Episode 247: Freeing Teams from Operational Overload with John Cutler

In this episode, Melissa Perri is joined by John Cutler to explore the often overlooked yet crucial role of product operations in driving organizational success. They dive into the balancing act between having the right people and the right processes, emphasizing how both are essential in managing complexity and fostering innovation.

The conversation takes a deep dive into strategic planning, discussing flexible frameworks and the balance between simplification and nuance. They also touch upon the potential impact of AI in product operations, addressing the opportunities and challenges it presents for product managers.

Curious about how to enhance your product management approach through strategic product operations? Listen to the full episode!

You’ll hear us talk about:

14:10 - The Balance Between People and Processes

John Cutler explains the false dichotomy between having great people and needing processes in product management. He emphasizes the importance of both elements to effectively navigate uncertainty and complexity in product development.

28:05 - Simplification vs. Nuance in Product Operations

The discussion revolves around how to balance simplifying models for broader understanding while retaining the necessary nuance to capture the complexity of operations. John Cutler shares his perspective on maintaining this delicate balance.

35:20 - Leveraging AI in Product Operations

Melissa Perri and John Cutler discuss the potential for AI tools to streamline processes in product operations, reducing the need for large teams and enhancing productivity. They also address some of the skepticism around the necessity of these roles.

Episode resources:

John on LinkedIn: https://www.linkedin.com/in/johnpcutler/

TBM Newsletter: https://cutlefish.substack.com/

Other Resources:

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Episode Transcript:

[00:00:00] John Cutler: I use this portfolio approach with most people when I'm talking about product operations. Where right now in the current environment, if you aren't spending 60 to 80% of your effort or thought process, pain killing, and basically removing friction. You're not gonna get to that 20% or 10% or 30% of upleveling or maybe changing the organization.

I think that the challenge right now in this environment is, what can you do that doesn't boil away all the helpful complexity and all the nuance that is in reality?

[00:01:40] PreRoll: Creating great products isn't just about product managers and their day to day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you find your way.

Think like a great product leader. This is the product thinking podcast. Here's your host, Melissa Perri.

[00:02:18] Melissa Perri: Hello and welcome to another episode of the Product Thinking Podcast. Today we are welcoming back, John Cutler, who's the head of product management at Dotwork. And he is a very prolific writer about product management, product operations, and forming great product teams. Before that, he ran product enablement at Toast and was a product evangelist at Amplitude.

And today we're gonna talk all about what he's learning by talking to hundreds of companies who are standing up product operations. Welcome back, John. It's good to see you.

[00:02:44] John Cutler: Yeah, it's good to see you. Glad we could make this work. Between fires and outages and yeah.

[00:02:49] Melissa Perri: California burning up.

[00:02:50] John Cutler: Costumer demos that I needed to run. Yeah, so this is pretty good.

[00:02:53] Melissa Perri: Yeah, I'm excited. It's been a while since we caught up. So you decided to go in-house to Dotwork, and you're working on this product that you are very opinionated about, which deals with product operations and operating models. Can you tell us a little bit about what made you wanna go in-house and how you ended up there?

[00:03:12] John Cutler: Yeah, it was funny. I'd sworn never to get involved in these tools ever again. I was at Amplitude and in theory, that's there to help product teams and then, I thought I had just burnt out on this stuff. But what was really funny is there were layoffs at Toast. I got laid off. Fun, for those of you who also got laid off. And I was, I had that summer and I was thinking about different things I wanted to do, and I was building things and I was talking to people about this problem, this nut that I couldn't crack about operations and in particular, just the really nerdy part of tooling. We don't need to even talk too much about that today, but there's this, if you're in operations and you have to suddenly map together the organization and connect things, truly, there's this sort of quest that you can go on. So I was back kind of thinking about different startup ideas. And then kept persuading myself not to do it because it was in this tools type thing. And I actually met someone at Dotwork and I kept sharing these ideas with them. Oh, do you know a developer out there? Or do you know anyone who might want to maybe make a prototype?

And they just kept coming back with versions of what I was doing of a point of it being annoying oh my God, like every they're really fast at doing this. And so that piqued my interest and so I jumped back in to do it. So yeah, I think that it happens to be a company with people who have, are really thoughtful about tools and that, tools are only one part of the puzzle. I really like that aspect of it. So yeah, I'm back. Maybe a glutton for punishment for out there talking to product teams. Although it's funny, at Amplitude I would talk to 'em about being data driven and now it's like I've even stepped back even to 20 or 30,000 feet. It's just being more effective, overall or spending our money more wisely or being more efficient or we want to do AI or something. So it's even up another 10 or 20,000 feet from amplitude, whereas be data-driven. Um, so that part's really interesting, hearing people talk about their operating systems, talk about exactly how they work. I used to have a pretty good hand for data-driven. Now if people say You wouldn't believe how my company works, it's typically like, I probably can believe how your comp, like I'm, it's very rare that I'm surprised now even about very specific details about how people work or how they're structured. I'm always learning. So that's what it's about.

[00:05:30] Melissa Perri: It is funny 'cause I'll do the same thing. I'll jump on a call and a company wants to say, Hey, we're not doing product management super well, but let me talk you through it and I'll go, oh, are you doing X, Y and Z? Does it look like this? Does that? And they're like, how do you know us?

It sounds like you know us. That's exactly us. And I'm like. I've seen this 18,000 times. Like you can show me a pattern and I'll tell you how it's gonna end up in five years, 10 years. And it's all pattern matching, which I know you love too, but it's exciting to me 'cause you're like, I see these things and then you know what will help, you know what can work, but then you have to figure out all these other criteria as well, or these other things around it to actually make sure like certain solutions work for certain people.

