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Help Me Understand Why: How "Dumb Questions" Might Save Your Product and Your Strartup

Practical Product Management · 2025-04-09 · 46 min

0:00--:--

Key moments - from our scoring

Substance score

55 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality9 / 20
Guest Caliber16 / 20
Specificity & Evidence12 / 20
Conversational Craft8 / 20

Sam Zabarjani, formerly global product lead at Moderna and founder/CEO of healthcare startups, discusses how "dumb questions" - really smart probing questions - can unlock innovation in heavily regulated industries like healthcare and fintech. The episode explores how product managers can partner with compliance and legal teams rather than treating them as blockers, using framing like "How can we make this work?" instead of "Can we do this?" Key examples include how telehealth succeeded by borrowing familiarity from FaceTime, on-demand house calls mimicked Uber's interface, and healthcare scheduling borrowed from OpenTable. Sam emphasizes that innovation in regulated spaces isn't about choosing between compliance and creativity - it's finding ways to do both. He and hosts Leah and Marilyn discuss how strategic experimentation, regulatory sandboxes, and building conviction across organizations enables companies like Amazon, Plaid, and Moderna to push boundaries while maintaining safety. The conversation stresses that tech should fade into the background, enabling better patient outcomes and user experiences rather than being flashy or beautiful for its own sake.

Key takeaways

  • →Frame regulatory constraints as forcing functions for creativity rather than obstacles to innovation, shifting from moonshot ideas to incremental, iterative testing.
  • →Change the vernacular when engaging with compliance teams - ask 'How can we make this work?' instead of 'Can we do this?' to shift conversations from blockers to problem-solvers.
  • →Borrow familiar design patterns and experiences from adjacent industries to build user comfort with regulated product innovation without needing flashy features.
  • →Use strategic small-scale pilots, limited releases, and regulated sandboxes to de-risk innovation while proving value in highly regulated spaces like healthcare and fintech.
  • →Success in regulated industries requires organizational conviction and teams willing to test boundaries, experiment, and fail rapidly - not companies that claim to innovate for optics.

In this episode

  1. 1Understanding Regulated Innovation in Healthcare and Tech
  2. 2Shifting Perspective: Regulation as Framework, Not Enemy
  3. 3The Power of Dumb Questions and Collaborative Compliance
  4. 4User Experience Without the Flashiness: Tech as Enabler
  5. 5Familiarity Over Originality: Borrowing Patterns from Other Industries
  6. 6Breaking Through Regulatory Barriers with Conviction and Pilots
  7. 7Industry Reset Moments: From Square to Pandemic-Driven Change

Mentioned

ModernaAmazonOpenTableUberFaceTimePlaidSquareTwitterSam Zabarjani

Guests

Sam Zabarjani

Topics in this episode

Healthcare product innovationFDA regulation and complianceTelehealth platformsPayment processing and fintech regulationAmazon One MedicalPlaid compliance automationPCI compliance requirementsKYC (Know Your Customer) regulationsModerna commercial productsTwo-way door vs one-way door decision frameworks

Questions this episode answers

Why do product managers ask "dumb questions" in regulated industries like healthcare?

Asking seemingly simple questions - like "Can we build a wallet that stores credit cards securely?" - reveals regulatory assumptions that may be outdated or overly cautious. These questions force teams to understand the actual risk, not just inherited procedures, and can unlock paths to innovation that regulators will actually support if framed as collaborative problem-solving.

How should product managers talk to compliance teams to drive innovation?

Instead of asking "Can we do this?", ask "How can we make this work?" or "Help me understand what it would take to make this work." This shifts the conversation from a defensive "no" to a collaborative exploration, turning compliance teams into partners and co-conspirators rather than blockers.

Why do successful healthcare tech products often copy familiar interfaces from other industries?

Using familiar patterns (OpenTable for scheduling, Uber for on-demand services, FaceTime for telehealth) reduces user friction and builds trust with both users and regulators. In healthcare and fintech, familiarity signals safety and reduces perceived risk more effectively than novel, beautiful design - trust matters more than aesthetics.

What's the difference between innovation that succeeds in regulated industries versus innovation that fails?

Successful companies like Amazon, Plaid, and Moderna combine conviction about the idea with willingness to test rigorously through pilots and regulated sandboxes, de-risking innovation while proving value before scaling. Haphazard companies that ignore regulatory constraints or procedure for procedure's sake tend to fail or get shut down.

How did the pandemic change innovation dynamics in regulated industries?

The pandemic created moments where some industries tightened regulations further out of caution, while others - like telehealth and self-administered medications - opened up space for creative solutions. It reset industry assumptions about what was possible, creating opportunities for companies willing to work with regulators on new models.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

10 / 20

There are a handful of genuinely useful ideas (regulation as forcing function, familiarity design borrowed from other industries, building compliance-defensible IP), but they're diluted by extensive mutual admiration, throat-clearing, and generic 'find your why' platitudes.

regulation isn't the enemy of. Right. Of innovation, but it's really the framework within which sustainable innovation can happen
if you can solve problems inside of the regulatory framework, you just create more defensible products that competitors can't easily copy

Originality

9 / 20

The reframes (regulators as partners, dumb questions, 'help me understand why') are reasonable but widely circulated, and the design-familiarity point (make it look like Uber/OpenTable) is a well-worn observation rather than fresh thinking.

a product is a lifestyle. Um, I don't know if somebody ever said that
we literally made it look like OpenTable because that made people feel comfortable

Guest Caliber

16 / 20

Sam is a genuinely senior and relevant operator: led global commercial product at Moderna, was digital health lead at Amazon, held health-system exec roles, and is a multi-time founder with exits, making him well-placed to speak on regulated-industry product.

most recently I was at Moderna where I was leading their global product team on the commercial side
I've been a multi time founder, CEO, exited a couple of companies

Specificity & Evidence

12 / 20

The episode offers several named companies and a few concrete figures (telehealth jump, Hims & Hers value drop, Amazon wallet, Plaid, Lilly DTC), but many claims stay at the anecdotal level without hard data or timelines.

only about 3 or 4% of the appointments were over telehealth across the system. Overnight it went to 99
the company loses like 40% of value overnight

Conversational Craft

8 / 20

Hosts occasionally probe ('poke the bear', 'help me understand why', the role-play as a junior PM), but the conversation is dominated by mutual praise and unchallenged agreement rather than genuine pushback or hard follow-ups.

