YouSaid · the spoken record

Sarah Stein Greenberg

lines on the record: 45
first: 2025-08-21
most recent: 2025-08-21
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Actually, it turns out to be a part of the value of this service. And that all happened because they focused and focused and focused. And then also like as a very early stage startup, you can't spread your resources too thin. And so it helped them realize like that's the point of leverage. Now, of course, they want to move upstream in the whole process because a lot of these denials should never happen in the first place. I think really have been successful at using design to find the right problem to start with that's really going to matter to people. And that is critically important, especially if you're in some kind of entrepreneurial context.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“And so they refocused their startup around that particular moment in the process. And they have now built some proprietary software that helps compare like what your insurance policy looks like, what your medical forms say you actually need, and then actually do the writing with a human in the loop to make sure that it comes out well. The reason that that was so important is it also led them to some of the more human insights, right? It turns out it's not just about the monetary value that you might recoup, although that financial piece is important. It's that the feeling for people of having someone on your side and knowing that even if you get denied, you put your best foot forward. You did everything that you could.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“That's right. So Haley and her co founders came in with this kind of broad premise. And one of the things that they had to do in the class was write down who they thought their user was and what they thought the pain point was. And that process of really focusing, one, it helped surface a bunch of assumptions. But two, what they realized is the most important pain point is for people to write the appeal and to get support while they're writing the appeal.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Claims are denied, and only one percent of those people appeal. But what her team has learned is that 40% of the people who do appeal are ultimately successful. So they're trying to increase the number of people who do appeal. Because like if you think you're getting covered for surgery and then you get hit with a $40,000 bill and 80,000, that is a life-changing financial event for most people.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Well, one story I want to share with you is a story about a recent grad named Haley King, who is an awesome entrepreneur. And I think her story gets at something that is really at the heart of design, which is about the difference between problem finding and problem solving. You know, human beings are great at problem solving. We're all wired to do that, but we pay a lot of attention in design to what is the actual problem that we're trying to solve? What is the pain point for our customer? What is the opportunity space? And so Haley has started a company with two other co-founders called Paxos Appeals, and they are trying to help more people who get denied a claim with their health insurance company to actually appeal that denial and then be successful in getting covered. And this is a huge problem, something like 10 to 20% of clients.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I am finding is incredibly useful in fast flaring. And then I still think it's on the human to really think about what does that mean, right? How do I connect that with the human needs that I've been uncovering? And how do I use my human intelligence to make sure that I'm using all of these new ideas in a way that's going to benefit the core needs that I've uncovered”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I asked it to think like a futurist. And to then go deeper on particular use cases. So I gave it a user profile that the organization had created and then said for a person like this, help me think about what is the future of flood insurance going to look like, right? What are multiple scenarios? What are people going to be thinking about? And every time I'm asking it to come back with five different ideas, come back with 10 different ideas or more. And then I can pick and choose and decide which ones I want to go deeper on. So in design, we talk a lot about flaring and focusing, right? There are moments where you want to broaden your aperture and then there are moments where you want to converge around a particular idea or a particular prototype.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So I was designing a session in partnership with a nonprofit called Commonwealth, which works on financial inclusion. And they were really interested in thinking about the future of actually financial inclusion, the work that they do with the coming wave of AI, because often people who are not well served by our current financial structures are left out of the kinds of tools that are going to benefit customers of all kinds of financial services. They wanted to get smarter about it. And so we used AI to help me design different future scenarios in which they could Really push kind of the edges of my own thinking and come up with far more divergent scenarios than I would have been able to on my own.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“What would we design? And that allows you to, one, it allows you to check your assumptions, which especially if you've been talking to a lot of experts or even if you're kind of getting close to the launch of a product or service, you have a lot of assumptions about what might happen. So some people use this practice to de-risk that launch phase. But it also can just invite more creativity and open thinking. It's like, okay, if we didn't hold on to this assumption, what could we create is a very powerful way to challenge orthodoxies and to kind of get beyond mental models that might be outdated.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“They do still have value in the world In my opinion, and in many people's. And it's also tricky because they will give you a kind of filtered view of the world. And part of your job when you're trying to figure out a new design space is to go abroad, is to make unexpected connections. So you want to engage with experts, but you also want to treat that kind of lightly, at least to begin. So the practice of assumption storming is You might have collected a whole bunch of expert opinions. You're getting smart about the space. Then you list out all of the assumptions that you've heard about that particular space. And you categorize those assumptions as some of them are facts. A lot of them are opinions and some just might be guesses. And you pick some that are in the opinion or guess realm and you challenge those. You just say, okay, if that were not true.