How to Survive Change Management in the Age of AI (with Sheryl Cababa, Author of Closing the Loop)

This is called systems thinking, and it's a thought process that takes into account the complexity surrounding a specific challenge, as opposed to linear thinking, which is like saying, "oh, it's easy, just throw the marble and it'll land in the cup." And while this metaphor is obviously a huge oversimplification, the crux of it is that complex circumstances call for more holistic approach to problem solving. My guest today is Sheryl Cababa, author of Closing

She also shares some useful tools for leaders and designers to develop better, more functional systems—whether that's a product feature, a team, or even an entire organization. Let's jump in. Oh, by the way, we hold conversations like this every week. So if this sounds interesting to you, why not subscribe? Okay, now let's jump in. Welcome back to The Product Manager podcast. I'm here with Sheryl Cababa. Sheryl, thank you so much for joining us today.

But I was also doing projects in global development, so global health that. You see a lot of like philanthropies developing or funding efforts in places that are in the global south to solve problems there. Things like eradicating malaria and things like that. And I was feeling like in both spaces in different ways that the design process for me was falling short.

I've always described it as human-centered design, and so the idea of, designing first and foremost for end users and making sure that you work iteratively to engage them within the process of design saves lots of time and money. Obviously, when you're developing expensive things and you want to make sure that you're designing the thing right before you build it.

But I was seeing that there was a lack of thinking around, for example, if we're thinking about technologies that aren't heavily integrated into, let's say like society today, it's really important to think about like unintended consequences. It's also really important to think about with intent about the kinds of use cases that you're thinking about those technologies should be solving for. Even if it's still like a wide world and you just want to figure out what a new technology is good for.

And then on the global development side, it sometimes felt like there was some lacking cultural knowledge or there were people from Western places like coming into places in the global south and not having a great handle on how things work in a place like that. And so you'd see a lot of interventions failing because there wasn't a great understanding of how communities operated. Either like culturally or economically or what have you.

And so I started doing a lot of reading around systems thinking specifically Donella Meadow's book, thinking in Systems. I found really inspiring this idea that, you expand your lens towards thinking more broadly when you're looking at like the world as it exists today and the problems that are inherent. And how you can analyze that from a systems perspective to think about how potential solutions or ways of changing things might affect things broadly.

And that means like a lot broader notion of who your stakeholders are, as well as thinking about different forces, like what people and groups are incentivized by. So that's the long story short. That's where I started really thinking about systems thinking. But as a designer, I was like, I don't know how to actually integrate this in my work in a real practical way.

So I started experimenting with different frameworks and things like that, and I. The result of that is the book that I wrote is a reflection of my own journey through the intersection of design and systems thinking. It's the book I wish I had when I was going on this journey to begin with. And so hopefully it's useful for other people too.

So to kick us off, what have you found to be the biggest challenges around organizations that are trying to implement systems thinking during a time of organizational change?

And basically every aspect you can think of when it comes to, let's say, steep analysis, which is social, technological, economic, environmental, and political. And I think when, if an organization is rightfully thinking about using systems, thinking methods to think about how to create organizational change. I think there are, some key sort of tenets and frameworks to engage in. One of the ones that I refer to a lot is Peter Senge.

Has this kind of like principle that, and I always say this wrong because I think it's, I might be saying it backwards, but the idea holds true. It's like today's solutions are tomorrow's problems. So constantly thinking about how the dynamic forms of problem solving means that you're, you might have to anticipate or mitigate for the kinds of problems that problem solving might cause. I think that's a really important thing.

Causality is like a really important concept for people and practitioners to think about as they're looking to integrate systems thinking as what are the things that kind of happen as a result of either decision making or problem solving that you might have to account for later. So that's one thing. If folks are thinking about systems thinking as a method to hold that idea behind how they approach it.

I also think like in terms of the shifting technology landscape, I think, it's really about interrogating our assumptions about emerging technologies and, knowing, like your audience is oriented around like product design development. I. I think organizational leadership tests see either only the good or harm to new to technology, just depending on what kind of organization it is. If it's a technology that we're developing, there can only be good to it.

There's possible great things will come of it. If it's a kind of technology that an organization is thinking about using or being forced to use. I think there's a lot of skepticism and there's oh my gosh, this is like. How can this harm our organization? That happening today with AI, right? It's or not developing AI, they're looking for opportunities to use it. Or you have like companies and organizations being like, we don't wanna use this.