I'm going to go back and poke the bear with Sam now a little bit here
You're both amazing, amazing, inspiring leaders

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B53%
  • Speaker C24%
  • Speaker A24%

Most-used words

product52love23tech21super18experience18innovation16different15build14marilyn13didn12healthcare12care12back12regulated11space11feel11

Episode notes

In this episode of Practical Product Management, Leah and Marilyn sit down with Sam Zebarjadi, a product leader with deep experience at the intersection of healthcare, tech, and regulation - including roles at Amazon, Moderna, and multiple startups. Together, they dig into what it means to drive innovation in highly regulated industries, the power of “dumb” questions, and how to partner with compliance and legal to build great (and safe) products. Sam also shares what makes a great PM today - and why staying practical, curious, and adaptable is more important than ever. Key Takeaways 1. Regulation Isn’t the Enemy of Innovation - Sam flips the script on the typical tech vs. regulation narrative. Instead of viewing regulation as a blocker, the best product teams use it as a framework that forces better, more sustainable innovation. 2. Ask Better Questions - Especially the Dumb Ones “Help me understand why…” can be the most powerful phrase in a PM’s toolbox. Dumb questions often reveal flawed assumptions or outdated procedures that are ripe for change. 3.

Full transcript

46 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome to Practical Product Management. It's a podcast that Marilyn and I do where we talk about the practical side of product management. So there's lots of great books out there with good theory, but we think that product management happens in context and so we love to talk about that. Today we get to talk to Sam, which is super fun. Sam has the dark, distinguished, um, opportunity of being someone who Marilyn and I have both worked with but didn't know together. Which is we know lots of people together, but we didn't. But I was like, you know Sam. And she's like, you know Sam. So that's really how, that's how, um, special he is to this podcast and to us. So Sam, tell us a little bit about yourself and then we'll dive in.

Speaker B: Sounds good. Well, first off, thank you. Um, I will say I've done a lot of like, media stuff. This is actually the most nervous I've been because you guys are awesome. Um, and the bar has been set very high apparently. So I even dressed up for you guys today.

Speaker A: Fancy.

Speaker B: Yeah, I've taken it up a notch. I've broken out a jacket, um, because I thought that you were that special. But anyways, thanks for having me. Um, yes, I'm Sam Zabarjani. Um, like you said, I've spent most of my career at the intersection of healthcare and technology, um, focused both on the product side and the business side. So most recently I was at Moderna where I was leading their global product team on the commercial side. So really think about any therapeutics that are ready to go to market and everything that happens from, um, marketing, selling, supporting in life and managing that across a global footprint. Um, and I had the privilege of doing that together with Marilyn there and working under her amazing leadership where she managed everything. And I was just taking a look after our product team. Um, before that I've been a multi time founder, CEO, exited a couple of companies. Um, I've held executive and leadership roles in a few different health systems. Um, and then I've also worked in big tech, uh, where I was the digital health lead at Amazon for a couple years. So it kind of gave me a little bit of a different perspective on what healthcare means in that context and when you have, you know, customers all around the world. And so for me, um, you know, product is, it's something I'm super passionate about. It's, uh, didn't you guys want to say this? A product is a lifestyle. Um, I don't know if somebody ever said that, but like, it sounds about right. So I'm super excited to dive in with you guys today and, um, yeah, have some fun with it. So thanks again.

Speaker C: Uh, I love it. It feels like kismet, doesn't it? Like the world are coming together in really interesting ways, which is cool. Um, this is going to be a thrill of a conversation, so buckle up, my friends. Um, Sam, I think you have a really unique perspective because you've been driving innovation, um, through technology, uh, in a heavily regulated industry. Um, so why don't we sort of like just dive right in and talk about, um, the opportunities, the complexity. Um, what is this whole space about, Sam?

Speaker B: It's interesting, right? Um, typically when you think of product and innovation, people typically think about just like the big sexy tech, right? Let's go build something fun. Let's be super reckless, let's throw something through the wind, and then we'll build an mvp. If it takes off, cool. If not, we'll pivot, we'll figure it out. Doing that in highly regulated industries and again, I'll use my, my background in healthcare. It just doesn't work that way. Right. Um, and I think part of what happens is that regulation, compliance, risk, all of those things come into the picture and what I found and there's this bit of a negative rhetoric, right? Um, people often say that regulation gets in the way of innovation. I like to think that regulation isn't the enemy of. Right. Of innovation, but it's really the framework within which sustainable innovation can happen. And so really figuring out how regulatory constraints can actually be a forcing function for creativity and really helping product teams think a little bit differently. And in that way, I think it's a matter of changing your perspective. It's like, how do I turn these little wins into game changers? Right? How do you compound the small wins into game changers, um, in highly regulated industries? And it's all about like shifting your frame of reference. Like, instead of these big moonshot ideas, incremental innovation, iterative testing is the way that you get there. Um, and the other thing is like, you know, and I think, Marilyn, we've had this experience together, um, in some of these regulated industries. It's about turning the regulatory teams and compliance folks like, looking at them as partners, not blockers. Right? Can they become co conspirators, not adversaries? Like, right. How can we use them as partners in crime, um, and do it early and often enough so that it doesn't get in the way downstream? And I think that's just some of the biggest key learnings I've had and it's very different for product people coming in from traditional tech or you know, non regulated industries. Again, you know, you've worked in fintech, right? That's a side of the world I haven't been on. Um, but in healthcare there's so much to it and it's funny, right? And um, in some of those cases you can always tell the people who come in because they always ask the silly questions which uh, aren't really silly, they're the smart questions to ask. And somebody kind of pats you on the head and says, oh, that's really cute, that's super illegal. We can't do that, right? Figuring that out early enough is actually

Speaker A: going to jail if we do that.