[00:06:07] John Cutler: Yeah, that long tail thing is the, one of the biggest lessons that I've learned is it is there's sort of an 80 20 really. The Pareto Principle is alive and well where, at some core level, every company's kind of operating the same. I love making drawings and I love analyzing how people use words, but pretty much every company has, at Dotwork what we call an intent graph, or something that expresses intent, something that has pillars at the top and maybe work at the bottom. If you step back, it's there and in fact I'll be on calls and they'll say, and we've got this pyramid. And I'm saying let me guess. There's time along one side, but I don't say it like that, but it's pretty much, yeah, I've I've seen the pyramid before.

The really cool thing at the day job currently is I end up doing a lot of sort of research. I'll guide them through a workshop about how they actually work. And what's really funny is, they start with this pyramid. This is how we work. Then an hour later, there's, 70 stickies with all these lines connecting things.

And I love that. I love the fact I love these idea of these abstractions. Like obviously if you went into every meeting or if you had a slide and said, here's the 70 sticky notes, everyone would say no that's impossible that we don't do that. That we would never work like that. But It's reality, but you can't put reality up on every single slide. So see these operations leaders always struggling with how to frame what they're doing at the right level of complexity or simplicity, depending on which side of the coin you're looking at it to get the right conversation to happen at the moment. One thing that is fascinating there though, you realize that our simplifications often really, uh kill the nuance that's important. So I just talked about that, like, you know, there's an intent graph of some kind, most companies have what I would call like a value model. They have some underlying model and we call that, we call those context graphs.

Those are, that's context. It's not a mission, it's not your yearly goal. It's not your annual thing. It's not your objective. It's not your work. It's not your task. It's not your to-do item. It's not your bet. It's not, I've heard every word for the intent graph. The context graph is about like your value model, your capabilities, your strategy. What's so funny is how people conflate those ideas. they they look at the pyramid and say. That's it, that that's strategy or that they even call it their value hierarchy, which is really funny because there's nothing inherently valuable about all that hypothesized work. It's actually all waste until it becomes valuable.

So the value hierarchy is value, but really the value is in these other conceptual models that people have. So we can talk a lot more about that. But yeah I just love nerding out with teams about words and how people perceive them and how people, their mental models for their company. It's really fascinating.

[00:09:02] Melissa Perri: Is so much going on right now, in tech, obviously with ai I find like product management is first. Everybody thought AI was gonna replace it. Now it feels like we're swinging back out and going, oh no, we do need product operating models, which is great, or we need to figure out our product operations.

What are you seeing out there with all of these companies? What are people dealing with? What are some of the major themes that are coming out of your talks?

[00:09:24] John Cutler: It's scary out there. Even in the last week, I met two people who were just leaving tech altogether. They've just had enough of it.

[00:09:31] Melissa Perri: Why?

[00:09:32] John Cutler: they've just, it's, it's, um, it's a very hard time to be in these companies.

Um, and I think what the hardest part about it is, it's almost the best time too. Like it's the. Perfect time for thoughtful people and systems thinkers to be able to be thoughtful operators and to help their companies be more efficient and be effective at the same time, and wrap their head around the many implications of AI in their company and be thoughtful. It's like the perfect time and then it's not the perfect time at the same time.

There's just a lot of, just reactive things, reactive layoffs, reactive... it's easier now for a leader to do something very rash and bold that not thinking it through very carefully than it is to trust that things can work out if they help their people. So that's one of the major stressors at the moment, especially for people who are really thoughtful about this type of stuff. That it's like the best of times and the worst of times. At the same time. And I think that's what's getting to a lot of people. However, the bright spots I think, is in companies that a more generative approach to it, or who are more thoughtful. You're just seeing awesome things, you're seeing awesome ways of working together.

You are seeing, silos breaking down or maybe they needed more silos. You're seeing silos building up, like you're seeing a lot of things. So that's how I put it in a nutshell, like the best of times and the worst of times, depending who you're talking to. I wrote a post recently from Three Perspectives. The post said that the founders like why isn't everyone have a sense of urgency?

[00:11:16] Melissa Perri: I saw that.

[00:11:16] John Cutler: What's going on? And then the VP in the middle is I don't know why isn't anyone telling me anything, but yet, why isn't this the founder giving me some slack to do this?

And then the front lines are just looking at and saying, I'm underwater. No one will make a decision. In this particular situation, they all talk about being bold and doing whatever, but no one's willing to make the hard decisions. It's oh, you've got your day job and spend your evenings learning about AI, and then why don't you spend your mornings learning about X? Or there's only so many hours in the week.

[00:11:46] Melissa Perri: Yeah.

[00:11:46] John Cutler: For the front line so that it's just a lot all at once and in call after call. That sort of tension between all these amazing opportunities and big opportunities mixed with just the zeitgeist and reality at the moment is super difficult.

[00:12:03] Melissa Perri: Yeah, I've been seeing that too. It's the, there's more fomo I feel like now being expressed than I've ever seen before. Ever. And I, there's this crazy sense of urgency. I feel it too. Every day I'm like, ah, what's going on? We're all gonna miss out. Like it's all gonna go away.

And I get that from all sides, from investors from, people on the ground floor, from leaders, from all over. And I just feel like everybody's like, if we don't jump on this wave, we're all gonna drown. And I see that everywhere yet that, that's like everybody's hammering in that urgency, but you can't just spin up a completely novel way of working or a new product or something like that overnight without the intentional thought and like the design behind it.

And I think in especially large companies, everybody expects like this gigantic ship to just turn right on a dime. And even smaller companies that you know haven't maybe had this practice or haven't been as like, agile in the past or as creative or fluid with their ways of working.

And you can't just go, when you've been going in a different direction. And I see the frustration that comes out on all sides about it and exactly what you're saying, like from those three different levels. Hey, we're all underwater here, but we all know something needs to happen or this time is urgent, but nobody can express the direction clearly.

Or the intent to behind you clearly. Or where we're going.

[00:13:25] John Cutler: Yeah. One of the, and I've done a couple talks on this and talked to friends and in, in mentor relationships, I've used the same thing where I, I call it the, the, just the button, the cans. so the just Justing is basically, we just need to do this. We just need to have a sense of urgency.

