(highlight:: Coordination Challenges Grow Superlinearly Based on Required Information Throughput
Transcript:
Speaker 2
Why fundamentally do organizations get slower, and then we'll go into talking about what the right solutions are.
Speaker 1
I think this is one of those problems that shows up. People assume very often it's like, oh, it must be somebody who gets lazy or there's some villain. It happens even if you assume absolutely everybody is very good at what they do, very hardworking, very collaborative. It arises for almost a fundamental reason due to the shape of networks. In the way that people have to coordinate across many different priorities they could be working on that has a very fundamental super linear acceleration. I think hardest about it, honestly, is it shows up just because there's inherently uncertainty. There's different information that different people have in it, and the conditions are changing pretty often. That makes it extremely hard to coordinate. The amount of effort it takes, the overhead it takes to coordinate can become a huge portion of the underlying effort. That just makes everything significantly harder to do.
Speaker 2
Let's compare a startup to a large organization. Is the idea that in a small startup, let's say there's only two people working on it, all the information is already in their heads about what they need to do. Whereas in a large organization, maybe 10 or 15 or even more people have to coordinate in some way in order to get the task done?
Speaker 1
Yes, so there's both the amount of people that are already pre-share the same information or share context or trust so that they can share information that you have to see a full picture Of it. Then it's also just something where you have to communicate with lots of different people across the team. It goes up kind of sort of with the square of the number of people in that team. As teams get larger and larger and larger, it just goes up at a super linear rate. It gets worse when you're working with lots of different people across many different teams.)
- Time 0:01:58
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(highlight:: 1min Snip
Transcript:
Speaker 2
Let's compare a startup to a large organization. Is the idea that in a small startup, let's say there's only two people working on it, all the information is already in their heads about what they need to do. Whereas in a large organization, maybe 10 or 15 or even more people have to coordinate in some way in order to get the task done?
Speaker 1
Yes, so there's both the amount of people that are already pre-share the same information or share context or trust so that they can share information that you have to see a full picture Of it. Then it's also just something where you have to communicate with lots of different people across the team. It goes up kind of sort of with the square of the number of people in that team. As teams get larger and larger and larger, it just goes up at a super linear rate. It gets worse when you're working with lots of different people across many different teams. If you sometimes work with, okay, this team of 15 people, and then you also work with this other team of 40 people, that makes it even harder for this effect.)
- Time 0:02:54
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(highlight:: How the Fundamental Attribution Error Impacts on Trust and Coordination in Large Orgs
Transcript:
Speaker 2
So going back to the main thread, you were mentioning at the fundamental attribution error, you want to tie that in with the sort of issues of large companies operating slowly?
Speaker 1
Yeah, it just, I think that it is when everybody's working really hard in these large organizations, everybody's, you know, got 150% of like their overcapacity. They don't have time to think about it. It's really easy for people to jump to the conclusion of, oh, that other team, those people just don't care enough or they're just trying to get out of extra work or they just don't understand X. It's really easy to jump to that conclusion. What a convenient conclusion of, oh, it's the other person's problem. And so that creates that leads to this almost default state that if you aren't careful, you'll lead to lack of trust. And then over time that will compound, it will get worse and worse and worse and worse. And an ambiguous environment is fast moving. If you're already looking, already assume it's so another team or another person isn't going to do a very good job, you'll find all kinds of signal in the ambiguous, you know, cloud of All the ambiguous stuff that's happening that will reaffirm that hypothesis. So it's really easy to get stuck in this trap where people aren't trusting one another across the large organization.)
- Time 0:13:16
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(highlight:: Tradeoffs Between Top-Down v.s. Bottom-Up Organizations
Transcript:
Speaker 1
There are it's not like there's one true answer. Like bottom up organizations are extremely hard to find interesting shelling points or other coordination mechanisms. So you get kind of this wild, very challenging to predict where exactly it's going to go, but they tend to be much more resilient, much more able to adapt to circumstances way more way Less likely to die as one way of putting it. Whereas top down control can create shelling points very actively, very, very straightforwardly, very cheaply for things accorded around, but they can get very caught off guard By things. I think a lot of things are trade offs, fundamental trade offs that we treat as black and white or there is some right answer. And when you see that basically everything is a trade off, then when to realize it's a trade off, you can start asking yourself, are we contextually at the right balance point right now? Because there is no one true balance point for every context. It is highly contextual. And so then you get a sense less of like, oh, you feel like you're surfing that balance point. Hey, are we a little bit too top down right now or are we a little bit, if we were to choose a little bit too top down or a little bit too bottom up right now, which one would you say? And then if everyone goes, yeah, I feel a little bit too top down right now. Cool. Let's nudge a little bit towards that as opposed to people think of it as being this binary thing, this big, huge shift that has to happen, but doesn't have to be actually can be relatively Small nudges continuously, can keep a system in balance.)
- Time 0:23:09
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(highlight:: Creating Resilient Orgs: Serendipity, Autonomy, and Creative Flexibility
Transcript:
Speaker 2
So what does that look like in practice to actually empower that kind of slime mold-like model inside a larger organization?
