Practical Product Management · 2025-07-30 · 51 min
Key moments - from our scoring
Substance score
41 / 100
Five dimensions, 20 points each
Greg, SVP of Product Management at Sheer ID and host of the Powerful Introvert podcast, argues that great product leadership begins with listening - and that organizational structures often silence the voices most likely to offer critical insight. Drawing on research from Susan Cain's Quiet and his own experience scaling three growth-stage companies to 70M+ ARR (including Jive Software's IPO), Greg identifies a systemic problem: traditional brainstorming, open-office dynamics, and meeting culture are engineered to favor extroverts, causing companies to lose the reflective thinking and self-critical rigor introverts bring. He distinguishes between product-market fit (where pull from customers makes everything feel easy) and the harder work of scaling, emphasizing that humility matters more than formula-replication. For product leaders, designers, and engineers - many of whom mask their natural introversion or neurodiversity to fit in - the episode offers practical frameworks: asynchronous idea submission before meetings, deliberate space for quieter voices, and understanding that inclusive contribution structures yield better decisions. Greg's thesis challenges the assumption that visibility equals influence, showing instead how the most impactful individual contributors often succeed by working differently, not harder.
Academic studies show that giving people time to think through ideas in advance before bringing them to a group discussion yields better results than traditional in-room brainstorming, which is calibrated to silence introverts who process internally rather than thinking on their feet.
Leaders need to deliberately ask quieter people in the room for their input and create asynchronous collaboration structures where ideas can be submitted before meetings, rather than relying on real-time discussion that naturally favors extroverts.
True product-market fit shows pull from the market - orders come in and customers are willing to work with you despite product problems, almost in spite of all the issues that exist.
Introverts spend more time in reflection and self-analysis, which naturally leads to more self-criticism, so mentors and leaders should provide positive feedback to balance their tendency toward being harder on themselves.
Individual contributors often have more influence than many titled leaders because they've found ways to voice ideas effectively and communicate their thinking, regardless of whether they hold a formal management position.
Our reviewer’s read on each dimension, with quotes from the episode.
A handful of usable ideas (brainstorming is ineffective vs. pre-thinking, customer success as the driver of enterprise maturity, signs of product-market fit) are buried in extensive personal anecdote and repetitive introvert/extrovert chatter that a smart operator would already know.
giving people the chance in advance to think of their ideas and then bring them in
typically that's the function in the organization which is driving maturity throughout the organization
Much of the framing is lifted directly from Susan Cain's 'Quiet' - the Alex Osborne brainstorming story and the introverted-leaders-in-plain-sight (Obama, Gandhi, Eleanor Roosevelt) examples are recycled verbatim from that book rather than fresh thinking.
this is also like an environment that is perfectly calibrated to uh, tune out all of your introverts
We forget about, even forget about people like Barack Obama
Greg is a genuine practitioner - SVP of Product at SheerID with 18 years across three growth-stage startups including a Jive Software IPO - but the transcript leans on his introversion-coaching side-project more than his operating experience.
The first one went IPO jive software
I'm currently a SVP of uh, product management at Sheer ID
A few concrete anchors (Jive IPO, SheerID, 30-300 person / 70M ARR ranges, Amazon Chime vs Zoom, Teresa Torres) exist, but claims about product-market fit, enterprise negotiations, and scaling remain largely abstract with no real data, timelines, or dollar figures.
up to 300 people, you know, up to 70 million ARR
Amazon should have bought Zoom or one of those companies instead. They tried to build their own interface called Chime
The hosts ask some reasonable questions and one good challenge about staying humble, but the episode is mostly a warm, mutually-affirming ramble with hosts inserting long personal stories rather than pushing back or probing claims.
how do you stay humble in the face of that?
How should product managers help their customer success people understand the balance
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of Practical Product Management, Leah and Marilyn are joined by Greg Weinger - SVP of Product at SheerID and founder of the Powerful Introvert podcast and newsletter. Greg shares his journey from engineer to product leader, revealing how introversion and deep self-reflection became the unexpected keys to his leadership success. Together, the trio explores what it takes to scale product in growth-stage startups, the push-pull between customer success and product strategy, and how to work with enterprise clients without losing your soul (or your roadmap). They also dive into why companies often overlook quiet leadership and how to build inclusive teams that surface better ideas. Key Takeaways 1.Introverts can be exceptional leaders - but the workplace must create space for them. Leaders don’t have to be loud. Influence often grows from reflection, calm, and clarity. 2. Customer success and product must partner - not compete - for priority. When enterprise customers make asks, product teams must balance strategic focus with relationship value. 3. Scaling a product doesn’t mean scaling chaos.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Welcome to Practical Product Management. This is a podcast where we talk about all things practical. Uh, theory's great, books are great, frameworks are great, you should read them all. I'm sure the authors of all of those things will be really happy to have your money. We talk about how product management is done in context and needs to be done practically. And today we have great Greg who's going to talk to us about some really interesting things. Uh, we're super excited to meet you and to chat with you. So Greg, I'll let you introduce yourself and then we'll dive in.
Speaker B: Yeah, really glad to be here. A little bit about myself. I kind of grew up in the dawn of the World Wide Web. Cracked open the first web server on one of my first jobs and really uh, fell into tech because I was, I was writing HTML. I initially I got into coding and on the engineering side I wrote Java for a number of years. Really enjoyed it, um, but found I continually was questioning why are we building this thing? This is so stupid. Typical engineer. I could do better at this. And so then I started like moving into, it's like asking about product. I got a product role and found it was like, oh, it's not as simple as all that. There aren't obvious answers. Um, but I found I really loved product management, got into leadership. I've really focused in growth stage startups. So in the past, uh, 18 years I've been in three. I've been really fortunate to have three, uh, awesome companies I worked with. The first one went IPO jive software. I've uh, you know, generally working in companies. I start when they're small, like 30 people, 30 to 70 people, up to 300 people, you know, up to 70 million ARR. I'm currently a SVP of uh, product management at Sheer ID. And here I am, um, I'm ah, moving into product leadership and I can tell you guys a little bit more about my journey. But I wanted to leave it there.