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, this is a really fun one. So everybody's heard of brainstorming, but there's a lesser known practice called Assumption Storming, which was developed by a guy named Craig Lauchner. And I mean, it's important to talk to experts when you're trying to design something new.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I really think it is a useful tool. I mean, it's a kind of a lightweight after action report, right? With a little bit more of a personal and human dimension because you want both the team learning and the individual learning, and you want to be having a dialogue about that. I think there's also something very powerful about framing those moments as not just like, what do we do wrong? What do we do right, but actually like how can we learn from the things that didn't go as well as we wanted to. And so. Creating the vocabulary around a learning journey, I think can help open up a little bit more of the vulnerability that you need when you're really trying to get people to be open and reflective as opposed to it just being an evaluation in which like somebody might feel penalized for having done something wrong.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“And that's because design is hard and creativity is hard, and innovation are going to be real low moments. And you want to make sure that there are experiences that students are having that don't edit that out because those are often the most fruitful learning experiences that we have.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“The thing that happens that's quite interesting is where you see a student who said, wow, this was a moment in the project when I was learning a lot, but it was really hard. I was struggling. I was mad at my team. I was uncertain about my own skills. And that gap between when learning is high and feeling or affect is low, I think is reflective of a concept I'm really interested in and have written about, which is productive struggle. So productive struggle is like, it's actually more beneficial to us when we're trying to learn how to do something new to have to struggle a little bit. If it comes really easily, it's not as likely to make that big of an impact for us. And when you see that gap where someone's like, oh, this was hard. But actually, I was learning the most. That's what you want to see as an educator, right? You want to create those moments deliberately where that can happen.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“These should not be straight lines. If they are straight lines, it would be a very weird human being that was filling this out. And what's really interesting is when you see where those lines intersect.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Learning journey maps are one of my personal favorite tools for reflection, and that falls into this kind of big broad category of reflection. So a learning journey map is a visual tool in which you think about a particular learning experience that you've had or project that you've worked on, for example. So I use it in my classes, but you could use it in a team at the midway point or the end of a big project. And you use an axis that basically is like negative to positive and then think about the kind of big milestones of the experience over time. That's the x-axis. And you draw one line that reflects your journey in terms of how much you learned. So like when were you learning a lot? When were you learning a little? And another line that reflects how you were feeling at the moment.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Exactly. Exactly. And then to be able to test it and get real feedback. So that is hugely beneficial. It's going to speed up that time. But then there's another category of things where it's hard to do in a classroom because they're labor intensive, they're time intensive, but they're really, really crucial for learning. So another example is a tool that my colleague Leticia Britos Cabinaro created, which is a tool that helps you reflect on your own progress as a learner. And reflection is one of those unbelievably helpful but critically underutilized approaches in education. And it's actually not just education. It's like, we should be doing this after every team project, for every quarterly review that you have, instead of being only evaluative, if it could also be a tool that is actually helping you learn better.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Well, you can play with this tool now. I mean, we're actually looking to test it with teams and different kinds of companies. So that would help us. That would be exciting to partner on. I think what we're most excited about are the ways in which AI can help augment what we do, right? And there will be certain things that get much easier and much quicker. And I think some of that is going to be really beneficial in design. Like, for example, if you think about building quick prototypes to be able to test your ideas, now you can build quick prototypes that actually work, right? It's not just like a fiction. So we're seeing that in classes where students are just much more likely to, in a very positive way, like break a stalemate on their team by just building the thing very quickly.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Exactly, exactly. And you can imagine how, you know, thinking about what could this be if you're trying to figure out the future of fintech, right? It's like what scenario might you design? And then, of course, at some point, you're coming up with your ideas. And then there's a big tilt, right? Like something goes wrong. One of your ideas fails spectacularly. And then you have to keep figuring out what you're going to do. And the thing that we're trying to figure out is how can you help people prepare and rehearse being creative under those kinds of uncertain circumstances? Because when you're in the moment, you're under lots of stress. And so if you haven't actually built that capacity and those skills, you're less likely to be able to really respond in that kind of resilient way.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So we're working on a tool that is kind of like if a textbook were more like a movie that you were starring in with like details and characters and plot twists, like think what you might be able to learn. So imagine this is a kind of a generative case study tool. Imagine that you maybe you and your team are using this tool and you're placed in some kind of future scenario that's very alien to you. And the only way to find out about that world is to interact with the people who are there. So through this interface, you're interviewing people, you're asking them about their lives, what's going on. And then you're coming up with ideas that might help them solve some of their challenges, maybe the challenges about C-level rise or maybe the scenario is like on an exoplanet or something that you are not familiar with.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“For all of the uncertainty that AI is creating, there are some things that it's going to help us do better than we ever could before. And for us, one of the things that's really hard to do is to help human beings imagine the future in really vivid ways and really creative ways. And it's also hard to retain your ability to be creative when things are changing so fast and then they keep changing and then they keep changing some more.