Speaker B: But okay, um, and here's the thing, right? When you think about like innovation in these industries, again, you're not talking about technology where you're like, oh, we're just going to make it easier to share pictures or we're going to make it simpler to buy stuff. Like there's this Amazon concept of like a two way door, um, you know, or a one way door. In healthcare, a lot of the decisions you make in certain product areas can actually be one way doors, right? There can be severe, severe impacts where you can't reverse course. There are things that might affect patient safety, regulatory challenges, risk. Like you might put the company in a really, really uncomfortable situation. Right? And so those are all the things that I think really good product managers like, uh, if I had to encapsulate the question, um, I'd say that being a product manager in a highly regulated industry isn't about choosing between innovation and compliance, it's about finding a way to do both and harmoniously.

Speaker C: So I love the notion of the dumb question, um, because as you both know, I'm a huge fan of the dumb question. Um, and I think that by the way. Pardon?

Speaker B: There's no such thing. But that's okay.

Speaker C: I love the dumb question because sometimes like really what you're trying to do is build a beautiful customer experience and sometimes that means challenging assumptions. So when someone often pats me on the head and says, oh, cute, uh, no, we're all going to go to jail. My follow up question is help me understand why.

Speaker A: Right?

Speaker C: Because sometimes there's a whole basket of assumptions or, um, I don't know, previous, uh, previous notions from a compliance perspective, um, that you don't actually understand why you can't do something, um, and why I think I feel like innovation happens and that helped me understand why, um, and I know you've seen this too. Both of you actually have seen this too. And you've both been able to change the games in pretty fundamental ways by thinking differently. Um, and so as you're thinking about, you're talking to a whole group of product managers today, um, how do you do that without pissing everybody off?

Speaker B: So it's a really good point, right? Again, I think a lot of this is, it's about just changing the way you talk. It's about changing our vernacular, right? Like going to a compliance team or a legal team and saying, can we do this? Right? How about saying, how can we make this work? Help me make this work. Help me understand what it would take to make this work, right? And so it really shifts the conversation from being no to let's find a way, right? And I think that's really the key. It's again, product manager. Being a product manager means so many different things. But in this case you're in this driver's seat, right? So you have to learn how to deal with all the people from the different parts of the business and speak their language. And I absolutely love what you said, Marilyn, right, Because at the end of the day, like, it's all about the user experience, right? No matter who the user is or what it is, it's all about that experience. So like in the health care setting, patients, customers, consumers, providers, nobody cares about regulations. All they care about is the experience that they have, right? And so whatever it takes to get that done. And so I think a lot of it is just about asking those questions and understanding and then having just that, um, you know, background, having some of that regulatory knowledge, the ability to strategically experiment and then be able to bring that cross functional collaboration to actually unlock some of those like, tests so that you can actually learn whether something will work or not.

Speaker A: I love what you just said there. Again, I think harkening back to sort of the healthcare system you and I both worked in, I remember having conversations and saying, nobody cares about our tech. What they care about is that the patient is seen in a healthy and safe way and the doctor can do their job and the medical record is updated and all of these things matter. Our tech needs to just disappear. So don't get fancy about it being like the uh, most beautiful and has to be perfect and everybody has to be like, oh my God, I'm in love with this user experience. It's not about the user experience in the healthcare environment. It's about does the person get what they need in order to feel better? Heal or, you know, get diagnosed in a way that they can move forward, you know, or whatever. And I, I think as product managers, we often, um, especially in the more traditional space, we're like, I want to build the flashiest thing, the sexiest thing, the best thing. And it's like, does not matter, right? It has to disappear, it fades. Because the experience of the patient with the healthcare system, with the doctor, with whatever they're interacting with is the experience we're concerned about.

Speaker B: Totally. And it's uh, about how does tech become an enabler. Right. And we always used to talk about this in kind of that traditional care delivery setting where tech was there. It's like, how do you make the tech operate in the background and bring back the human element. Right. And so that was the user experience to your point, Leah, it's like the user experience was bringing back that FaceTime, that sacred relationship between a patient and a provider. Right. And that six minute setting when they're there so that somebody's not heads down, punching away on their computer. Right. And so those are the kinds of things. And I think when tech becomes a part of that journey, then you can start thinking about the user experiences. And in highly regulated industries, again, I think what I've seen work out really well. And there's a guy we both worked with, Leah, who would always say you don't get points for originality. Right. Uh, and I think, you know, I didn't know, agree with everything he said. Um, but that was a really interesting one. So when we actually looked at then building that familiarity with those products and getting people over that like level of discomfort, it was really simple. It was like, okay, if you're building a healthcare scheduling system, we literally made it look like OpenTable because that made people feel comfortable even within a new context. Um, you know, with the company that I had, we were doing like on demand, like house call doctors, right? It looked exactly like Uber. Like you had this, uh, familiarity, but instead of ordering a cab or food, you were getting like a doctor to the house. Right. But it looked, felt comfortable, um, when telehealth became mainstream, it was, you know, because it was very similar to making a FaceTime call and calling your grandma. Right. And so again, you had that comfort and familiarity. And I think part of that narrative was really helpful with the regulatory folks and compliance folks and just people all across trying to get them across that, you know, to cross the chasm, if you will, around, like, hey, this is new and different, but like, it's really not new and different, right? We're borrowing concepts from other industries that have worked and now we're bringing this age old industry to the new era when it comes to technology. And oh, by the way, we're not doing it because tech is awesome. We're doing it because it's better for customers, it's better for people, and it's better for the organization. And we can show you why.