Speaker 1
I think it often looks like creating space for serendipity, creating space for a little bit of autonomy. One way looking at this is having, hey, culturally, like Google famously had 20% time. And this is a well-known thing about how it worked. In practice, 20% time was always basically a cultural myth. It didn't really exist. It was always 120% time. But it did two really useful things, in my opinion. One, it allowed space. Sometimes that space people would use it to do things like create a knitting club or something, some kind of social network thing. And a knitting club isn't useful to the company per se, but what is useful is having a high trust, very diverse social network overlay that is different than the organizational structure That makes it significantly more likely the right information flows to the right places at the right time. The second thing that 20% time did really nicely is a lot of things that have tons of indirect value over time are really hard to make a legible case to lots and lots of people succinctly. And I would argue they're fundamentally impossible in many cases. And so what 20% time did in practice is someone could set me working on a P2, a lower priority item. And someone comes over and says, why are you working on that? And they kind of waved their hand and go 20% time. And a number of those things might turn out to be hugely useful and have tons of indirect value down the road. So maybe somebody builds a little prototype where they duct tape together a couple different systems internally just as a hobby project on the side. And so when most people go, wait a second. That actually would be a really good fit for this other thing we have. Or wait a second, we should get that from some users. And then a UXR you realize, oh, wow, this thing is extremely successful, extremely interesting. We should make this a real product. And by having that little bit of space, a little bit of awareness of like, yeah, it's okay culturally for you to be doing a few things that don't fit in the broader plan that creates the Possibility of these little seeds to be planted by people that might plausibly grow into something really interesting.)
- Time 0:26:36
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(highlight:: Leveraging Serendipity: Give People Space and Time to Explore Their Intrinsic Motivations
Transcript:
Speaker 1
One thing that plays really important, when people have intrinsic motivation, oh my gosh, it's unstoppable. It's amazing. They get in these flow states to do all kinds of cool stuff. When it's extrinsic motivation of like, well, you have to do this to get promoted, it really messes with it. And you get like much less value out of it. So like, my rule of thumb was don't try to make people have extrinsic motivation on the things I cared about. Look for the people whose intrinsic motivation was already roughly pointing in the direction I believed was somewhat interesting and give them a little bit of encouragement. Fan the flames. Say, wow, what a really cool, that's a really neat thing that you just wrote up. I wonder how that fits in with this thing or you should go talk to this other person who has a similar idea. Maybe the two of you can collaborate on something. That was a very different approach. Even the downside to this, by the way, is when it's working really well, it just looks like luck. So when you have these miracles happen, people go, oh, you just got lucky. And it's like, well, kinda, yeah, but on a meta level, I've been sarcastically increasing my luck surface area. So like, likelihood that I have a lucky break is significantly higher than if I didn't do this.)
- Time 0:36:07
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(highlight:: Increasing Luck Surface Area: Let People Indulge in Their Curiosities
Transcript:
Speaker 2
But what are some other ways you're thinking about increasing this luck surface area?
Speaker 1
I think a large portion of it is a lot of innovation, I think, comes from people combining existing stepping stones, existing ideas into novel combinations. In the more diverse those things are, the farther I feel those existing stepping stones are that are duct-tipped together, the more likely the insight or the innovation is significant And game-changing. So a lot of it really does come down to allow people to indulge, do things that feel self-indulgent about like going down rabbit holes that they're super into or doing these kind of extra Curriculars or hobby projects. A lot of it really does come down to that. And I think that it sounds so simple, it's like, that can't possibly be it. I don't know, that's certainly what I found is creating situations where people feel that they're able to thrive, that they're able to not try to be a cog in a machine, but rather to be The best versions of themselves and to lean into the things that makes them weird. Like, I think that people look at weirdness in a large organization. Weirdness is bad. Weirdness means that you don't fit in, that you don't want to measure you. The weird stuff is where all the cool things happen. And so I kind of encourage people to be like, what is the thing that makes you weird in a positive way? And like, lean into that. Like, don't be ashamed of that. Like say, yeah, I'm kind of a weirdo about this thing. I'm really into board games. I'm really into this dabbling with this kind of thing. Cool, great. Like, lean into that and find other people who might find interesting combinations with that.)
- Time 0:37:31
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- [note::Reminds me of "all truth and beauty come from the union of the unlike"]

(highlight:: Doorbells in Jungle: A Portfolio Approach to Experimental Product Development
Transcript:
Speaker 2
So it's fair to say that this idea is around, if you're not sure whether to do something, instead of debating it endlessly, do some really cheap version of it that allows you to essentially Like assess the demand. And it doesn't even have to be optimized to, you know, get people to use it. You can just like wait around and see if people do use it. And as long as it's cheap enough to put it out there, the cost effectiveness could still be really good.
Speaker 1
Yeah, exactly. And then crucially, the other thing you want to do is any one of these doorbells that you put in the jungle, like you've got to climb through the jungle to get there. Like there's very low likelihood that actually that someone does that. So one is a diversity of them. You want them in lots of different angles, lots of different directions. They're almost like a sensing network for you. So you want to sense where the demand is. And that allows you to be in a reactive position to it as opposed to proactive position. So you don't want to just do one. You want to do a number of these of various forms, you know, in different directions.)