We just need to do ai. We just need to lean in. We just need to get into the details. And then on the other side, it's, budding is, yeah but did you consider this, did you consider that, but did you think about the implications

[00:13:52] Melissa Perri: Mm-hmm.

[00:13:53] John Cutler: of AI? Did you think of but we're gonna burn people out, but we're gonna do this. And I think each of us has our own internal justing and budding. So we've got the things where we're always like, well, we just, you know, mine in 2015 was like, we just need to get together and visualize the work

[00:14:07] Melissa Perri: Yeah.

[00:14:07] John Cutler: and everything will be okay. Later I learned that that was sort of a pipe dream. but we all have our just and our butts.

But I think that the challenge right now in this environment is, what can you do that doesn't boil away all the helpful complexity and all the nuance that is in reality?

But at the same time doesn't let you spin in circles. So the funny part of that's almost the definition of agility, that's almost the definition of how to make decisions under conditions of uncertainty. It's almost the definition of how to feel your way forward. And it's almost the precise definition of where having. A reasonable operating system or like a reasonable way of working could be effective. But I think people in their mind, they think it's this trade-off between on one side, we could have amazing people and then we don't need process, we don't need X, we don't need y, we don't need all these things. If we could just have 10 X players, we wouldn't need any of that messy stuff. And then on the other side is, it's a similar Just, you know, if we could just agree to what our words, if we could just agree to our definition of done, if we could all just use sprints, if we could all just use this, if we could just all do these particular things. So it's like these and either side, and I think that that's a false dichotomy. I've been talking to a lot of people who I would regard as thoughtful operators. Like thoughtful operations people tend to, they find their way forward in conditions of uncertainty without either boiling away all the complexity or on the other side getting caught in a spiral.

It is fascinating. Like I said, it should be the best time for a lot of situations.

[00:15:52] Melissa Perri: So when it comes to having those different layers, right? Not obviously we can't just have great people, right?

I've always said that I think there it's funny 'cause it this is like repeating itself again, right? Where when we were talking about Scrum, all the leaders were like, oh, we can just have Scrum and then we have really good people and then the whole company will work. And it's no, that's not how we build software.

You have to make good decisions and set good strategy as leaders and give them. Direction and then we can figure out like what's build. So now we're going in, oh, let's just use AI and throw like some people at AI and get rid of a bunch of roles as well. And as long as we have good people, they'll just AI this into wherever we need to go.

And again, it's going back where I feel like all this backlash is coming back on operations or having any kind of structure there, even if it's not rigid. What have you been seeing out there with how people are thinking about operations now? What they're doing with it? 'cause I think it's a there's so much more that we can now do with these tools to help our operations and streamline it, but I feel like now it's getting into.

Do we care so much about it or we don't care about it at all?

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[00:17:28] John Cutler: Yeah, I think that I use this portfolio approach with most people when I'm talking about product operations. Where right now in the current environment, if you aren't spending 60 to 80% of your effort or thought process, pain killing, and basically removing friction.

You're not gonna get to that 20% or 10% or 30% of upleveling or maybe changing the organization.

So I think that what a lot of people are finding and sometimes the hard way because they just, remove whole departments or whatever, is that, ultimately they were hoping that folks in product operations and enablement would help uplevel the org. And then the narrative now, depending on the org, is "well, that takes too long. That's gonna take too long." So I was chatting with someone recently and their whole, they had a product excellence group and that whole group just got laid off along with other PMs and just a whole group because they had the right idea, but it was taking too long. And so I think that ultimately for any product operations team now to just thrive and the current zeitgeist is if you aren't putting, 60 to 80% of your time into how we can reduce friction?

[00:18:43] Melissa Perri: Mm-hmm.

[00:18:44] John Cutler: How we can make it easier to do things? We do analysis at this at work. We'll go in and workshop with people and they are spending, one day a week updating a million different decks, updating a million different tools. There's goals over here and then there's work over there.

And even though all the tools are integrated, they're not really. They're not really connected. They're not really connected to the context, and they're not really connected to the rituals that the company's using. And when you talk to companies that are doing really well, one thing you notice is this focus on rituals, the tools and all that are almost, and this reminds me of Amplitude too. We, we talked about this in amplitude, you know, uh, dashboard. That no one looks at,

[00:19:27] Melissa Perri: Yep.

[00:19:27] John Cutler: and uses in a meeting to make decisions is like a tree falling in the forest. And the thing with all the tooling that you do in product operations, where if it ultimately isn't freeing up time for great thinking or enabling great thinking in the right places with the right bits of information, it's a waste of time.

[00:19:47] Melissa Perri: Yep.

[00:19:47] John Cutler: It's, you're not gonna, you're not gonna just add. And that's another thing that a lot of operations leaders are realizing is, all they were doing was just adding to the cognitive load of teams.

[00:19:58] Melissa Perri: Yeah.

[00:19:58] John Cutler: And if you're not subtractive, if you're not, leaving mental bandwidth. But then, like I said, I was chatting with the product operations person, this is the best of times. Realized that they were recontextualizing their release notes for eight different customer segments. And they had pmms who had to look at it and they had a release calendar and there was just a mess of wired ideas and hopping between tools. They just automated it. All the announcements are sitting there waiting for a poll request.

So you just go into Slack and you just go, I've checked over your rewrite of this for our enterprise segment. You nailed the tone perfectly. Our enterprise customers don't need to be treated like they're our SMB customers, but you've put the spin on it that the enterprise customers will love, deploy. That's an amazing that's an amazing example. So you know that's that's a big. Opportunity right now to buy yourself the room and space to do the more generative upleveling, tweaking the OS kind of work.

[00:20:59] Melissa Perri: I see. This is what makes me so excited about AI type tools, right? Like when Denise and I originally were writing product operations, and this is the way we had to do it at many companies I worked at before, like we didn't have the ability to have people be able to interact in their common language with tools and get the answers they needed.