Speaker C: I love it. I love, um, there's so many directions to take this conversation. I'm really excited to meet you and have you join our little tribe here. I feel like you fit right in.
Speaker A: Great.
Speaker C: Um, the first question I want to ask you though is you actually host a, uh, podcast and a newsletter called Powerful Introvert. Um, and I know that this is sort of something that's come up before for us and something that we hear from the people that we work with is, is, you know, a lot of people in technical jobs are either extroverted introverts, or introverted extroverts. And there's a level of exhaustion that comes with putting yourself out there every single day. Um, and so why don't you tell us a little bit more about what, what your newsletter and podcast are, um, and why, like what led you to start this?
Speaker B: Yeah, absolutely. As you may have, you know, may have guessed, you know, starting out on the engineering side, I am an introvert and I was just continually kind of baffled. Uh, I'm super achievement oriented. I could always study my way through anything, did well in school and I think like a lot of engineers, like, oh, I'll just solve brute force my way through this problem. But, you know, things weren't that easy. So over my career I've had to develop a lot of skills and a lot of trial by fire because, um, a lot of my natural personality, I didn't come out of the barrel of the cannon or shotgun, whatever it is, um, presenting as a leader. So I really had to acquire a lot of those skills. And in particular I rose to middle management, director, VP on an executive team, just encountering levels, increasing levels of, uh, chaos, ambiguity, confrontation, um, that, you know, just at each stage it kind of would push me beyond what I could handle. And so I just had to do personal work and figure out how to manage my emotions and calm myself into situations until I could rely on my natural strengths, which as I come to find out as introverts, it's you, you know, it's thinking on your own, uh, having the time to think through a problem and um, you know, a little space there which isn't always available when you're in the chaos of a company. So kind of at that, coming around the end of it, I really felt like I wanted to give back and like, oh, I wish I had someone who could give me some of this information when my 30 year old self was kind of embarking on the leadership journey. And part of what I discovered is that there is a tremendous amount of information out there. Uh, I first really came up, uh, across it, uh, a book by Susan Cain. Quiet. She has an amazing TED Talk. I think a lot of people have seen it. But even then it didn't really sink in until I really read that book and absorbed that information. And so my mission with this podcast and newsletter is to try to amplify the message and really get it out there. I want more people to hear this. And you know, ultimately I would love to help change the culture a little bit because we have so many biases against introversion. You know, introverted leaders. Um, a lot of the way we run our meetings and the way we structure our business processes aren't favoring, you know, introverts. And so we talk about introverted to extroverts, vice versa. Um, know, really, uh, the statistics are up to 50% of the population are introverts. We, a lot of us kind of in the middle, really find ways to manage it and, you know, or we deny it or cover it. And so that's where I find, I keep finding people who say, like, I'm an extrovert. But I find more and more I like to have my quiet time. I need my time to recharge. Well, that's your introverted side. And I personally think that the, you know, the introverted extroverts are the most interesting. They spend time in reflection, they create room for creativity, that sort of thing. Um, so anyway, that's, uh, in a nutshell, why I created this podcast and get to talk to amazing people like yourselves.
Speaker C: I mean, I love it. I think this is, ah, I mean, this is something that really speaks to my heart. And I know Leah and I have talked a lot about diversity in teams. Um, and really when you talk about the business processes not supporting, um, I would just say, like, diversity in general, um, I think that's something that I've sort of tested a lot with a lot of my teams. How do I allow for space? How do I introduce an idea, allow space for thought, space and time for thought. Other than like just getting everybody in a room, letting only two or three people debate the idea, and then making a decision, moving on. You're not making an informed decision. You're not, you're not actually serving, um, your customer and you're not leveraging the skills of your people. You're not, you're not bringing the whole team to a problem when you just use typical processes. So how do you use, you know, asynchronous collaboration tools? And I don't know, I like, um, now I'm going to go and, like, listen to all of your podcasts and then I'm gonna, I'm gonna be that extrovert that like, sends you emails. It makes you crazy. There's an exclamation point on the end of my name for a reason, I think.
Speaker A: Um, it's true. It's true.
Speaker C: I am the chaos monkey.
Speaker B: Yeah, yeah, and I appreciate that. And there's, um, one of the things that you'll, you'll see in some of the work. I wrote an article. It's actually on the on the podcast about, uh, brainstorming, um, like brainstorming is broken. Why are we still doing it? Um, ah, after all these years. And this is actually a story from the quiet book. Um, there was an ad man, Alex Osborne, who's like Don Draper, um, in the 40s and 50s, uh, like this king of Madison Avenue. And he actually popularized, he came up with, is credited with coming up with brainstorming and popularizing it. Um, and the idea is just, he has a book where he describes it. You know, the wilder the ideas, the better. You know, you get everybody in a room and you know, you can kind of imagine the madman scene. Um, but um, that has really stuck. I mean it's a great story, um, and it is fun in certain environments, but this is also like an environment that is perfectly calibrated to uh, tune out all of your introverts because they can't break in. They're sitting there, they're thinking internally and processing. Um, and it turns out, you know, just academic studies back it up. This doesn't work. Um, but what does work is giving people the chance in advance to think of their ideas and then bring them in. It's a little bit more of a triage and a building upon ideas when you get everybody in together. But that's the recommended path for getting the best ideas out of everybody.