- Time 0:42:28
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(highlight:: Individual Incentives Disincentivize Complexity-Based Approaches to Product Development
Transcript:
Speaker 2
So why don't organizations do this more often?
Speaker 1
I think it's funny, a bunch of these approaches are extremely repeatably successful. We work really, really, really well in a number of contexts. And they have pretty large returns and generally like very positive returns. I think the reason that they aren't done is it feels so backwards. It feels like instead of saying, well, I have a plan and like, you know, my plan is really well researched and we're going to heroically execute on this plan and I figured out exactly what's Going to happen in the next five years. You're saying, I don't know. I don't know what's going to happen. And that requires vulnerability. It requires you to say, I don't know what's going to happen specifically, but I trust I'm confident that this will lead to good outcomes for us in general. And honestly, if you're someone new in your career, for example, and you say this people like, what the heck are you talking about? Like, are you just trying to get at like the way that we always do it is we come up with a plan. We have spreadsheets tracking the plan and interdependencies and then we actually get on that plan and you have to have some, you know, quote unquote strategy behind it. I think that strategies are often better versions of them are meta strategies. These kind of meta approaches that you can take that give you positive exposure to luck. But they again, you know, I mentioned earlier that when you do these kinds of patterns in large organizations, when it works, people go, oh, you just got lucky. So it's really hard to get promoted for these in organizations. How can you make it legible that you didn't just get lucky that you had actually structurally increased the likelihood of this kind of luck happening? You can't run the counterfactual and that's why it's so much simpler to say, look, we came up with a plan, we executed on the plan, we shipped that thing. Give me a promotion. It's like, but you don't know if you did a good thing that users actually want or that's going to have a ton of usage. So I think it's just it requires you to acknowledge that you don't know to lean into this sort of indirect value in a way that's really hard for people to reward or acknowledge in a very Concrete way. And so I think there's like, it's like the world tilts in a certain direction. It tilts towards more concrete, more specific, more plans than it should. And it requires you to put in some effort to tilt the world in the other direction. But then that's going to mean that you're going to stand out a little bit as an oddball.)
- Time 0:43:18
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(highlight:: Pluralistic Ignorance in Organizational Strategy
Transcript:
Speaker 1
I've seen this at many places in these larger organizations where you actually talk to everybody individually in a trusting one-on-one environment where you're being very authentic And candid about about what constraint you see. And absolutely nobody believes that the overall strategy is coherent or good or moving in a good direction. And yet the entire system is moving in a direction that like is to one direction. It's like, wait a second, the, if you play that forward, doesn't that get us almost without question to jump off a cliff? Like that's, that way doesn't work, right? He can convince every person, individual person behind the scenes. That's true. And we go, well, shouldn't your product be different than like your sub feature in this product? They go, listen, I'm not going to change this entire ship. I'm not going to do this entire ship. And if I go and do something totally different that goes at that bucks the trend and goes in the direction, yeah, we probably all would individually agree as the right overall direction. What's going to happen is I'm going to be fighting upstream the entire time to everybody. It's probably going to fail and I definitely won't get promoted. Whereas if I add ship a feature inside of this bigger system, this whole ship that doesn't actually make it, is going in direct, it doesn't make any sense, then like it's totally legible To the best of the organization. I'll probably get promoted. So like I'm going to do that. It's like, ah, but that totally does happen quite often. By the way, this is when a system is like this, it's in what I would call a super critical state where every individual person actually disagrees with the overall direction, but the overall System keeps on moving in one direction. These are can have massive upheaval with the right inciting incident.)
- Time 0:53:50
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(highlight:: The Challenge of Establishing a Coherent and Plausible North Star
Transcript:
Speaker 1
Yeah, and so in practice actually, you, this is why you don't just have a slime mold. You also have to have a north star that everyone is pointing off of that is actually plausible, coherent and good. And so like if your north star is pulling you off over a cliff, like it's a bad north star, it's bad. Those north stars are very hard to move, especially in bottoms up organizations and often the north stars are coming from the top down and like this is the official plan and we're going This way. It's like, okay, but everybody knows that this doesn't work. So that's actually having a plan that is official that everybody pretends that they believe, but actually nobody believes is worse than having no plan at all because now you're kind Of it's very hard to reconfigure. It's very hard for some of the bottoms up stuff to do little local experiments that pulls it in a different direction. So in practice, you get this kind of this worst of all worlds kind of thing. So like I agree that like if you don't have some kind of coherent plausible north star that everyone is sighted off of, a sign will by itself just it goes that and kind of explores into everything And does nothing. It can't coordinate anything. So you do need them to be pointing in a similar direction to get better things coming out of it. I think that people often think that those directions, those north stars have to be a lot more planned, a lot more like top down, you know, exactly features all planned and a big spreadsheet That's been coordinated in the massive planning process than people actually, then it needs to be. I have rarely seen organizations in my experience, my personal experience, but also talking to lots of folks, mother industries who have reached out where the north star is actually A good one. It's really, really, really hard to do a north star that is plausible and good, a good outcome.
Speaker 2
Why is that? It's not intuitive to me why it's so hard to do.
