The missing layer in government tech? A real operating system.

The problem with most improvement efforts isn't the framework. It's that the organization never built an operating system.

In this Livestream, John Cutler (Head of Product, Dotwork and author of The Beautiful Mess) joins Bryon Kroger to examine what actually slows teams down. John has spent his career diagnosing the uncomfortable, messy patterns of product organizations— and his first instinct when entering a company is never to audit the tools. It's to watch the rituals: the daily and weekly interactions where information actually moves (or doesn't) between front lines and leadership.

The conversation covers:

• Why rituals—not tools or frameworks—are the first place to look when something isn't working
• The gap between the official process and how work actually gets done—and what happens when those drift too far apart
• Why one delivery model rarely fits every type of work, and how to name the parallel motions your organization is already running
• The critical difference between a framework (SAFe, Agile) and an operating system—and why treating them as the same thing leads to endless failed transformations
• How capable leaders move between multiple organizational lenses—systems, political, informational—to navigate complexity without getting trapped in any single worldview

The thread running through everything: an operating system isn't something you implement. It's something you build together, iterate on, and actually live. As John put it—reading the D&D rulebook and playing D&D with your friends are not the same activity.

Watch the full livestream, and then check out Bryon's free course on shipping outcomes in government.

Bryon Kroger (00:02):

All right. Well, hello everyone and welcome to the Mission O/S Livestream. I'm your host, Bryon Kroger. And for those that don't know me, I spent 10 years active duty Air Force, First Seven as a targeting officer using really terrible software to conduct really critical missions. And then the next three fixing that over in the Air Force at a successful transformation project called Kessel Run that I co-founded. And I got out and started Rise eight to help other people do the same thing. And so we've launched Mission O/S to share all of our lessons alongside this live stream where we extend the conversation with leaders from government and from tech. So we want to explore what it really takes to ship across people, process, and technology. Joining us today, I'm really excited, is John Cutler. He is someone who has made a career out of sitting with the uncomfortable, messy parts of product work and turning them into some of the clearest thinking in the industry, in my opinion.

(00:58)
So you might know him from his newsletter, The Beautiful Mess, which pretty much sums up what he's all about, the overlaps, the patterns, and the honest realities of building product. John's currently head of product at. Work, which is a platform for instrumenting what I'll call your product operating system. Before that, senior director of product enablement at Toast. Prior to that, product evangelists and coach over at Amplitude, where he got to work with teams and leaders from all over the world. So he just has great experience with a lot of different operating models. Spans B2B SaaS, I think Zendesk, Pendo, AppFolio. Before that, B2C, ad tech banking and media. So when John talks about patterns across the industry, he's really not guessing. He has seen them. He'll also be joining us in just a few weeks at ShipSummit, by the way, leading a session called the Practitioner's Edge: Using AI without Losing Your Craft.

(01:51)
So if you like this conversation, be sure to attend that talk. Really glad to have you here today, John. Welcome.

John Cutler (01:58):

Yep. Thank you so much for having me. Very excited.

Bryon Kroger (02:00):

Yeah. So I want to start with what you're working on right now at. Work, which you all refer to as a strategy and operations platform for product-centric enterprises. And it's really about helping organization connect the dots without friction. So when you go into an organization, what's the first thing you usually notice that's missing or not quite right?

John Cutler (02:22):

I always look first at rituals, which is the interactions people are having with each other on a daily, weekly basis. And that might seem counterintuitive given the tooling background of the company. You'd think we'd go straight to the tools and ask, what's the stack? But it really does boil down to interactions between people. Sometimes those interactions are through tools. They might be through a dashboard. They might be through Slack or Teams or something like that. But often they are over Zoom or in regular cadence rituals, we call them. And that's really where I start observing. And in terms of what's missing, it's very, very interesting. You mentioned you had a military background, but if you think about situations where information has to move through a number of layers fluidly in really uncertain situations, it's often a part of well-honed rituals and things that people show up for and communicate and backtrack what they know about.