So you had to hire people who had the skills to be able to go do that do the inbetweens. Now with a lot of these products, like you can go natural language and just ask for what you want and get the information back. Or you can ask like the program to go make itself do that. And now we can generate text, we can get the data out, we can do all those things.

So it's exciting to me because. I'm like, we don't need a gigantic team to go do that. Which creates more process, more go betweens, all of that stuff. We can keep it small, but I'm still getting like pushback going, do we even need product operations at all? And every company I've seen implement it correctly is yes, this is a role.

Because those friction points still exist. There's always gonna be more friction points you have to solve for, right? So it's not oh, somebody's still gonna be doing this off the side of their desk trying to implement these things, which is what they're doing now. You need somebody to go in and actually understand like the culture, the processes, everything, and say what can we do to get some more leverage so we can just free up people to think about: what is the work that's going to create the best product for our customers at the end of the day? Like, how do we just get that work done instead of all the bureaucracy and all the red tape around it, which is necessary, but annoying, right? And it takes you away from the deep thought from the stuff that you actually wanna get into.

And I think it's such an interesting time because there's still such a like push of people being like, we don't need operations, we don't need this, like you were saying, or we don't need people do that, look at operations, but at the same time, the ones who are doing things successfully, they have operations people in there helping.

[00:22:48] John Cutler: It's one of the reasons too, like with Dotwork, we don't, there, there's sizes of orgs. I guess you could say the number of users matters but we'll be on calls and say, the goal is for you not to be using Dotwork. If we're doing our job, you might not even imagine that you're using our product. And that kind of blows people's minds sometimes.

They're saying, oh, we were being charged by users for this and that, and, we had everyone doing this and we had all these different tools and we try to challenge ourselves internally that there, there is a future here where no one wants to log into these tools. no one wants to do data entry in these tools. No one wants to map together that epic with this thing, with that thing, with this thing, and then turn it into a launch and release calendar or a roadmap. a lot of that stuff involves, not just copy and paste, it's copy and recontextualize. So the number one opportunity for a lot of AI stuff that we're finding is the copy and paste problem is just a data plumbing problem. And that sucks. Sitting there in a spreadsheet and then exporting out of Jira and then doing this like all, so low leverage. Let's just imagine, okay, let's fix that particular problem. And there are ways to fix that problem. The problem is more the copy and recontextualize. So when you go, we'll talk to a company, they'll show us the slide deck, and it's easy initially to be saying why do you use slides? But you look at it carefully and all they're doing is creating a dashboard. All they're doing is using a slide to create a consumable dashboard that you can go on a meeting that it looks the same and facilitate an amazing meeting. And, but it's the copy recontextualize. It's the thing that they're pulling together a lot of information. We talked to a company that's spending maybe $4 million in staff hours per quarter around just spending time, copying and prepping for all these types of things. And so I think that's just a massive opportunity for AI to be able to help with that kind of stuff.

[00:24:52] Melissa Perri: How would you see that play out? What? Where do you think there. What's an example of one of those opportunities there?

[00:24:58] John Cutler: Yeah, I'm not trying to sell our particular product, but we tend to, and this is actually helpful from an ops perspective in general, so we have these three pillars. You have to have a good model or of reality. So that's modeling data. You need the data in there, and for many different sources.

And then third, you need to enable decision making. It's the same thing at Amplitude. Uh, you know, data insights action. So in this case it's just, but, but the model is kind of important. You need a, an underlying model of how your org fits together, which is very important for AI to do what AI does best. So if you don't really explain how your org fits together in how you operate. It's very difficult for AI to preempt things and understand how it's working. So if all you had was data, but you'd have no model of how you work, you wouldn't be able to make use of the data. But if you had an amazing model and a great miro board, but it's not actualized and you can't get any data in it, that doesn't help you, and you could do both of those, great, but if you can't actually guide decisions and make the decisions that matter for the people out there who are working. It's all for nada. So you could have amazing model of the world. You could have amazing data through integrations, et cetera, and then you could do that. And so the way I tend to think about AI is very simplistically like AI can help you keep your model of reality a little bit more accurate, can help map things.

It can help determine when you're talking about new concepts, it can help, of just a simplified pyramid, it can actually flesh out a realistic model of how it works. It can keep the 60 stickies in its mind, whereas most humans can't. That's why they use the simplified pyramid, right? data, there's all kinds of opportunities, so it just makes it easier to manually enter data.

You can just hit people in Slack and say, instead of updating eight objects, just tell me how things are going. Then I'm gonna update eight objects for you.

[00:26:49] Melissa Perri: Yeah.

[00:26:50] John Cutler: So you get the model is right, but the interface to it doesn't involve going into 8 different screens of a system and then logging your I don't need to give a status on my goals and a status on the initiative and a status on the pillar and a status on that. So that, that's good. AI is also really useful for helping with integrations. So like a lot of the lossiness with integrations out there is just manual mapping. You see these, I met a company recently that had, a scheme of 20,000 feature labels in a huge tree. This product's been around for a long time. No one's gonna maintain that, in that system. They also had five priority fields. It's ironic if you think about it, you should

[00:27:30] Melissa Perri: Five priorities.

[00:27:31] John Cutler: your priority

[00:27:32] Melissa Perri: Yeah.

[00:27:33] John Cutler: able to do it. Yeah, the AI can help with the integration stuff and then obviously the insights. It allows to leverage great data and a great model of things to do it.

But forget our tooling for a second. You could just apply that generally as product ops, you could have a mess of data sitting somewhere, but if you have no mental model for how it all fits together, it's not gonna work. You could have that mental model, but if it's really difficult for everyone to give you updates and keep you on track and no integrations, it's not gonna work. And then if you can't act on it in your rituals and your habits, and maybe people lack the skill to act on that information, that's a place to focus as well.

[00:28:09] Melissa Perri: You keep talking about the model. Let's dive into what does a good model look like? Because

[00:28:13] John Cutler: Yeah.

