the knowledge of the organization.

[B]

Right.

[A]

I'm curious to see how many people just sit there like paralyzed.

[B]

Yeah, no, totally. Well, you mentioned DOT work a couple times. Let's spend our last couple of minutes digging into that a little bit more. So for, for those of us who aren't familiar with DOT work is high, kind of high level. What, what is DOT work and what's, what's the problem you all are trying to solve for organizations?

[A]

Yeah, it's probably good to, from history of the company because it's kind of interesting or history of the people in the company. It's, it is a new company now, but they were originally involved in this product called agilecraft which was purchased by Atlassian. And that product went on to become solid. Something like Jira Alignment and Jira Line was sort of rode the scaled Agile hype train basically, and so did agilecraft in that sense. It wasn't originally conceived that way, but at a certain point, you know, it was really, everyone wanted to know, how do you scale agile? How can you roll this up? How can you do these things? And so they got really heavily into that space. I think one thing they realized later though is there's a reason why you would never find leaders in those tools. There was a reason why it was some like PMO or some group that like ultimately was figuring out how to get some number to put into some other system.

[B]

Some sort of translation layer.

[A]

Yeah, translation layer of doing that. And because those weren't like sense making systems, it was, it was mostly like roll up systems, you know, do stuff down in JIRA and then if you're successful it will get rolled up into some legible but frankly completely illegible summary.

[B]

Right.

[A]

Like you feel good that you're looking at the number. Like, wow, it looks like we put about 62% of our hours last year into this particular thing. Time is just like one tiny component of the overall picture of capacity to be able to do it.

[B]

Yeah.

[A]

So they realized that and mostly they realized it because you had people coming and saying, oh, we're working out with customer journeys or oh, we want to do North Star Framework or oh, we're not really like we don't want to morph what we're doing into the predetermined models that those products have. And they started to rethink like how they left ultimately they left Atlassian, but they had to kind of rethink how these products were put together, these kind of strategy goals, contextual systems. That was kind of the impetus, which is, you know, with AI coming onto the scene and generally rethinking like what, what these. It's naturally very much a graph. It's not these big trees of roll ups. Like what would it look, would it look like if a team could be like, oh, let's test out a journey map view of the world, capability view of the world and the work hierarchy view of the world and different, you know, just a more thoughtful thing. Now the funny element of it is that in the meantime I was at a company trying to use no code tools to do this stuff and you start to hit the real limitations of it not being kind of a graph. There's all sorts of like interesting domain problems in this space that you can go pretty far with the no code tools but you sort of hit a wall. And so I felt the problem firsthand and it took a little bit of me learning more about what they're doing in the approach to think it's a cool thing. But for me as well, the cool thing now is that I'm sure, you know, anyone who's done it's, you know, a head up product, but there's also scratching the super nerd itch about how companies work. So it's just like, like yeah, I'm getting that sense. I have like watching you write about it. Yeah, I'm on sort of like on another Level in terms of the understanding about how different companies manifest all this stuff into how they actually work, which has been really, really cool.

[B]

Yeah. It feels like from it. From an outside perspective, a major part of your day job is like really pushing your thinking forward about how organizations actually work work so that it can then be reflected back in the product.

[A]

Yeah. So you seem like you're having fun. Yeah, I mean before I showed up today, I was in a couple hours of workshops and in two hours I'll be in another workshop. So it's kind of a cool role. You know, one could argue well, no one really intentionally designs their org and I don't know, it's just extra work and can you just give the roll up and just make people stop talking about it? But then when you do go out and talk to leaders and the kind of puzzles that they have, they understand on some deep level that. That they don't want lot. Like they know that legibility is often there's some loss of local context in any effort to make something legible for leaders. But they are thoughtful about the idea that you have. There's a spectrum between you're just not looking at something real. Like an epic is not real. An epic is a label you put on something. Like there's only a couple things real in product, like humans sitting down and making changes to files that then get deployed. And like there's real things and then there's all these other words we use for stuff like bets and epics and all that kind of stuff. Those aren't real bets and epics are not real things. They're labels we put on things. So there is that kind of trade off in any company between how deeply you want to try to persuade yourself that the words you use for things are actually real. So that's an interesting byproduct of this.