(03:27)
And so that's where I look first because often what you see is you see that the frontline has very established rituals. In fact, sometimes they have people telling them exactly what they should do, exactly how they should show up, what tools that they should use, whether they should call things stories or tasks or anything like that. And then the leader rituals with other leaders are highly honed, highly political, highly crafted, highly slide supported rituals, basically. It's what happens everywhere in between that and how information moves through those different layers that often is really the weak spot from a ritual standpoint. So just for background, when we go in there as a company, we're looking at the rituals to see how we can support them because that's really where a lot of the magic happens when people start to move information more fluidly and more effectively.

Bryon Kroger (04:22):

That's awesome. I am curious, do you see a big gap between what's documented and what's actually getting done in the organization? And if so, why is that?

John Cutler (04:31):

Oh, I sort of call it the ... It's the real and the ideal, but it even goes more than that. There's the ideal that leaders talk about how it works. There's the sort of the idealized real. It's like most of the time things on the frontline are working this way reasonably. Sometimes there's the real real, which is just legitimately, even if you include the edge cases, exactly what's happening, which is very, very difficult. And then often there's the aspirational talk track about where people are trying to go. And so what's fascinating for your average knowledge worker or person working in an organization is they're juggling that incoherence sometimes. I do think a little bit of incoherence is actually what moves us forward. If all we did was sit there in the real world every single day, say, "Oh my God, today was so difficult because X, Y, Z, A, B, C." And you had no vision for what it might look like in the future.

(05:30)
I think you could get actually pretty stale. It's when those different realities that I discuss get too far out of whack that you get people on the front line sort of saying, "Well, I spend half my time working around the official way of doing things." I end with that observation is that for the most part, people on the front lines want to do a good job, they want to show up, they want meaning in their work. They will work around, to some degree, they'll work around whatever reality exists at the moment to get their work done, which then causes, of course, other problems because people say, "Well, we thought we were doing sprints, but we aren't." And the frontline is saying, "Of course we aren't because that's not a great way for us to get work done right now." Well, you're not following the rules, therefore it's not working.

(06:12)
And so it can kick off this bad cycle, but you have to navigate those different realities in any organization, for sure.

Bryon Kroger (06:21):

So for listeners out there who maybe are either leading the organization or on the front lines, they're running into some of these problems with adopting an operating system or refining theirs, what's some practical advice you have for them? What have you seen work?

John Cutler (06:35):

Well, I can go on what I've seen work. I mean, there's a lot of stuff that doesn't work, but I've discussed this in the past. It's the reverse anti-carina principle, which is like everyone can point to the problems in their org. They were like all happy families of the same and all dysfunctional families are different. And the reverse intercrena principles like all dysfunctional family. You can fool yourself by pointing at patterns and say, "Haha, I saw the anti-patterns," because they are pretty common in different places. I'd say that the practical tips for leaders is, first of all, get the cadence of moving information up and down your org and across the org dialed in. And that seems so simple to say, but it is so difficult. It's so, so difficult.

(07:22)
In my neck of the woods of these sort of product selling technology organizations at the moment, it's especially hard. People are worried about layoffs, people are wondering what's going to happen with AI. They're maybe hesitant to share the bad news necessarily. They're being pressured a lot to share the good news around the experiment that worked. It is a somewhat difficult time for moving information up and down organizations at the moment, but that's where it all starts, right? Is that first thing is just being very deliberate about the design of those meetings, the design of those things. And people get nervous when I say design because they think it's a bit of Big Brother, "Oh, if we just had competent people, we wouldn't need to design these situations." But what I would invite people to think about is think of the best experiences of your life, the best wedding, the best restaurant, the best maybe church group you're a part of or anything you're a part of is an intentional experience.

(08:16)
So intentionality is what it's looking for. I think people conflate documentation with intentionality, especially now with AI, I can create lots of documentation. That does not mean that any of the documentation is intentional. So being highly intentional about those rituals and how information is moving is probably the first one. I think that the second one is, in my opinion, is resisting the need to say there's only one way things work at your company. And you and I have talked about this too, where it seems like we chase simplicity for simplicity's sake before asking whether simplicity is really serving us. And so I do think there's a role for leadership of what I would call strategic oversimplification. Sometimes to make a point, you do need to crystallize things in a way that maybe your most passionate, thoughtful frontline person would be like, "I don't know, not that simple." Ryan, it's not that simple.

