S2E17 – Exploring the Territory with Douglas Squirrel

Show Notes

 This episode of the TTL podcast features Douglas Squirrel, an expert in making tech teams insanely profitable. The discussion delves into David Snowden’s Cynefin framework and the concept of entangled trios for navigating complex situations by leveraging diverse perspectives. Mon-Chaio, Andy, and Squirrel cover various tactics for tech leadership, including encouraging exploration within product design and the importance of external communication for generating novel ideas. By drawing parallels with historical explorations like Lewis and Clark’s expedition and examining modern examples like Roblox and LEGO, the episode elucidates ways in which tech leaders can foster an environment of innovation and experimentation within their teams.

Squirrel​ has been coding for forty years and has led software teams for twenty. He uses the power of conversations to create dramatic productivity gains in technology organisations of all sizes. Squirrel’s experience includes growing software teams as a CTO in startups from fintech to biotech to music, and everything in between; consulting on product improvement at over 200 organisations in the UK, US, Australia, Africa, and Europe; and coaching a wide variety of leaders in improving their conversations, aligning to business goals, and creating productive conflict. He lives in Frogholt, England, in a timber-framed cottage built in the year 1450.



Andy: Welcome to another episode of the TTL podcast. We have Douglas Squirrel with us today. He is an expert in making tech teams insanely profitable. And Squirrel and I actually have a long history. He was the first CTO I had when I worked in London.

And now he’s gone off and he’s done what he did at that company. He’s multiplied it several times and, and he’s now doing that for anyone who will hire him. Well, that’s

Douglas Squirrel: Yeah, not anyone.

Andy: won’t just take anyone.

Douglas Squirrel: Give me credit here.

Andy: Yeah, yeah.

Douglas Squirrel: Discerning customers only need apply.

Andy: Yes, discerning customers. Yes, you want customers who actually want to take your advice and change.

Douglas Squirrel: That helps.

Andy: Yeah., Before we dive into our topic, do you want to introduce yourself a little bit so that I don’t continue to butcher , who you are?

Douglas Squirrel: I’d be happy to. So, I’m not butchering anything at all. So, the brief version of Squirrel is that I’ve been writing code for 45 years. I’ve been some kind of senior technical leader for 25 of them. And the first few, which included the one where I was Andy’s CTO, I kept getting fired. And I got fired in this really nice way, where the founder would come to me and say, Squirrel, you’ve built this amazing team, and they’ve got a fantastic leader, and they’ve got a great direction to go, and everything seems to be ticking along and there’s not much for you to do.

And you’re expensive, so would you please go be wonderful somewhere else? And I, I really enjoyed getting fired that way. It felt really good. But I figured the third or fourth time that maybe I should plan for it. So what I did at that

Andy: It does sound like a very nice

Douglas Squirrel: very comfortable. But I got the point.

That I was actually a person who was good at setting things up, making them run well, and getting the heck out of the way. And so I started doing that as a fractional CTO, so I’d work with multiple companies but three, four days a week with each, and over a long period. And then I’ve just got faster and faster, so the, the pattern has always been that I, I try to do the next one significantly faster than the one before.

And I’ve, I’ve settled around three months. As a typical duration, but for the kind of transformation work, coaching work, strategy work that I do for companies. And my record, however, is three weeks. I had one extremely motivated person I was coaching. We got him to a completely different level because he worked very hard and met me every day and did all the homework.

But I don’t promise that. So my goal is to transform organizations as quickly and effectively as possible, leave a lot of skills behind, and help a lot more. And so far I’ve done that for over 200 different companies around the world.

Andy: Nice. And now we’re going to be talking about something related to transformation and quickly and effectively doing that. Which is David Snowden, and his ideas around entangled trios, and then wherever the entanglement takes us.

Douglas Squirrel: Excellent. Yes, Snowden is an amazing guy. Your listeners might know him from a framework called a framework that’s hard to pronounce. I’m gonna test you guys. Do you know how to pronounce it?

Andy: Yeah, I do.

Mon-Chaio: I think

Douglas Squirrel: Give it a try.

Mon-Chaio: we give it a go? Is it Cah nevin?

Douglas Squirrel: got it. Perfect.

Andy: it is Kinevan.

Douglas Squirrel: good. You can speak Welsh. Dave likes to give strange names

to things.

Andy: We have, talked about the Cynefin framework a little bit. It’s, it’s a very useful framework for, for talking about what kinds of approaches might be reasonable in different

Douglas Squirrel: You got it. So the next time you come up with a framework, either of you, and I’m sure you’re going to come up with great ones, please do not use Welsh to name it, so that people will actually remember it and they know how to Google it. Okay? Can you promise me that?

Andy: At least he isn’t using the double L or double

Douglas Squirrel: don’t get

Andy: which I don’t know if any non Welsh people can

Douglas Squirrel: No, that’s completely hopeless. So, if any listeners don’t know about the Cynefin framework, very briefly, it has four quadrants. There’s more. Snowden keeps adding things. Just ignore that. And the four quadrants tell you how to behave in different types of situations. In a simple situation, everybody knows what to do it’s very well known how to act.