[00:28:14] Melissa Perri: think that's something where, people are always, questioning like what is a model, right? If we think about product operating model or this type of model, like what is a model?

And when you think about how you work, what's required for you to start thinking about it?

[00:28:27] John Cutler: yeah. I'm letting the nerdiness out here when I talk about the model stuff, but when I say model, I'm talking about, literally, conceptual models of how it works.

[00:28:38] Melissa Perri: Mm-hmm.

[00:28:38] John Cutler: So the minute that you have a slide that says, this is how we work, you've created a model. The minute that you come up with a customer segmentation scheme, you have a model. the minute that you have a capability tree or jobs to be done tree, or the minute that you have an opportunity solution tree or you have a customer journey or you have a North Star framework, I'm just lumping it all under models.

[00:28:59] Melissa Perri: A model.

[00:29:00] John Cutler: all kinds

[00:29:00] Melissa Perri: Yeah.

[00:29:00] John Cutler: of conceptual models that model some sense of the reality of how you work.

So even those value pyramids are one type of model. They're incomplete, but they're helpful. So when I use model like that, I'm talking about generally these, what I call them, frames. Also, there's different frames to look at the org, so an amazing example of this, this will be nerdy for the product operations people, but how many times the company has all the tools and that yet marketing has a launch spreadsheet and you ask them, what's going on with that? Don't you have all the information? They say no. We have a model. We have a tiering system. Oh, you know what your initiatives, sometimes we bundle them into one launch. Oh, your releases. And so that's a model, so marketing's model, mental model is launches and releases and tiering. And it has a one to many relationship with many of your initiatives. And yet. So companies are filled with models. Way too many for any one person to keep track of, but that's the type of plumbing, that AI needs to generally understand to be able to make sense of how to operate. If that makes any sense

[00:30:14] Melissa Perri: Yeah,

[00:30:15] John Cutler: to anyone listening.

[00:30:15] Melissa Perri: Totally. Yeah. And it's what is our ways of working? And in that,

[00:30:19] John Cutler: yeah.

[00:30:19] Melissa Perri: There is a bunch of different models that you rattled off and we could think of models for like the way that you set and deploy strategy, models for opportunity solution, trees model, right?

Like all of those things when you go and talk to companies and try to map out their models with them, right? Where do you find that models are? Like what categories of models right, do you find are maybe not very thoughtfully laid out or like unintentionally laid out? And I say that because

[00:30:47] John Cutler: Yeah.

[00:30:47] Melissa Perri: usually there is some kind of model, but sometimes there, maybe sometimes there isn't.

But what are the ones where you say Hey, you need this, but like you haven't really thought this one out.

[00:30:56] John Cutler: One of the interesting parts, there's not thinking it out, but there's just conflating models.

[00:31:00] Melissa Perri: Hmm.

So,

[00:31:00] John Cutler: start with the, the latter problem. So that's, I alluded to that a little earlier on where, for example they conflate the value pyramid with the organizational structure of teams, with the product taxonomy. So you ask, what's a product? They name a team. like, is that a product? Yeah, it's a product team. Therefore it's a product. Is that a product? it's a product team. there we've talked about three different, and what are they working on? They're working on X, they're working on this part or whatever.

That's three different models. That's the what we have these four, it's, I'll write more about it, but this is four graphs, which are context graphs, intent graphs, collaboration graphs and investment graphs. Models you could put graphs for models. so one of the biggest errors is conflating, like I said the conflating those things, massive one is investment. Most companies have implicit funding models. They might, they, and then, but then when you ask finance and then you ask the teams, sort of a mess,

[00:32:04] Melissa Perri: Yeah.

[00:32:04] John Cutler: So you think those teams were funding them, like product teams? We fund these like projects, but actually we need a breakdown by the strategy five, which is intent. Oh, we need a breakdown by capabilities. Okay. So now you're mixing investment with the, context graph. Super nerdy, but once you wrap your head around this, you start to see all these problems. So that's one of the big outputs from doing all these workshops is like my pattern matching abilities for the dys.

I didn't have a name for that before. I would say things like, cascades are bad. And then now I'm deep into it. I'm like no, it's not a cascade problem. It's that that company's implying that the intent graph or the intent model is a decision rights model. That's the problem there. Yeah, not to get too nerdy, but that's what you should look out for when you're thinking about these orgs, is just mental models for things that are, easy to conflate, but that ultimately get your organization confused.

[00:33:05] Melissa Perri: I think one of the like hard things that I hear, especially in like larger enterprises is those models. Sometimes, like the investment model, for example, is owned by finance, not necessarily product, but it has such an impact on how product actually operates and is able to get things done. When you are like working with companies and trying to think about like these different models and how they interconnect.

If you were giving advice to, let's say, like a head of product, what do you tell them when they come and they say, Hey that's great, but I don't own that model. Like, how do I go get influence to, to change it or to bring people to the table about it?

[00:33:40] John Cutler: I love that question because I was talking to this leader the other day and I said, if you don't offer a better game, someone will give you a game. And so many product leaders just scoff at the finance model and they're like that's the finance model. But we use the North Star framework on our team and it's super helpful. And I say to them like, look, that other group doesn't believe in that.

[00:34:00] Melissa Perri: Yeah.

[00:34:01] John Cutler: you are not accommodating space. You're not leaving space for how they think about investment. And then when I talk to finance people, they'll say, oh, I totally understand. This nature of product, I, I understand that we're investing in teams that then work on capabilities and build those.

I know it's a multi-year thing. I know that what we do right now isn't gonna close this particular quarter and they'll see, but the product team seems to completely ignore us and talk this crazy language that we can't even agree on some basic ideas. Yeah, I was doing a workshop the other day where there was a person from finance in the call and the product leader was talking and the finance person was talking, it was so obviously like a battle of the models instead of, wait a second, i'm hearing you, but could we agree this?