(09:14)
So there is a role with leadership of strategic oversimplification, but I think ultimately your company or your organization or whatever mission that you have is probably juggling a couple different motions. And if you lean into that and name it to tame it, I think that that can be very effective. So very practical example, maybe some of the things you do are big, messy projects, involve lots of people in your company, involve a certain kind of governance to make happen. It just does. Some things are like that. And then you've got other work streams in your company that are highly iterative. You can pretty much just leave those three people alone and just come back and talk to them every two weeks about and talk to them about a metric, at least for some period of time to do that. Pretending that your organization is one or the other and not both is damaging, in my opinion, because if you don't name it to tame it that first one, you don't really acknowledge the hard work required to make those large high coordination efforts go.

(10:11)
And if you don't name to tame that iterative motion, you sort of don't acknowledge that that exists. So I would say that's the second one is parallel, admitting that you probably have parallel motions within your company at once and name it to tame it is the second one. And then the last one is, in any sociotechnical system, the things that we work, the environments that we work in, you do need to jump between the kind of systems view and the individual view all the time as a leader to make it. And I wrote a blog post about how capable leaders navigate these complex systems we're in. But what it really boils down to is what I would call multiframe thinking. There's a great thinker who, and I'm struggling for the name now, but her first name's Althea, but she promoted this idea in the Australian government in Australia where she lives called Dragonfly Thinking.

(11:10)
And her whole thesis is that a Dragonfly has many, many lenses. And so I'd say that as leaders, we often have our default lens. Like my default lens is sort of a systems human sort of sociotechnical, messy human lens. Now, maybe my engineering friend tends to maybe think about the organization as a bit more of like a machine. I might have my poly psy friend is down with the idea that our organization is a political structure as many organizations are. My information theory friend is all about the organization as an information conduit. Now, we all have like our default happy place. And so one of the big evolution in my career was realizing just how deep I was in my own lens of this sort of ecosystem thing. I hadn't even considered the political lens. And I have friends who only consider the political lens who've never thought about anyway.

(12:09)
So I'd say that if you boil down this sort of leadership and conditions of uncertainty and complexity thing, a lot of it is not just, I'm a systems thinker. It's the ability to move between those lenses, the anthropological lens, the political lens, the sort of machine or systems lens. That's really the power skill we all have to learn, especially today. And it's not easy because we all have our ... You probably have your default place. What's your default place? What's your default vision of your organization?

Bryon Kroger (12:38):

I think I'm aligned with you. I definitely view it as kind of like a messy system. I like to accept some level of complexity and try not to oversimplify, but I also will fall into the trap of oversimplification. So yeah, I think it's really interesting to think about those lenses because I can see, I have people coming to mind right now that definitely have very different lenses than me.

John Cutler (13:05):

Yep. It's also the different ... I think for a lot of us in this community or different communities, our identity gets tied to that lens. So you see, for example, there's, let's just take something like lean and theory of constraints, for example. Now, it might view a certain type of system from a perspective of constraints, really, really valid perspective and especially tuned into some systems that we're working in. But people often get so grounded in that community. So let's say I'm in the Kanban community or I'm whatever, that becomes part of our identity and the only way they see it. Now, I'll give an example for those folks. How many times in my career I can remember if I was deep in that space of saying, "We just need to visualize the work. How great would it be to just visualize the work?" And literally having leaders coming and like tearing down the sticky notes from the wall because they're saying, "I don't want us to visualize it.

(14:01)
" No. And so you could imagine I'd so self-identified with being the person that's like, "Well, this will just agree to improve together. We'll visualize how things are today and then we're going to improve it. " Become a trap of our own perspective sometimes. And so I think that probably everyone can relate to that trap and you could flip that around. Friends of mine who are very into sports analogies and high performing A+ teams and things like that, it's great for many situations, but it also like, this isn't a sport. There's not clear rules to this particular game. We don't have necessarily a definition of winning all the particular time. So they're going to ... I'm just giving an example of another setting where people will have trouble.