It feels like there's very little control and then the kind of like companies that are developing it are like, oh my God, this is like game changing for everybody on earth. And I think it's really, it's around thinking about, how can we with intentionality consider the potential outcomes of using a technology or developing a technology, right? If you're an organization that is using new technologies, AI is a good example.

I do a lot of work in education and I think it was EdWeek just a few months ago, released a survey of K 12 school districts. Found that the majority of teachers said they weren't clear on the AI policies of their district. For example, I'm like, this is a big deal because a lot of students are just using AI. A lot of teachers are using it. And I think for an issue like that, AI or systems

thinking is a good approach for unpacking with intentionality, the problems that AI is meant to solve. So you can create a theory of change about. How this particular technology will affect your organization. You can look at the status quo of what are the problems today in your organization, let's say like you are running a school district, and where are the sort of points of intervention that when we think about AI as a possibility that it would have an impact.

Then creating sort of principles for use. In addition to that, you can use systems thinking methods I use the Futures wheel a lot, for example, to unpack potential consequences both intended and unintended as an approach. And I think it helps you make decisions about your organization with intentionality in a way that you might not. Have thought about before and that you can do this with intention instead of just things being used organically and like finding out the hard way.

It's not really like a cure-all solution is just, we're moving the goalposts around a little bit for where exactly we need to be focusing on, correcting different things that have moved as we make new developments. This is actually also reminding me a lot of a conversation we had some time ago with Samantha Gonzalez around I. Ethical product strategy and having to really audit your approach when you're in this space around. This was recorded before AI was even popular, by the way.

Like we were talking all about how it's so important for product leaders to be really evaluating the impacts unintended and intended of their product strategy. And that's something at this point that's you're relying on product leaders to take that approach. Of their own volition. So yeah, it's, it is a very interesting time to be in this space. But I wanna dig into this further. 'cause I think that this is, like you said, this is so applicable to the space that we're in, the time that we're in.

So in closing the loop, you're talking about expanding stakeholder considerations beyond just end users. So I'd like to elaborate on that a little bit. How can design leaders identify and map the broader stakeholder ecosystem when they're planning organizational change? What exactly do you mean outside of just the end user.

You have to be all these different stakeholders. You have to be thinking about all these different people, like beyond just end users. So I, I'm just acknowledging that's not super easy, right? Yeah. And it's a really big task, which is one reason I try to like, engage in those kinds of activities.

In that kind of thinking in a really accessible way, which is like you should be able to do like a one hour workshop where you do some of this analysis and then try to figure out like, are there takeaways from this? So when I talk about something like stakeholder mapping, it's basically in many ways, like awareness is the first step. You might be thinking, especially if you're in product organization, that the main stakeholder you're thinking about is an end user and what their experience is.

When they're in the moment of using a product that you're designing. And we test products in that way too. It's oh yeah, how do, is this usable? How can we ensure that it's quality, experience, et cetera. But there's all these potential kind of repercussions. So go back to my work in education and with optimistic. It's we have product teams who are in ed tech and they're developing maybe software courseware for.

A teacher to use or deploy or for students to walk through, but they're not always explicitly thinking about all the different stakeholders in the system for whom there might be incentives and they might not even be thinking that much about, to be honest students. And what students might need from these systems because maybe they're not the primary user, maybe they're secondary users. So one way that I try to get certain of product teams to engage in the syncing is to.

Put your end user in the center of radiating like ecosystem map. And you're gonna think about primary sort of relationships, secondary relationships and tertiary relationships. And think about who are all the people who have an impact on that student's experience? And then you can do this as well for your organization. So for your product team, who are all of the primary, secondary, and tertiary stakeholders that we should be thinking about? And you might be thinking about.

It might surface for you that your buyers are really different than your end users, or that you have a huge intersection and are affected by regulation or by policy makers and like how do you understand what their incentives are? And oftentimes what this means is bringing them into the mix. So you might want to be doing like interviews with policy makers or even engaging with them. In workshops or something like that, and we do like a lot of that in our own practice.

And I think that goes a long way in just gaining alignment for what's the broader picture in which we need to be thinking about our product and kind of the impact it has on the world and not just the impact it has on end users.

So the people who are buying the course Rev, like very different incentives. They're incentivized by okay, is this system cheap and does it integrate well with our existing digital ecosystem? And then you have, teachers or instructors or what have you, and they are motivated by. Okay. Does this make my job easier? Does this make my life easier? And when we think about those kinds of incentives, do they actually align with the kinds of things that result in good student outcomes, for example?