Speaker A: Well, and I think, I think on that point, I mean, Marilyn and I've talked about this before, similarly in the payment space, like when you, you, uh, know, I've worked for a fintech company who was always like, we're going to push the edge on the experience. And I'm all, if it looks different than Amazon, it'll make them nervous. Yeah, so don't do it. Right. It's like, well, but we're going to do this and we're going to move this and we're going to have this field. I'm like, good luck. And every time they tested it, if it was dramatically different than the payments experiences we're used to, it made people, the trust signals went like, like tanked. I don't care if it's ugly, it works. I get that that real estate and the Amazon checkout isn't great. Like, we all, even Amazon knows that. Right? It's like, it's, it's functional, but it's not beautiful. But should you try to change it, your trust signals collapse.

Speaker C: Well, and also I think, um, I mean you both, you both like, let's just beat a dead horse. I'm coming on to help you beat the dead. Um, and I think that product and design teams forget this.

Speaker A: Yeah.

Speaker C: Um, it's not about beauty when you're testing. And I always get like, I was funny, I was having a conversation yesterday and someone's like, I want delight. And I'm like, do you know what delight is? It's done and you didn't even notice it.

Speaker A: Yep.

Speaker C: It's not like I don't need a, I mean I kind of want. But I don't need a unicorn to fly over and drop sprinkles everywhere. I need it to just happen. And for me to be like, wow, that was super easy.

Speaker A: That was easy, right?

Speaker C: Yeah.

Speaker A: I mean we talked about like, I think in certain contexts, I think healthcare and, and payment, fintech payments are the same in this regard. I will jump through hoops to get to what I need if you make me. And I'm like, that's annoying.

Speaker C: But whatever, we all do because there's no alternative. Like, think about what a pain in the ass it is to find a primary doctor to set up an appointment, a dentist, like everything's a friggin nightmare. And then they want their insurance and you got to fill out a form and then you got to show up 10 minutes early to fill out more forms that you already answered online. Like, this is a, this is the base case scenario and we all accept it because there's no easy alternative.

Speaker A: Right, Right.

Speaker C: And when you think about the opportunity, and this is. I'm going to go back and poke the bear with Sam now a little bit here. When you think about the opportunity to really change the game in this space, you're fighting against a couple things. You're fighting against regulators.

Speaker A: Yeah.

Speaker C: Uh, and, and let's be honest, there are companies who, most companies that are regulated have a set of procedures, um, that they follow that keep them safe, but they can't actually tie the procedure to the risk. They've lost that because they've wound up like procedure over procedure. Um, and there's a whole ton of fear around everything. And because it's a little ambiguous, there's a lot of resistance to innovation.

Speaker A: Yeah.

Speaker C: So how do you break that, Sam? How do you. Like, like I know you, I know you're super energetic, but I want you to tell your story to the rest of the world. And you know, it's hard, but like, you've done it multiple times.

Speaker B: Yeah. And I think part of it is, um, you know, it's, it's not easy. Right. And I think depending on the, the industry you're in or what you're trying to crack, it's, um, A, it's having a lot of conviction. B, I think it's finding people who are willing to take that ride with you and take the gamble. Right. Like organizationally, you know, as a, as a dumb young entrepreneur founder, it's really easy to fall in love with your own idea and your own cooking. You know, that confirmation bias. It's awesome. I highly Encourage anybody under 30 to, you know, have a high level of conviction for an ID and go do it and then, you know, come back to earth. M. That was awesome. Right. I used to have a full head of hair at one point. And then, you know, life happened and startups and all that stuff. Right. Um, but working in an organization, I think you've kind of seen this with the companies that have done well and the companies that haven't. Right. The ones that have that conviction to face some of the pressure to swim against the current and to try things that and fail and rapidly learn, like, push the boundaries of what can be done. They're the ones that succeed at the end of the day, right? There's companies that say, oh, we want to innovate and don't end up actually innovating. Or they say it because it looks good in the proxy report. Or, you know, they think it looks good to go to a conference and have somebody present on AI, but they're not willing to actually invest in it. Um, you know, those are not the places where innovation happens. And I think part of this too, if you look at some of the companies that have come out on top, again, we'll use the Amazon example, right? Like, part of what made them be as successful as they are outside of prime and all those great things that E commerce experience, right? They were one of the first to actually master having a wallet where you could securely store a credit card. Right? Like, that was crazy. PCI regulations, like back in the day, like, oh, lock up your terminals, do this. Everything has to sit in a, you know, mainframe somewhere. Like, that whole process was crazy. Or even think about, like, all the new fintech companies, the banking regulations with kyc, like when Plaid started out, they had two choices, right? They were like, we can either add a bunch of compliance teams or we could figure out how to build an automated compliance solution and work with regulators and again, see if we'll get in trouble or not. But let's try to build the technology and tools to make that happen that can verify users in seconds and not take hours and days. Right? And so those companies that have that conviction and then bring people in that are willing to, again, test in, um, you know, small, little, like regulated sandboxes. Yeah, that's where, you know, you can actually see the biggest success, like in these highly regulated spaces. Pilots and limited releases. De risk innovation while, like, proving value. Right. And showing that things can be done. And then, uh, figuring out that snowball effect, I think, has been really, really critical. And if you look at every company that's been successful, they've all kind of done it that way. No one's done it haphazardly, Right. The haphazard companies have all gone out of business, right? Um, they spacked a lot of them. They became kind of overnight successes and then they went away. So, you know, there is a level of, um, I guess maturity that comes in being able to actually innovate in these spaces and do it well. And, um, I think it's only going to get easier as time goes on. But it's also going to get more noisy. Right. And so I think that we will see. My prediction is we'll see regulation start to clamp down a little bit more in all these industries. Tech is becoming more ubiquitous. Um, and, you know, it's going to be interesting to see what happens.