Bryon Kroger (14:44):

Yeah. Yeah. We've gone back and forth on LinkedIn on the A player

(14:47)
Conversation. So I know it's interesting how those lenses show up. I'll say ... Well, actually, there's so many jumping off points, but I want to go back to something you said earlier, which you said it's much easier for me to name all the ways that it fails. And actually, before I even go to that one, there was one other thing. You talked about how simple your first point was. You wrote an article back in December about what you said ... Let me just find it here. Feels so simple that it's probably dumb and maybe I'm crazy for writing a post about it, but I'm going to. And the basic idea was that you should label the relationships between things. I don't know if this is related to the kind of name it to tame it, but it's kind of like a much more micro version of that, but really great article.

(15:32)
And I think as you get more into the weeds of mapping out your operating system and looking at it, talk to me about why labeling things is so important. What does that make visible? Why is it important?

John Cutler (15:43):

Yeah. And a lot of it is about collective sense making. So that article was basically, I'm just going to riff on it a bit, but if you've ever seen the slide deck that says, "This is how we work." And it has a pyramid on it and it says one to three years at the top or whatever your timescale is. And the mission's at the bottom, I don't know, however it works. And you're looking at it and you're like, "Well, that's not ... Okay, that's one view of how it works, but that's not necessarily how ... It doesn't really represent everything. It maybe underplays that real org chart like we were talking about, or it might underplay how you think about value really, or it might underplay how people are working on the front lines." And so I think this is an activity that just people who have a more like a process mindset tend to take one lens into kind of mapping things out.

(16:30)
It might be like a linear lens. And what I was trying to do in that particular post is just exercise. If you click on that and you go down that rabbit hole, it's like, go down the rabbit hole with me. It's all about different ... It's how the words we use and the relationships we describe things between can be so telling in terms of understanding how your coworkers think. Let me give a very, very clear example. A lot of times people have those hierarchies. I was on with a leader and she had this great line. They had something up at the top and they had stuff worked down at the bottom. She had this great line like, "What if the person at the front line can just finish the thing that knocks out the thing at the top?" Why would they need to go to those particular ... It's fake.

(17:16)
It's not real to say that you're doing this little task because it dries in this story, it tries in this epic, that dries into this thing that drives into this thing. And this leader was just right on point. It's like, I don't ... Hey, we have a business metric up there. I don't want to ask the frontline people to purposely, forcefully move things through all these layers if they can impact that. What if we could do that in one day? And the whole team was ... It's the classic should versus can. Absolutely right. Why do people imagine the things at the bottom or one day that have to ramp into three quarter things or three year things only to achieve the thing at the top? It's a really interesting thing, but it's a little bit riffing on the statement there. In that post, you'll talk about some creative ways to think about the relationships between things in your operating system and challenge you on how you think about those things.

Bryon Kroger (18:07):

Yeah. Yeah. Oh man. I'll say for those of you that don't follow John on Substack, you should. It's one of my favorites. It definitely challenges me on a regular basis. All right. So going back to ways that you've seen things break down, or maybe even you call some things like traps people fall into. What are those? What do they look like?

John Cutler (18:29):

Oh, geez. Yeah. I mean, there's so many. That's what I'm saying.

Bryon Kroger (18:36):

What are some of the top ones or

John Cutler (18:38):

One that you? It is the why behind those in those. So there's the symptoms like what we're observing and then the really rich cultural reasons why it's happening. I mean, I'm going to give people an example of something everyone can relate to. You get together with a couple team members, you spend just one hour starting to forge a working agreement of how you're going to work, how you're going to show up. Someone makes a spreadsheet with a couple rows in it that you're going to try to keep track of how you're doing on those things. Everyone feels good in that first meeting, and within a week or two, it all falls apart. People go back to their day job. And so the anti-pattern is basically like people vastly underestimate how much energy it takes to build any new habit. Yes. So the number of things in any organization of like, "Oh, this week we're going to try listing them this other thing.

