Making Pigs Fly - Turn early career lessons, empathy, and curiosity into product success.

Speaker A: Hi everyone. Welcome back to Practical Product Management. This is a podcast where we basically uh, talk about how there's lots of theory about product management, how is product management done? And there's lots of great books and, and articles. But really product management is done in context. You know, the company you're in, the team you have, the customer, you have all of that. So today we're interviewing and talking to Ali. We're so excited to have you here. Um, why don't you introduce yourself and then we'll dive in and chat.

Speaker B: Awesome. Thank you for having me. Leah. Marilyn. Um, again, my name is Ali Rakimov. I've uh, been in product management about 13 years. Um, I jumped into product management without knowing there was the word product management. I started my career at a college from Keithville Trenches, Dean of students, business manager, uh, really hard work, really stressed work. So uh, one thing that I observed, observed in my kind of career was um, um, as I was doing my master's in accounting, uh, there's a lot of fraud like little Johnny's lunch money, getting stalling and all that stuff. And so I was like, well there should be a better way to kind of collect parents payments, uh, and uh, have access to this financial data instantly for business managers like me. And so long story short, went to China with my co founder, built uh, a kiosk that accepted cash, checks, cards brought to us, went from Arizona all the way to New Jersey school to school, kind of selling that kiosk, uh, to accountants, school accountants. And so that was my first kind of portrait entrepreneurship and also kind of product management. Because behind the scenes I was mocking everything myself. I was designing myself without knowing what UI UX was, without knowing what product management was, anything about software or payments. I just had a mission to make it easy. So um, through that career, um, kind of once we exited it was bootstrapped the company. Uh, I learned a lot of things about, um, kind of problems and solutions. One of them being I was very confident in myself. Um, being eight years in schools, I thought I knew everything about the problem. But as I went and talked to customers face to face in the middle America, east coast, West Coast, I thought that like problem is different shapes and different sizes and it's not just me. And so it was very like, that kind of gave me like, okay, I need to be, get out of my bubble more often and know that it's like there's some different patterns of the same problem that others are trying to face. So one thing we found out that it's like Hardware is very expensive. So we pivoted into more SaaS and mobile and kind of exited to a strategic. And by that time I learned a lot about payments. I learned about product management. I was like, okay, so I started consulting and that's how I got into product management. So I was, yeah, that's very interesting experience. But um, I mean in that career then, um, made a lot of mistakes. Uh, and so one of the reasons kind of wrote the book is because when I communicated, when I did stuff, I did a lot of mistakes. And it also shows me, kind of goes over the observations, uh, of how to improve yourself doing simple things.

Speaker C: M. I like that you just mentioned your book. So you have a book coming out called Make Pigs Fly, um, which is described as, and I love this description by the way, a no fluff guide for outsiders in tech looking to avoid costly mistakes and build things that actually work. Which is all we really want to do as product managers is like build cool things that actually work and maybe make a few less mistakes because we've all made them. Um, so what, like, what drove you to this book? Um, I think you said a little bit about it, but tell us more about the no fluff guide that will help me from making costly mistakes. Because I'm in.

Speaker B: Yeah, I mean I wrote the book for myself, for old Ali, uh, because um, it took me like years and years and years. Perfect kind of my craft. How to communicate. We always hear about web PMs have to be really amazing influencers, storytellers, communicators. But as uh, an immigrant, I came, I know I can speak the language. There's not a lot of granular details. So like how you do it, right? So that came through observations and uh, like observing very smart people, executives, leaders, how they really communicate a mission objective or goal and how they kind of uh, make sure that, how they cheerlead that mission. Right? And so one example kind of where all of this started is uh, I was in the room with a lot of executives, um, for a private Equity backed company, McKinsey folks come in and they talk about stuff and one of the stuff's like, hey, juice is not worth the squeeze and we have to do it. I'm like, wow, that's amazing. Like it's, it's so. It looks kind of uh, immaterial but for me it was like, wow, this is like just not worth the squeeze. Like, wow, this is very impressive. Like really memorable. And all it's all about like when it comes to communication, retaining information, having that memorable aspect is very important. And so after all this presentation, the only thing that stuck with me was juice is not worth the squeeze. I'm like, wow. And I knew that this project, juice is not worth the squeeze, right? So I was like, I like it. So I kind of took it, adopted it, and I said, I want more of this. Like, I got really hooked into idioms and phrases and so started kind of having a little paper of like my own, like, oh, I'm going to start using those things. So that was it, like, for me, as an immigrant, as somebody who wanted to kind of better myself, really, uh, kind of go up the ladder in my kind of PM career. Uh, I started using it in my emails, in my pitches, in my meetings, and I saw the benefits of it, so. And I wanted to share.

Speaker A: Yeah, I mean, when I moved, I. I just made me think. When I moved to Sweden from, from living in Seattle, I would sometimes use idioms and everybody would just stare at me. The chief architect at Corner, who was about 6 foot 8, he came to see me and he said me and that other guy were the only people in this whole company who know anything about basketball. So every time you use a basketball idiom, it doesn't land. He's like, before you start, don't talk about baseball, don't talk about American football. Nobody knows anything about it. He's like, you can do hockey, you can do soccer. Those are the two options you've got,

Speaker B: right?

Speaker A: Like, there are things that we. That are come very natural to us in terms of terminology we use, depending on where you're from in the country, where you're from in the world, and when you're trying to communicate articulate to some someone, you have to know who your audience is.

Speaker C: Right?