That’s like driving your car. I can drive my car even though I don’t know where the engine is. But if a situation is complicated, then experts know what to do, but ordinary mortals probably don’t. And that’s the situation where you have an F1, Formula 1 car, and there you can get somebody like Lewis Hamilton to sit behind the wheel, and he knows what to do, but you put me in there, I won’t be able to find the gear shift. So, that’s the world of complicated. In the complex world, there are rules, but nobody knows what they are. There are no experts that you can rely on. That’s and that’s the world that I think we’ll talk most about here because you have to do a lot of probing. You probe, you sense, you respond, you do something else.

And then the final, and that’s like a test pilot who goes up in an airplane that no one has ever flown before. It’s just been in a wind tunnel. And when she turns it left, it might turn right. He moves the wheel left and it turns right or spins or blows up. And you don’t know that until you try it.

The final area is chaos. And in chaos, there are no rules. There is no connection between what you do and the results. And the only thing you can do is act randomly. And an example of that is an airplane in a tailspin. The control surfaces aren’t acting you, you, you really can’t do very much. You better figure out a way to bail out or something that you can do to shock the the system back into so one of the other quadrants. So I, I hope those

Andy: as fast as you

Douglas Squirrel: exactly. Yeah. ’cause you want to get out of the tailspin. That, I hope the, that kind of brief summary will set us up for what we want to talk about today, which is snowden’s new ideas about how to explore those quadrants.

Andy: Yeah. So, so let’s, let’s dive into that. The one we started with, and I don’t know what others went into. I, I started with Snowden and then I went off into ethnography and other things.

Douglas Squirrel: Because you’re you, Andy.

You can’t stop yourself. That’s great.

Andy: yeah, yeah. The one, the one we started with was entangled trios. Mon Chiao or Squirrel, do you want, one of you want to give us a quick rundown of what he meant by entangled trios?


Douglas Squirrel: Chaio, why don’t you do it? Because, because I brought it to you, but then I went in a different direction myself too, so go ahead.

Mon-Chaio: So in some ways the three of us might be considered entangled trios. And so you all can correct me in my sensing of how I explain entangled trios. So the way that I would explain it roughly would be that they’re, well the trios would be three people.

And they all come from different points of view. I think Snowden generally says one should be an expert another should be more of an operator and a third should be maybe more Connected to the business or customer side something around that end Where when they get together because they have different points of view they can offer a Better impact than each individually alone could offer

Douglas Squirrel: And another example of that, that I found evocative and has been helpful to me in understanding it, is a case where, for a local government, Snowden and his merry crew got together and arranged trios of grandparents teenagers, and local government officials. And these trios would go and explore and try new things, which I’m sure we’ll talk about, and brought, talk about different perspectives, right?

A teenager sees the world very, very different from somebody, differently from somebody who’s 70 or 80 or 90. And by getting those people together with someone who had some local power, who had some knowledge about what things were possible, and giving them a small budget, they discovered a lot of initiatives and a lot of things that the local government, who was the client, could do.

A lot of optionality that they had, that they hadn’t thought of before. And I think that’s the crucial thing. What Snowden is trying to help us to do is to explore the complex quadrant, where you don’t really know what the rules are, and you want to probe, but how do you probe?

Andy: And there were a few things about how you probe that caught my eye. So one was that in the setup of the Entangled Trio, you need to pick an incentive. You need to pick some sort of motivating thing that keeps people participating and active in it. It doesn’t just magically happen. And the other one was that it’s not always the trio. That he also, he says, actually you don’t even need three. You can do it with two. You can do dyads. And that also that the dyads may change because you’ve got three people, so you may have, you have two different trio. Two? Three different dyads. I just had to do the quick math in my head. You have three different dyads, three different group pairs of people, and as they work on their problem, they’re not always going to be together in those threes.

They’ll might, they might split off into those twos, and one of them might even go, just go away for a while. And that, that’s part of the, the mechanism as well. Those, those times of being separated as well as coming

Douglas Squirrel: So, so what Snowden is really bringing together here is two of his ideas and as, as usual they have at least one of them has a kind of whimsical name. What he’s doing is he’s bringing together estuarial thinking that’s thinking like an estuary. I’ll explain that in a second.

He’s bringing that together with the idea of safe to fail probes. And, and as he brings those both together, he, he gets these kind of trios. But he’s not attached to the idea that, that There, there have to be three of them, which is another very Snowden kind of thing to do. He’s not, he’s not very precise.

He doesn’t keep things the same. He wants them shifting around. Which is the idea of estuarial or estuary, estuarine thinking. I may be saying these things wrong. I’m learning about this stuff as we go too. But if, if you have an estuary, that’s a, an area at the end of a river that is not a delta. In a delta, the river actually splits up into different pieces.

An estuary is all water. And, and not kind

of land around. I think I’m saying this right. If any folks who are geographers are welcome to correct me. But the idea of the estuary for Dave is that it’s tidal. So there’s water flowing in sometimes and it’ll move around in a surprising direction and kind of flood a little area.

And then there’ll be a tide that goes out, and so, some land will be exposed, but it’ll only be exposed at low tide. And the, the,

notion that

Andy: the Thames, around London is

Douglas Squirrel: has an estuary, that’s a perfect example. And it’s the area at the mouth, so it wouldn’t be the part at London, but it’s the part where the Thames flows into the, the, into the sea.