(19:29)
Oh, it didn't work. Oh, geez." And you see this too in retrospectives, it's like communication sucks. And then you ask the team, "Have you actually run any experiment over one hour to improve that? Tell me what you did to do it. " So that's one that comes up all the time. And frankly, this is the human condition too, because in our personal lives we're like that all the time. Building a habit takes however many reps, probably someone knows who's listening. I forget what the number is to do that. So that's one of them comes up. I would say that especially around product work, and someone kind of started to allude to this too in a question that I saw, but one is really not considering the shape of the thing you're working on and trying to ... Monoprocess in general, and I alluded to this before, is just generally that kind of anti-pattern where someone says, "Well, we do discovery for two weeks, and then we do this for this.

(20:30)
" And I don't know about you, but I've definitely been in situations with highly qualified people that we do like a three day offsite and everyone feels great. And then the next week, it's like we still kind of feel great. And then you've got that smart person. I always remember a meeting I was in, I was facilitating a workshop in a large South American bank and everyone had gone through all the whole workshop and this really soft-spoken UX researcher, she'd been sort of sitting in the back observing the whole thing and she just dropped this truth bomb on everyone about the research. This is like 40 hours in of workshop time. But what's so funny is how many times when that happens, it's like, "Oh no, no, no, no, we got to wrap this up. We got to do this thing." People leave those things.

(21:15)
Now, flip that around and how many times do you just got to let a team make some decisions? Geez, just let them go. And yet you run them through the 40 hours of things. So that's another thing is that people are amazingly beholden to whatever boundaries they have and don't say to themselves like, "Wow, if all these risks are high, we better sit with that uncertainty until we forge it. " And you know what? A week later, we'll still drift apart, so we need to do that. That's the second one. And I think that the third antibody is mostly around ... And this is one of the great things about. Work that it's kind of part of our mission, which is we have such a recency bias on what's going on. I mean, the number of companies you see where it's like they documented the problem four years ago, and then they're documenting it again, and then they're doing the research on it again.

(22:09)
It's like the collective memory problem is really, really hard. Now, I think that the problem with that is that there is a little bit of a tooling issue, but it's ... I wrote recently that remember, context is co-created with the people you're working with. It's not like you document one thing in one place and document another. And if you just throw those documents together, you have the truth. It's really, we're co-creating that context over time. So the collective memory thing is just, you just see in organizations all the time, it's like, "Oh, we're doing this again." And the amount of just locked in knowledge in the organization and people have something to share there who can't necessarily be involved in that conversation again, it's just staggering. It's really, really difficult.

Bryon Kroger (22:51):

Yeah. That goes kind of hand in hand with what you said about just letting teams make decisions sometimes is discovery as an example will often do like a two to sometimes up to six week discovery depending on the complexity of the problem we're looking at. And we always say, you produce all these artifacts and decision briefs for leadership and everything else, but we say none of that really matters. The important thing is the collective context that we built over the course of the two to six weeks. But if you aren't then allowed to turn around and act on that context, like the organization starts making all the decisions, then you go down the wrong route, and then a month later you're doing another discovery, identifying the same problems that you discovered the first time around. And this is the

John Cutler (23:30):

Issue too. I would add to that one of the challenges is that I think that there's a lot of leadership advice, which is like leaders have the long horizon. Somehow the frontline has the short horizon. And while I think that there is some truth to that, because with experience, you're able to grapple with longer horizons a little better. Example, you're a massively experienced movie director or producer. You're on one of those three year movie shoots, like you're Stanley Kubrick and you're going to do something for the umpteenth time. They've done it enough that let's say the problems in the near term, they've like, "Okay, we're going to keep the course here. I see how this is going to play out. " So that is a form of things. But one thing that's happening a lot in organizations I think now is there's sort of a flattening in a lot of organizations where there's a layer or two of management coming out is that I think there's a little bit that's off about that where, look, if the strategy involves action now, then action now is the leader's responsibility.

(24:29)
And so there was this kind of collective absolving of responsibility by being quote unquote strategic. In my mind, strategy is creating the conditions for the best decision, quality and velocity at all times, not like, "Oh, annual planning, we're going to spend..." In the standard corporate environments like, "Oh yeah, just look, annual planning sucks. We do our long range financial plan in March and then by the time we're done with that in May or June, we start to do H2 planning and then we replan and then we start again. In one month, we're doing annual planning for four months and everyone despises the process and literally it falls apart the first month of the year." But I think part of that is because the systems and mechanisms and rituals that people had in place for that just sort of were never really ... People just phone it in and then that's sort of like, okay, job done for a little bit, the slides are done.