Speaker B: Exactly. Exactly. And so, yeah, knowing your audience is important. And as somebody who was like, I, uh, when I, when I had my startup, I would go and pitch and I was like, why is. Like, why is it not attracting an attention? What am I doing? It's like, I need to slow, uh, kind of speak slower. I need to use certain words. It's a keyword, smarter words or some other words, you know, like more strategic or tactful words. So it comes like through the learning, just making mistakes, and that's fine.

Speaker C: I hate that, though. Yes, yes, yes, yes. I do not have the ability to speak slowly when I am either nervous or super jazzed about something. Like, I will like, I like, kick into the super burner, like, whatever, super fast talking. Because I'm like, passionate about it and I want to, like, I'm excited and I want to draw people in, and I just, ah, uh, gross. All right, I'll read your book. It'll have lots of good tips for me. Um, and I'll try to talk slower.

Speaker A: Do you think so? One question that comes to my mind, Ali, as you're talking, is, do you think that it requires that across time as a product manager, that you learn when to be very direct and when to sell a little softer and how. How. What's your experience with that? Like, when. When are you, like, I'm gonna go straight at the conversation versus kind of sneak up on it a bit. Right. Like, how do you think about that?

Speaker B: I think it all comes again. Like, I use my background in K12 a lot, and that's why I feel that teachers, educators would be amazing PMs, because they deal with stress, they deal with different audiences, and they have to adapt. Like, you have to speak certain way with administrator. You have to speak certain way on a kid's level. On a. With little kid. Right. Uh, and with parents, you have to be slightly different. Right. So adaptability comes to mind. Me, uh, personality. Every. Every one of us are unique. Every one of us have a personality. I am very direct person. And that's why, like, I've, uh, boiled the ocean and burned bridges because of that in the. In the past in some meetings. So it's like, over time, I learned to, like, okay, kind of recognize maybe when not to do it. And that kind of maturity comes again through making mistakes and being yourself, which is fine. And then. Then thinking, okay, if that was. Would have happened again, is it something I would die on the hill again? You know, type of stuff, you know, like, is it worth it? You know, so it's. It's always kind of it. Like, it never stops. Like, I don't think I've ever perfected myself. I still sometimes feel directness is important. Uh, one of the cultures that I, like, I've read about, and I forgot the book name, but the Netflix culture, they're, like, very direct. Like, hey, we care about bottom line, we care about this, we care about customers. Uh, we don't have time to do photos, fluff. So I loved it. And some different cultures that are more like, hey, we need to care about people, we need to care what we say. So it's very different, uh, where you work. Ah. And just, like, for families. Right. So I have four kids, so I try to experiment some of my product management with them. And sometimes it works, sometimes it doesn't. And you Learn.

Speaker C: I've done that too. Leah can tell stories. Uh, my son is now 29 and I can't believe he got that old. And I did not. Um, but I, I used to when he was a teenager, like, it was really rough. Like, raising a teenager sucks. Teenagers are monsters. Um, and if they're not, like, you got a magic one and I don't want to hear about it. But, um, I used to do family standups every single day because otherwise I would never hear what he needed from me. Like, never. Um, and I did. Leah loves to tell this story too. I did put him on a performance improvement plan one time. I like down.

Speaker B: Oh my gosh, Marilyn, you're very intense.

Speaker C: They had a scrum board.

Speaker A: Yeah. That I had a pip. But one of my first memories of Marilyn was she's like, I gotta go home. I gotta. I'm m. Put my kid on a pit. And I was all, I'm sorry, you're gonna do what? Like, I'm sorry. I so wish you could find that.

Speaker C: I was just trying to use the tools that I had at my, like, disposal to, to manage a situation to me that felt unmanageable.

Speaker A: Uh, uh, Ollie, I think one of the things you just said, like, you know, I'm, I'm one of five kids and my parents, while they at the macro level, parent at us the same at the micro level, they did not. Right. Because we needed very different styles. Like, I was the kid who, if they, if my dad said, I'm very disappointed in you, I was devastated. Right. My brother was like, yeah, I don't care. That's cool. I'll be, I'll be disappointing you some more in a minute.

Speaker B: Right?

Speaker A: Like, it was just totally different styles. And I think sometimes as, uh, a product manager, um, you know, and a leader really having. Realizing that when I'm leading others, um, whether it's the product at the product team level or, you know, more strategic, I also have to think about that. I have to think like, every single person I'm leading doesn't need me to be really single threaded leader who only behaves in one way. Right. I think a lot of times as leaders we say things like, this is my leadership style. And we think that that means everyone's going to rally around us and understand it. But really a good leader goes, all right, this one needs a real transaction. This one needs some servant leadership. This one needs some transformative leadership and a coach. Right. Or whatever. And I think it requires us to also be adaptable as leaders. Right. I mean, that's just my thinking. I don't know what you, what you would say to that.