Speaker A: Yeah, I love that. Do you think that by just following on to what you just said, do you think that there is, um, because. And again, I'm generalizing. Introverts are more self reflective and do spend more sort of quiet time thinking about like, how is this going? What's going on? How did it, you know. Do you think that introverts are harder on themselves?
Speaker C: Mhm.
Speaker B: I haven't lived in inside the mind of an extrovert. I can certainly attest that I have. And I do, I do find that that's, that's true. I think spending time in reflection, um, does lead to more self criticism. Uh, and I, I mentor a lot of introverts in my profession and so I'm, I'm always trying to, you know, build them up and give them a lot of positive feedback because they, they really do. I mean they like direction on what they could do better. But you know, a lot of times they are harder on themselves.
Speaker A: Yeah, yeah, yeah. I mean, I think that what's interesting about that is that I think, you know, I am, um, Marilyn has known me a long time. I am a very natural introvert. I want lots of alone time, lots of quiet, lots of I'M going home now. Leave me alone. I, I am the queen of disappearing from parties. Right in the middle of the party and people are texting me like, where'd you go? And I'm like, oh, I'm home. I'm in my pajamas. I'm already, I'm already going to bed. See you later. Right. Like I'm that person. Um, but I can, I can extrovert as a, as a verb. Right? Like it is a thing. I can. Right? Um, um. And people are then like stunned when they find out I'm an introvert, you know, But I also wonder if it doesn't, you know, I think in this, I think Susan Cain talks about this a lot in quiet. Like the, the thing we miss out on when we don't make space for introverted leaders, introverted team members, is the brilliance that can come forward because of that, that self reflection. The person who's like, yeah, I hear what you're all saying, but I don't think it's going to work. Often in my experience has come on my team from the person who has the least to say most of the time. But when they say that, we all go, what? It's not going to work. Right?
Speaker B: What do you mean?
Speaker C: Yeah.
Speaker A: Why? Right. And so they, when they speak, everybody's like, oh. So I, I, uh, you know, I think, I wonder how often we are missing opportunity, um, because we're not m. You know, giving that space, building that space in as leaders for people to, to really lean into their ideas, their thoughts, what they're concerned about.
Speaker B: I, uh, think it's pervasive. I think it's per. Even I will do this, you know, because I'm like, I'm, um, the extrovert. I'm the extroverted introvert. You know, so in the land of introverts, I'm. I'm the extrovert. And you know, I'm. And especially as a leader, you know, it's in your position. And so I have to remember to make time to ask people around the room who are, who are quieter. And it's, you know, it's a deliberate. It's, you know, I think there's something that's natural. I think some of it is culturally ingrained in order. It's just what happens as you have a leadership position. But it's so important. And then you, you know, it was a, uh, wake up call for me when I started moving into product and spending more time in marketing and especially a lot of more time in sales and, and you really have to dial up the energy. You really have to amplify the version of your personality that comes out to just to be heard and just to be on their wavelength. Cause they're on this. This other, you know, wavelength.
Speaker C: Um.
Speaker A: Um.
Speaker B: So. So, yeah, I. I think you're right. I think that we. We do miss out on that. Um, but it. You. You clearly are. You've been listening.
Speaker A: Trying.
Speaker C: Trying. Yeah. Ah. I think I'm on the other end of that spectrum, Leah. I feel like we're two sides of the same coin, because I'm the. I'm. I'm an extrovert. Um, I don't know if you guys noticed or not, but I'm an extrovert. But I also. There are times when I want to go crawl into a hole or I don't want to walk into a room where I don't know anybody. Like, it takes that moment of, like, all right, I gotta do this, and I gotta pretend like I'm. I'm already friends with people. Um, but, yeah. Um. Yeah, so it's really. It's really interesting, and I think there should probably be more dialogue, actually. I feel like the three of us should get together and do, like, a Tools for Teams episode, um, on how to, like, get the best ideas out of team. I think that would be sort of a fun conversation. Sorry, Leah, I interrupted. You. Go ahead.
Speaker A: No, no, no, it's okay. It's okay. You know, one thing as we're talking about. I think that's a really good point, though, Marilyn. I think there is, you know, there is how. So there's two things. Two thoughts come to my mind. One is that so many of the folks we're working with as product leaders, um, with engineers, product managers, designers, etcetera, so many of them are. Are going to be somewhere in this space. And quite frankly, many of them are also going to be somewhere on the spectrum. And so masking is a huge part of what people do. In order to feel like, okay, I can show up, I can fit in, I can try, and I know I do it. Like, uh, there's an element of, like, okay, to your point, okay, I'm gonna go speak on this panel. I've got to walk in this room. I'm here, right? It's a totally different person who shows up than the person who's on the. If you walk, if you have to go into those things and I'm on the elevator with you, you wouldn't know that I was going to be the speaker, right? Because I'm in The elevator, like, don't talk to me. Right. And then I walk into the room like, I'm ready to be talked to. Right. It's like jazz hands. Right. You get 90 minutes before I disappear and turn into a pumpkin. Right. So I think that there's something to be said for our teams. Giving. Giving space for, hey, we see you, we hear you, we understand you. Um, because probably a lot of the people that have been on my teams over the years think that I am an extrovert and that that's how I've been successful, and they couldn't do what I'm doing. And I'm all welcome. You know, I'm a quiet. I was a quiet kid who had to teach myself to talk. Right. Openly in front of people. Right. And so I wonder. There's an element of this that I think is very much not just the introversion extroversion spectrum, but also just all of that comes into the kinds of things we build and the kinds of people. The people build software, as Marilyn often says.