Speaker 1
A lot of the constraints are not obvious. They are hard to get to make legible to a lot of people. So one of my rules of thumb is the way I look at this is if you just had a north star and you had no plausible path there, well, you're going to end up designing castles in the sky where you go To build them and go, oh, wait a second, gravity, it doesn't work. And if you only explore through your adjacent possible, then you're going to get going, and just kind of exploring in no way in a direction. You need to have a balance of both.)
- Time 0:56:29
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(highlight:: What is the Adjacent Possible How Does It Relate to Organizational Strategy?
Transcript:
Speaker 1
So adjacent possible is this notion of the set of actions that you as an entity or a person as an organization, instead of actions that you might plausibly take in the next turn and in the Next short term. So after you resolve all the different constraints around you about what things might you might plausibly be able to do your power dynamics in the organization where you currently Are what people currently believe, your adjacent possible is a set of actions that you can actually that you can actually choose from. And adjacent possible are often way smaller than people think they are. So a lot of plans kind of say, and then we're going to do this massive thing that we're going to ship in three months. And it's like, no, wait a second. It is definitely not in the adjacent possible. That's going to take us four years to do or whatever. So your days and possible are often much smaller than people think they are. But the critical thing is once you pick an action in your adjacent possible, your adjacent possible shifts, because you are now in a different spot. Like, okay, cool, we wrote the code for that thing. And now we have a different sort of actions available to us. And so if you cite through what you want is your, your iterated adjacent possible, do you have a smooth path that could plausibly deliver you towards your north star? So in practice, people have these like heroic things that will just magically force of will themselves quite far into the massive jumps forward, which are basically not possible in Practice. And I would argue, I would argue for various like fundamental reasons. But that's one of the reasons it's so hard is people go, that sounds like incrementalism. And it's like, yeah, fine, sure. But directed incrementalism is the way that basically anything interesting happens in the real world.)
- Time 0:58:42
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(highlight:: Balancing Specialist and Generalist Roles To Increase Organizational Agility
Transcript:
Speaker 2
So another thing I think about when I think about why organizations slow down as they get larger is that people specialize more. And so you imagine you're a startup founder, maybe you have a co-founder and you kind of have to do everything. And then you hire maybe a few people and then maybe they are taking some of the things off your plate. But you're still doing a ton of things and they probably also are doing way more things than they would be doing in a larger organization. And then when you get to a really larger organization like Google, you might literally have a person whose job is to handle just one page on one particular product that's super, super Specialized. And it makes sense because if you're Google scale changing a button actually could have like massive consequences. In fact, it could affect millions of users, right? If you're a tiny startup, like focusing on optimizing just one little button or one little feature probably doesn't make sense because there's just so many important things to do that Are like kind of are going to have more impact at that level. And so because at larger organizations you get increasingly smaller and smaller focuses, it means that sort of everyone is responsible for like less and less. And so it's like hard to take large actions because like if your whole domain is just this little thing, how are you going to like move the whole organization?
Speaker 1
Yeah, that totally tracks to me as well. I think of this as like one way of looking at specialization in that context is a form of structure, the form of structuring the problem to some degree. Okay, you're going to be responsible just for the precise drop shadows of this button or whatever. And structure is a liability. It allows you to go faster and be more efficient. But it also means that if you need to change direction, it's now a liability that makes it harder to change direction. And the more that you would create this structure, at each point it's like, oh, let's make this thing that we're doing slightly more efficient. Yeah, that's totally for sure. But then if the world changes, if the context changes and it will definitely change because the context that you are in is always changing based on what your users are doing, based on What your competitors are doing, based on what technologies are there, based on what you know, global pandemic, it kind of is always changing. And that means that that structure will be really, really hard to get out of because everyone will kind of snap back into that exact sort of specialization. I think that generalists are super useful in these kind of contexts. And you can think of it maybe like a balance. What's the balance of the overall amount of specialist versus generalist that you have across your entire organization? So to your point, you know, it's mostly generalists at the beginning for small startups because you got to be. I mean, you got to be wearing multiple hats. As you get to a larger and larger organization, it gets more specialized. But how can you inject a little bit of randomness into that? And so you get this naturally when people move across the company. So if you encourage, yeah, hey, after you spend a year or so on your project, yeah, it's kind of totally fine for you to go find another project within a company if you want. That's something that you shouldn't feel embarrassed about. Something that's great. And that allows you to have a little bit of cross pollination, a little bit of these ideas flowing through the system and slowly changing it over time. You also sometimes find there will be a departure of a lead that kind of, whoa, hold on. People is a big shock to a system. Those shocks can cause them to kind of those systems to reconfigure and go into a little state of chaos for a bit, but then re-a needle maybe into a interesting other shape. So I think that encouraging that kind of like people to dabble, to be a little bit more generalist, to switch to things that are, ah, it's kind of outside my existing wheelhouse. Maybe I'll switch to a role that does that. Is it really useful to do it? I think it was GE that famously had this program that would deliberately cross-pollinate a small number of people across very disparate business units as a way of injecting kind of That structured noise. And you can think of 20% time in a similar way of like deliberately inducing or injecting a little bit of structured noise kind of.)