Speaker B: No. 100, 100. And, um, I think one of the stuff that I, right out of college, I was about, I think 22 when I started. Then they hired me as a business manager. And one thing I learned is like, never look, look, I've never read fine print, but there's like, other duties as a sign, remember? And then I was like, oh, our school needs a dean of students. Ali, I think you fit the bill. Hey, our school needs a, uh, you need the PE coach. Like we were trying to find a PE coach. So I did a lot of different things. And as a dean of students, I was like, I was just pushed in that position. Like, hey, here you go now. Now you have to kind of take care of disciplinary actions. You have to talk to parents, all of this stuff. And I'm like, oh, my gosh. Uh, and I was, um. Then I found a person nearby. I was like, trying to get some get up to speed with what does dean of, uh, becoming dean of student means. And he was like, he just said one thing and it just stuck with me. And it's like, there's a Belgian philosopher who said, don't be afraid that kids don't, um, listen to you be afraid that they're watching you. And that was. That's all I needed. So, like that. That's like, yeah, how I held myself, how I communicated, what I did, even little things. Did I throw something in trash? Did I pick up something in the hallway to throw it in trash? Those little things kids watch. And that's kind of what creates kind of contagious stuff within the school ecosystem. And we've saw it firsthand because all of the educators and me would try to kind of lead by role, by, uh, actions.

Speaker A: Yeah.

Speaker B: So for me it's about really being a, uh, like doing little things consistently well. And uh, yeah, it's like for leaders. One, uh, of the other stuff that I always say, like, anybody can be a captain when the sea is calm. Right? Anybody can give themselves a title and do stuff. But what really matters when your startup is failing, when your project is like getting stuff, how do you handle that? Right.

Speaker C: Yeah.

Speaker B: When you get punched in the face, like, do you stand up? How do you, uh, do you give a counter punch? Or do you just stay and cry and stuff? Titles don't matter. That's why when I talk about book, like fluff and stuff, there's a lot of examples where I give of failed startups. Stuff to say, hey, it's normal, it's failure. Rejection is part of life, part of your personal life, professional life. Uh, but just keep going. You know, making mistakes, that's one of the beauties of United States. When I came, like I grew up in the Soviet Union, um, I mean I didn't experience a lot of stuff, but it was like, hey, America is a land where you can make mistakes. And I love it. That was how it explained to me, like, what does democracy, it's like, it's a learn to make mistakes. I'm like, okay, I love it. I'll make mistakes and I'll grow.

Speaker C: I feel like you entered the perfect role for making rapid mistakes and test and learn. So like you, like, you've embraced product management. I think that's really what product management is. Like, how fast can you learn? Um, I did also see uh, Ali in your bio, um, something else that spoke closely to my heart is like, you say that you've scaled enterprise platforms by asking stupid questions. I am the queen of stupid questions. I think, I think that I like, I have no fear of asking stupid questions. Tell me a little bit about what that means to you and how you use that as a tool.

Speaker B: Um, so all of us have been probably right. Like, experience doesn't just appear right? Like one of the stuff that really pissed me off early on in my career is like, oh, it's an entry level job, but we need five years of experience. It's like, how the hell am I getting, getting experience if I don't even have like, like why is it entry level to begin with? Right? And um, uh, when is it? I think I was at T Mobile when I joined T Mobile, so I've already become a product expert by selling my own enterprises, working with other companies. And uh, I didn't have any background in engineering, but um, Enterprise Payments group within T Mobile hired me as a consultant like for fun of their payments. And they're like, they saw within a few months that wow, this is, he's really awesome at what he does. So let him give him some several pods and put him a technical product manager. I was like, I was good at APIs, but wasn't that good, you know. So when they talk about, hey, we have this and there's a group of people go in like architectural sign off meetings or whatever and they're like, and it's like, like, okay, uh, I kind of understand what resilience means, but what does it really mean? I understand what scalability means, but what does it really mean? Like, why are we doing it? So. And it's times like, even I'm a. Like, someone to me goes, like, scared, like, man, like Ali. If you ask this question, you undermine your credibility because you have a title. Like, if you shut up and ask any questions, maybe you'll come across as at least somewhat competent person. So I think everybody goes through that and always say, like, you have to overcome that. Like, you should screw whatever title is. I really care about my craft. I want to understand all the in and outs of what there is, and I don't care how people perceive me. So I think I went through it myself, through the journey is like, I really could care less what other people think of me. I want to ask these questions, understand why are we doing this? And so, but you have to really be a little bit fearless and you have to really love your craft to a point where you're like, you really don't care, uh, how, like, whatever the others say is not going to kind of change your mindset. And so I think that's where I was. Like, I would ask questions because technical product management was net new to me. I didn't know anything about engineering. Like, yeah, I've done it. I work with engineers. I knew to be dangerous, but it wasn't kind of granular level. So in those meetings, that's kind of one example where, like, people, they go in and have imposter synergy. Like, everybody's like, trying to speak less. But if you really love your craft, like, and you really want to know what's going on under the hood, you have to ask questions.

Speaker C: I think that is such a key skill. Um, and it's where I've really seen product managers go from, okay, um, to incredibly, ah, incredibly skilled and really successful. And like, I mean, I'm not gonna lie, like, I care if people think I'm dumb or not, but I care more. I'm more curious than I care. Um, and I also know that sometimes if I ask the question, I'm actually poking at the place where the team doesn't agree. Um, and. And, uh, I just think having that ability to ask the question in the moment is so key. And, and so maybe if I, like, talk to all the product managers that are listening, even though I, you know, in my head, there's no one that ever listens to this. Um, otherwise I would be too scared to have this podcast. Like, if you're not asking the dumb questions, if you're not the person, like, being curious, if you're not finding the people that are willing to teach you, then you're not, you're not, you're not getting all you can out of being a product manager. So that for me is one of the key skills, one of the key unlocks. And I know, Leah, this is something do incredibly well. And you believe in.

Speaker A: Yeah, I mean, I. So when I often I have a pretty hard and fast rule for product managers on my team that they have to understand the basic architecture of their, of what they own.

Speaker C: Yeah.