Speaker C: Right.
Speaker A: And so how do we make space on our teams for that? Super, super important.
Speaker B: Yeah, yeah. And it's. It's my work. I'm focusing on leaders or people who realize, oh, well, I want to have more influence, but. But it's not necessarily leader and title. I mean, it's really that drive. I want to have more influence, which I think a lot of people who don't want to have the title, they just really love what they're doing, but they. They want to have more influence. And, um, what I've just. In my career, I'm sure you've seen the same thing. People who are individual contributors have tremendous influence, more influence than a lot of titled people. And it's just because they've found the way to. To really voice these things, communicate their ideas.
Speaker A: Yeah.
Speaker C: I've also found some of the most impactful leaders are people who don't want to lead. People. Like, I've, um, had people. I know that there's several people that are, like, top of mind for me right now that are just such incredible team leaders. And they never wanted the role. When I suggested it, they were horrified. Like, they did it for a while and then took a step back and then realized, oh, well, that was actually pretty good. And I built a great team and went back to it, like, so they had this sort of, like, I don't want it. I'm out of it. I'm. But you're right, I'm a good team leader. I do build a good team. So I'm coming back to it. Um, and I don't think we make enough space or leave enough support for the people, uh, for people that are less extroverted and do make friends, fantastic leaders and are inclusive and build these teams that just, that just are so together and so cohesive. So, yeah, we're missing an opportunity as business leaders.
Speaker B: Yeah. And I like the word you said, inclusive. And one of the things I realized when I started talking to people on my podcast and including extroverts was that it's not just about this. It's really about diversity of opinion. There may be multiple reasons why. There are many reasons why someone might not feel comfortable speaking in a situation and could be, um, gender, uh, race, ah, other dynamics or. You mean even to your point. Um, you know, people on the spectrum. Um, and creating that structure for inclusive contribution is really how you're going to get the best out of everybody and the best results for your company.
Speaker A: Yeah, 100%. I mean, I was definitely what Marilyn just described. Uh, even when we were at Amazon, I was like, I don't want to manage people. What are you talking about? I went. I was the ic high flying, IC track all the time. And then when I managed, people made me. People made me manage people. And I was like, oh, yeah, actually I'm not so terrible at this after all.
Speaker B: Right.
Speaker A: I guess. And then, then I fell in love with it. But it took a long time for me to make that mental shift into, like, you want me to be in charge of people's holidays and stuff like that. That's how I felt about it. Like it was an admin task instead of. So like management, not leadership. Right. Was a different. That was a different, uh, a different set of skills for m. Me.
Speaker B: Yeah. There's the set of annoyances. I had that experience. I actually was an engineering manager first, and then it was kind of like, ah, ah, this isn't. This doesn't feel right, you know? Yeah. I mean, I love engineers. You know, they're my, my favorite people. Um, very comfortable with engineers and all that. But, um, I realized it wasn't the, the kind of influence or the kind of problems I wanted to be focused on.
Speaker A: Right, Right. So I want to shift gears a bit. One of the things you mentioned in your introduction and that we've talked about before was like, you've mostly worked at kind of growth stage startups, and I'm curious. I've done some of. Some of both. Right. And. But I'm curious, what do you think is sort of common And I am sort of tailored, taking a hard left here. But what do you think is common in the DNA of products that can grow and scale across time? Like is there something that is like ah, uh, there's a theme that you're looking for when you're looking at these kinds of companies or is it kind of each one stands on their own.
Speaker B: You know, uh, there has to be a core of product, market fit and you know, in an enduring way. And least the companies I've, I've been in and um, you know, it's, it's like impossible to find. Like once you find like when you see it, you know it and when it's, when it's there, like it's like it's just. There's nothing better and everything is easy, you know. And you're like, I'm a genius. You're not a genius. Yeah, you stumbled at uh, upon one of these things and that's great. And I think you're just fortunate when you do. So that's why it's so much easier to like I haven't done the true startup myself and I've really kind of jumped in after the hard part is over and you know, okay, I can help to scale up this product. And um, so it's, I mean you know it by the signs where you know, like it's, there's pull, pull from the market, the orders come in. It's almost in spite of all, you know, the problems with your product that, that you know, are there and uh, customers are willing to work with you. And so that's one of. I do also work with enterprise. I work with SaaS, uh, companies and usually we're a small company working with large enterprise companies, Fortune 500, Fortune 10 companies. And so you really sit down with your customer and teams and you get to know them and you have these long term relationships and um, it's, you know, they, they're, they're so grateful and, and you know, because you're solving this deep pain for them and you're actually making them look like stars. You're the, the products of, for the companies I've worked with have. They make the careers for the people in these companies like they, they, they kind of catapult them. So that's the kind of problem that you're looking for in uh, to be solving for in the market at least in this type of company I work in.
Speaker C: Um, so thank you for the left. Leah. I think this conversation is fascinating. It brings to mind, uh, so what you said is like These sorts of products, these sort of product market fits are magical. Like when you find them, they're like, you have to run to keep up. Um, what, how do you stay humble in the face of that? Because there's plenty of Silicon Valley unicorn leaders that don't and they think, they think it's some personal attribute come up with instead of like a lot of hard work, a little bit of fortune and being a little bit smart.
Speaker B: Right.
Speaker C: The ratio of like the ingredients it takes. Um, so you've clearly been a few of these rides, Greg. Uh, how do you maintain the humility to like then go back to a very small company and you know, lean into a new problem space and not just bring a formula and smack it on top?
