The Exchanges

Q out to me was they litigate the details. Are they litigating sort of like a different lens into the same problem, and they keep rehashing their point of view because they think the other person doesn't see it, but they're coming at it from a completely different lens. How do you get out of that? How do you become productive in that, in that sort of litigation or argument then?

A Look, what, what we end up doing when we feel like that the other party is not listening is, uh, that we just keep repeating our message and we do it louder each time. Hoping it will stick, and it doesn't, and then we are frustrated that it doesn't. It's like, you know, I've told you this five times. We've had this meeting three different times, and I just don't understand why you don't get it, right? Like, that's at least the feeling, even if it's not vocalized. The real solution out of this is take a step back and recognize what is going on. Recognize that Oh, I see this other team is really concerned about the optics of the situation, so let me explore that more, right? Like, you know, one of my challenge, my personal challenges in my own kind of, you know, journey and growth as a leader was, um, it was easy for me to judge Other individuals or other teams saying like, oh, these people are only focused on optics, whereas I am focused on impact and execution, which are the right things to be focused on. Um, and when you start with that sort of feeling, it doesn't Create or make any room for true collaboration. So instead, uh, you know, later on in my career, when I had this vocabulary and this way of looking at things, when I saw these situations where perhaps somebody else, some other team leader that I'm trying to collaborate with is really focused on optics. I wanted to ta…

AI assessment note: “The real solution out of this is take a step back and recognize what is going on.”

Q It seems, maybe I'm wrong here, but it seems from the outside, the professional managers would sort of gravitate towards quantitative, uh, indicators, whereas founders would gravitate more towards the qualitative. What do you, what's your reaction to that?

A I think if we were talking about general patterns, um, that matches my understanding and my observations too. Uh, but, uh, I'll add an interesting additional observation, which is, uh, what happens when, uh, the company starts to scale, right? So, so now we are going to have to rely on other signals. Uh, and one of the things that, uh, you might end up learning along the way is that, uh, oh yeah, so from this point onwards, you have to manage by the numbers, right? Because You know, you, you're not close to the customer anymore. Uh, you don't have as much, you know, strong empathy for customers as you used to. Uh, and, uh, at, at certain scale, your instincts, uh, may actually be wrong, right? The instincts that actually worked for you early on may not work. The challenge though is sometimes, uh, some founders will kind of lose their way entirely. Right. And they, they, again, they make the mistake of treating the proxy as the goal.

AI assessment note: “that matches my understanding and my observations too”

Q I want to switch gears from writing, come back to decision-making for a second. What do you know about decision-making that most people miss?

A You know, there are certain truths, uh, or maxims, uh, that, um, we learn or we discover about the world and how the world operates, uh, and then we use, uh, those maxims for, uh, making many decisions. Sometimes we should use the antithesis of that truth or maxim Uh, when it applies to us. Okay, so I call this the antithesis principle. One kind of truth that we might know about the way the world works is that most people learn better when the content or the teaching is entertaining, right? When, when it's entertaining, it's like, it's got great stories, amazing analogies. Uh, people just learn better. And there are many people who proudly say, right, like, you know, and I come across such folks all the time as a teacher myself or as somebody who writes online and so on, is, uh, that, well, I only learn through engaging writing. As a smart person who wants to make a big impact, On yourself and on the world, right? If you think really deeply about this kind of truth, let's just say, right, which is most people learn better, learn the best when the content and the teaching is entertaining, is, uh, that if you want to help people learn something, Make it very engaging and entertaining. So that's the obvious conclusion that almost any smart person will reach. But it turns out there is actually one more conclusion you should draw to be a better decision maker and to have better resu…

AI assessment note: “I call this the antithesis principle. One kind of truth that we might know”

Q who's the arbitrator of a tie in those situations? How does that work when you have maybe two people who are both looking out for the customer, but they're coming at it from very different perspectives and you have to pick one path and you can't have both. In the case where all functions are sort of equal and everybody's responsible for the customer, how do you make that decision?

A So in practice, I'll observe a couple of things. Number one, this is where a writing culture helps intensely, right? So Stripe famously, uh, has a writing culture, and, um, uh, a lot of these discussions, uh, would start with a document, right? And they're asynchronous discussions. And, and the reason I think it's key is because just having to write these things down forced a degree of clarity that is often missing when you are kind of having just these debates verbally. By forcing ourselves to kind of write down our thinking, it enables us The reaching of consensus or a decision, uh, better than if we were trying to do it all just verbally in a meeting. Uh, cause again, oftentimes, you know, uh, when we are doing it in a meeting, we, there's also like other factors that come in, right? Like it's not just the lack of clarity and the lack of comprehension, uh, but also ego factors, uh, that become quite, uh, you know, Prominent and dominant in how then we decide, right? So, so I think that just like, you know, that writing culture helped address a lot of this, where, yeah, we might disagree, but now we understand the root of our disagreement better, because you're trying to optimize for this metric, and I'm thinking of this other metric. So let's have a conversation about that first, instead of, again, litigating the minutiae of whether there should be a three-step Flow or a two…

AI assessment note: “By forcing ourselves to kind of write down our thinking, it enables us The reaching of consensus”

Q One of the things that you said online that was interesting is that there's a difference between evaluating how something is going and measuring how it's going. Can you expand on that?