Speaker A: And uh, especially non technical product managers get really anxious when I tell them that. They're like, what do you mean? And I'm like, I need you to be able to draw the boxes for me of what's, what sits under what you build. And they're like, oh, I don't know if I can. And I'm like, yes, you can go ask those engineers to teach you. And then you come teach me. Right. And the reason I do that is that the reason I was a technical product manager was because I did that. Right. The reason I could hang with really smart engineers who could outshine me intellectually. The, uh, reason I could hang with them was that I asked questions and they love, and they love to draw pictures and explain it to somebody. Right. And then. And one, one of my, one of my tricks. And so I'll show. I think I've shared this before, but I'll share it here. Um, early on, one of my tricks was I would get an engineer to draw. If I had a question, I'd be like, how does this work? I get them to draw it. And then where they would draw the whole thing and then I would erase it to where I understood it. I would just erase the board and be like, I understood to there, can we do it again? And they would start where I understood it and they would move forward. And we would keep doing this over the course of, you know, days or hours or whatever until I was like, awesome, now I understand it. And then I could draw it and that. And uh, the one of the best engineers I ever worked with, hey, Rob, said, can you draw this now? And I was like, I think so. And so I drew it and. And I missed a few pieces. And he's like, not yet. You missed the, uh. And so he went in and filled it in. And then a few days later he would try it again, draw it for me. You know, until, I mean right now, some of the stuff I drew with him, I could draw it right now. If there was a whiteboard right here, I could stand up and I can absolutely Draw out exactly how the Federal Reserve of the United States works in detail. Like how many files go and when they go and how it works. Because I did that back then, which is a really weird skill to have, but it's a skill because I was, we were so meticulous so that I could understand it, so that I could speak to stakeholders about how it was going to work. Yeah, right. And that, that and so I really push product managers and say like go ask them and then ask them to let you draw it for them and then fix it.

Speaker C: Right.

Speaker A: And I think that there's no. You're not gonna, no one dies drawing architecture diagrams on a whiteboard.

Speaker C: Yeah.

Speaker A: You might be embarrassed. Right. But you'll be all right. You're not gonna die from that either.

Speaker B: And just to add to that, you know, sometimes, um, and I've been in those situations. That's why like I want to like if there's PMs are going through rough time with this because it's a culture. It's sometimes you find an engineer who's really open minded and he, he will do it. And there's. Sometimes you'll find engineers who know. And so I've been in places where like you would go and they're like, oh no, no, no. Like they're like this, they treat you as like, like dumb person or they don't want to share. This is like, it's, it's. That happens. You know, this is the reality. And so like what I would suggest is like, okay, don't stop trying. Find another engineer, find somebody else. Go to qa, go to some other like hey, I just like quick question. Can we do a 30 minute sync? I'm just having this questions and. But yeah, I mean reality sometimes. And also this is um, two way street. Sometimes engineers might not share. Right. So and that's uh, it's really kind of hard to understand. And sometimes they don't even have one of the stuff. The reason one of the, in one of my experiences is like they don't have any documentation, they don't have a diagram, they don't have nothing. So sometimes asking questions is like unearthed dirty laundry. And like nobody wants that.

Speaker A: You know, like they wanted had teams that wouldn't draw for. Draw the architecture with me. And when I was like do you not understand it? They would, it was, it would sort of leak out that they didn't exactly know. Right. It was like, okay, then we all, we have to all go figure it out. The other thing that I've done when I'VE had that. I think it's a really good point that you call that out. One of the things I've done when I've had that happen is if it is documented somewhere, I would say, can I have the architecture documents? And they'd be like, oh, yeah, they don't know why I wanted them. They're like, you'll never understand it. And like, okay. And I would take it, and I would literally take the diet, the architecture document, and draw it myself on the whiteboard and like, be copying it on the whiteboard, right? Because along the way I would make connections, right? I'd be like, oh, that's what this thing is. And then if I drew it out enough and understood it, then as I was learning things, I'd be like, oh, I know where that is in the architecture document. Like, it was a. It was a visual in my brain and it's how I learn. I'm not suggesting everyone learns that way, but, um, even when no one would necessarily help me, I would at least take whatever they had and be like, okay, I can figure this out, right? Like, I may not understand it all, but I can figure it out. And so I agree with you 100. Like, just keep asking. Ask someone.

Speaker B: There'll be some amazing M moments, uh, which I had. Like, if he was like, they think you don't know, so they just throw something, which is not true. And they're like, actually, this, this response doesn't have this attribute. And they're like, oh, my gosh, what are you talking about? So I was like, okay, now, now we can take him seriously.

Speaker A: It's true. I mean, I was a ctpo, and I know Marilyn has led engineers as well, and I certainly let engineers be like, lady, you don't know. You're not an engineer. You're not going to be able to hang. And I'd be. And I would always say, try me. You might be right, but try me. Explain it to me. And let's see. And often, not always, but often, I'd be like, yeah, all right, I understand that. Here's. Here's my question. Mhm M. And they'd be like, all right, those are pretty good questions, you know, like, okay, we're gonna give her a little bit of credit. And so I could build a. I could build credibility across time by asking sometimes dumb, sometimes good questions, right? Because they knew at least I was willing to ask.

Speaker C: So I think one of the superpowers you have there, Leah, uh, is something that I also am fond of, and that's how you connect everything to the whole. And so you can get really smart engineers working on their thing, but if it doesn't fit well in the entire architecture, it doesn't really matter. So you can be like a brilliant jerk on your thing and like think everybody else is beneath you, but if you can't play in the ecosystem, you're not really worth anything to the team.