[B]

What has been interesting as you have been selling and introducing this tool to organizations, helping them get up and running in it. Like, what has been surprising to you as you embark on that work?

[A]

Well, first this guy of this intentional design. So there are. There are companies with extremely ingrained operating systems where the culture there wasn't about making it explicit. So that's kind of. You could imagine a two by two, like explicit and implicit and intentional.

[B]

I'm a consultant. I can imagine a two by two.

[A]

Yeah, you can imagine a two by two and it's explicit and implicit. On the other side, it's basically intentional or not. So there's a lot of intentional implicit operating systems that there's A high degree of intentionality from leadership. But they're just not into making the OS really legible. They don't want to talk about designing the operating system. And then you can imagine there's also people who have highly incongruent. But. But the effort to make it legible is there in the two by two. So that's been one kind of thing is that there's many, many different perceptions of how an organization works and the degree of intentional thought that needs to go in to these things. I stress out about whether something's called a bet or not or the fact that initiatives can be used for everything. But there's a lot of product leaders who like, I could care less. I just want to have an impact for customers. We don't need shared language here. Like it doesn't matter. So that, that kind of. That's been one of the interests.

[B]

Does the tool let them kind of be laissez faire about that or does it. Do they have to like.

[A]

Well, ideally because the. Yeah, I mean ideally because the relationships can be less structured, you can be more lazy. Fair about that particular thing. The other thing too is that like. Yeah, I mean the ability to be more flexible with the presentation. I mean we were, you know, we have an MCP server. You could go in and like vibe code out a visualization of something you've always wanted to see for a customer journey map. The nice thing about visualizations is often it's the structure of the data behind the scenes often takes a second seat to like, is this helping us make decisions that we need to make? So by kind of, you know, there's a reason why decks exist and it's not all bad. It's because you basically are custom designing a dashboard.

[B]

Yeah.

[A]

You're giving a job aid to other people that can be crafted the way you want to craft it. The problem is that most decks are incredibly expensive to just try to assemble. And you know, you look at your Average slide has 10, 15, 20 data objects in it that could be much more legible if you put. Put more thought into it or at least legible in different places. So that's kind of the. But the hunch is that those leaders who could care less and are more laissez faire about it actually have a point that usually some, some of them are just, you can't save them. But other ones are more like they want to focus on the rituals and the decisions and the people. And they do rightfully see that often tools get in the way and efforts to make Things legible often replace building shared understanding for teams. And so they have like a level of process aversion that's completely justified and well earned for where they've gotten to them, where they at. So a little bit's kind of on us to persuade them that you could hopefully have the best of both worlds, that you're just, you don't need to sacrifice one for the other, if that makes any sense.

[B]

Yeah, it doesn't have to be binary. We can have a third way here that gets you both of what you want.

[A]

Yeah, that's the hope at least I

[B]

think for one last kind of question here since I have you here and I, you know, I'm currently thinking big thoughts about, about the next phase of my career after having left the ready. I'm a selfishly use you for a little bit of career consulting here. I'm curious, have you thought about your career as having a longer arc and each specific experience you have as kind of contributing or building to that arc? Or are you just kind of exploring the most interesting opportunities as they present themselves or maybe a third way since I presented that as.

[A]

I don't know, I mean I wish I put more thought into it. I wish I was sort of patient and more. More but, but not in the kind of like oh, set the three decade goals, but more like just trying to be a really hyper aware of what's giving me joy in those particular settings to do that. The self awareness side of it and, and, and just being like you know, over the years these types of contexts give a lot of like using that historical data as a good guide but then allowing yourself to maybe like accidentally fall into that, you know, to do those things. But I've had the kind of luxury, almost accidentally maybe through the writing of not having to worry about it too much because it's all, you know, whether it's workshops or this gig or something that certainly helped me to do it. One thing in the current market and job market is the hypergenalists are probably more valuable than ever. But they also have the hardest time to explain.

[B]

Yeah.

[A]

How their hyper generalism helps in the particular environment. So it's like you've been looking over

[B]

my shoulder and all the conversations I've been having for the past month and a half.