Speaker B: Yeah, it, I mean I think some of it is, you know, the wiring, but back to the introvert wiring. Um, but also like I wasn't the founder, I think it's the hardest for the founders because they worked so hard and they stumbled on something and it's like, well I, I did it once, I can do it again, I've got it. And that's super rare. I mean it's rare enough to find one, but then to be the repeat founder, I mean those people are so impressive and you see more of people who have been there and done that and then um, kind of failing to see what were the things that they had control over. Um, that said, there's a lot of thought to be said for pattern recognition and experience and so they can advise, uh, other companies that are going through that.
Speaker A: Yeah. So I think one thing that is super interesting to me is like in that journey, when you are joining a company that is moving into that, you know, out of, out of sort of startup land, into scale up land. What do you think? What advice would you give to product managers who want to make that shift from one to the other? They need to have a different, maybe a different set of gears to move into different skill set that they need. Or is it all transferable in your
Speaker B: mind, the transition being from a, uh, stable company to a new one or.
Speaker A: No, No, I guess I like if I'm a start, if I'm a product manager who's been with a startup and it's successful and now needs to kind of move a gear into being a scale up, you're m. Often your focus is kind of shifting. Do you think that those product managers are like, I, uh, need to go back and find another startup to work at? Or can they make that growth pivot with a company?
Speaker B: They absolutely can uh, they, it does require, you know there's, there, there are processes. We, you know, we talked about this and, and so there does require a lot of learning. If someone is highly motivated, loves learning. Loves, wants to understand. Uh, okay, well this is a new, a new situation. And so I, I'm, I'm all in. I really want to learn. Right. Really helps to have experienced people come in and then, then they, they absolutely can make the shift. Um, but I have, you know, I've seen it go either way in, in, in these companies. Some people are like, well I really prefer the 10, 10 to 20 person company. I'm not good with a hundred uh, plus person company. And, and you know, you, I mean I'm, I'm one of those people. I'm, I'm not one of. I, I don't want to be in a 500 plus person company.
Speaker A: Right.
Speaker B: And, and so it's good, you know, take some self awareness and understanding. Where do you want to play?
Speaker A: Yeah, no, I think, and the reason I say this is I think I've had the similar experience where I often am coming in when there's 50 to 150 people and they need some, they need product to sort of level up. Like there needs to be a. And, and that can then feel like there's a criticism of the product units. There's. And what I always say is like no, you got it to here and now to get it to the next step we need to mature some of what we do and how we do it. And uh, I think sometimes those folks can feel like it's a bit of a slap in the face to have to bring somebody in who's like I know how to do this and I can do the really small but actually I'm better at what's the next like what is that next step? Um, and I think uh, so that, that was why I wanted to ask that what you see, because I do think people can make that leap but they've got to want to.
Speaker B: Yeah, yeah, yeah, yeah. It's really interesting. It's, it's, there's. Whether it's anti authoritarian or you know, I mean it, but there's, there's something of a buzz to the early stage where like there aren't defined roles and you just, you're someone who sees a need and you fill it and you know, you're a glue person and those, you know, a company of 150. There's plenty of those opportunities. Like there's like it's, it's not a Mature, that's not a mature company. There's so many problems to solve, you know that. Um, so there's. Those opportunities exist, but it's. Yeah, it's really uh, up to the individual.
Speaker C: Yeah. Curious though, because you have so. Yes, yes, yes, yes to everything you guys said. But think about the companies where you described working. You are a tiny company and Leah, you face this too. So you're a tiny company and you're scrambling to make a product. On the other side of that deal by friends is an enterprise with lots of people and lots of processes and defined roles. So two things. One, you have to build a product that fits those customers. Um, and so that requires a deep understanding of like what are the problems of those people and the roles in the company. Um, and two, like interfacing with people that do have hierarchy and strict roles and care about things like that. So what are some of the really interesting um, opportunities and difficulties that you see with that sort of like, relationship?
Speaker A: Mhm.
Speaker B: One of the things I've seen so you, it's a lot of hinges on, at least in my company, is in the customer success manager role. And so typically that's the function in the organization which is driving maturity throughout the organization. And I've had the fortune to work with some amazing customer success leaders. And um, even in my current company, that is the lever that's pushing the company forward. Okay, we need better collateral, we need better um, engagement plans. We need enterprise. Companies expect this and that and you know, they, you know, just out of necessity, that's where the, the change comes from, isn't it?
Speaker C: Isn't it? So that makes that relationship between product and customer success really critical. Because if there is strong product market fit and you are trying to build the airplane while you're flying, like stupid analogy, everybody uses it. I'm leaning into it. Um, what you want to do is for the product you have, maximize the number of customers that can use it. Um, but it's often the case where an enterprise success group will go after as many customers as they can. And that actually puts a lot of pressure on a very constrained team to build lots of stuff. Um, and so how does it, how, like how, how have you seen that relationship work? And what, how should product managers, because again we're talking to product managers about product management. How should product managers help their customer success people understand the balance between blowing out the doors and going after everybody and creating a bunch of features and product capabilities that don't exist and doubling down on the core that they have today? And going deep in a particular market.