And the point is that you get eddies, and you get things moving in all kinds of different directions. It’s not like the river has a single flow that goes one direction and all the water molecules head west. What actually happens are in the Thames case, east. You’ve got some that are heading northwest some of the time, and some that are heading southeast, and then they’ll go southeast, and they’ll go southwest, and then they’ll go north, and then they’ll go down, and then they’ll go up.

And because there’s a lot of moving around in lots of different directions, you get an awful lot of movement of silt, and of material that’s in the water, and so on. So, if I understand it right, Dave’s idea is what you want when you’re exploring the complex domain is exactly that lots and lots of motion in lots of directions, lots of eddies in the, in the flow.

And that ties in very nicely to these entangled trios, which may explore in all kinds of different directions. And because there are three of them, they have lots of different influences that might take them in to explore. In the, the local authority example, they might some of them might explore.

Fun things for kids to do in the evening so the city center is safer. They might look for improved policing. They might look for better parks. So they might explore all of those different possible projects rather than somebody saying, we’re part of the better fire service initiative.

We’re going to think about how to prevent fires and that’s the only thing we’re doing.

Andy: Now that, that was a lot of interesting talk about rivers. How do we bring this back to software development? What, what does that, what does this mean for a company or a group that’s trying to run a, a engineering team? How do they, how do they take rivers and turn that into leadership?

Douglas Squirrel: me suggest a not very river like example. And that is a company called Roblox. Do either of you perhaps have kids or know people who play Roblox? Or is this a complete mystery to you?

Mon-Chaio: No my kid plays

Andy: You, okay. I’ve, I’ve heard of it, but I’ve never

seen it.

Mon-Chaio: And when I was working at Meta it was one of the one of the competitors to their metaverse idea.

Douglas Squirrel: Oh, sure. So can you tell me what sort of words, what’s not the metaverse side but the the founding principle? How does Roblox work? How does it make money? Do you know? And you probably know more than me. So you can tell me in our listeners.

Mon-Chaio: I only have a small idea. So for our listeners who don’t know Roblox, Roblox you could think of as a massively multiplayer environment or game. And what users can do is create their own worlds or create their own games with the mechanics and tools that are offered by Roblox. Now most of those environments end up being free but then there’s also

micropayments and things that you can buy within those environments and games. And so as a player you go in and you have a whole set of things that you can look for. You say, oh I want to play the pizza making game, or I’m interested in animal adoption, or there’s, there’s quite a large number of these.

Douglas Squirrel: Key thing there is that users can create the experiences, or the games, I think they call them experiences, and encourage people not necessarily to try to have something that you can win, that you can just go make pizzas all day and have a fun experience. But the, the point of that is, you can go in and with a programming language create a game. Roblox really encourages people to do that in lots of ways, they make it easy to do, they promote it heavily and so on.

And the specific reason they want to do that is very similar to something like YouTube, which has user generated content, or any of the other social platforms, but in a slightly different way. Because it might be that I make a video on YouTube, but most people who use YouTube never make videos. Or if they do, that’s very very small. Roblox really is all about the users creating things. And the benefit of that is that they get even more exploration of an unknown territory. What games are fun? So nobody might ever think that a game, I’ll make one up now, a game where you throw rocks at your friend would be, or even better, a real example, a game where you tap the button and you make your bird wings flap and you try to stay in between some pillars that have holes in them.

That’s a game called Flappy Bird that showed up, not in Roblox, but in the Apple App Store. I don’t think Roblox was so popular then. And nobody would think that this was popular. There would be just no way that you could from first principles say, this game, this is going to capture the attention of the world and it’s going to be super duper successful.

But because in that case, Apple and in Roblox is case consciously there, they’re trying to push for this. There’s an encouragement. There’s a force in the direction of exploration, in the kind of entangled trios, probe sense respond way. Try a thing. Failure is just fine.

If you create an experience and only you like it, Roblox isn’t unhappy, you aren’t unhappy. You can go on and make another one. Maybe that one will be the next Flappy Bird. So, it’s safe to fail. There’s nothing wrong with trying it and not getting anywhere. And what Roblox gets is exactly what the Thames gets from having an estuary.

You have, , water and eddies and, and loops and things happening all over the place. Rather than, say, I’ll take Meta, right? So, Meta has lots of user generated content, but all in very, constrained ways. So I can put up pictures of my cat, then I can go to the metaverse and play around, or I can go live with a video or something like that.

There’s certain things that you can do within Facebook, and those might become popular, but there’s not the kind of organized chaos. That you get in something like Roblox. And the benefit of doing that is that Roblox can watch a huge number of different experiments, a huge number of different probes all happen at once.

And the ones that are interesting, guess what? Those get monetized. And YouTube, I think, I look at now, and it’s friends, Instagram and so on. I think of those kind of creator platforms as poor cousins of Roblox because, again, they, they constrain what sorts of things you can try. Whereas Roblox is intentionally making it as open as possible and continue to try to make it more open.

And I don’t know whether they have something like an Entangled Trio. Maybe you could get Roblox’s help with something I’d like to research to, to make something that’s an even better Roblox and an even better experience. I bet if you do well, you’ll you would get some advice and help so that you can become even more successful.

You can get an even better game that makes more money for both you and Roblox. That’s an example within software of a company making their experience, making what they’re selling, their product, really, really friendly to exploration. And as a result, they get a lot of exploration and therefore they find out things that you would never guess in a million years.

Anybody would pay money for or enjoy or visit because they have the, they’ve created that pressure, that encouragement, that opportunity to experiment.