And then on top of that, there's organizational

leadership that are completely incentivized by other things. And I think it's just making sure that. People let you have a good understanding of where people want to be and what they want to accomplish. And I think it's, you might not always get like a win-win situation. And I think that's where things get complicated, but at least you can acknowledge that. And I think, yeah, there's the, these kind of other dynamics too that come up when we talk and think about power.

We oftentimes do in some ways self-reflection with product teams that we work with because we're like, okay, what are the power dynamics with you, for example? And where you sit in the system, you're not just like an outside observer of the system. You have your own incentives as well that are driven by things like quarterly profit or where your funding is coming from and what are the kinds of things that.

Your funders are demanding, especially that you might have friction with, and how do you resolve that? We recently did this project called Modernizing Math, and you can actually look at it. It's on modernizing math.com and it is really around like the future of math education. And one of the most interesting things that I felt like I took away from that was, it was a futures thinking and systems thinking project where.

We were working basically with middle school students to think about what would you want out of math education for 20 years from now? And we're thinking about different technologies and different scenarios that would exist at that time. And one thing that constantly came up was they were like, when it comes to AI, like they don't wanna be just like users of.

AI or any other important technologies, like I wanna be able to make that technology, like I wanna be in the room and they will point out like, people who look like me are not in the room, and you're doing this work with mostly black and brown students and they're like, we know who's making AI right now. Not representative of who I am.

How do we change it so that I can get in that room and not just be like a user of these things that are coming and trying to figure out like, how would we use this in math education? I want to think about math education in terms of like, how can I be empowered to actually create it or create things in a way that is not as like super centralized the way it is now, where like these companies, where there's very few people are designing these technologies for everyone else.

I thought that was just like such a clever way for the kids to be thinking about this as well as just it made you sit up and just go yeah, kids are really smart. Like they, their system thinkers inherently, I think, and bringing it to that, even though that's not how we necessarily post it to them, was really interesting exercise.

I feel like we could really dig into just anything here, but we'll keep moving. Let's say we're talking about AI adoption and platform shifts. How would you say that system thinking can be helpful in avoiding common pitfalls? You describe a system archetype called success to the successful in the book and some other systemic traps.

If you wouldn't mind just summarizing what success and successful means and then just how can we use systems thinking to mitigate some of these kind of tendencies for organizations to create we mentioned before, unintended consequences.

And you can think about that as we also described that as vicious cycle. And I think it's about thinking about ab an abstract concept like that. Oh, a vicious cycle. Are there like vicious cycles in our ways of doing things where we're maybe incentivizing the wrong things or it's. Counterintuitive, what do they call those? Perverse incentives, right? Or, yeah. We're rewarding certain things that are actually resulting in an outcome that we don't wanna see.

And yeah, if you overdraft fees are, just sending people spiraling and there's basically, it's a race to the bottom that's a sustainable system and they're, it's like worthwhile to think about what are different potential solutions for this?

An example I use from like sort of city policy sometimes like plastic bags, because this, there's no wrong answer here, but it does help organizations maybe think about what if we're trying to institute a policy, like what are the actual long-term outcomes we want? So some plastic bag policies.

There have been studies that show when there's a plastic bag ban that people buy more plastic bags for just things like lining their trash cans and things like that rather than just using the reusable or the plastic bags that come from the supermarket. And the problem with that is the sort of garbage bags you're buying, those use more plastic. So is the goal to reduce the use of.

Plastic bags that you're giving away for free, or is the goal to reduce the use of overall plastic entirely in the long term and it's like forces organizations to think about what are the choices we're making about that?

And those I'm sure are just absolutely the worst as far as by gradability. So it's just to me like I'm thinking there's only a few grocery stores in my area that have just started using paper bags in lieu of the reusable ones, which to me is kinda like it's an obvious choice. That's probably the first thing that people are gonna opt for if they.

And it makes you more intentional too about metrics. I feel like in my book, I didn't write enough about metrics. I, I, another edition comes up, I'll write more about it. I do think like sometimes we measure the wrong things and a lot of organizations are guilty of that too. So I think it's like thinking about what are the long-term outcomes that you want and how constantly mapped that in a way that even the small decisions you're making, you can keep that in the back of your mind.