Speaker B: Yeah, there's a lot of tension there. And, um, it's a lot of providing context. And honestly, whether it's engineers or CSMs, it's really about the context with a strategy. Here's our current plans, here's our amount of resources we have, and help us, partner with us to prioritize where we have space, um, to move the needle. And with the enterprise, particularly some of these Fortune 100 companies, they're used to getting everything they want and they really throw their weight around. And so as a little company, you kind of have to put on an attitude and you're like, look, I'm the innovator. I'm, you know, I'm the expert here. This is what we've seen work with all your competitors. And then they listen, they're like, oh, is that what they're doing too? And, and so, so, yeah, so we. But, but it's still. They can throw their weight around. And um, so it's, it's a really delicate balance. Uh, I try to make sure that we have capacity to, to deal with the unexpected things for just related to, uh, maintaining critical customer, uh, relationships. Um, but every one of those customer success managers, clients have special pet requests. And that's where you have these really challenging conversations where like, yeah, we're not going to get it because the really big Papa bear over here, um, is getting theirs this quarter.
Speaker A: Yeah, it's, it's interesting because I think, um, I feel like I've been on both sides of the table. I was at Amazon making deals with small companies and trying to figure out how we could take advantage of every, every penty penny we could get out of them in order to, um, to squeeze. And you could just say, well, if you don't want to do that, then we don't. We'll. We'll figure it out another way. And it was, I remember feeling kind of gross in those scenarios. I've also been on the other side of the table where I'm trying to build something and get an enterprise to participate. And I think one of the things you just said is some of this is remembering that now that I've been on both sides. When you're on, when you've done that, you realize that on both sides of the table, there are some insecurities that are at play. On one side, the small guys are like, oh, this big company is going to take advantage of us and they know more than we do and they have more. Their pockets are deeper and they can say, no. And so we have to say yes to everything on the other side of the table. There's a little bit of like, we probably should be able to solve this ourselves, but we can't. And so we need some help. And so these guys are faster than us. They have less processes than us. They're. They're more scrappy than we ever can be. Again, we used to be like this, and we're not. That's on our DNA anymore. There's insecurity on both sides. And if both players will come to the table and be like, let's figure out how to make this work, like, we need each other. Because if it's the, you know, if, if the big guy could do it, they would do it.
Speaker C: Right?
Speaker A: Right. But they all. But, you know, listen, every time, you know, I don't know if you've ever used my, My big example of this is that, you know, at the outset of the, of the pandemic, Amazon should have bought Zoom or one of those companies instead. They tried to build their own interface called Chime. And the last time I used it, it was still terrible. And I'm like, why didn't you guys just buy something? Right? But they had a. They, they have gotten into a spin of, um, make it. Make it ourselves. Make it ourselves. Make it ourselves. Right? And it's, it's more important if we do it ourselves. When, like, guys going into a pandemic with an, With a diverse team spread around the world, you should have bought somebody who was already good at this. Right? Because your features are terrible. Right? So, so I just say that because I just, you know, I mean, Google did that. You know, they had Google Meet at the outset of the pandemic. They were like, okay, we got to get all the feature parody to so that this will, this will be a tool that gets hosted and it got better fast. Right? And so, like, I use that example because, like, I mean, not that particular example, but I just think that there are insecurities on both sides. And it's important to recognize that you have some. If you have something to offer, you have something to offer. So, so going I often tell clients when I'm working with them is like companies that I work with, I'll say, like, uh, you're not an apology. You have an offer. Don't go in as an apology. Like, you are not a walking apology. You're a company. You have something to offer. Go in and offer it.
Speaker B: Oh, yeah, Ah, absolutely. And you're not going to serve that customer if you're doing something which you think is not in their best interest, like uh, for one, you have to be viable. Like you have to stay viable as a company, which means you have to sell to other companies and they should want you to be as strong as possible just to deliver them the best quality solution and helping them, uh, to keep innovating. And usually so it is a partnership conversation and usually people are behind it and but then sometimes they're just facing other pressures and so they like yeah, but I really got to have this thing.
Speaker A: Yeah, that's super true. So one of the things that I think is. Weaves the whole conversation we've been having together is, you know, Marilyn and I have talked in the past on past podcasts about how much we have loved product managers who have joined our teams who came out of engineering.
Speaker C: Yeah.
Speaker A: Um, they're often they get it and we don't have to. It's like all we have to do is help them be product managers. What would you say? Neither of us has an engineering background, so that's. Yet we have run very technical teams, very platform heavy teams. Lots of engineers have worked. We've both led engineers as well. Um, I'm curious, in the move from engineer to product, what do you think was the toughest thing for you?
Speaker B: Yeah, I mean it was really, uh, some of these more challenging situations, uh, dealing with confrontation, um, really learning to speak up and be comfortable in those situations, um, being able to sit in the hot seats. But was for me, I mean, yeah, the like talking with engineers, uh, is easy. Like I'm like they don't consider me technical anymore, so I can just ask questions and be like kind of gee whiz and, but, but I'm, but I, you know, I'm onto that. Like, do we need this? I was like, oh yeah, but, but, yeah, but, but do you need to do this now? You know, like, or could we do this? You know, I just know how to keep, keep drilling in in a way just because I do understand more, which I see some of my non, you know, people who haven't, you know, sat in an engineering. They'll get to a certain point in questioning, but they won't go further because they're. They're not sure and Right. Um, that's an advantage. You know, I won't say it's not an advantage but um, there's so much more to product management than like all the these other aspects where I think it all, it balances out and you know, I see both technical and non technical people be really Successful in that role.
Speaker A: Yeah. I guess the other side of that question is, what did you. In moving to product management, what did you love about it that made you go, I never need to go back to being an engineer? What made you stuck?
Speaker B: Yeah, that's. Yeah, giving up the coding was hard. There is certain. There's such a satisfaction in making things. And, um, yeah, it was the creativity. I'm trying to think of a way to make this more specific. There are fewer constraints on what you can bring to solve the problem. Your problem is more constrained. As an engineer, you just figure out this, and it's usually technical, and you can create new products, open new markets. Uh, it's like endless learning. And I just. Just love that about product.