Mon-Chaio: Yeah interestingly Meta does that as well, but in a different way.

Douglas Squirrel: Hmm.

Mon-Chaio: They build platforms. And I would say this is something that we probably don’t want to talk about here. But they build platforms in a way which makes me a little bit uncomfortable at times. Because what they’ll say is they’ll say we’re building this platform that has 18 different possible use cases and maybe more We don’t know if any of them are going to be successful but because we have reach we’re simply going to release this out to the world And people will use it or they won’t or they’ll find new ways to use it and they won’t and after five years maybe we’ll find that there’s portions of this that are monetizable so that makes me very uncomfortable from a customer focus point of view.

Douglas Squirrel: Yeah. What happens to the other 17?

Mon-Chaio: Yeah, they just, they go away, right?

So I think that’s an interesting thing. We can talk about that if we choose. Another path we can go down that I was, I’ve been thinking about with regard to this type of Roblox exploration is when is exploration not good enough? And so I’ll give a couple examples for this, if we want to talk about it.

One is my daughter being a big Roblox user. Very, very few of those experiences are actually great. very much. They’re all in some sort of half finished state, right?

Douglas Squirrel: And, and I, by the way, I’ll say, I think that’s intentional by Roblox. I think they are happy with that. You’re going to say Mon Chaio, why that might not be a good idea, but they, they know that and they aren’t

Mon-Chaio: I, I mean, I would say that that there’s both good and bad to that. But to me it raises the question of when does exploration stop and what is the next step? And what happens if we never figure out the next step or if we let exploration go on too long? Another example that you gave, Squirrel, is the Flappy Birds game, right?

That was a game that was super successful, except none of its clones were ever successful. And so that might be a also an interesting thing to explore about well was it that flappy birds was an exploration and then all of its clones were derivatives? And the exploration had already been done, but nobody understood that that’s what it was So, those are a couple things on my mind, but i’m happy for others to chime in about what other things they’re thinking about what other directions we can take this discussion?

Andy: the Flappy Birds one I think is interesting, Mon Chaio, because it’s like this problem of you try all of these things. How do you know if what just got some traction was purely novelty? How do you tell the difference between just novelty, it was new, and so it got some traction, and this is something that can, can have a future to it.

Flappy birds,

Douglas Squirrel: I have an opinion about that. I’d love for you guys to question me, and for our listeners, too, to get in touch and say, I don’t agree. I’ll, I’m sure Andy and Mon Chaio will say how to get in touch with them. I’ll make sure to do that for me as well, because I’d love to hear different perspectives.

This is an area I’m exploring. But what strikes me about it is we’re in the complex domain. That’s what we’re assuming. Roblox doesn’t know which experiences are going to work, and they’re going to try a lot, many of which will suck. And then they’ll try ones that work. And where we’d like to get is into the complicated domain.

Because if we could get into the complicated domain where there is a rulebook, and we do know what will work, then we can do that again, we can try to even stabilize it further and improve it. But to do that, we’re going to have to have a predictable, repeatable kind of activity. It doesn’t have to be perfectly repeatable, but it has to be clear enough that there’s a pattern.

That we’re really in the, in the domain where we could write down how Flappy Bird works. And the thing about Flappy Bird is, it didn’t work. It wasn’t repeatable. Exactly as you say, Mon Chaio. It’s clones and other things, Flappy Fish, Flappy, I don’t know, Crab, whatever else there was. None of those worked, which means that the mechanism of creating an exciting game that people really want to play, and have fun doing, it isn’t repeatable if you start with Flappy Bird.

Flappy Bird only works once. And once you’ve discovered that, once that piece of exploration is settled, and you’ve, you’ve drawn that into your map, there’s no point exploring that any further, and your exploration in that area can stop. So that’s my suggestion about how you know when to quit in your software or product exploration.

Mon-Chaio: But I think the, the other question I have around that is how do you avoid becoming chaotic by switching between the complex and the complicated domains? I don’t know that I personally have seen a great framework for saying, this is the time to switch and this is the time to stop. And if you’re switching and stopping all the time, that doesn’t allow you to focus, right?

I think, there’s not just flappy birds, but examples abound. about Explorations or what people might have thought were no longer explorations that just stopped working one that comes to my mind is Did you all ever play that trivia game that live trivia game that paid out prizes? That was really popular sort of in 2018 2019.

I think it was called I remember masterminds or something like that

Douglas Squirrel: I missed that

Mon-Chaio: essentially

Yeah, essentially what you did was you logged in every day at noon, or whatever time it was in your time zone, and there was a host who would host a trivia game. And what happened is if you were in the top some number of the trivia answers for that day, You would win a cash prize.

And so it’s elimination right of like people would get eliminated out as they guess the wrong answer And that was super super popular. And then all of a sudden it stopped And people stopped going to that experience and then on the other side, I think a lot about something like apple newton, right?

Which I think many folks would say was ahead of its time But that was an exploration that people said, Eh, it’s not really going anywhere. We productized it, but we had to stop it. But years down the line, it came back in iPad form or whatnot. And so I have these questions around. If you, if you don’t take enough time, you don’t explore for far enough or you explore too far and you’re not executing on trying to make that experience great and someone beats you to it.

So how do we prevent ourselves from falling in any of these traps?