A little saturated, there's it, there's really more of a emphasis on quality of output and how can you measure the actual impact of what you're putting out, rather than just blasting out as many items as possible and then just hoping that they'll perform. Yeah I think that this is like a, it's a really important thing, as a main takeaway for this conversation is to really be evaluating, it's not just about what you're doing, but what's the intent?

What are you trying to achieve with what you're investing in here? And being really intentional with how you're mapping out the pathway to get there. Okay. So I wanna talk a little bit about something that you mentioned in your book again about designers as facilitators rather than solution creators. I wanna talk about that a little bit and what exactly you mean by facilitator role versus solutions creators.

I think that we've long thought about designers as solutions creators, so how do you kinda describe that change in mindset and what are some of the processes that you'd suggest to support that kind of a transition in the organization?

This has everything to do with AI as well and as well as things like design systems, right? Design systems are meant to make everybody's jobs easier, but I do feel like everything becomes systematized in a way that it's oh, what does that mean for designers? As practitioners? Really, at the end of the day, as I'm thinking about educating future designers. I think being able to have a strategic lens on how decisions

are made and how maybe we educate others or think strategically about how things get made and built is maybe a better like long-term spot to be in, which is like the area in which I work, which is just thinking about, how do we bring together different stakeholders for problem solving purposes.

And basically facilitate and make explicit the decision making or the broadening of the lens that design can help facilitate, which is, yeah, things like making explicit, a theory of change, making explicit, like what does a systems map analyzing today, and where the intervention points, where can we look to potentially problem solve? How do we imagine the future? In a way that, we can articulate through design.

So I, in my book, I write a lot about, I don't write a lot about it, but at the end I write about speculative design because I do think there is an intersection with thinking and systems and being able to create provocations around what the future might look like and what the future might hold. And that's what I think about when I think about design as an act of facilitation. It's like, how can we.

Help people make more explicit their ideas, whether it's organizations we're working with or various stakeholders who are coming together to problem solve. We would do a lot of work in my studio with philanthropies and thinking about where to direct their investments. And design is actually a very good tool for facilitating those kinds of conversations because one, we can use like our. Visual communication skills to create frameworks, principles, et cetera, for decision making.

But we can also do design concepts, right? So even if we're not building like a shippable thing, it's about how can we imagine the future through artifacts that are around what might screens look like in the future? Or how might people move through a journey of using different kinds of products? These are all acts of design that I think get me really excited because they're used for like really upstream decision making.

And so I encourage anyone who's designer and if if you're like a product designer, there are ways of integrating this into your work as well. That I think is like maybe doing some of that facilitation work, holding workshops with your team, et cetera, that might get them into the space of. And thinking more broadly about where work in general sits.

I think there's often, especially when there's a lot of excitement and investment riding on an outcome, there can be a tendency to ignore or, optimism away your potential negative consequences. And if you have an anecdote, I think that'd be really helpful. But how would you advise? Design teams to try to start mapping out some of those unintended consequences before implementing new technologies or even organizational structures.

I know we have to think about it, but it's not fun to think about and it actually puts people in a very defensive spot too, because they're like, oh, you're, what you're accusing us of is that we don't think about harm or we don't care about it or something. So several years ago I worked on this thing called the Tarot Cards of Tech.

It was with my previous firm, and the goal was to get people to have these conversations, but it's like these fun little characters that are a little bit like tarot cards. And they had like different personalities, like one was called Mother Nature and there were prompts on the back of it that were like, what if Mother Nature were your client? There was like one that was called like the forgotten.

Who's being left out of your thinking when it comes to the product or features that you're designing? Yeah. People are using those cards to this day, which is really interesting because it's very simple and, I found that people are using it for strategy, for education also, for basically product feature design. And it's, I think because it takes the blame away from you as a technologist. And puts the onus on like this toolkit that is like prompting you.

It helps people have those like really tough conversations about what unintended consequences are without it feeling accusatory. The other tool I really like using is doing a futures wheel. A futures wheel is here's the thing we're gonna do, and then you think about the primary, secondary, tertiary, et cetera, effects of those decisions. And like good things can come out of it and bad things can come out of it.

When I've worked with organizations for example, that are think, I was working with one organization that was considering their work at home versus comeback to the office policy and we did an exercise around a features wheel around the comeback to the office policy and then did it as well for continuing to let everybody just work remotely.

And it was really interesting because in those scenarios, like really, I. Like teams tend to, especially technology teams, they're like very optimistic people. I, this is why I call, we called my studio Optimistic Design, but they start with the really positive potential effects.