Speaker A: Yeah, yeah, 100%. And so how can you. If I understand this piece and you're off building this piece, how do you help me connect that? Yeah, if you can't, then we have to figure out who can. Who's the connector in there, right?

Speaker C: Yeah.

Speaker A: Makes total sense. Yeah, I love that.

Speaker C: So you also ali talk a lot about, um, translating user empathy into technical systems. Like how. And so like now we've talked about how you understand technical systems and how you ask a lot of dumb questions to get a lot of know how. Let's talk about the user side of that and maybe some tips to help our product management audience translate user empathy into those technical systems. And Leah, I know you've done this a lot too, so I expect you to have some good stories as well.

Speaker B: I mean, it used to be when I got into, uh, PMing, um, and I was like, okay, let me get a certification. And you go to certification about all the Scrum and agile and there's 50 different organizations and you kind of do it and like, here's agile, here's stuff. There's a lot of theory. There's like, Write a PRD. Write a PRD. I was like, to be honest, I hated writing PRDs. I was like, there's so much documentation at like the Soul, uh, as a visual person, like, I liked something more kind of with some pictures, with some stuff because I would retain it faster, I would understand it easier. And so that was kind of boring. And so the only way I learned it is like once I actually went to like, oh, you don't know what stand up is. No amount of text can explain what stand up is or retro is until you go and actually in that environment and start talking about whiteboarding and all this stuff. So like, oh, that's what it is. Okay, I get the premise now. Uh, but, um, uh, for me it was, um, getting out. Like again, I always go back to my kind of startup story is. And it correlated to existing kind of problems where a lot of PMing in the last five years, like everybody wanted to become PM because it pays good, because it's easy to kind of get in relatively. Right? So everybody like from college, like PMing, PMing. And it's all theory, it's all documentation. Like right now, ChatGPT can write PRDs, they can do test cases, all of this stuff. Right? But what really matters is it's not you writing, there's a user. I want to do this so that blah, blah, blah. No, what matters is do you, have you seen a user? Have you observed the user? Have you got of your bubble? And so for me, like, again, I thought I knew all the uh, in and outs of business management because I lived seven years. But despite that, I had, when I went to, kind of drove to like one of the schools in, I think it was Missouri or Tennessee or like, and the superintendent is wearing 50 different hats. It's like, we don't even have a website. Ali, what are you talking about? What payment are you talking about? Like, I can't even do, like, I have to do 50 things. Can you set up a website for us? I was like, oh, you don't even have a website. So those are one of the stuff that comes up where like, there's a lot of intangibles and you need to understand your user who you're selling to, like, why they're buying all this. Then you start creating different user Personas. And so that's, I think what's uh, what, what I, when I, when I say I'm a blue collar product manager is like, I really love spending time with actual users, not like in my office and doing stuff. You really have to kind of put yourself in their shoes and, and kind of go through that. So, uh, that's, that's what I mean by empathy. Empathy is that the word is not just writing it, it's actually knowing all the potential edge cases and kind of observing multiple, kind of maybe m. Have a cadence of visiting once a week or whatever. Um, and seeing what they go through.

Speaker A: Yeah, yeah. So it's so important because I do think I, and especially technical product managers. I've had this conversation with several technical product managers who are like, well, but what I build doesn't directly touch the, the customer. And I'm like, does it not?

Speaker B: Right, Let me explain.

Speaker A: Yeah, think again. Are you sure it doesn't.

Speaker C: Right.

Speaker A: If they, if the button gets pushed and nothing happens, you're the one who built the thing that doesn't happen.

Speaker C: Right.

Speaker A: So, so I just, I think there's so much, what you just said is so important. Like, we have a lot of ideas about who customers are and what they want, but those ideas are worth nothing. If you don't actually talk to them.

Speaker C: Yes.

Speaker A: Right. And, and let me listen. I have been in so many boardrooms and so many investor conversations and pitches and things like that. And a lot of times people are handing out money on a business idea, but they don't have any idea who the actual customer is, what they're going to look like, what they want, who that, you know, and, and it's like that's the job of the product person.

Speaker C: Yeah, right.

Speaker A: I mean, I lose my mind anytime someone says that they have a chief customer officer and I'm all, oh, is that person run product? No. Oh, um, why, why do you have them?

Speaker C: Yeah, right.

Speaker A: Like what do they do?

Speaker C: Usually they leave the call center and they think they're in charge of the customer experience, but it's really only the people that are pissed off enough to call.

Speaker A: Right, exactly, exactly.

Speaker B: And I mean going to your button example, for instance, right. Like I remember my days at Macy's, right. Macy's app. Um, we're leading Macy's app. And you talk about that button and there's a lot of rage scrolls. Like sometimes some iPhone or Android app doesn't. There's no, nothing happens. And we're like, hey, these are like loyalty customers. Somebody wants to like just think about it. And this is something as PMs we did reinforce and I highly recommend everybody reinforcing the same story to engineers and others because it's okay to over communicate. But like, hey, some mom wants to buy a birthday for her daughter and she comes to Mesa, she opens. If she logs in, she goes to all this forgot password nonsense that we go through and she's already pissed, but she wants to buy that skirt or whatever and she goes and it's like by the time she listed 50 items, scrolled and stuff, uh, once she had to check out, once she goes to checkout, it's not available. This is the dumbest thing. Like she would spend so much time. Do you think she's gonna like, what do you think she's feeling? She's gonna just close it and maybe go to like some like brick and mortar store or somewhere else. And that stays with her psychology says like, okay, it's not reliable. Like I can. Yes. So those are the stuff like when we talk about, well, stability or lack of crashes. That's what happens behind the scenes is there's like moms or dads or somebody is trying to kind of buy an item, give, trying to give you your cash. And we're saying, wait a second. So that's Why I would talk to you, like, listen, we have people coming, giving it, trying to give us their cash, and you're telling. You're slapping them in the face and saying, get out of here. I don't need your cash. That's what it is.