Douglas Squirrel: If I understand it right, the question is, when do we know how to stop and to say, okay, we’re going to switch from probe sense respond into a more linear That’s the term Snowden would use, linear or liminal approach, which is like scrum, that’s going to be headed toward an end, instead of estuarial where there’s eddies going in all kinds of different directions.

Have I understood right?

Andy: Although. Yeah. Although I want to check something because I think this might be really good. I think we might be working from different understandings of the Cynefin domains.


Douglas Squirrel: Tell us, more.

Mon-Chaio: me more.

Andy: Yeah. So Mon Chaio, I’m hearing from you one along the along the lines of it’s a choice about whether or not you’re probing and responding or sense respond, all that.

I don’t remember the exact sequence that he gives. And so Mon Chaio, you’re like, when do we switch from one domain to the other? But Squirrel, you’re talking about it in terms of, well, it’s just, it is the way things are happening, and you’re coming up with all these new ideas, and grasping onto some of them, and holding onto them for a while, and then maybe letting them go.

Does that describe the, the ways that you guys are thinking about it?

Douglas Squirrel: Certainly accurate for me.

Andy: Mon Chaio?

Mon-Chaio: I think it’s accurate for me as well, although I don’t see that they’re different. So maybe if you think they’re different, I’d love to hear how you think they’re

Andy: it’s a difference of choice. It’s a difference of whether or not you have individual choice. And in Mon Chaio, the framing you gave, we have an individual choice about whether or not we’re in one domain or the other.

Douglas Squirrel: Ah, well I think I know the difference.

Yeah, I think I know why we’re looking at it differently. Mon Chaio is focused on what you can do. So you always have a choice about what you can do. And for example there are, folks that we could all think of who are very happily existing in very, very deep in the complex domain.

And they are working in a very linear way as if there is a source of expertise. I’m always having to tell my clients that they can’t say the words best practices. Because somebody will come along and say, well, Spotify have figured everything out. There’s the Spotify model. I just need to structure my team like that and then I’ll be as successful as Spotify.

The problem is Spotify never operated that way. But even more so there’s no reason why your little corner of the complex domain will respond to anything like the exploration that happened years ago in the area of streaming music. It’s in fact, very unlikely that there is an expert to whom you can apply in any form of new software.

I mean, if you’re building a bog standard e commerce website, no reason for you to use any software. Just turn on Shopify. But the moment you start doing something that’s more complicated, like the e commerce site that I was CTO for, where we had 4, 000 new products showing up in the warehouse every week, there isn’t anything off the shelf, and therefore you’re going to be in the complex domain, whether you like it or not, there’s nothing that stops you acting as if you were in the complicated domain and you might win, you might happen to get lucky.

My coauthor, Jeffrey Frederick likes to say, get lucky is always a possible plan. It’s just not the way to bet. So you might get lucky and pick the right direction and something that’s repeatable and you wind up with flappy bird by just dumb chance. But Snowden’s recommendation, and certainly mine, is that you until you are really sure, until you can see something that’s very repeatable, that you can write down in a runbook, that you can follow very reliably, and you can say, this product, if marketed this way, will result in this many sales, and all I have to do is now roll it out to new markets and new geographies and new experiences. Until you’re there, I think you’re in the complex domain, and you better stick with ProbeSenseRespond.

Andy: Right. So, so it’s a thing of the, the domain you’re in is not a feature of the way you want to operate. It’s a feature of the world around you.

Douglas Squirrel: That’s

Mon-Chaio: is correct, but it is also on how, it’s also on how you sense that world, right? Two different people could look at that world and one determine that it is in the complex domain and another determine that it’s in the

complicated domain.

Douglas Squirrel: Indeed, and that’s the source of lots of great business success, is somebody detects some nuance and figures out, Hang on a second. We’ve been renting out movies for a nice long time, and people are very used to going down to their corner Blockbuster. That’s a complicated domain. You just need to understand how do you build Blockbuster, and how do you make sure people rewind before they bring back the videos and stuff like that.

That’s pretty simple. But what if we put them in the post? What if people didn’t have to actually come into the shop? And you know what, in the future we might actually be able to download these movies once that internet thing gets faster. So actually that way of looking at the video market is looking at it as a complex domain.

And a lot of people have been tremendously successful by realizing that something is complex where somebody has found a little corner of it that’s actually complicated.

Mon-Chaio: Right. And I think my question around that is, in my experience, I’ve certainly seen, again, my judgment, right, which is not the it’s not objective truth. It’s simply my judgment I’ve seen places where I think that they live in the complex domain for too long And they should have moved into the complicated domain earlier as well as the other way around where?

People have judged it to be in the complicated domain but it’s more in the complex domain. I think that’s more that’s more that’s less rare than the other one. It’s it’s more frequent

Andy: I want to put a little nuance in what you just said. It’s not that they were in the complicated or complex. That is a fact out there. It’s, it’s that they judged that they were in one or the other, and they behaved as if they were in that one.

Mon-Chaio: Right. Whereas my judgment perhaps was that they behaved incorrectly because I judged their domain to be different than how they judged their domain. But I, I think what interests me is in a, in a podcast titled Tactics for Tech Leadership. How do

we give tactics for this so people avoid that error or do we say, look, it’s not an error.

Anybody can judge it however they want. The important thing is to understand where you judge it to be versus where you what your actions are dictating.