- Time 1:02:25
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(highlight:: Coordination Challenges Grow Superlinearly Based on Required Information Throughput
Transcript:
Speaker 2
Why fundamentally do organizations get slower, and then we'll go into talking about what the right solutions are.
Speaker 1
I think this is one of those problems that shows up. People assume very often it's like, oh, it must be somebody who gets lazy or there's some villain. It happens even if you assume absolutely everybody is very good at what they do, very hardworking, very collaborative. It arises for almost a fundamental reason due to the shape of networks. In the way that people have to coordinate across many different priorities they could be working on that has a very fundamental super linear acceleration. I think hardest about it, honestly, is it shows up just because there's inherently uncertainty. There's different information that different people have in it, and the conditions are changing pretty often. That makes it extremely hard to coordinate. The amount of effort it takes, the overhead it takes to coordinate can become a huge portion of the underlying effort. That just makes everything significantly harder to do.
Speaker 2
Let's compare a startup to a large organization. Is the idea that in a small startup, let's say there's only two people working on it, all the information is already in their heads about what they need to do. Whereas in a large organization, maybe 10 or 15 or even more people have to coordinate in some way in order to get the task done?
Speaker 1
Yes, so there's both the amount of people that are already pre-share the same information or share context or trust so that they can share information that you have to see a full picture Of it. Then it's also just something where you have to communicate with lots of different people across the team. It goes up kind of sort of with the square of the number of people in that team. As teams get larger and larger and larger, it just goes up at a super linear rate. It gets worse when you're working with lots of different people across many different teams.)
- Time 0:01:58
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(highlight:: 1min Snip
Transcript:
Speaker 2
Let's compare a startup to a large organization. Is the idea that in a small startup, let's say there's only two people working on it, all the information is already in their heads about what they need to do. Whereas in a large organization, maybe 10 or 15 or even more people have to coordinate in some way in order to get the task done?
Speaker 1
Yes, so there's both the amount of people that are already pre-share the same information or share context or trust so that they can share information that you have to see a full picture Of it. Then it's also just something where you have to communicate with lots of different people across the team. It goes up kind of sort of with the square of the number of people in that team. As teams get larger and larger and larger, it just goes up at a super linear rate. It gets worse when you're working with lots of different people across many different teams. If you sometimes work with, okay, this team of 15 people, and then you also work with this other team of 40 people, that makes it even harder for this effect.)
- Time 0:02:54
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(highlight:: How the Fundamental Attribution Error Impacts on Trust and Coordination in Large Orgs
Transcript:
Speaker 2
So going back to the main thread, you were mentioning at the fundamental attribution error, you want to tie that in with the sort of issues of large companies operating slowly?
Speaker 1
Yeah, it just, I think that it is when everybody's working really hard in these large organizations, everybody's, you know, got 150% of like their overcapacity. They don't have time to think about it. It's really easy for people to jump to the conclusion of, oh, that other team, those people just don't care enough or they're just trying to get out of extra work or they just don't understand X. It's really easy to jump to that conclusion. What a convenient conclusion of, oh, it's the other person's problem. And so that creates that leads to this almost default state that if you aren't careful, you'll lead to lack of trust. And then over time that will compound, it will get worse and worse and worse and worse. And an ambiguous environment is fast moving. If you're already looking, already assume it's so another team or another person isn't going to do a very good job, you'll find all kinds of signal in the ambiguous, you know, cloud of All the ambiguous stuff that's happening that will reaffirm that hypothesis. So it's really easy to get stuck in this trap where people aren't trusting one another across the large organization.)
- Time 0:13:16
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(highlight:: Tradeoffs Between Top-Down v.s. Bottom-Up Organizations
Transcript:
Speaker 1
There are it's not like there's one true answer. Like bottom up organizations are extremely hard to find interesting shelling points or other coordination mechanisms. So you get kind of this wild, very challenging to predict where exactly it's going to go, but they tend to be much more resilient, much more able to adapt to circumstances way more way Less likely to die as one way of putting it. Whereas top down control can create shelling points very actively, very, very straightforwardly, very cheaply for things accorded around, but they can get very caught off guard By things. I think a lot of things are trade offs, fundamental trade offs that we treat as black and white or there is some right answer. And when you see that basically everything is a trade off, then when to realize it's a trade off, you can start asking yourself, are we contextually at the right balance point right now? Because there is no one true balance point for every context. It is highly contextual. And so then you get a sense less of like, oh, you feel like you're surfing that balance point. Hey, are we a little bit too top down right now or are we a little bit, if we were to choose a little bit too top down or a little bit too bottom up right now, which one would you say? And then if everyone goes, yeah, I feel a little bit too top down right now. Cool. Let's nudge a little bit towards that as opposed to people think of it as being this binary thing, this big, huge shift that has to happen, but doesn't have to be actually can be relatively Small nudges continuously, can keep a system in balance.)
- Time 0:23:09
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(highlight:: Creating Resilient Orgs: Serendipity, Autonomy, and Creative Flexibility
Transcript:
Speaker 2
So what does that look like in practice to actually empower that kind of slime mold-like model inside a larger organization?