Speaker A: Your money's no good.

Speaker C: I think that that really highlights the danger that. That. That companies will face. Why? Why? One of the reasons companies lose product market fit is because they get big enough that they stop listening to their users or, Or. Or really focusing on all the users. And you get this, like, stupid artificial title. I'm sorry for everybody that's got this title called Chief Customer Officer. Chief Experience Officer. And they run only the call center.

Speaker A: Yeah.

Speaker C: And that's a fraction of the customers who are pissed off enough to call, but they may not be the customers that matter. Right. To your point, Ali, you could have so many shitty experiences. Sorry, language. So many shitty experiences that actually have a bigger impact on your customer user base, your loyal user base, the ones you want to keep. Um, and you don't know anything about it because no one from a product perspective is looking at what's happening holistically and. Or looking for new opportunities. You're just trying to. Like, you're taking a patient that's on the ER table and you're putting band aids over small cuts and they've got a million. Yeah, it's like, it's.

Speaker A: It.

Speaker C: It infuriates me that people don't pause long enough to really think about, like, what are all the challenges, especially with a big enterprise, especially with a big, complex product. What are all the challenges we're trying to solve? What are the ones that matter? And go after those freaking. First, stabilize the patient. Stop putting Band aids on cuts that don't freaking matter.

Speaker B: Yeah, root cause. Address the root cause.

Speaker A: Yeah.

Speaker C: No. Kills me.

Speaker A: I mean, the example that I often use. And I mean, people get mad when I do this, but the example I often use is, like, when anybody wants to get flashy about a payments experience, I say, do you know why Amazon doesn't change their payments experience? Because it's invisible.

Speaker C: And it works. Works.

Speaker A: And if I. And you know what, you know what I can do if I'm in Sweden or Germany or Spain or France, if I want to buy on Amazon, I can go through the entire checkout process without having to translate anything on the page. Um, they have not changed a damn thing. Right. And I. And my credit cards have never been lost. Right? They've never. They've never been. They haven't been Hacked into. So there is a sense of trust. So when I worked at Klarna and they wanted to get fancy fancy, I was like, listen, this is the set of fields. Put them in this order, do it like this. Don't change anything.

Speaker C: Yeah.

Speaker A: And when they tried to test it with, with customers, customers are like, I don't know what's going to happen. I was like, who wants to not know what's going to happen when they enter a credit card? Like, I'm okay with some surprises in some parts of my life, but not when I enter a credit card. Right. And so I sometimes think we get so caught up in being fancy and thinking we know what customers want. But what customers want is when I give you my, my financial information, I want to trust that you know what to do with it. So it needs to look like every other time I've put that information into the universe.

Speaker C: Exactly right.

Speaker A: Hackers don't go make up. They mock up those exact same experiences so that people will put their information in. Right. These guys aren't dumb. They get it better than we do as product people people. So I mean, that's the. Sorry, I just, that's my example I give. A lot of times is like, you, uh, know.

Speaker B: But that's what happens in a culture where all like when you're tasked with, hey, let's improve 0.3% like somewhere else. And you like go and pick a little features, feature, sub feature. And you're like, okay, we're gonna do a b testing. I'm m. Like, why are you wasting your time on this? Like when, when you, when people cannot even make a payment. So like we had this. People had to go to actually Macy's store to give their cash and checks to make a payment on their card. And I'm like, this is dumb. Um, this is the biggest problem. Why are we talking about some other stuff? Like this is like, this is our customers, loyal customers who cannot make payments on their Amex. Like, why, why is this not a priority?

Speaker C: And so, I mean, it's probably, I think that some of those things are endemic and companies not thinking about the experience from end to end. Right. Because I'm sure there's someone who's like, well, if we make them come in to pay their card, they'll buy something when really, like, do you really care where they buy something? Maybe you just sort of offer shopping recommendations in your app where they're making a payment. Like, don't like, think about who you're trying to serve. I think this, this comes Back to the three things Leah and I always, always talk about from a product management perspective. You have to know three things. You have to absolutely know your customer. Um, you have to understand the business. Um, and you have to understand what's technically possible. Now those three things are going to play with each other, right? The customer might want really easy payments, but the business needs that recurring revenue. So you need to bring them back again. Um, but you can't make it so difficult. That's too big of a hassle to make their payment. Right. There is a balance there. And there will be a moment when you're going to decay a business result to bias on behalf of the customer. And you have to know what those choices are going to be in advance. Uh, because team A in a corner who's just doing like one part of the experience is going to really care about that customer experience, but they're not going to think about the overall business problem. Um, I think that it's really. A lot of these things are super interesting and complex. Um, and as a product manager, you're obligated to think about it. You're obligated. You have to. You have to understand the business context in totality.