Douglas Squirrel: Well, let me suggest some actions that are, that are fresh from the, the, the thinking of Squirrel. You guys are getting an exclusive here because it’ll be in my newsletter in the next few weeks, and some, some new ideas that are coming out. But I wanted to share them with you first, since you were kind enough to invite me on to talk about this fascinating topic. And I’ll do one of them by describing another historical parallel, but a long, long, long way back further into history. You guys both know, I think two folks named Lewis and Clark. Do you remember them from your history lessons?

Andy: Yep. I’ve even, I’ve cycled the Lewis and clark way

Douglas Squirrel: Oh, did you? Fantastic. Andy cycles everything. I think you probably cycled up Mount Everest, or you will soon. But Lewis and Clark, if for anybody who doesn’t know, are, two they’re mostly military leaders who had a little force that traveled across the United States when that was not something people had done very much at all in the early 1800s.

This is even before the settlers and the wagon trains and so on. And so in this very hostile environment, very complex, right? Nobody had, there weren’t any maps for them to follow. They encountered all kinds of difficulties, which they solved by doing multiple safe to fail experiments. These probes that I’m talking about.

And I’m going to say in a moment what you can do that’s like their action. So I’ll just tell you one story about them. They came to a place. You can go to this place. I would like to go there, maybe, and uh Uh, and check it out it’s called Decision Point. And it’s called that because they were following a river. Some Native Americans had told them, just follow this river, you’ll get to where you want to go. What the Native Americans forgot to mention is that the river forks. It goes in two different directions. There are two rivers there that join together. And they said, well, which way are we supposed to go?

And they couldn’t just phone up the Native Americans back a hundred miles and ask them. They had to figure out which way to go themselves. So what they did is they went both ways, and they split their party, and they sent half of them on one fork and half of them on the other fork, and they didn’t go very far, they just went far enough to figure out if they were on the right river or not, and they came back.

After a few days and said, okay here’s what we observed. And Lewis and Clark between them as the leaders decided to take the South fork, they turned out to be right. The point of that story, the way we can apply that as technology leaders is by taking both forks where we have that opportunity. I had a client of mine phone my Squirrel phone and chat to me about this problem.

He had where he’s making an architectural decision. He says, Squirrel, there are good arguments on both sides of this. We could do A or we could do B. They both work. I’m just on the horns of a dilemma. He sounded really anxious about this. He sounded really worried. And I said, do A and B. He said, how the heck would I do that?

I mean, I’m making an architectural decision here. Do I use this cloud provider or that one? It was that kind of decision. And I said, well, get a trial license with both. Build a little bit on each one. You don’t have to go very far down the river. To figure out more information that will be valuable to you.

And that’s a perfect tactic for the complex domain that involves doing the the probes. The probes go down each branch of the river. And of course you could do three or five or ten. And you’re looking to discover more information. It’s a mindset that’s very different to how you might work in, say, a scrum environment, where you say, Well, what’s our sprint goal?

How are we going to achieve our sprint goal? What are we going to prioritize out of our backlog so that we can achieve this outcome of getting to the end of the river? Lewis and Clark didn’t have a backlog. They didn’t have a sprint meeting. They said, We’re gonna do both things, and then we’re going to figure out which way to go.

So that’s one tactic that listeners could try out.

Andy: so to, to follow on Lewis and Clark. So I, I, the town I grew up in is on part of the path. Lewis and

Clark traveled and so I, I got to grow up hearing parts of their history.


Douglas Squirrel: know much more about it than me. Tell us.

Andy: one thing they did is when they got so what they were doing is they were following the Missouri River for a large section of it, and at some point they hit another fork.

They hit the Yellowstone Missouri fork. And at that point, they followed both rivers the full way. This came about when the United States had bought the Louisiana Purchase. And the question was, what have we just bought? And so they sent out Lewis and Clark to figure this out.

They were going out to map and survey. They were doing surveys the entire way. And so they wanted to cover all sorts of land, but they couldn’t go over land. That would just be too much work. They eventually had to, to cross the mountains, but for as long as possible, they wanted to stick to the rivers. So they stuck to the rivers, and they followed the Missouri River, but they sent half their party to follow the Yellowstone River. And at some point, both of those rivers ended, and then they, they had to start figuring out how do they find each other again. And they must have come up with some system about how they’re going to find each other. But the idea was they were exploring a domain, and so they wanted to spread out. They wanted to go down those different paths.

And, and, and that’s what they did. They came up with ways of going in all these different directions and collecting information and bringing it back together.

Douglas Squirrel: And this is just such a different mindset. It is really an exploratory mindset, which is why I like the Lewis and Clark way of thinking about it. And it’s so different from what people would like. And I think this is what Mon Chaio was saying. There are lots of organizations that say, Boy, I wish I was in the complicated domain.

And it seems really clear to me what the right way to go is. It looks like we should be going west. After all, the Pacific Ocean is that way, and that’s where we’re supposed to wind up. So I think we should go west, and it seems really obvious to me, and if I’m the highest paid person around and people are listening to me, this is dangerous.

Then I may say, let’s all go west, and we run into a big ravine. Or bears, or hostile Native Americans, or something like that. And so, what I’d encourage listeners to do is to, to question that bias that they have toward the complicated. And to encourage them to create more opportunities for exploration, for discovery, for, and I think this is crucial, doing safe to fail probes.