Speaker A: Yeah. Yeah. We were talking about. I was in one of our last podcasts, we were talking about engineers who come out of product, uh, managers come out of engineering. And I had a guy that worked for me who was an amazing engineer and a really great product manager. He's turned into an amazing product manager, but he. We had to turn off his GitHub access.
Speaker C: Yeah.
Speaker A: Because he. I was like, turn his shit off. He was like, working on pull requests and doing that. I was like, stop writing code. His. His engineering manager, Lee, his engineering partner, came to me and was like, he's got you. You have to tell him to stop. And I was like, I have. Turn it off. And he was like, okay. And I was like. He came in, he was like, hey, I wasn't done. And I'm like, you are done. You were done months ago.
Speaker C: You were done a long time ago. Remember?
Speaker B: I could just. I can just fix it. I can just. It just take me an hour. Like, I'll just. I'll just move this along. Oh, God, the temptations got to be terrible.
Speaker C: Like, I've had product managers that were not engineers, um, that would constantly come up as one of my largest code contributors. And I'm like, how the hell do you access, like, get out of the freaking code? To your point, I think he just got tired of waiting for what they weren't picking up in the sprint. So he's like, okay, I'll go in there and look around. No, you will not.
Speaker B: You just have to work on your influence skills more.
Speaker A: Exactly. Well, I wonder how much more dangerous product managers are now with AI and being like, I'll just vibe code my way into the stack. And it's like, don't touch anything, for God's sake. Oh.
Speaker B: Oh, no, no, not that.
Speaker A: Yeah, because I about. I would say about maybe 10 years ago now, which sounds crazy. I was like, I'm going to learn to code because that'll help me be a better product manager. And one of the engineers I was working with like, please don't. We don't need you to know how to code. And I was like, what do you mean? He's like, you won't be more helpful if you can code. You'll be a bigger pain in the ass. And I was like, all right, am I already. Yes, you are already a pain in the ass. We don't need you to be a bigger pain in the ass.
Speaker C: That was Hans.
Speaker A: Yeah, it was. It was someone we both know. He was like, you don't know. That's not necessary. And I was like, oh, uh, hello to Hans.
Speaker C: If you're listening, we're talking about you still.
Speaker A: Yeah, yeah. Very interesting. All right, shall we lightning round?
Speaker B: Sure. I'm ready. Wait, let me, let me take a step.
Speaker A: Everybody stretch. We're gonna lightning round.
Speaker B: Okay, Lightning.
Speaker A: All right, Lightning interjected here. What is a product you wish you had built?
Speaker C: Mhm.
Speaker B: Uh, you know, I just. My life is so much better in Slack. You know, I wish that that happened sooner. Um, but I'm glad it's here.
Speaker A: Yeah, that's a good point. Marilyn. Do you have one?
Speaker C: I don't actually. You know what? I do. Um, and it's dumb because um, like I am. I am a spoiled brat. I'll just like my car syncs to my phone and magic happens. M. My father's card is not.
Speaker A: And how annoying for you.
Speaker C: So it does become my problem. I know it is very annoying for me that my father's. So he will get somewhere and for some reason his maps will go out and he's 88. He only moved to Massachusetts to come live with us about a year ago. So he still doesn't know his way around all. And this is if big deal in his life. And because it's a big deal in his life, it becomes a big deal in my life. Right. And there is this little dongle. Heidi Smeller. I said dongle just for you. Um, there's a little donger called Auto Kit, um, that plugs into his USB port and it Bluetooth to his phone and it makes magical things happen and it has completely illuminated this problem. I sorry, Toyota. It's your problem, not mine. Um, but it actually makes Toyota is very compatible with Apple and it is magical and I wish I would have solved that problem.
Speaker A: That's a good one.
Speaker C: Yeah, it's great.
Speaker A: Nice. How about you yeah, I'm trying to think if there's anything. I mean, listen, I. There's almost nothing in the world I love more than a good book. So uh, there are. I mean, I think after all these years and we've talked about this before, Marilyn, after all these years, the paper White is still my favorite thing that Amazon's ever created. And they've done a lot of things that I've taken advantage of over the years. But I still love, man, my paper White is never far away. It loads all those books. The battery lasts better than any battery on anything I own. Right. So, so that's my. I'm like. And so sometimes I'm like, man, I wish I'd been on Dorothy's team when she was creating that. And I'm always like, man, I just feel a tiny small image of like I wish I'd been on that team. So.
Speaker C: And the tap to turn the page. I will tell you when I get really tired and I'm reading, I'm reading a physical book, I'll tap the page. Then I'm like ah, no, this has
Speaker A: a page, I have to turn it. I love to tell people that story that Marilyn taps pages just like I do. Greg, do you work better in the morning or at night? Or is it dependent on what you're. What's going on and what you're working on?
Speaker B: 100% the morning? Um, yeah, I wake up at 5:30 and I meditate and then have coffee and breakfast and then I'm, I'm gone.
Speaker C: Oh, it's horrible.
Speaker B: Yeah, you should not, you should not bother talking to me about anything important after 3pm M. Okay, good to know. Marilyn's not advised.
Speaker C: I work best when I'm caffeinated. Um, and I do not get up at 5 o' clock without a lot of prodding. But you know, I like to stay up late. But I also like it's that I'm a night owl but also not too late now that I'm getting old like moderately night owl. How about you Liam?