Speaker B: Um, hopefully you're backed by your leadership because that's one of the stuff that happens. Like, which I hate. PMs are CEOs. Like, no, you're not. You're. A lot of times, like, we see it's order takers, right? So, and that's like. So. But I mean, you can push back. Like, if you really care again, you can lose your job. But, but I mean, that's, that's the reality is like, you have to be. And that's like kind of communication comes in. Like, how tactful, how strategically can you push and influence others to think certain way, right? So that's kind of where the communication comes in. And, um, sometimes you can be successful. Um, sometimes you might not be.

Speaker A: I don't want to be. I don't want Ems to think that they're the CEO of their product. And I don't want them to think that they're a waitress. No, I'm like, they're, uh, somewhere in the middle is the job, right? Neither. The job is the job.

Speaker C: And it happens in context. I think it goes back to our whole premise.

Speaker A: Yeah, absolutely. Absolutely. No, I think that makes total sense. Do so. Shifting subjects just a little bit and then we'll, we'll lightning round it up in a minute. I'm curious, what do you think? Um, you know, you've said it a little bit. But I'm curious, like, when you think about coming into, um, this work, into product management as an immigrant, what do you think some of the biggest lessons are that you've. That you've learned along the way or that you've maybe brought in because of that?

Speaker B: So, I mean, we talk about certain kind of negative scenarios and stuff, but overall, the. The thing is, the tech was like. I mean, with different companies, it's very beautiful to work with a lot of different, diverse folks, different time zones, different kind of backgrounds. And so it was really beautiful. Like, I had a, like, really beautiful journey. Uh, very blessed, uh, to have those kind of contacts to learn from a lot of smart people. Like, I look myself as a bee, like, trying different kind of flowers, you know, like, oh, this is it. And more different flowers. You try, like, the honey becomes even better. And honey for me is that intellectual growth. And so, uh, overall, it was amazing. Journey challenges is like, uh, initially I looked at challenges as a problem and couldn't sleep. But then it's like, listen, Ali, like, one of the stuff that I learned, like, early on, and it's like, we stress a lot about stuff that really doesn't matter. The most important thing, uh, is my family and my health. That's number one thing, like, job and everything is good. But, like, for me, once, I kind of understood that, once it was cemented in my brain, like, it doesn't matter what I did, it's like, okay, so nobody in 20 years gonna care about your architectural design and this API, that API, that button, this button, that app, whatever. Like, you need to realize that. And of course, uh, you have to be a good human being. And that's like, if you're a good human being, uh, it's contagious. So told other PMs who are going through, like, some cultural issues where there's like, very bad stuff. Continue being yourself, be a good person, uh, and you'll see slowly, like, you. You will have an impact. But for me, like, the biggest thing that I learned was, like, um, it's good and bad. I'll talk about good. And is that there's a lot of amazing people, uh, who can help you. You just need to ask. You need to ask, you need to be humble. If you put others before yourself, uh, that will kind of recalibrate certain psychologies. Because it's. Sometimes you go to a culture, you don't know the background, and it's been cutthroat. Like, engineers went through so many times where they were uh, the scapegoat that they just hate PMs. Right? So you have to understand that, you know, like, the reason that they're done doing is not because of you personally, but there's background, there's history to it. So. And I learned it through, like, through time. I was like. I didn't know. I was, like, clueless. And I was like, why they're not sharing this? Why are they doing this? And so instead of just pointing fingers, you say, hey, can we spend 30 minutes? Like, hey, can I take you to lunch? Just if you do, like, those basic humanly stuff was like, building relationships, like Dale Carnegie talks in his book. It's like, I think you'll be fine.

Speaker A: Yeah, no, it's a really good point. I really appreciate that. I do think that, you know, I. If. If the job, if you're a product manager. So if you're listening to this and you're a product manager and the job has beat your humanity out of you, go do something else. Like, if the toxicity, if the job, if it's beat out your ability to be human, to be kind, to be, to have fun, go do something else for a while. You can always come back, but go do something else. It's not worth it, right? This job is. It should be fun, it should be challenging, it should be hard some days, but it should not beat us down to not ourselves.

Speaker C: Right?

Speaker A: So, I mean, that's. That's. I 100% agree with that and that.

Speaker B: And yeah, for those PMs who are going through this right now, like, just know that there's some other. Like, there's some other kind of greener grass, definitely. And I went through it. You probably went through it. So sooner or later, the stars will align, you'll find that place and you will love it, and you'll have amazing experience. But wherever you are right now doesn't mean that, like, that's the only thing.

Speaker A: And, yeah, uh, it's not the end exactly. No.

Speaker B: True.

Speaker A: Cool. Shall we. Shall we do a lightning round?

Speaker C: Let's do it.

Speaker B: Yeah.

Speaker A: All right. All right, so let's start with this one. What, Ollie? What's the first product you remember loving? Like, um, what product did you love first?

Speaker B: Probably, like, as an immigrant, like, first thing is, like, Craigslist. It has to be Craigslist. Like, where do I find my M. Car? Where do I buy this textbook cheaper? You know, all those things.

Speaker A: Yeah, no, true. What about you, Marilyn?

Speaker C: I mean, I think that there's. There, uh, has been some really cool innovations around Global Entry and like, E Passports, anything that can get me out of that endless line to go through passport security, like, I'm a huge fan of.

Speaker A: Yeah. Yeah, for sure.

Speaker C: How about you?

Speaker A: Um, yeah, I was trying to think, like, I think I've said it before. I think the first product I ever like, one of the early products that. When I think about products that I loved, I really loved Microsoft's version of the, um, of the, uh, I. What was it called?

Speaker C: The Palm Pilot?