And realistically what an another finding of mine is that. A company can only really keep a number of models in its head at once. So the reason why you probably see the simplified Parthenon slide with the pyramids of strategy, or the reason why you see these oversimplified artifacts in your company is not because the people are stupid. typically because the population overall of the company only has a limited bandwidth, to understand all these nuances. So if you're a leader, it's like you better you. You can either get people to a seven by just showing them the Parthenon slide, or you can lose everyone completely by showing them little nitty gritty detail of a particular strategy. But that doesn't stop. So I would say that for any leader doing it, you're in the game building business. You are gonna invent a game and co-design a game with finance. That ticks the boxes that they, you, you're building a product. Your funding model is a product. So if you're a product manager you're freaking out about your customers and all the crazy product tactics that you're gonna use in product thinking.

Apply that same thinking to the funding model that you agree on with finance. And if you can't answer basic questions for them or if you can't layer in their concerns and meet their needs in some way you'll lose them. There's many more tactical sides of that about how exactly to do that. But I think that the higher level advice is you're co-designing a game, you're co-designing a model, and if you get it right, that thing could stick for years.

[00:36:26] Melissa Perri: Yeah.

[00:36:27] John Cutler: which is also the zombie model problem, which is you, that's good and bad. Companies and they said why are you doing it like this? Five years ago there was this one deck and it had some horizons on it and it had this thing. And so since then we've logged everything, we've tagged everything in the system with no one really knows what they're tagging exactly. And then we put allocations in this other system and we tag it to X and then some reports are generated, but I've never really seen the reports.

That's finance. That's insanity. So you have to keep redesigning the model as your company changes.

[00:37:02] Melissa Perri: Yeah.

[00:37:02] John Cutler: Its another way to think about it.

[00:37:03] Melissa Perri: The one thing that's been frustrating for me, I think for doing this for so many years, and I'm sure you feel this way too, is I don't know how many times I have to go into a company and be like, Hey, actually, like we're all one team. Like you're talking about finance over there. Like

[00:37:19] John Cutler: Yeah.

[00:37:20] Melissa Perri: it's another organization that's your competitor.

[00:37:23] John Cutler: Yeah.

[00:37:24] Melissa Perri: If you wanna be successful, like you gotta go to finance and tell finance, like work with finance and say, Hey we're all here for the benefit of the business. Like of course you're gonna have slightly different goals than you do, but you all have a joint goal at the end of the day of making the business successful.

And I still feel in this day and age, some of those things come down to the biggest issues trying to get companies like just moving in the right direction. And this kind of learned helplessness sometimes at the leaders where they just go, oh, that's not my area, i'm not gonna deal with it.

[00:37:56] John Cutler: It is intimidating. It is,

[00:37:58] Melissa Perri: yeah,

[00:37:58] John Cutler: you're in a place where you know, finances it's

[00:38:02] Melissa Perri: finance has to be welcoming too,

[00:38:03] John Cutler: sometimes it's like

[00:38:04] Melissa Perri: Yeah.

[00:38:04] John Cutler: you'll talk to someone from, sometimes you'll talk to people in finance and they'll just be like, that's too complicated. The world doesn't work that way. This is how the world works. And this is what you need to do. So I understand people's frustration, but there does seem to be there does seem to be stepping stones to that.

[00:38:20] Melissa Perri: Yeah.

[00:38:21] John Cutler: And I think people often get a little bit, even me, they get too purist about certain things.

[00:38:26] Melissa Perri: for sure.

[00:38:26] John Cutler: if you can get, if you could get the finance. If the horizon model is what finance needs to wrap their head around with the idea that like, oh, I get it. They get this, they get the idea that you're gonna invest in things and see money later. They understand that concept a thousand percent. Or for example, a lot of people have luck with almost like a startup funding because people in finance might understand, they understand their external m and a. They understand the idea of maybe investing in a company. So the idea of investing like with a funding model, with different tranches of funding or that you can move that matches their particular mental model. You imagine the person in finance, they're sitting there and seeing how high and maybe the cost of acquisition is becoming, or they're seeing, they're getting investors asking them, why are you spending 30% of your revenue on RD. They're under a lot of pressure. So if you know that's

[00:39:18] Melissa Perri: They have to answer those questions.

[00:39:19] John Cutler: to

[00:39:20] Melissa Perri: Yeah.

[00:39:20] John Cutler: is important. And coming up with answers that, I always do this thing as like, is it a perverse game or

[00:39:25] Melissa Perri: Mm-hmm.

[00:39:26] John Cutler: a reasonably good game?

[00:39:26] Melissa Perri: Yeah.

[00:39:27] John Cutler: And the perverse games are things like, we're gonna do quarterly planning and we're gonna max everyone up to a hundred percent and play a huge game of Tetris. And Mary's doing 11% and Bob's doing 2%.

And Joe is doing 17 different allocations. That game is demonstrably bad. It serves no one except, I guess it must serve someone and I think it's just the people who need to like get through that quarter or something. But from a business standpoint, it's terrible game. You're gonna just burn up your money on low, like low value things or context switching. From a human standpoint on the teams.

It's a terrible game.

[00:40:04] Melissa Perri: It's also,

[00:40:05] John Cutler: that's the, yeah, it's just not

Way.

[00:40:07] Melissa Perri: it's forcing like fake certainty too when you do planning that way, right? It's oh, if we say we do this, we're gonna get that. And that's never the case. So it's just, people feel more comfortable and that's not the reality of the situation.

[00:40:19] John Cutler: yeah. One of the interesting aspects of that, actually this is a perfect example for people about what we're talking about where, but then put your shoe self in the shoes of someone in finance. No one's given them a better game. So I was chatting and coaching with a leader a week ago, and this is something we do really well in our product too.

So it's like I can show them in the product, which is really neat. what I put up on the screen is look, the question is not dependencies, the question is prioritization. And I just gave them an example in the product and said, look, you have this team and they're spending 30% of their time on something that's one 10th the leverage of the thing that they're doing. And that's the game. And I reframed the game for them. I actually even just created like a funny score. It's called like the leverage score. And the leverage score is basically the allocation related to the leverage of that thing from just an opportunity cost standpoint. And I'm looking at, it's like the leverage of that is a 0.1, and the leverage of that is at 3.2. This is the new game.