Speaker A: Yeah, you know, it's interesting because I think, you know, I think we have these moments. And I have a question here somewhere. But, like, I think we have these moments in time, in product, where things happen in the industry that sort of reset something. So I, you know, for me, as a payments person, it was when Square dared to build a, you know, something into their phone and go to a, uh, trade show. It was the Twitter guys that did it. It wasn't even square. They didn't exist. Right. The guys at Twitter were like, we need a terminal on our phone and they built something, you know, and it. It changed everything. Right? And then sometimes things happen to us, not. We don't do it from within the industry. And I think the pandemic was an interesting moment in time where everybody sort of came to a halt. And I see some things in industries like in travel and some care and some of these spaces where things have gotten confusing. We're like. It got locked down even tighter, and now we're trying to, like, re, like, get the fulcrum out and open the door again, right? We're like, somebody go get the jaws of life. We're stuck in here, right? Like, and then I think there are other places where it's opened up some space. Right. And some creativity. And I'm, um, I'm just curious for both of you, given kind of what you've done, like, how has that played out in what you're seeing in this kind of regulated space?

Speaker B: Marilyn, I'm curious to get your thoughts. Um, you look like you're dying to say something, so jump in. I have some thoughts as well. I always have thoughts. They might not be good ones, but

Speaker C: I. I am an I. So. Yeah, um, I think so. I think a couple things. I think first and foremost, um, a lot of innovations like you just described, Leah, come from someone having a problem and having the skills to solve the problem.

Speaker A: Right?

Speaker C: And if I think about health care in particular, you know, people didn't. People still don't go to the doctor. Let's just be super clear. Like, not a lot of people just go to the doctor. We all avoid it. It's. It's pain in the butt. Um, no one really wants to find out they have something terrible wrong with Them and we don't usually go until it's far too late. And uh, you know, and then there's something is wrong. I think the, the invention of telehealth was kind of a game changer and it helped a lot over Covid. People I know, um, called the doctor, right. They didn't have to go anywhere. That didn't have to be a big thing. You didn't have to go into like the instacare and sit next to someone that's hacking up the plague. You can just call someone and be like, I have this horrible rash. Can you help me?

Speaker A: Right.

Speaker C: Um, I think that uh, we're seeing some of the same things as it relates to some of the new medications that are on the, you know, that are on the market now where people can self inject. And that notion of giving yourself a shot now has become a lot less scary. There's millions of people that are self administering in these little pens or whatever. Um, now I think that opens up risk to your point. Now there's all these telehealth groups spinning up that are compounding and like they're doing all of these crazy things. And as a consumer you don't really know if they're credible, yes or no, but they are kind of solving a problem. So there are things cracking open and there are companies like Lilly for example that are looking at more of a direct consumer relationship for their products.

Speaker A: Right.

Speaker C: I think we're on the verge of seeing some more things sort of crack open, I think for two reasons. Um, one is I feel like some of these industries are finally realizing that tech is not it.

Speaker A: Right.

Speaker C: Um, and the people that can build these experiences, that help solve these experiences are technologists. They're not an IT company that someone in business writes a spec and gives and they only do that and there's no thought, there's no innovation. So I think, I think that there's a fundamental premise there that is changing. Tech is not it. And if you've got an IT group, you're probably not going to get a lot of innovation out of it. And um, if you have a tech group, they're not going to sit in a corner and do what you tell them. So there's a different operating model that needs to evolve there. And secondarily I think tech is changing at such a rate, rapid pace that it allows for people, um, like product, um, or others who haven't had the ability to code to now rapidly prototype in a way that they haven't been able to before. So they can express an idea in a working prototype rather than a doc. So now we're starting to leapfrog over some of the things that actually got us here.

Speaker A: Right.

Speaker C: Um, which means innovation can happen faster and you can get something into someone's hands a lot quicker and you can actually validate if it's going to work or not. I've, you both know that I have like this passion for like rapid testing and getting things into the hands of customers. That's my opinion on what's going on here. So I think it's both really good because we're starting to see like a little things that are going to change the game and it is, it absolutely is going to add noise into the, into the system for a while. Uh, but I think that the big guys, the big guys, um, will either have to adapt or, or purchase because they'll get disintermediated.

Speaker B: Yeah, yeah, I completely agree. I think, I think that's been the direction it's going. Right. I think part of what's happening with these big legacy companies, to your points, right. Innovation has not been at the top of their minds. And so they've historically been going out and they've been getting kind of, you know, disrupted or like the Lilly example is a great one. Right. Manufacturer, um, working through a bunch of channels direct to consumer, healthcare becoming a thing, tech becoming ubiquitous. Like why not go and actually build that direct to consumer brand and cut out the middle. Right. Um, and now it's become easier than ever. Now it's not a, you know, go spend tens of millions, bring in a third party company to build it. We can actually test something out. And I think what's happening too, you know, kind of going back to your point, Leah, like going back to the pandemic, um, that was a forcing function where telehealth adoption skyrocketed. Like at that point I remember I was a executive hospital system in the Midwest. It was an IDN mid sized organization at that point only about 3 or 4% of the appointments were over telehealth across the system. Overnight it went to 99. Right. And so we basically had to go and figure out how to scale the system. Train, um, the doctors, do everything and then the regulations were changing daily. Like how do we bill for this? What's happening, what's not happening?

Speaker A: Yeah.

Speaker B: So on one hand you have those forcing functions of like what happens, you know, at like the global level, the macro level. And then you've got some opportunities where companies are just like trying to figure out the gray Area. And you look at the hims and hers, right? What they're compounding the stuff, they're doing the GLP1s. Let's go and figure this out.

Speaker A: Yeah.

Speaker B: All of a sudden, you know, FDA is like, actually, that's not going to fly. Right. Cuts that off, effective, you know, this month, and then the company loses like 40% of value overnight. Right. And so, like those regulations, there's companies and you're kind of playing with fire. Some of the times you're reacting to the regulations. Some of the time you innovating in spite of, like, not having any regulations that you can be aware of.

Speaker C: Right.