Speaker A: No.

Speaker C: The BlackBerry? No.

Speaker A: So it was the. It. It had the little. It was the little tiny square that held all your music right back before.

Speaker C: Yes.

Speaker A: And I loved that, uh, it was really easy to use. The user interface was super simple. It was. And I was like. And I wasn't an Apple user yet. So for me, it was like, this is amazing. And I. But I remember just being like, I can have all these. All this music playing in my office at any time. It's amazing. So. But yeah, that was one of the first things I remember just loving as an adult, for sure. So. Very cool. Um, so do you. Have you ever. Do you have a feature that you regret shipping?

Speaker B: Oh, um, I think I'm gonna take a long time to think about it.

Speaker A: I know that's a tough one, right?

Speaker B: But I'll go back. I'll go back to my startup. I think that's where. In my startup. Startup, uh, with a lot of features. Um, one of the biggest mistakes that I've made, again, for anybody who wants to do a startup and who's desperate for customers, one big advice that I give them, uh, just because customers tell you, hey, if you build it, we will kind of sign up. Don't do it. Get a customer for what you have. Like, if you have value, like, they will sign you up. Uh, and only do stuff for your existing customers because they're actually paying customers. So I went to the drawers, like, hey, can you build this other map? Stuff like that had nothing to do with kiosk and payments. And like, we did it, and they still didn't sign up. So I was like, yes, there was a lot of stuff that I tried to appease customers, prospective customers. Let's put it in that bucket. Uh, and it always failed.

Speaker A: Yeah, yeah.

Speaker C: Uh, like, fortunately. So the answer is always yes, fortunately. A lot of my biggest learnings. Maybe not. Maybe not. Regrets have been under controlled testing. So rollback is an option. Um, but I think that most of the things that did not work spectacularly. Um, and one of the reasons I'm so biased against letting anybody from inside the company suggest too many features is most of the things that didn't work. Um, where were passion projects by people inside a company instead of looking at real user behavior? So I, I think those are the ones that usually underperform.

Speaker A: Yeah.

Speaker C: How about you, Leah?

Speaker A: Same. I mean, I was thinking the same thing when I worked in a. I worked at a healthcare startup, uh, that was incubated inside of a giant hospital system. And we let the neurologists tell us what to build more than we should have. Right. Because they were the sponsors and they often, uh. So they would say, well, I'm a neurologist. And what I always wanted to say was, was, yeah, and you're not an engineer.

Speaker C: You don't.

Speaker A: You don't know about. You want to write some code, right? Come on over. Right? But. But we did, uh, we made some mistakes. We made. We made some bad decisions in terms of what we launched and what we did because we let them bully us a bit. And we didn't have. I. I didn't at the time. I. I should have backed them down. And I look back sometimes and I'm like, why didn't I push back? Right? Like, I could have backed. I could have backed them down a bit. And now that's often why I don't back down. And when my instinct is saying, don't do this, I'm like, I'm going to fight you now so I don't have to fight you later.

Speaker C: My answer is always like, let's test that.

Speaker A: Let's give it a shot, see what we learned. All right, last question for you, Ali. If you were going to, um, take one lesson from raising your kids that you would apply to product management, what would it be?

Speaker B: Listen more.

Speaker A: Yeah, that's a big one.

Speaker B: Yeah, I think, uh, I tell them, like, hey, God gave us one mouth and two ears for a reason. So I tried to. That's one of the, uh, things that I'm working on myself, so I'm not good at it. But, like, yeah, it's probably listen more. So they might be telling you the problem and everything. And it's just. You have to. You have to listen.

Speaker A: Yeah, it's a good. It's a good one.

Speaker C: I am stealing that. That's your answer exactly right.

Speaker A: Yeah. I love that.

Speaker C: I got.

Speaker A: The one thing that comes to my mind is similar, I think, you know, I always think that as a parent, I don't have kids, but I helped raise my nephews. But I always think that there doesn't come a day when your kid is the one that pursues you. You're always the parent in pursuit of the relationship with your child. Right. And I think there isn't a day where your customers are going to pursue you. You're always chasing what they need and want. Right. And so you have to always be the one who cares about that relationship, because if they stop caring about it, you're not going to have a relationship. So if you expect them to chase you. Right. And so with customers, like, they'll go somewhere else if you don't chase the relationship. Right. And I think I feel the same way about kids. Like, if you take your eyes off of them and say, uh, I'm not going to pursue them, they'll go somewhere else. They'll find someone else.

Speaker C: Right.

Speaker B: To something else will fill that vacuum. Yeah.

Speaker A: Yeah. So that's the other one, I would say. Well, this is such a fun conversation.

Speaker B: Yeah, I loved it. Thank you, Leah. Thank you, Marilyn.

Speaker C: Thank you.

Speaker A: Yeah, thanks for coming and talking to us and for sharing kind of what's going on with you for sharing your book. Um, we'll post your book and the information in our resources on this, this episode so everybody can look on the website and find it. We'll also mention it when we, when we post this so everybody can make sure they can find you and find the book.

Speaker B: I'm super excited, and I don't know if I connected with you on LinkedIn. Are you on LinkedIn? Do you have it there?

Speaker A: We're on LinkedIn, yeah. And we'll post this out there and everybody can, uh, get to. Get to know you and find you that way.

Speaker B: Thank you.

Speaker A: Thank you so much for doing this.

Speaker B: Thank you so much, Leah. Thank you, Marilyn.

Speaker A: We'll see everybody else next time. Sam.