(25:23)
And there's only one sweet spot in the year where anyone gets anything done in a corporate environment. It's like a little bit after long range planning before annual planning starts. So I think that there's an element of being in the here and now as leaders, that's a super skill and the little bit of the long horizon. The horizon pace layering view is helpful, but like all models, it's wrong.

Bryon Kroger (25:47):

Yeah.

John Cutler (25:48):

And you have to think that through a little bit in many cases.

Bryon Kroger (25:51):

Yeah. Yeah. That leadership note, I mean, this is like a can of worms because I want to get to one question before we close up here, but I'll just mention that I think it was widely misunderstood Brian Chesky's like founder mode thing. I don't know if I agree with all aspects of what he said, but a couple of the things you highlighted there are things he said is really important. Founder mode's not about swagger and like being a founder, but it's about being in the details and being able to help teams take action right now, not just the long range. And so I think that is like a bit of a lost art. It almost got discouraged for a while, as you said, and

John Cutler (26:23):

I think. Well, and the things that he said, he notes it. Now, I would say as a leader, it was his responsibility to see that the change was happening underneath his chin. So what I didn't like about that was like, I suddenly woke up one day from vision questing and it turned out that my organization had turned into a highly political and bureaucratic mess and like only through my great acts of leadership could I tone it down. So that's where I'll take my life. Fair enough. I can poke at that. But to your point, realize that those rituals and those environments where people could make sense of things to make faster decision making had fallen apart. And so I think that there's a lot of truth in that.

Bryon Kroger (27:01):

All right. In one minute or less, this was the one question that I saw here that I thought was super important to cover because I'm kicking myself. We're not opening up with definitions. They said we've tried AgileSafe and a lot of other frameworks over the years. How is thinking about an operating system different?

John Cutler (27:17):

Yeah. I mean, here's my take on ... Remember, frameworks, our models and all models are useful, but wrong. They are thinking tools. We hire our frameworks for a couple things. One, to teach, two, to communicate across boundaries, to create lower cognitive load, to create interfaces between groups. And then three, even for experienced people is like a heuristic check, like am I on track? It's almost like even the best doctors have checklists is another way to think of it or have frameworks the way they think about it. And so the difference between that and an operating system is cultural. It is about all the rituals that you have. So Safe literally lays out a huge book of must do this, must do that. The problem is that real operating systems are like the intentionally designed and iterated on game in a sense. I use game design as a thing.

(28:09)
So the equivalent of frameworks is that when someone gives you ... There used to be these old school games where they hand you a huge manual and say like, "This is how to play the game." And you actually to get together with your friends and you're like, "This makes no fricking sense. I'm like moving my pieces, this game is not that great." So this idea, if you document every single little part of the game that makes the game, no, you learn with your friends. If you play D&D with your friends, you iterate on your rules together. You create the culture around sitting there and playing the game. So I would say that is that an operating system is layers. It's the artifacts you use. It's the culture that used to show up. It's the systems that you have to do that. It's also different than an operating model.

(28:53)
Models are pretty broad. They're just general principles, but the operating system is almost by definition uniquely yours. And when that drops on people, I think that that's the critical part.

Bryon Kroger (29:06):

That is a perfect place to end this. I absolutely love that. John, thank you so much.

John Cutler (29:11):

Yeah, my pleasure. Looking forward to being in Park City and chatting with folks. It's going to be exciting. Yeah.

Bryon Kroger (29:17):

And if people want to follow you, I mentioned your Substack, but is there anyone else they should follow along?

John Cutler (29:22):

Oh, that's it for now.That's probably the best place. LinkedIn. I know LinkedIn's hard to be in lately, but that's where I am. And then obviously, if you ever want to talk operating systems, I'll talk all day with you about that kind of stuff.

Bryon Kroger (29:39):

Awesome. Well, thanks again, John. Appreciate you. And thank you all for tuning in. Have a great day.

John Cutler (29:43):

Thank you so much.