It would have been fine if one of those expeditions up the Yellowstone, say, had hit a giant waterfall that they just couldn’t pass. That would have been a good outcome. We can map the waterfall, say, Hey guys, don’t go this way. Not passable. Not going to get to the Pacific Ocean this way, and then head back and see the other guys.

That would have been a good outcome. It was safe to do. So many organizations today in software have decided that failure is terrible. I always tell people that an experiment that doesn’t come out the way you expect is a successful experiment with a negative result.

Andy: If you guys are okay, I was going to try to take this now a little bit in the direction of some research I found about brainstorming, which I think, I think connects. So when I heard this whole thing of entangled trios, I I went down the path of, okay, you, you want this to come up with a wider range of ideas.

And it seems, intuitionally, it seems kind of like, sure, why wouldn’t it? But I, I doubt those things. And so I looked up is there any research in whether or not diverse groups actually come up with more information in brainstorming? Because that’s what these Entangled Trios are, is they’re almost like brainstorming, explore this thing, come up with these ideas, maybe do some of them, but mainly it’s come up with the ideas from what I could tell. The interesting thing turns into, what are the factors that are actually needed to make that work? Is it purely that they need to be different? Do they need to be together all the time or what? And I found a meta analysis that covered, I think, over a hundred different studies into brainstorming. And they asked the question of, okay, what does it show?

So, the things that were most influential to getting a wide range of ideas was one they have to have a vision. They have to have some sort of thing out there that they know that they’re trying to go to, which is why in the Entangled Trios, something that caught my eye was the idea that you have to pick an incentive that will motivate people to participate, is what he says.

So you need that vision. Squirrel, you’ll probably like this one, because I remember you used to have this whole saying of, bring the outside in.

Douglas Squirrel: Oh, yes.

Andy: And they said the second most impactful thing was external communication. It had nothing to do with the diversity of the group itself. It had to do with the external communication of the group.

In fact diversity of the group seemed to have very little impact on their ideas.

Mon-Chaio: So I, I’m gonna ask a question about that. My understanding is that when they said whether it was bring the outside in or something else, they were talking about bringing in people that were not in your normal network. Was that, was that

Andy: Yeah.

Mon-Chaio: Okay. And so one could say that that leads to diversity of thought, that they have other ideas being, being in other networks, but you’re saying that’s not it at all.

Or am I misreading what you were saying?

Andy: I, I think it’s, it’s not, it’s not purely that it’s three different people from three different backgrounds. I think the important part is that it brings in external views.

Mon-Chaio: I like that. I like that. So it’s not just that it’s an engineer, a product manager and a customer service person from your AAA team. It’s actually, you should go out to other different AAA teams and bring those people

Andy: Those people go out into the world and find, find your customers, find the people who aren’t your customers. So squirrel to the, to the story that you had about the, the council and the grandmothers and all of that. What What was in that was that you had a council member getting external communication from teenagers and grandmothers or grandparents.

And that was the key, probably, to that one working.

It was the fact that you had someone who was the insider and getting external communication.

Douglas Squirrel: This makes loads of sense, and it’s certainly the sort of thing that I tell my clients all the time to do. For example, a really good way to differentiate a truly exceptional technology team from a not quite so exceptional engineering team is to ask the engineers whether they’ve ever met a customer.

And it’s rare that I get even a single positive response. Engineers don’t tend to like talking to customers necessarily. It doesn’t really occur to anyone. It doesn’t seem very efficient to have somebody not writing code, but instead talking to some person who uses the software.

But my god does that give you new and interesting ideas. It really makes your estuary wider. And causes you to get more inputs and more suggestions. So I’m a big fan of that. As you said, Andy, bringing the outside in, but it’s become even more clear to me over many years since I first promulgated that rule.

Andy: I’ll, I’ll read a quick quote from this paper where they were talking about this external communication. They said particular group of researchers “underlined the importance of interpersonal relations with people outside one’s own team or organization. Interactions with other functional areas enhance the likelihood of obtaining new knowledge and disclose new perspectives, which spark the development of new ideas or the adoption of new ways of doing things.” Yeah, it’s that. It’s bringing that external perspective in, not necessarily just different roles from within the current, the current group.

Douglas Squirrel: But I want to add another tactic, if that’s alright. Can I head in that direction?

Andy: Mm-Hmm. . Oh, of course. In fact, we probably should. We’re

Douglas Squirrel: We’re coming toward the end. I know, but I wanna, I wanna fit this one in ’cause it’s so valuable. And it’s another example that’s very close to Roblox, but just a little bit different. And that is Lego for adults.

So, we all know we played with Lego as a kid. I love playing with Lego myself. I actually do it with my wife that we construct Lego sets together. But there are people who are even more into Lego than me. And one of them is one of my clients who has, when I see him on Zoom, I see just a whole shelf full of Lego.

He’s done an incredible amount with it. And people who are real fanatics like that, who are really excited about Lego, tend to get their own Lego bricks. They get lots of individual items, and then create something themselves. And Lego let these people order, but really ignored these folks for a long time.

They said, look, we’re all about making sets. You get the set. You build the set. If you want to build more stuff, that’s great. We’ll give you a bunch of bricks and you can make whatever you’d like. But we’re not going to do very much with that. That’s, that’s your business over there doing your thing.