Speaker B: Um, and so there's kind of this balancing act. And I think that organizations, big organizations, part of what they benefit from is that they're often on the leading edge of these things. They sit on these working groups, they have direct line of sight into government agencies. They hear of regulatory changes coming. And so if you think about that in terms of like, not the effect that regulation will have just on you developing a product in healthcare or manufacturing it, um, but really thinking about that as like a product life cycle thing of if I can actually have my product people involved early on and often enough, uh, think about how that impacts your product roadmaps and how much more effective you can be. Right. I now know something that's going to happen. I know this big industry change that's going on. I know something is coming off patent in, you know, a year. Like, how do we actually change the trajectory of where the company's going? And then technology and digital become. It becomes ip. Right? And I think one of the really, really interesting thing is, like, if you can solve problems inside of the regulatory framework, you just create more defensible products that competitors can't easily copy. Right. And so how do you use that to your advantage and as a product person, how do you quarterback that along the way so then give your company that lead? Um, and also keeping your head on a swivel. Right. I think that's the most important thing a product person in this industry can do. You have to be. You kind of have to be a Swiss army knife. Right. Like, you have to take on and learn more things than you typically would in a traditional PM type role. And I think those superpowers are really incredible once you find the people who can do that.

Speaker A: Uh, you know what's coming to my mind, and I'm curious what you both think about this, but what you both said that strikes out, kind of strikes a chord with me is all of Us that got us to hear all the companies, all the product people that got us to hear. We sound like we're sitting on our porch, like, get off my lawn. To all of the companies out there that are doing what we taught them to do. And we're sort of like, I was young and agile once, right? And I'm going to get in your way and I'm going to help the regulators get in the way. And it's like, no, if you would capitalize on all of the skills we developed, you can also stay current, relevant and ahead. But we, it's almost like we're annoyed that we got everything to hear and now we're like, hey, those kids are taking our space, right? And I'm like, come on, product people. Our job is to stay relevant and on top of things and go with the pace. Like, we are pace setters.

Speaker C: Yeah.

Speaker A: That's our job. And if you suddenly go, oh, I'm just gonna get my walker out and go for a little stroll, like, carry on. Get out of the, get out of the way.

Speaker C: Yeah. Retire, go to the park. I actually feel like I fundamentally feel the opposite. I feel like I did a lot of stuff to get me here and it is not going to help me in the next five years.

Speaker A: No.

Speaker C: Because the next five years are going to do nothing but accelerate. And I think that, um, being adaptable and being able to use the tools and having to do more and understand more and test faster, um, and push the boundaries are all super key. I actually feel sorry for, for people coming into this role now because what you. This is the premise of our entire podcast, Leah. What you read in a book or learned in university about what product management is, if you get too rigid about that one framework, right. You will most likely be a terrible failure because it depends on so many factors. You need so many skills.

Speaker A: Yeah. Ah, totally. And I wonder if, Sam, for you having had sort of the CEO hat and worn that, but also really strong product skills, how do you, how do you navigate what we're talking about like this? How do I stay relevant? How do I use what I'm, you know, stay current and learning and curious. How do you think about that? Because you obviously have worn a hat that I haven't worn and that Marilyn hasn't worn. So I'm super curious about that.

Speaker B: Um, albeit a small size hat, but yes. Um, you know, I think at the end of the day, right, I think we kind of started talking about this like, yeah, product is all about the user experience, right. As like. And I Think there's actually a lot of parallels between, like a CEO role and like a product leader. Right. At the end of the day, you're trying to figure out how do I bring value? How do I do it in a meaningful way? How do I create these incredibly delightful customer experiences and really good product people and really good CEOs. Also think about the entire value chain. Like, how does that affect the business? How do you think about unit economics?

Speaker A: Right, right.

Speaker B: This actually something that's meaningful. And I think that, you know, those. There's a lot of parallels there. And I think now, um, more than ever with the technology gap that's kind of shrinking. Like, again, it is about being adaptable, right? It's about what do the customers, excuse me, what do the customers want? What are you trying to deliver on? Um, how do you bring a differentiated experience that's really sticky, that's engaging, that's delightful. And then, you know, how do you use the technology to help you along the way? Like m. You know, to Marilyn's point, you know, like the gap to building demo able and kind of workable MVPs. Now it's, you know, the days of, like, user stories. Let me go draw, you know, draw them out and build figmas and this not like Gen AI can do all of that for you now. Like, I could literally go from, like, you know, my problem to what I'm trying to solve for, to some user stories, to some sort of mvp, to some sort of workable code that actually doesn't look awful in, like, hours and days. Right. And so now I can get something in front of my customers. Now I can actually test things out in real time and get real immediate feedback. Right. And see what works. Oh, and I can, by the way, I can model how it's going to impact my business. I can, you know, model the roi. You can do all of those things that, you know, 10 years ago when I was a young, naive CEO, that would have been awesome to have. Right. Um, but again, I think the industry that we're in, the space that we're in, the people who are going to be the most successful are the ones that are keeping their eyes open. They're reading, they're researching, they're studying, they're having conversations. And I love the first word in your podcast. Practical. Um, it is about being practical, right? You can't do everything by the book. Like, you have to bring in some of the street smarts with the book smarts, uh, especially now. And I think that that is like the biggest key I would have for like any, anybody getting into like PM M right now is how do you actually practically see the world? Right. What do you want to try to accomplish? And at the end of the day, attention of users and customers, whether it's an internal user, it's a doctor, it's, you know, like an 18 year old kid, it's a 70 year old, you know, man. Um, you have to think about what they want and how they are going to use your product and what else is like taking their attention day to day and how do you actually compete for that attention? Right. And so those are the really hard questions. It's actually kind of bringing back, it's silly. It's like it's almost Bringing back web 1.0 vibes. Right. When like you're starting to build these products, everything is kind of new and interesting and innovative and like how do you actually build those really sticky kinds of things that people want to rant and rave about?

Speaker C: Yeah.

Speaker B: And so that is the biggest thing that I kind of think about now. Like if I were starting a company, it would feel, look and be completely different today.

Speaker A: Yeah.