Speaker 1
I think it often looks like creating space for serendipity, creating space for a little bit of autonomy. One way looking at this is having, hey, culturally, like Google famously had 20% time. And this is a well-known thing about how it worked. In practice, 20% time was always basically a cultural myth. It didn't really exist. It was always 120% time. But it did two really useful things, in my opinion. One, it allowed space. Sometimes that space people would use it to do things like create a knitting club or something, some kind of social network thing. And a knitting club isn't useful to the company per se, but what is useful is having a high trust, very diverse social network overlay that is different than the organizational structure That makes it significantly more likely the right information flows to the right places at the right time. The second thing that 20% time did really nicely is a lot of things that have tons of indirect value over time are really hard to make a legible case to lots and lots of people succinctly. And I would argue they're fundamentally impossible in many cases. And so what 20% time did in practice is someone could set me working on a P2, a lower priority item. And someone comes over and says, why are you working on that? And they kind of waved their hand and go 20% time. And a number of those things might turn out to be hugely useful and have tons of indirect value down the road. So maybe somebody builds a little prototype where they duct tape together a couple different systems internally just as a hobby project on the side. And so when most people go, wait a second. That actually would be a really good fit for this other thing we have. Or wait a second, we should get that from some users. And then a UXR you realize, oh, wow, this thing is extremely successful, extremely interesting. We should make this a real product. And by having that little bit of space, a little bit of awareness of like, yeah, it's okay culturally for you to be doing a few things that don't fit in the broader plan that creates the Possibility of these little seeds to be planted by people that might plausibly grow into something really interesting.)
- Time 0:26:36
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(highlight:: Leveraging Serendipity: Give People Space and Time to Explore Their Intrinsic Motivations
Transcript:
Speaker 1
One thing that plays really important, when people have intrinsic motivation, oh my gosh, it's unstoppable. It's amazing. They get in these flow states to do all kinds of cool stuff. When it's extrinsic motivation of like, well, you have to do this to get promoted, it really messes with it. And you get like much less value out of it. So like, my rule of thumb was don't try to make people have extrinsic motivation on the things I cared about. Look for the people whose intrinsic motivation was already roughly pointing in the direction I believed was somewhat interesting and give them a little bit of encouragement. Fan the flames. Say, wow, what a really cool, that's a really neat thing that you just wrote up. I wonder how that fits in with this thing or you should go talk to this other person who has a similar idea. Maybe the two of you can collaborate on something. That was a very different approach. Even the downside to this, by the way, is when it's working really well, it just looks like luck. So when you have these miracles happen, people go, oh, you just got lucky. And it's like, well, kinda, yeah, but on a meta level, I've been sarcastically increasing my luck surface area. So like, likelihood that I have a lucky break is significantly higher than if I didn't do this.)
- Time 0:36:07
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(highlight:: Increasing Luck Surface Area: Let People Indulge in Their Curiosities
Transcript:
Speaker 2
But what are some other ways you're thinking about increasing this luck surface area?
Speaker 1
I think a large portion of it is a lot of innovation, I think, comes from people combining existing stepping stones, existing ideas into novel combinations. In the more diverse those things are, the farther I feel those existing stepping stones are that are duct-tipped together, the more likely the insight or the innovation is significant And game-changing. So a lot of it really does come down to allow people to indulge, do things that feel self-indulgent about like going down rabbit holes that they're super into or doing these kind of extra Curriculars or hobby projects. A lot of it really does come down to that. And I think that it sounds so simple, it's like, that can't possibly be it. I don't know, that's certainly what I found is creating situations where people feel that they're able to thrive, that they're able to not try to be a cog in a machine, but rather to be The best versions of themselves and to lean into the things that makes them weird. Like, I think that people look at weirdness in a large organization. Weirdness is bad. Weirdness means that you don't fit in, that you don't want to measure you. The weird stuff is where all the cool things happen. And so I kind of encourage people to be like, what is the thing that makes you weird in a positive way? And like, lean into that. Like, don't be ashamed of that. Like say, yeah, I'm kind of a weirdo about this thing. I'm really into board games. I'm really into this dabbling with this kind of thing. Cool, great. Like, lean into that and find other people who might find interesting combinations with that.)
- Time 0:37:31
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- [note::Reminds me of "all truth and beauty come from the union of the unlike"]

(highlight:: Doorbells in Jungle: A Portfolio Approach to Experimental Product Development
Transcript:
Speaker 2
So it's fair to say that this idea is around, if you're not sure whether to do something, instead of debating it endlessly, do some really cheap version of it that allows you to essentially Like assess the demand. And it doesn't even have to be optimized to, you know, get people to use it. You can just like wait around and see if people do use it. And as long as it's cheap enough to put it out there, the cost effectiveness could still be really good.
Speaker 1
Yeah, exactly. And then crucially, the other thing you want to do is any one of these doorbells that you put in the jungle, like you've got to climb through the jungle to get there. Like there's very low likelihood that actually that someone does that. So one is a diversity of them. You want them in lots of different angles, lots of different directions. They're almost like a sensing network for you. So you want to sense where the demand is. And that allows you to be in a reactive position to it as opposed to proactive position. So you don't want to just do one. You want to do a number of these of various forms, you know, in different directions.)