A Yeah, it's often the case, Shane, that, um, You know, you hear in business meetings, right, that, um, if you can't measure it, you cannot improve it. In, certainly in most of the highly rational, uh, company cultures, uh, that I have seen, uh, these kinds of, you know, statements are taken as, uh, truths. And, uh, Over time, I realized, used in the wrong context, they, they tend to, uh, you know, cause a lot of damage that we don't even realize, because we feel like we're being smart when we say, oh, this thing must be measured before we can improve it. Really, the way I, I realized some of the flaws in this thinking of you cannot improve something that you don't measure is, uh, Kind of looking at my personal life, and sort of evaluating. So I, I'm a parent, and so at one point, I asked myself, um, am I measuring how I'm doing as a parent, right? Or, or am I measuring how I'm doing, uh, as, uh, as a spouse? And while, you know, there, I clearly improved in certain areas of parenting, um, I had not done any measurement there. So then I started asking myself, well, if I've clearly improved in this area of parenting or this area of being a spouse, um, but I, I don't measure it. I don't track it on a daily basis. I don't have any metrics associated with it. Uh, and yet I can tell that I'm improving in these areas. So, so how am I doing that?

AI assessment note: “if I've clearly improved in this area of parenting... but I don't measure it”

Q can systematically grow your competence, the role of opportunity cost, the antithesis principle, the agency talent matrix, and so much more. It's time to listen and learn. I think when I was thinking about where to get started, I want to start with the three levels of product work. So the execution level, the impact level, and the optics level. Can you expand on these levels and where conflict arises?

A Yeah, for sure. So, uh, this took me many years, almost two decades of working on products at, uh, mainly at high tech companies, uh, to really realize that Oftentimes conflict between people and teams arises mainly because, um, we're not talking at the same level. Uh, and, uh, we might have, uh, you know, similar missions and similar goals and OKRs and whatnot. Uh, but if we are not aligned on the level at which we are talking, that can lead to a lot of confusion, a lot of just stress, uh, among individuals and teams. And so the three levels of product work, uh, that I discovered through my observations were, uh, the execution level, uh, the impact level and the optics level. Oftentimes, uh, there would be product managers or other folks on my team who would be very nervous before presenting to an executive. Maybe it's a product strategy, uh, or something else, and, uh, they'd be very nervous, and so I'd have a conversation with them about, like, you know, hey, nervousness is normal in these situations, et cetera, uh, but what's really going on? What is your real concern? And so they'd often point to past examples where they, they would say, oh, you know, I was talking to the CEO in this last product review, uh, and I shared with them exact details of how, uh, Uh, we can, you know, make this, uh, these goals more ambitious or whatever the case might be. And that just did not l…

AI assessment note: “conflict between people and teams arises mainly because, um, we're not talking at the same level”

Q you're doing, uh, with, with their, I guess not of approval, depending on where you are at some level. Uh, and if you're in a culture that is very measurement oriented, Saying that, you know, we're going to improve this, but not being able to quantify or demonstrate how it's improved is very tricky to get the buy-in. How do you, how do you, how do you go about that?

A Yeah, it is very tricky. And, uh, I would say this is why the solutions to some of these problems lie, uh, not with, uh, an individual, uh, or individual contributor within the company, but they lie with the company leadership, right? Like, so ultimately, The company's leadership needs to have the judgment, and if they do not, things are just very hard. This is why a lot of the work, the, both the writing I do, the coaching I do, and so on, is focused on leaders and leadership. Without leadership understanding these ideas and these principles, it's just very hard. Now, all that said, What I've found interesting is that it is possible sometimes to pivot, um, this kind of intense desire for, uh, you know, showing, uh, you know, numbers on a graph with, uh, other ways of showing impact, because ultimately the measurement is not the goal, right? The impact is the goal. Uh, we hope that the measurement is, uh, just a proxy, uh, for the impact we made.

AI assessment note: “possible sometimes to pivot, um, this kind of intense desire for, uh, you know, showing”

Q in, Stripe is one of the most interesting and considered to be one of the most, uh, well-run companies in the world. We've had the good fortune of having Patrick on the show. I'm curious, uh, we're talking a lot about the lessons that you're offering. I'm curious as to what did you learn being inside that culture that you've taken away with you and how do you use it?

A Yeah, I, I just learned so much at Stripe. Uh, you know, I was there for, uh, over five years, uh, and, uh, I joined as they were just, uh, thinking about what product management means at Stripe. And so, you know, this was a company of a few hundred people at the time. And, uh, you know, already building a really had, had already built a very compelling product and sort of, you know, at least by Silicon Valley standards was adding product management a little late. Uh, you know, usually you'll have product management added at, uh, you know, several dozen to a hundred or so people. Uh, so Stripe was adding product management a little late, um, and, uh, had done just fine without product managers. So one of the reasons I joined Stripe was because I saw this as what a wonderful opportunity, uh, to really understand if product management can create unique value at a company that has already been very successful without product management.

AI assessment note: “I just learned so much at Stripe... I joined as they were just thinking about”