Speaker A: I um, think I do my best work in the morning but I'm better socially in the afternoon or evening. Like I'm, I do great alone work in the morning and I don't really want anybody to talk to me before about 10 in. I used to, I worked for a CEO during the pandemic. Um, and right after that man, he used to schedule meetings for 7:30 even when we had to be in the office. And me and his co founder man, we were pissed off. Neither of us like to be anywhere by that time of morning. We would come in and the co, the other co founder would hand me a cup of coffee angrily. And I would take it angrily. And the co founder, CEO would always be like, how come you didn't give me a cup of coffee? He's like, yeah, that's retribution.
Speaker C: Yeah.
Speaker A: So one of us would buy the other one coffee every time and the CEO be like, I want a cup of coffee. We're like, get it yourself. You made me get up and go across Berlin at seven in the morning. This is your problem, not mine. So, so, yeah, so I'm a, I socialize better from about 4:00 on, but I'm really, my work is much better early in the morning. So. Yeah. Okay. Greg, what do you think is one thing that um, one or whatever, however many. But what do you think is most misunderstood about introverts?
Speaker B: Yeah, um, it's really about their capabilities of being leaders.
Speaker A: Hm.
Speaker B: I think people forget the leaders who are introverted. Introverted who are in plain sight. We forget about, even forget about people like Barack Obama, like, who's a very inspirational leader. We think about spiritual leaders. He was also a political leader. Gandhi, Eleanor Roosevelt. Um, there's just profound influence in these people and I like to say they're hiding in plain sight. So look around and you'll see them.
Speaker A: Absolutely, absolutely. No, I think I 100% agree with that. I think for me, I also think one of the, When I say I'm an introvert or when I need to walk away, I think one of the things I feel misunderstood about is that I don't like people or that I don't care or that I'm not, you know, but I do, I deeply, I deeply care. I deeply am invested. I just need energy in order to invest. Mhm. And so I need to walk away. You. And you need me to. Right? Because if I keep going, when I'm, when I run out of energy, when I hit the wall, if you keep pushing me, you're gonna, you know, poke the bear. You'll get a roar. Right. Like a grumble. So and so. So for me it's not. I, I love people, I love my teams, I care deeply about, about how they feel and about culture. But I think it can be misunderstood that I gotta walk away. Like we'll have, we had an off site recently and uh, at the end of the day when everybody else wants to go out, I'm like, I'm going back to my room. I'll see you guys in the Morning. And everybody's like, you don't want to hang out? I'm like, I've hung out with you for the last 10 hours. I'm all hung out. Right.
Speaker B: It kills, it kills me. Yeah. We'd go in these off site meetings and 7:00am or, you know, till, you know, you stop talking. Like 6pm you go to dinner and then after, you know, happy hour, like, I'm, I'm done by dinner time.
Speaker A: I was done talking to you at four.
Speaker B: Right.
Speaker A: But I guess I'll go for four more hours. Like, it's like. So.
Speaker B: Yeah. Uh, and some people love it. That's good for them.
Speaker A: Um, totally. I mean, I watched my team just light up because I have a, um, I have a handful of extroverts. And I loved watching them interact and get more and more energetic and more and more fun. And I was like, have fun. Don't spend all our money. Gotta go.
Speaker C: Right?
Speaker A: So. So, Marilyn, what do you think?
Speaker C: I, uh, can tell you what I think. People misunderstand about extroverts rather than introverts. Since I'm not. Since I don't think I'm an introvert. Yeah. Um, I think a lot of, I think a lot of people sometimes will think that extroverts don't care because we're bouncing forward and we're like, sometimes we forget to listen or we don't slow down enough to listen. Um, and it's not that we don't care, it's just that we're super jazzed and we're full of energy. And think of it like, in the case of myself, I equate myself to Tigger from Winnie the Pooh. I am gone, man. I'm one woman party. And I want to bring everybody with me and we're going to have the best time. And I don't see people hanging back. Sometimes you have to actually tell me or ask me to slow down a minute. Yeah. Um, and I, I will because I want you there.
Speaker A: Yeah.
Speaker C: I just am. I'm ready to bounce. Right?
Speaker A: Yeah, for sure.
Speaker B: That's, that's. I just had an episode with a woman who's extroverted. And, and it's really the lesson out of that was like, have empathy for people who are extroverts. You know, even the person who might be steamrolling you, they may not know. They may not realize it. And this woman talked about her story. When she realized it, she was like, oh, my God, you know, I didn't realize I was doing this. And she worked on that so have that empathy.
Speaker A: Yeah, I love that. All right, last question. If you do have a favorite book, um, or author or writer that you follow that for that you would recommend
Speaker B: to product managers, to young for products. Uh, I always love, uh, the work that Teresa Torres does, the customer discovery. Um, so customer, um, discovery habits is a good place to start and just get you in the practice of being curious and asking questions and talking to customers in a way that doesn't bias with the things that they tell you.
Speaker A: Love that. Thank you for that one. Marilyn. Do you have a new one you want to share or anything?
Speaker C: No, no, I'm going to go buy that one.
Speaker A: Me, too. I've heard. I've. I've seen some of Teresa Torres's work, but I haven't read the book, so I think that's a. That's a purchase. Hold on, I'll get my paper white and put it on there. Tap. Yeah. Tap, tap. Greg, thank you for coming and talking to us. This was so much fun. It was interesting. We got to ramble, ramble and wander together a bit, and that was really fun for us. We really enjoyed it.
Speaker B: It's awesome. I, uh, enjoyed it, too. Thanks for having me.
Speaker A: Yeah, for sure. All right, everybody, we'll see you next time.
Speaker C: By, uh,
Speaker A: Sam.
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