Speaker C: This whole conversation makes my heart happy. But now I'm going to turn to you both as product leaders, um, and as a. I'm going to assume the role of very junior. I don't, I like, I want into this, I want into this, you know, this, this career because it sounds amazing. Um, I know where to get the book smarts. Right. There's book on every corner. Um, as my newfound mentors, how. What are the top two or three things I need to do to start to develop those street smarts? Um, and what would you give as guidance to some of your more junior people? Because it sounds scary.

Speaker A: The one thing that comes to my mind as you're saying that I think is something we've talked about before. Don't think of product management as this one kind of job. Go do other things. Go work in platform, go work in data, Go work somewhere outside of the shiny sexy UI and learn deep product management so that you can go wide. Right. And I think, I think I just. All we've been saying for me, like what you just said, Sam, was super important. It does feel today like it felt like when uh, I started my first year as a product manager was 2003, it was a new thing. I didn't even know what it was. When my boss said, do you want to be a product manager? I was like, I don't know what that is, but probably right. Like I don't I don't know. And, and I think, like, it does feel now like it felt then. And the reason I'm still relevant is I still, I'm still super curious. I still care deeply and I'll say yes to almost anything that's interesting and I haven't done before. So do that. Right? Say yes to something that isn't like, oh, uh, I want to build the front end for this mobile app. Like, that's fun. Do it at some point, but don't only do that, that. So that, I mean, that's my, that's my, my. I implore young product managers out there to open, like, crack open the thinking on this.

Speaker B: Yeah. And I would also. I echo that hundred percent. Right. Um, especially as somebody that I admire in the product space. Right. So I'm always learning from Leah, honestly. And so, um, that's good advice for me to take today as well. And I say, you know, to anybody kind of coming in or the more junior PMs, like, like, first off, the best PMs are translators. Right. At the end of the day, it's about turning business goals into, like, tech execution and customer needs and a product strategy. And go and study. Like, don't just ask customers what they want, watch what they do. Like, don't look at what they say. And then more importantly, go look at all the products, all the things that have failed. Go learn. Go ask why. Go understand what has not been successful. Go ask why all these companies that have been complacent with their products because they thought they were first movers, like, why didn't they get ahead? What were the key decisions in knowing that, like, engineers, designers, execs, everyone is going to have an opinion. But your job as the PM is the one who understands the customer the best. And that's what is going to make you either succeed or fail.

Speaker A: Totally. I love that answer. I love that answer. What would you say, Marilyn?

Speaker C: I love both of those. I would also, I would also say, uh, you know, Sam, you said you need to know your customer. Leah, you said you need to know the ecosystem. I actually think you also need to be really empathetic to both your business partners, which Samuel alluded to, but also your tech team. Are you sitting on the, um, Are you sitting on the, on the, uh, the outages? Are you getting on the call and understanding what your team is fighting through? Not your job to talk, my friend, but at 2am you can shut up and listen.

Speaker A: Yeah.

Speaker C: Um, but do you know how hard it is to run your platform?

Speaker B: So.

Speaker C: So you're trying to create these invisible, beautiful customer solutions. But if your engineers are killing themselves and it's not working. Still not working.

Speaker A: Yeah.

Speaker C: You can sort of wizard of Oz it all you want, but no one's going to work on this shit and it will fail.

Speaker A: Yeah. One of the things I did in my career, kind of early in my career was I put myself on the. I, I got a call. If they got a call.

Speaker C: Yep.

Speaker A: And you should, if you're a product manager on a team that has helped, has a lot of problems, production issues and is struggling, put yourself wake up, get woken up in the middle of the night every time they get woken up and see how painful it is before. See how long it is before you start solving that problem.

Speaker C: Yeah. Multiple times the problem. I have, uh, I have issued pagers to my product managers.

Speaker A: Yeah.

Speaker C: Like if my engineers are up, you're up too. You own it.

Speaker A: And the empathy has to, to. To what Sam said before, like the translator, your empathy has to be able to, you have to use your empathy in that translation in every single direction. That's the job. Right. You don't get to be like, ah, uh, I'm not going to care about business metrics. You have to. I'm, uh, not going to care about this. Uh, you have to. I don't care about the engineering team. You have to. That's the job. If you don't want to care about those things, go do a different job.

Speaker C: Yeah.

Speaker A: You're not.

Speaker C: Get out of your building. Yeah.

Speaker B: And I think that's one of the best disciplines of like being a CEO of a company and seeing it grow. One of the absolute best disciplines is that you are like in, on the ground floor, you're building the 0, the 10 to 1, the 1 to end. But also like, I was there with the engineers. You're there like building, you're there during outages. You know. One of the great things, um, and Leah, you might remember this from the medicast, is like I would literally talk to every customer, every patient for like months actually for a year. Fun fact. I was the 24 hour call center. So like calls at like 3 in the morning, 5 in the morning. Like, I would literally talk to every single person who would call. Right. It gives you that empathy. It helps you understand. And when people are like calling and then they say like, you know, this is uh, the problem I have. And then the next day they call you and they're like, this was the best medical experience I've ever had. I had a sick kid who was throwing up. They couldn't get into the doctor for three days. I worked two jobs, like, thank you. I actually used to have that email printed here on the wall until not long ago. But hearing that right, as like, whatever you are, CEO, an engineer, product manager, it gives you that real understanding and it gives you purpose. Right? And I think there's nothing greater. Like my, my key takeaway in all of this would be for product people is find your purpose, find your why. I know it sounds really cheesy, um, but I genuinely believe it. Like I have a very, you know, altruistic lens on these things. Like, find your why, do it for the right reason and it will show in all the work that you do on the work product. Yeah, M. That's my cheesy take away from all this. But I genuinely believe it. I do mean that. And I think that's one thing that, you know, I think the three of us all shared when we work together in our different, you know, um, organizations. And that's actually kind of hard to find. And so I think when you find those kindred spirits, you want to stick with them and you want to do more work together.