[A]

Yeah, it's this unfortunate balance between some understandable narrative arc helps accessibility to people to understand what you're about. And at the same time, you know, it is, it is a good time for generalists. So having to kind of weave those stories together seems like the puzzle of the day. I think.

[B]

Yeah, I've always kind of thought of my writing publicly, which is I do, but to a much less prolific degree as you as kind of increasing my surface area for serendipity. And I look back at the cool things that have happened in my career. Almost all of them can be traced back to something I wrote publicly online. And I get the sense based on what you just said there, that your writing has played a similar role in kind of your.

[A]

Yeah, and it's also. But it's made things more difficult in some ways. Like I described that conversation with the manager and stuff.

[B]

But it's too transparent.

[A]

People know too much of your brain. Yeah. And I think. But you know, people unfortunately do it. They do like to put people in a box. I think it just the lowers the cognitive load of understanding that. And so I think that that's the interesting puzzle of the day. Right. It's kind of how to balance that sense of this solid arc with these. All these kind of cool opportunities that exist at the moment.

[B]

Yeah, yeah, I know that that makes sense. If you had to self define your box. What's. What's the box you're okay being put in?

[A]

I wish I could define it and that would be more helpful.

[B]

This is your chance right here. We can clip this and then.

[A]

No, I start the. I don't know, I'll have to think about it to be able to do it. No, but it is actually. I struggle with this a lot, which is, you know, like I have a friend who started a newsletter and they just hyper focused on one thing, you know, like, oh, we're B2B for this. You know, we're all about B2B. Or they just picked a lane and just pushed it. And frankly, like factually, it is easier to build a surrounding group of people if you focus on something. So people have often say to me, they're kind of like, you know what? I don't even know what you're about the last year, John. Like I've kind of. I don't know, I used to like it when you're the actionable guy or you know, or then the people are like, oh my God, oh my God. This post is way too actionable. I liked it when you're the philosophical person. So this kind of like I have been thinking a lot lately about the idea of we can pick the narrative and the package that we want for ourselves and design it. And we can design it with some flexibility in mind. As a Trojan horse, you can put yourself in a box. And it will definitely be easier to market yourself and do things, but it might not be in alignment with your priorities or who you want to be. And then there's ways to craft that box that at least make it accessible. It's like, there's some really good music that it has a lot of cool things going on. You could tell the person's a music nerd, but they, they put it in the context of also a really good pop song. Like, we have the options to do that. And so I think that that's something that everyone, you know, has to, like, lean into.

[B]

I think you do a great job with your newsletter. I mean, I, that's what I. There are people like me who I want all the versions of John because I'm not signed up for, like, just the actionable version or just whatever. It's like, you are the model. You're the model model of what I. I think of what it looks like to be very, very deliberate and very conscientious about thinking about organizations. Like, that's what I, I tune in for. And it takes lots of different forms.

[A]

I think that that's also. I guess what I'm saying is you. I think you can have. You can shoot for both.

[B]

Yeah.

[A]

In the sense that, like, there's. And a good example of that is someone like Matt Skelton or manual pace with this team topology stuff. Stuff like it's a Trojan horse because they care about, like, a lot of stuff and yet they're able to put something out there in the world that they can. That, that can build on itself. And you know, you see other people do things that it's. It feels very much like a one shot, like one trick pony. It's like once you go one level deeper into what they're doing, you're like, wow, you've really backed yourself into a hole here. But there's people who do seem to find like a. A bit of a packaging that does give them sort of almost like narrative cover in a sense, to explore different things. And so that's one thing I think a lot about that I don't have the answers to it. I just notice that, like, it's something that one can aspire to to enable the opportunities that we want in our careers and stuff. And so I think that that's an interesting question. Cool.

[B]

Well, we will wrap up here for today. You all know we're always looking for new topics for the show. So if you have an organizational pattern that you're having trouble changing, shoot us a [e-mail] the show is engineered by Taylor Marvin and produced by Jack Van Amberg. At Work with the Ready is created by the Ready, where they help organizations around the world change the way they work. Thanks for listening.