And then it just like organically goes into spaces where you're like, oh, that wouldn't work out that well. Or people are gonna start feeling really isolated if. We just let everybody kind of work from home in perpetuity, or if we force everybody to come back to the office, there's going to be some loss of autonomy that is going to

be something really hard to deal with as an organization. And so they're able to have conversations around decision making that go beyond how they were initially thinking about this. Because oftentimes a team making decisions, they'll be like, okay, we have to create.

Are back to the office strategy and it ends up being like a bunch of like rules and like what are like the rules around this and how do we need to execute on this rather than what's like the philosophy behind this and how do we need to approach it in order to think about those potential effects that we might wanna mitigate. And then you go into the tangible creating of the rules after that.

I think that analysis just helps broaden your thinking about, what are the potential things that can happen. And yeah, I think a lot of organizations are dealing with AI right now and aren't doing that sort of intentional, like what's our philosophy around this perspective before doing the policy work of it and the rules and regulation work of it. I really like the Office of Educational Technology.

I refer to this a lot, where they're like, we recommend a philosophy that's around treating AI like an electric bike and not a robot vacuum cleaner. You want it to be an assist that strengthens people's abilities versus something that just does a thing instead of the person doing it. And I was like, even that, which is like.

Very high level and maybe a little abstract gives you a little bit of guidance when you are thinking about that and creating your policies or your perspective as an organization with intentionality. So I think that's a big part of using these things that help you think about unintended consequences will get you to that principle or policy plays better.

Conducting stakeholder interviews and conducting workshops to make sure that you're not operating just on the assumptions of people who are making those decisions and really getting like a very holistic picture of the people who are being impacted by those decisions. And when we think about, normally in product, we usually think about stakeholder interviews and workshops as a user researcher product development methodology.

So how do we have to adjust our thinking and what's the difference in procedure as far as using those techniques? With the purpose of organizational change and facilitating better organization design?

And I think what's interesting is that, and this is maybe the difference between doing like more traditional kind of design research is it's really great to do co-design with those kinds of stakeholders because the decisions that are going to be made. Are going to have a direct impact on them in a way that they could be involved in designing the solution. Creating these workshops where they feel part of it.

One, it starts gaining alignment for the eventual decisions that you're going to make because people haven't been kept in the dark and you're no longer just like throwing something over the fence. People are aware that this is happening and then. Thinking about how to empower those who normally aren't empowered in these processes because organizations are made up of people from all different levels of power, right?

Some who don't feel like they're ever consulted on anything, and so even if they're just being interviewed, it is a way of consulting with them, and it does feel like they're being pulled into the process, even if at the end of the day. Maybe you're not entirely doing what they think should be done. There is some value in engaging with folks like throughout the organization in order to create policy that is intended to have an impact on them or their own ways of working.

So all of these systems mapping exercise is really good for that. So I've done like iceberg mapping, which is like thinking about what are the visible problems and then how do you look at the patterns below that, the sort of systemic kind of infrastructure and then the mental models. And I always find that members of an organization have. Just really meaningful reflection on things that go below the surface.

So if you're like, oh, we're having a lot of attrition in this organization, it's okay, you have to think about like, why is that happening all the way down to the mental model, and are we doing anything as like a sort of system infrastructure that is actually contributing to that, that we didn't intend to? So it forces you to look at your existing policies and things like that. All that to say.

I do feel like putting these sort of visual frameworks in front of people, help them have the conversations that maybe they wouldn't have if it were just like them sitting in a conference room just talking to each other. Things come out because you're making it explicit through the act of filling out a framework. It's it seems really simple, but I noticed like people have a lot of valuable conversations they might not otherwise feel like they could have without those tools.

Anyway, I really dig this, like the systems thinking approach is, I think so applicable to so many different disciplines and in the organizational design I can really see the connection is very clear between the work and the outcome. So I really appreciate your time talking about this today, Sheryl. For those who are like me and are keen to continue this conversation, where can people of all your work online?

You can find my book, which is called Closing the Loop: Systems Thinking for Designers at my publisher site, which is Rosenfeld Media. And so yeah, hopefully this has been an interesting conversation. Every now and then I talk about systems thinking. I feel like I'm just stating the obvious, but I think it's like just connecting the dots on these things I think is meaningful. But I, and I hope that people kind of experiment with these methods in the organization.