Speaker A: Yeah. Well, and I will say, I'll say this. I think one of the ways that CEOs and product managers are alike, that they don't always tune into, is that they usually really want to do the right thing for the right reason. Yeah, a lot of startups, you know, yeah, sure, there's some, there's some jerks out there who just start companies to make a ton of money, right? But a lot of startups, a lot of founders, a lot of those kind of folks are really in it for a vision. And product managers are the people in your company who will attach to your vision and go with you in a way that you're like, why do you think this is your company? Right? And, and if you can, if you can, if they can get on the same page, it can be really, really beautiful.

Speaker C: So my favorite part of, ah, that interaction, and I've never been a CEO and I don't actually know if I ever want to be a CEO. Um, but as a leader in the tech space, my favorite part of those interactions are when they attack the, the people attached to the mission so deeply that they take it further than you thought, than your expectations. And for me it's super delightful. I can see how that would be like an ego thing. Well, you know, this is my thing and I only wanted it to go to level B. And you're taking it to level F. Um, but for me, it's delightful because it means someone's really grounded themselves in what our problem space is and is thinking broader than I have, which is. It's such a. It's such a cool thing to experience.

Speaker A: Yeah, I love that. All right, lightning round, people.

Speaker B: All right, let's go.

Speaker C: All right.

Speaker B: I don't know if I'm ready for

Speaker A: this, but that's a lightning round, right? Marilyn's gonna play too. Um, okay, first question. It kind of came off of something you said, Sam, so I scratched out a lightning round question, and I'm gonna add this one. What's your favorite product that, you know that failed?

Speaker B: Oh, my gosh. Um. Holy cow. That's a really good question. Okay, so I actually love the first generation Pebble Watch. Um, it was super innovative. It was like light tech, would give you notifications for your texts. It had basic health stuff. I loved it. It looked super futuristic. It looked like an old, like, little Atari type watch.

Speaker A: Yes, I remember that.

Speaker B: I love that thing.

Speaker A: It was great. Marilyn, what's yours?

Speaker C: I don't know. I. I did have this conversation about bad tech recently.

Speaker B: Yeah.

Speaker C: Or what is a bad product? And I actually think that, uh, because it's such a learning journey, there's only products that make people's lives worse. And then. And in my, uh, answer, I was like, well, self checkout at the grocery store is pretty freaking bad because it does nothing but infuriate me.

Speaker A: Right.

Speaker C: And McDonald's and fast food, they're pretty bad because they're just like super unhealthy. But I think, I think products are learning journey. So I don't know if you just fail or you stop iterating.

Speaker A: Right, Right. I, like, I had the Microsoft version. I don't remember what it was called of like the ipod before, like, whatever they're. Yes. I loved that thing. Right.

Speaker B: I loved. Until it froze on an eight hour flight that I was on. I was an hour. And I was like. At that point, I was like, super anti. I was like, I'm gonna be different. I'm not gonna get an ipod. I'm gonna get the Microsoft.

Speaker C: Right.

Speaker B: And then I got it and I returned. I was like, this sucks. It was literally stuck on. So. Yeah. An ipod.

Speaker A: Yeah, exactly. That's my experience too. But I loved that thing when I first got it. And then I was like, oh, uh, this isn't gonna keep up. Right. So, yeah. All right, next question. Is there a leader out in the universe, a known leader out there that you admire?

Speaker B: Um, yes. Actually, there's many leaders that I admire. Um, you know, present company included, of course. Um, I. I've always loved Richard Branson. I've always thought that he's just like, a super down to earth, you know, like, loves his life, you know, finds missions that he's really passionate about. Um, and he stayed out of, like, the spotlight around any sort of, like, you know, weird stuff, which I always admire for somebody who has that power and money. Uh, and I've always thought he'd be a fascinating person to speak with, just because he's had his fingers in so many different business areas.

Speaker C: Totally.

Speaker B: So he's always been on the top of my, like, you know, celebrity dinner list.

Speaker A: Yeah, for sure. What about you, Marilyn? Anybody?

Speaker C: So the people that I would have dinner with. Aliber Dead. Astro Teller is at the top of the list. Like, huge fan. Um, BJ Fogg, obviously. Um, who I'm just a huge fan girl of. And then Stephen Levitt and Stephen Dufner.

Speaker A: Nice.

Speaker C: The guys from Freakonomics.

Speaker A: Oh, okay. Yeah. I love that. I love that. Yeah, I. I, um. For all of his insanity, I really like Mark Cuban. Like, I. On dinner. Right. So. So I like Mark Cuban. I also think Richard Branson is an interesting cat, especially living in the UK now and kind of seeing his fingers and everything, and then he just kind of pulled back and said, carry on, I'll go do this. Right? Like, which I love. Um, and then I think she's not a, uh, not a CEO in the kind of classic sense, but I would love to hang out with Brene Brown and pick her brain about kind of all of the. You know, I love her.

Speaker C: I saw her speak at a slalom event this year and she scared the stuffing out of me.

Speaker A: Oh, yeah. She's terrifying.

Speaker C: Yeah. I was like, I want to sit with her, but she's going to tell me I'm wrong and.

Speaker A: Oh, yeah, she'll tell you're an.

Speaker C: I would still walk in the door and sit down.

Speaker B: Awesome.

Speaker A: Yeah. Yeah, awesome. Ah, well, I think that's all the time we have, but that was fun. And thanks for lightning round. This is something we're doing now when we have guests, which is really fun.

Speaker B: So I love it, Love it. Thank you for having me. This was a blast. It's always so amazing to talk to you both. You're both amazing, amazing, inspiring leaders. Um, and I so privileged to have the opportunity to work with you both. And so thanks for inviting me on. This was great.

Speaker A: Yeah. We'll have you back anytime you want

Speaker B: to talk about something anytime.

Speaker A: We love it. Um, no, I think it's so fun for us to talk to people that we know, um, and hear a little of their story that we don't get to sort of dissect in this way and to do it together and have a good time. So fun. We're so glad.

Speaker B: You guys are the best. Thank you.

Speaker A: Thanks.

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