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Time Yeah, I mean, here's what I'll say one of my colleagues, Scott Dorley, who's our creative director, has this great phrase where he is describing how I think a lot of us feel around all of the tech change that's happening, which is like you constantly feel like you're not up to speed. And if you think about it not up to speed also spells nuts, right? And like that is the feeling, right? That's the feeling in the air, right? And feeling behind is a real challenge. So one of the things that I think we just all have to be doing is like actually all experimenting with the technology. And so a lot of us at the DSchool are doing that. And I'll give you one example of where I do think that”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Those first couple of classes coming out of the pandemic were just really struggling in lots of very material ways. And so I would say on the other side of that, we have kind of an interesting mix of both some of those habits that were acquired during that period of time, like maybe shorter attention spans. And then we also have this massive oncoming wave of how AI is like really going to change education in particular, right? And it's already influencing certainly our students now are so facile with certain tools and they also spend so much of their time in digital environments. And we're all trying to figure out like what is actually going to come next.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I think we're seeing some really interesting changes. One of them is that 20, 25 years ago, more students wanted to make things and now students like really want to make change. So their appetite for what kind of impact they want to leave is bigger. And also the kinds of challenges they want to work on are bigger and broader in scope and scale. You can't just be good at one part of product design and get to the scale of impact that we're talking about. We have seen a need to build more tools and methods and thinking around systems as well as around ethics and thinking about broader consequences into our curriculum. And that's really in part because the students want to work on those kinds of challenges. I will also say that the effects of the pandemic were really, really significant. It feels like a lot has repaired, but not entirely. There have been just some massive shifts that have happened.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Well, I mean, it could work even more easily in a remote work environment because you can literally shadow somebody in a Zoom room.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“And then I think as you get bigger and bigger, you could even create a situation where you use some of the same practices you would use to understand your customers with your colleagues. So one of those is shadowing, right? Beginning of the day to the end of the day. You sit with the person you're shadowing. You try to understand what their work is. You try to understand from their perspective. And that's going to help you bring insights back into your own work, both about how they approach their task, but also about as human beings how they're functioning in the particular part of the system.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“If they're having a lot of conflict about which direction to go, it is often because they have all gone out and talked to different people and they haven't found a way to really share their insights in a meaningful way. So one of the things you can do is to create some moments where you're making sure that your teams from across the organization are looking at the same raw data and trying to make sense of it and figure out what to do. That is a very just practical approach, making sure you're designing those connections in.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So, I think there is something that often happens early on in companies where you're all sitting together in the same room. The sensitivity that you have for your colleagues and what their jobs are and their roles and the challenges that they're facing is very, very high. The second you have two rooms or three or four or offices where you're not all together. Easy to lose a sense of empathy and caring and just even insight for your colleagues and what they're doing day to day. So I think knowing that that horizon is coming is really important.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“To be able to actually respond and to be prepared to respond and to be prepared to respond creatively This is one of those things that design does really well.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Yes, exactly. Rolls off the tongue. And that is a team that is facing new challenges all the time, right? Or is having to pivot or having to adapt very rapidly? And that is actually very consistent with what we see anecdotally, which is that design is actually a very powerful way to prepare yourself to be really good at learning new things quickly. And in particular, when you have a team of people who are confronting uncertainty and ambiguity, which let's face it, like that is what is happening right now in the world.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I mean, there are a number of studies that look at different ways that these behaviors manifest. So I just read a paper that was studying a large company in China. It's a very interesting controlled study in which they were looking at the effects of design thinking training versus after action review training versus other kinds of team building trainings. And they found that both the After Action Review and the Design Thinking outperformed the control, but that the design thinking training had a disproportionately positive benefit for teams that had what's called high task variability. Sorry to get so technical.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So instead of just wireframing in a digital environment, for example, you might actually physically draw something out. You might use a big whiteboard. You might put it on construction paper, right? You might cut it up and collage something. It creates a different sensitivity in your brain and helps you think of things creatively in different ways. We actually, we call that building to think. And I love to see how magical it is for people who are really right now kind of constrained to thinking on a screen to get out of that mode and actually start to work in some kind of physical medium. I think another thing that that helps with is that when you're building an analog materials, it leaves more open to interpretation. People can have misunderstandings with each other. But it's like very clarifying to work in those kinds of mediums.