And it was just funny once you showed them that, of course, they got the questions how would you evaluate the value of these? And I said, look, you don't need, you could just be rough.

It's a it's a log relationship. Like the things that are really valuable or a many multiple over the things that are even half the, as valuable as those things. So you don't need to be perfect. You don't need to be precise here. And it was like a light bulb went out off with them, where they realized that game made sense, they realized that I'd reframed the game for them.

As one of depend, oh, our job is to manage dependencies is not the game. The game is we have a certain capacity. It's likely not gonna change in the next month. There are definitely things you can invest in to change the profile of your capacity. It's not gonna happen in one month. So you only have, or in a quarter, probably not gonna happen in a quarter.

So your only leverage is where you can direct people's focus and who works together and who collaborates with each other. And once you frame it like that, it's not about dependency management, about how we can slot everything in. It's like, how can we both improve our capacity profile for the future, right now? And how we can work with the capacity profile we have right now to do the highest leverage work possible for the company to do it. And that's a great example of, I, maybe just talking through that example is helpful for people of thinking that is a game reframe.

[00:42:49] Melissa Perri: Yeah, for sure.

[00:42:50] John Cutler: And that changes the game from one of high utilization and loading everyone up and keeping everyone busy to value throughput, for lack of a better word. Interestingly though, I've also talked to people at companies that are often like really rapidly growing tech companies as well, that when you say that to them, they'll say. We hired all these VPs, we hired all these engineers. Like shouldn't have to work on people's like this is too much process. This is we shouldn't have this problem. And then I'll say you do have this problem. You are burning like 50% of your capacity on multitasking. What? We shouldn't have this problem. If we had just hired better managers who would push back, if we just hired better leaders who would push back, if we just did all these particular things, you wouldn't have this particular problem. And I said right now you have this problem. So that's the catch 22 there, that ultimately you can even think that you've got the game explained and then someone will say, that's not the game. So you gotta be graceful with it.

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And it, it's also the, as you scale, it gets more complex, right? So it doesn't, you can hire the best people, you can if you don't give 'em direction, they won't know where to go. They're not, they don't know what game they're playing, right? Again, it comes back to, and if they're solving the wrong problem, trying to read people's minds, they're not gonna be able to get things done.

I guess people listening to this, starting to think through their models, what they're thinking about their operations, how they work and things like that. You did mention you've got like the four graphs on there. There's this interconnected how our teams work together, type models, right? What are some other models people should be thinking through that will help unlock them?

[00:44:50] John Cutler: If it were me and I was designing an operating system from scratch, and I end up doing this actually for some people. First of all is I try to come up with two or three or four foundational context models that are gonna land with the company. So some kind of either a capability model, a value stream type model, or these can be related to each other, or maybe the jour a journey model is right for that particular company or something like a growth flywheel model or North Star.

[00:45:15] Melissa Perri: So it's like your value, like how do we produce value for our customers, like value customers? Yeah.

[00:45:19] John Cutler: Without getting into what the work is people are doing, I want to come up with those stable things that are gonna be even true in three years.

They give people a mental model. And like I said, what I've learned is that it's some combination of, you know, designers, it's very effective. The journey of the customer is very effective. Typically something like a capability tree is helpful for architects and then also helpful for grounding in stable things.

And then a growth type model, like a North Star framework or a flywheel something that incorporates maybe horizons of some kind of an, and that starts to become the basis of a thing. So I would just decide on a couple of those. You're not gonna get more than three or five of them because no one can fit all those into your head. you might as well, you could max get maybe three that really land with the company that they say when you talk to a company, they usually mention maybe three of those models. Like we're really big into customer journeys and we started to do a little bit of jobs to be done, which is basically capabilities. And it's set in another way. Or and the growth team does x or the revenue team. So you're only gonna get three models outta that now with the intent hierarchy stuff. I like to keep it extremely simple. If it were me, I would just have an object called bets. And bets can be more strategic and bets can be more tactical, and you could have really long bets of one to three years. You could even have really short bets of one to three weeks.

I like to keep the intent thing. I think one mistake is when you see seven layer cake of high level vision, then company strategic goals and the next goals and the next goals. But one thing I also advocate for when it comes to intent is thinking about more like a fabric instead of a cascade. So I have a picture that I drew recently that seemed to really land with people where on one side I said, I showed the collaboration graph. So I showed leaders, middle management, frontline, and then I showed the intent graph of something like. Strategy objectives work, and I compared that to more of a fabric where the organizational graph is still the same.

It's like leaders departments or orgs, and then the frontline. But each one of them had a strategy. Each one of them had goals. Yes, work was happening closer to the front lines, but it's hard to visualize. Maybe we'll share people. I can share the picture and the links of the podcast. But that was a very interesting reframe for them.

So instead of thinking of it as just like one cascade of intent, you think of it as a fabric. It's like a fractal type of intent. So I would do that for intent. You can keep the org chart pretty simple, but I would focus on the key rituals. So for the collaboration graph, you are gonna have how your groups and product areas and stuff are modeled. You're gonna need that. And then you're gonna probably have some set of rituals or decision rights and stuff. And then for investment, this goes back to the allocation thing, which is really funny, is, I just tend to keep that really simple. If a team, you should be able to ask pretty much any team and they should be able to say oh, we're about 50 50 on this, or, 30, 30, 40, or, or maybe we're in trouble. So it's 50% reactive work. No team is gonna if a team has more than like four conceptual blocks like that's too many. I like to keep it really simple with investment, which is like core, like big quarter chips. the team is just we're gonna roughly, it's gonna roughly be about 50% on that for the quarter.