- Time 0:42:28
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(highlight:: Individual Incentives Disincentivize Complexity-Based Approaches to Product Development
Transcript:
Speaker 2
So why don't organizations do this more often?
Speaker 1
I think it's funny, a bunch of these approaches are extremely repeatably successful. We work really, really, really well in a number of contexts. And they have pretty large returns and generally like very positive returns. I think the reason that they aren't done is it feels so backwards. It feels like instead of saying, well, I have a plan and like, you know, my plan is really well researched and we're going to heroically execute on this plan and I figured out exactly what's Going to happen in the next five years. You're saying, I don't know. I don't know what's going to happen. And that requires vulnerability. It requires you to say, I don't know what's going to happen specifically, but I trust I'm confident that this will lead to good outcomes for us in general. And honestly, if you're someone new in your career, for example, and you say this people like, what the heck are you talking about? Like, are you just trying to get at like the way that we always do it is we come up with a plan. We have spreadsheets tracking the plan and interdependencies and then we actually get on that plan and you have to have some, you know, quote unquote strategy behind it. I think that strategies are often better versions of them are meta strategies. These kind of meta approaches that you can take that give you positive exposure to luck. But they again, you know, I mentioned earlier that when you do these kinds of patterns in large organizations, when it works, people go, oh, you just got lucky. So it's really hard to get promoted for these in organizations. How can you make it legible that you didn't just get lucky that you had actually structurally increased the likelihood of this kind of luck happening? You can't run the counterfactual and that's why it's so much simpler to say, look, we came up with a plan, we executed on the plan, we shipped that thing. Give me a promotion. It's like, but you don't know if you did a good thing that users actually want or that's going to have a ton of usage. So I think it's just it requires you to acknowledge that you don't know to lean into this sort of indirect value in a way that's really hard for people to reward or acknowledge in a very Concrete way. And so I think there's like, it's like the world tilts in a certain direction. It tilts towards more concrete, more specific, more plans than it should. And it requires you to put in some effort to tilt the world in the other direction. But then that's going to mean that you're going to stand out a little bit as an oddball.)
- Time 0:43:18
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(highlight:: Pluralistic Ignorance in Organizational Strategy
Transcript:
Speaker 1
I've seen this at many places in these larger organizations where you actually talk to everybody individually in a trusting one-on-one environment where you're being very authentic And candid about about what constraint you see. And absolutely nobody believes that the overall strategy is coherent or good or moving in a good direction. And yet the entire system is moving in a direction that like is to one direction. It's like, wait a second, the, if you play that forward, doesn't that get us almost without question to jump off a cliff? Like that's, that way doesn't work, right? He can convince every person, individual person behind the scenes. That's true. And we go, well, shouldn't your product be different than like your sub feature in this product? They go, listen, I'm not going to change this entire ship. I'm not going to do this entire ship. And if I go and do something totally different that goes at that bucks the trend and goes in the direction, yeah, we probably all would individually agree as the right overall direction. What's going to happen is I'm going to be fighting upstream the entire time to everybody. It's probably going to fail and I definitely won't get promoted. Whereas if I add ship a feature inside of this bigger system, this whole ship that doesn't actually make it, is going in direct, it doesn't make any sense, then like it's totally legible To the best of the organization. I'll probably get promoted. So like I'm going to do that. It's like, ah, but that totally does happen quite often. By the way, this is when a system is like this, it's in what I would call a super critical state where every individual person actually disagrees with the overall direction, but the overall System keeps on moving in one direction. These are can have massive upheaval with the right inciting incident.)
- Time 0:53:50
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(highlight:: The Challenge of Establishing a Coherent and Plausible North Star
Transcript:
Speaker 1
Yeah, and so in practice actually, you, this is why you don't just have a slime mold. You also have to have a north star that everyone is pointing off of that is actually plausible, coherent and good. And so like if your north star is pulling you off over a cliff, like it's a bad north star, it's bad. Those north stars are very hard to move, especially in bottoms up organizations and often the north stars are coming from the top down and like this is the official plan and we're going This way. It's like, okay, but everybody knows that this doesn't work. So that's actually having a plan that is official that everybody pretends that they believe, but actually nobody believes is worse than having no plan at all because now you're kind Of it's very hard to reconfigure. It's very hard for some of the bottoms up stuff to do little local experiments that pulls it in a different direction. So in practice, you get this kind of this worst of all worlds kind of thing. So like I agree that like if you don't have some kind of coherent plausible north star that everyone is sighted off of, a sign will by itself just it goes that and kind of explores into everything And does nothing. It can't coordinate anything. So you do need them to be pointing in a similar direction to get better things coming out of it. I think that people often think that those directions, those north stars have to be a lot more planned, a lot more like top down, you know, exactly features all planned and a big spreadsheet That's been coordinated in the massive planning process than people actually, then it needs to be. I have rarely seen organizations in my experience, my personal experience, but also talking to lots of folks, mother industries who have reached out where the north star is actually A good one. It's really, really, really hard to do a north star that is plausible and good, a good outcome.
Speaker 2
Why is that? It's not intuitive to me why it's so hard to do.