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I mean, that is so fundamental to how the DSchool operates. I think one of the most important things is to remember that even if we're interacting with each other only online, we're still embodied human beings. And so some of the things you could do there are to insist if you're having a brainstorm or you're doing some kind of prototyping session, have people build in three dimensions. Even if that's happening, I'm in my living room and you're in your home office, we can still have a similar experience. Maybe we have the same set of materials in front of us. And that also helps you build those bonds, even though you're physically separated.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So, there's a lot in the literature around creativity and psychological safety, right? You have to have a real sense of connection and belonging and safety to get your best ideas out into the room. And so when you take the time to build those relationships, it helps people appreciate where other people are coming from. It helps you be more open-minded to hearing ideas that may not automatically make sense to you.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“That's right. And then Glenn will have his students actually take those individual photos and create a short video that they then do as a little mini film festival. And it's just a creative and playful way to try to bridge some of those connections.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, one of the activities that's in the book is actually inspired exactly by the context that you're describing. So Glenn Fajardo, who's been teaching at the D School for a long time, created this amazing assignment called the wordless conversation in which the goal is to have a rich empathy building interaction with a colleague or someone else in your class without using words. And so in this process, you set a timer and on the hour every hour you send a photo to your partner. And then that person responds. And maybe it's a photo exactly from their environment at that moment, or maybe it's a conversation. And we start to build interaction and a connection through something that doesn't require us to already have met or to be on the same page or to have even a language in common.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“A great title. Thank you. I think curiosity is kind of a necessary ingredient for creative work. And I wanted to really highlight that. And it contains 80 of my favorite assignments that we teach. And I think those assignments are not only useful if you're in school, if you're in a design program, but if you are in a business, if you're in a community, if you're trying to figure out like, how am I going to change some of the patterns?”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So a few years ago, we started a big project at the DSchool to try to actually share more of what was going on, more of the work that we do with a broader audience. And so we have actually released a series of 12 books. My book is a part of that series. It's called Creative Acts for Curious People. Which is an epic title.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“I mean, I have so many interests. And as the executive director, you know, some days I'm cleaning the floors and some days I'm, you know, thinking about the strategy for the future, it's just increasingly important that we equip our students with the ability to think critically about not just the near term effects of what they're doing and the potential for it to be successful, but what's the second order or third order effects? What are the potential unintended consequences that they could create and to be able to have a really rigorous conversation about that?”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So we now offer two design degrees an undergrad and a master's degree, and we offer a lot of classes for professionals as well.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“Combination of a lifelong passion and a ton of luck. I have always been really interested in how human beings come together and organize themselves in different ways to produce specific results. And the luck part is that I happen to be a grad student at the business school at Stanford right when the D School was getting started. So I took some of the very early classes. It was totally experimental. It was in a trailer on the edge of campus that was the only space available. And immediately I felt like, oh, here are my people that was part of it. And part of it was just that it was a group that was as obsessed with how do people actually collaborate, particularly under conditions in which there isn't a right answer. And how do you actually produce useful creative ideas from that?”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So we specialize in a type of design called human centered design, and it is a really flexible creative solving approach. It incorporates some elements of other kinds of design like graphic design and we're even intentional in thinking about like how might we construct the space in which these kinds of classes might be happening. So we have some other things in common. But design is a really big field. Everything around us is designed. Everything not found in nature has some kind of human influence in terms of how it came to be. And we really focus on how do you tune in to what human beings need, think about the context around them that might be the natural context, that might be the social context, and then try to figure out what are some solutions or some new opportunities that you could bring to bear.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“That's right. So I'm happy to. I think that's a first for me. Oh, really? Someone would think the D was divinity. So I appreciate that. Okay. So what is the D school? The D school is an institute at Stanford. It is a kind of unconventional place where people from all over campus, all different backgrounds, all different fields of study come together. And the goal is to develop creative problem solving and to apply that to a whole range of different kinds of opportunities and challenges. And we do that because we want to advance the spread of design. We think design is one of the most useful ways to create new possibilities. And it feels like a really important moment when human beings are doing that and equipped to do that. And that's what we're all about”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“So, in design, we talk a lot about flaring and focusing. There are moments where you want to broaden your aperture, and then there are moments where you want to converge around a particular idea or a particular prototype. And AI I am finding is incredibly useful.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT
“When you have a team of people who are confronting uncertainty and ambiguity, which let's face it, that is what is happening right now in the world Design is actually a very powerful way to prepare yourself to be really good at learning new things quickly.”
2025-08-21 · Masters of Scale · How design drives successful companies, with Sarah Stein Greenberg · IDENTIFIED FROM THE TRANSCRIPT