That's what we're anticipating. we'll let you know if we've gone way out of those bounds. Not like tracking time, not like tracking that stuff, but just invest in like large chunks of focus over longer periods of time at a very, um, core screen outcome focus, strategic focus level is usually enough for investment.

So I've just given those are the four graphs starting from left to we could share a picture, but yeah, I dunno if that helps someone.

[00:49:02] Melissa Perri: No. Totally.

[00:49:03] John Cutler: just come and chat with me if I, I nerd out about this stuff all the time.

[00:49:05] Melissa Perri: Yeah.

[00:49:06] John Cutler: That's the stuff I can help you out there. We have actually have a whole directory of them.

So at Dotwork we have these things called dot packs, which are basically almost like, for example, John Smart's an advisor, and then we're building out like a better, sooner, safer, happier dot pack that we would have. Or we have other things where you can get an opinionated dot pack, you could get into general dot pack, but the dots are these parts on the graph, and then we fit them together for an OS for people.

[00:49:32] Melissa Perri: Did you make the opinionated one?

[00:49:35] John Cutler: No surprise. So this is fascinating you said that because one of my personal realizations in all this. Was, so I came up with this four graph model really early on when I started because I was like, there's some sort of physics to this that's a little hard to explain. I've tried to explain it on the podcast, but as you do these workshops more and more, you begin to see it. so what I realized is that the, where you're opinionated in the OS is often just in small little details on these things. Like it's that fabric versus cascade thing I just talked to you about, or it's in the choice of the context graphs you use or it's in the rituals that you choose. So it's funny because the one that I created internally is just called Strategy Os, and it's just, it seems very unopinionated from the outset. But it's really flexible for people to use. So it's oth other ones tend to be more opinionated and specific about the names of things. Like the one that I made is just something that could just, you could just get going on quickly. And then just tailor it to your own needs over time.

Yeah, I don't know. Yeah, maybe we gotta get yours in there. Would be really cool if you're

[00:50:44] Melissa Perri: It is funny though, 'cause I have come to the same conclusion with naming. I used to go into companies and be like, I'm so specific about you naming the strategic intent. And now I'm like, I don't care what the hell you call it, as long as it's like, contextually what we're talking about here, like if the context matches, you name it, whatever you wanna name it.

Like I'll go back and try to,

[00:51:03] John Cutler: the fun.

[00:51:03] Melissa Perri: yeah.

[00:51:04] John Cutler: realized too. That's that's why I call it the intent. Intent as the second thing, because the differences are so interesting, like where you push the mandate down

[00:51:11] Melissa Perri: Mm-hmm.

[00:51:12] John Cutler: to the teams, all this stuff, like you've got work and goals and people. I'm like something's missing.

In that A, you have context, which is basically strategy, you know your context, but teams that are working really well, the line between working goals is really nebulous, and I just realized that at the end of the day, it's all intent. It's all in intent, and intent is linked to time and intent is some anticipated. It's you're setting intention for something to be true in the future of some change, to be in future that's very different from value model, which is like just a model of how things are. When you create intent, you're saying whether it's a 10 year vision or it's your one day task, a form of intent. So that's why I tend to think of it as to your point, I don't care about as long as it makes sense and it's structured and connected

[00:52:00] Melissa Perri: Yep.

[00:52:01] John Cutler: to the other parts

[00:52:01] Melissa Perri: Yep.

[00:52:01] John Cutler: of what people are doing. The names as long as it, it latches in with what people are talking about internally and makes sense that's all that matters.

It's less about the names of the things and more about, the thought behind how you're working to do it.

[00:52:15] Melissa Perri: For sure. So John, what are you excited about looking at product operations coming up for the future? What's your predictions?

[00:52:22] John Cutler: well. I'm just interested to see how this all pans out. I'm excited that I think that once there is some element that this sort of, that you're gonna get, this bubble is gonna pop and it's gonna be difficult. There's gonna be a difficult time. But in my experience, can be a real catalyst for right now we're still in, kind of moonshot mode, it's like high disorientation. But I think that I'm excited to see what people do when they come back down to earth and start... I think we, I, my hope is that we would be in for another cycle of thoughtfulness and stuff of people doing this type of stuff. So I'm excited to try to help people do that. And I also get excited when I talk to these leaders who are making it work, in their companies. There's people doing amazing things and you very rarely hear about them on podcasts or anything like that. We should get them more on podcasts. But it's just they're just given even all these crazy things that are going on, they're still doing cool things.

So that, that gets me excited every day to see that.

[00:53:23] Melissa Perri: Oh, I'm excited about that too. John, thanks so much for being on the podcast. If people wanna learn more about you and Dotwork, where can they go?

[00:53:29] John Cutler: Yeah, if I find me on LinkedIn, I'm, I don't even know what to do with the socials anymore.

[00:53:34] Melissa Perri: know just on LinkedIn now.

[00:53:35] John Cutler: yeah I'm lost with that. I think if you subscribe to my newsletter, you probably get access to my personal email somehow. email It's probably on, I think it might be there, if you need help, contact me and I just put my personal email. That's a good way at the moment.

[00:53:47] Melissa Perri: Cool. Okay.

[00:53:47] John Cutler: Yeah. I'm always up for doing these. Um. My call to action would be things about my role is that, we don't, we, we can't afford like a UX researcher now at the moment, or other folks. We're very early. So one way we do a lot of this research is just in almost like workshop settings.

And I'm always scanning it as head of product and thinking about what that means for our product. But if you just want me to, you wanna get together one time and just map it out. And then I can give you some tooling stuff after we talk about that. But we could start with what's the, what's your intent, for lack of a better word. And then we could go to that. So I'm always up for those research sessions if people are interested.

[00:54:27] Melissa Perri: Cool. So we will put all the ways for you to contact John on our show notes at productthinkingpodcast.com. Thanks so much for listening to the Product Thinking Podcast. We'll be back with another dear Melissa on Friday, and then next week we'll have another amazing guest. We'll see you next time.

Melissa PerriSeptember 24, 2025