Speaker 1
A lot of the constraints are not obvious. They are hard to get to make legible to a lot of people. So one of my rules of thumb is the way I look at this is if you just had a north star and you had no plausible path there, well, you're going to end up designing castles in the sky where you go To build them and go, oh, wait a second, gravity, it doesn't work. And if you only explore through your adjacent possible, then you're going to get going, and just kind of exploring in no way in a direction. You need to have a balance of both.)
- Time 0:56:29
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(highlight:: What is the Adjacent Possible How Does It Relate to Organizational Strategy?
Transcript:
Speaker 1
So adjacent possible is this notion of the set of actions that you as an entity or a person as an organization, instead of actions that you might plausibly take in the next turn and in the Next short term. So after you resolve all the different constraints around you about what things might you might plausibly be able to do your power dynamics in the organization where you currently Are what people currently believe, your adjacent possible is a set of actions that you can actually that you can actually choose from. And adjacent possible are often way smaller than people think they are. So a lot of plans kind of say, and then we're going to do this massive thing that we're going to ship in three months. And it's like, no, wait a second. It is definitely not in the adjacent possible. That's going to take us four years to do or whatever. So your days and possible are often much smaller than people think they are. But the critical thing is once you pick an action in your adjacent possible, your adjacent possible shifts, because you are now in a different spot. Like, okay, cool, we wrote the code for that thing. And now we have a different sort of actions available to us. And so if you cite through what you want is your, your iterated adjacent possible, do you have a smooth path that could plausibly deliver you towards your north star? So in practice, people have these like heroic things that will just magically force of will themselves quite far into the massive jumps forward, which are basically not possible in Practice. And I would argue, I would argue for various like fundamental reasons. But that's one of the reasons it's so hard is people go, that sounds like incrementalism. And it's like, yeah, fine, sure. But directed incrementalism is the way that basically anything interesting happens in the real world.)
- Time 0:58:42
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(highlight:: Balancing Specialist and Generalist Roles To Increase Organizational Agility
Transcript:
Speaker 2
So another thing I think about when I think about why organizations slow down as they get larger is that people specialize more. And so you imagine you're a startup founder, maybe you have a co-founder and you kind of have to do everything. And then you hire maybe a few people and then maybe they are taking some of the things off your plate. But you're still doing a ton of things and they probably also are doing way more things than they would be doing in a larger organization. And then when you get to a really larger organization like Google, you might literally have a person whose job is to handle just one page on one particular product that's super, super Specialized. And it makes sense because if you're Google scale changing a button actually could have like massive consequences. In fact, it could affect millions of users, right? If you're a tiny startup, like focusing on optimizing just one little button or one little feature probably doesn't make sense because there's just so many important things to do that Are like kind of are going to have more impact at that level. And so because at larger organizations you get increasingly smaller and smaller focuses, it means that sort of everyone is responsible for like less and less. And so it's like hard to take large actions because like if your whole domain is just this little thing, how are you going to like move the whole organization?
Speaker 1
Yeah, that totally tracks to me as well. I think of this as like one way of looking at specialization in that context is a form of structure, the form of structuring the problem to some degree. Okay, you're going to be responsible just for the precise drop shadows of this button or whatever. And structure is a liability. It allows you to go faster and be more efficient. But it also means that if you need to change direction, it's now a liability that makes it harder to change direction. And the more that you would create this structure, at each point it's like, oh, let's make this thing that we're doing slightly more efficient. Yeah, that's totally for sure. But then if the world changes, if the context changes and it will definitely change because the context that you are in is always changing based on what your users are doing, based on What your competitors are doing, based on what technologies are there, based on what you know, global pandemic, it kind of is always changing. And that means that that structure will be really, really hard to get out of because everyone will kind of snap back into that exact sort of specialization. I think that generalists are super useful in these kind of contexts. And you can think of it maybe like a balance. What's the balance of the overall amount of specialist versus generalist that you have across your entire organization? So to your point, you know, it's mostly generalists at the beginning for small startups because you got to be. I mean, you got to be wearing multiple hats. As you get to a larger and larger organization, it gets more specialized. But how can you inject a little bit of randomness into that? And so you get this naturally when people move across the company. So if you encourage, yeah, hey, after you spend a year or so on your project, yeah, it's kind of totally fine for you to go find another project within a company if you want. That's something that you shouldn't feel embarrassed about. Something that's great. And that allows you to have a little bit of cross pollination, a little bit of these ideas flowing through the system and slowly changing it over time. You also sometimes find there will be a departure of a lead that kind of, whoa, hold on. People is a big shock to a system. Those shocks can cause them to kind of those systems to reconfigure and go into a little state of chaos for a bit, but then re-a needle maybe into a interesting other shape. So I think that encouraging that kind of like people to dabble, to be a little bit more generalist, to switch to things that are, ah, it's kind of outside my existing wheelhouse. Maybe I'll switch to a role that does that. Is it really useful to do it? I think it was GE that famously had this program that would deliberately cross-pollinate a small number of people across very disparate business units as a way of injecting kind of That structured noise. And you can think of 20% time in a similar way of like deliberately inducing or injecting a little bit of structured noise kind of.)
- Time 1:02:25
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