But somebody clever at Lego figured out that in fact these people were great unpaid labor. These people were coming up with stupendous things. And publishing them on the web and so on to, to tell everybody about the, that they had made, say the the spaceship from the movie, from, I think it was the television television program Firefly, or something like that.

They had made some exciting thing from something that was more niche, that, that wasn’t, a Minecraft monster or something like that, that everyone would know. And so, Lego begrudgingly at first embraced these and they now have a whole mechanism where you can submit something that you’re excited about, that you’ve figured out how to make, and if you are successful at getting this through that process, then Lego will actually make it into a boxed set that other people can buy.

This should remind you of the Roblox example because again, they’re using this kind of user generated content, but they’re designing their product around making it easy to do that. And they actually didn’t realize it at first, right, for the first 50 years or so. We all got Lego and we might make our own exciting stuff, but there wasn’t a way to share it.

It was only when they added this additional element to the product, their whole offering, that you could submit something, you could submit your plans, and you could propose something, and other people could sign up to it and say this is exciting and vote for it or not, that they had this sort of competitive evolutionary kind of model, which allowed them to explore much more of the space That would have very surprising things in it that you would not expect would turn into very successful LEGO sets.

And it was risk free for them, because they knew it would sell, right? They, they had had people vote for it. This kind of participatory democracy told them that this free labor for them, people who were excited to do it, who loved LEGO, who wanted to make more LEGO, We’re coming along, doing the work, creating new exciting products for LEGO to sell.

What a deal! Man, we should all do this! So, the idea here, the tactic that listeners might try, and it’s one I don’t understand so well yet, so if you do it really well, please tell me, because I’m sure Andy and Mon Chaio will be interested too. I’m developing this tactic. But you can design your software, you can design your product, so that it makes it really easy for you to evolve it.

For, for you to do probe, sense, respond. For people to participate in entangled trios with your product. And if you do that consistently, if you do that across the board, You’re going to have a product with much more of the terrain mapped, right? You’re going to get the whole Western United States, not just the Missouri river basin.

You’re going to get lots more information and that’s going to let you outcompete everybody else. So can you design your product? So that customers participate in building more of it. And getting people to use more of it. It’s viral on steroids. And that’s a tactic I think not enough people are trying.

There’s only a few examples and I don’t know why. We should fix that.

Mon-Chaio: Well, and I think that’s an interesting area to explore. I actually agree with you a lot, Squirrel. I would love, and some of my favorite products are the ones that don’t constrain me down their use case, right? But allowed me to explore my own use cases.

Douglas Squirrel: There has to be feedback too. Remember, LEGO let you do that for a long time. This was the point of the LEGO story. That they let you explore your own use case, but not to share it. It was only when you could share it and there was this kind of voting and evolutionary process where the, the good ones floated to the top.

That was when LEGO really got a big advantage to it up from it and was able to expand further.

Mon-Chaio: Right. And I think we hear stories about exploration around the metric side, right? Measure everything your product does, even if you think it’s unimportant, because you might have some interesting insight. It just real quick me, quickly though, made me think of Yagni. And I think all three of us come from, the XP world, where if we ever heard a developer say, Hey, I want to make every aspect of this product customizable.

I think as leaders, we’d say, no, I don’t think so. So there’s, I think there’s an interesting conversation to have and not here. We’re, we’re, we are running low on time here. About how to, how to think about those differences.

Douglas Squirrel: That would be great. Let’s do that on another episode sometime.

Andy: All right. And with that, let’s try to wrap this up. So we’ve just had a very wide ranging discussion, starting from just the idea of the Cynefin domains and what domain you’re in, into Entangled Trios and Estuaries and how we can get new ideas flowing and collecting those and working with them to what kinds of things we can do to make sure that we’re behaving properly in those different Kinevan domains so that we’re not assuming that we’re in the complicated domain when it’s the simple domain or the complex domain when it’s the complicated domain and now we were just talking about product and how you can package up your product and do it in a way where you can learn more about what it is that your users really want Tactics we’ve had I remember there was the one about get the developers to talk to the customers.

Pull in the outside so that you can get these trios based off of what some research says is what’s really needed for finding new ideas, which is bringing in external ideas, external communication. What have I missed, guys? What have I missed here?

Douglas Squirrel: I think you got it covered pretty well.

Mon-Chaio: We didn’t, we talked about Lewis and Clark.

Andy: we got Lewis and Clark. We got a bit of American exploration history. All right. So, Squirrel, can you give uh, listeners an idea of how they can find more about you and get in contact and answer some of your questions?

Douglas Squirrel: Yeah, boy, if you’ve, if you’re experiencing with any, experienced with any of these, if you’re trying any of these methods or if you have a different perspective on it, I sure would like to hear from you because I’m doing a, a lot of active research on this right now. It is for a book I hope to be writing in the next year or so.

And I’m doing a lot of that in public. For example, I can also exclusively tell you guys. That I’m going to begin doing some marketing experiments in public and document what what I’m doing exactly this way. Discovering what people want to do doing many multiple safe to fail experiments and probes all at the same time.

So I’m documenting all of that, and I’d love for listeners to come along and join me on that. The way to find out about all that stuff is to start with DouglasSquirrel. com. That’s D O U G L A S, and then another S, Q U I R R E L, just like the animal, dot com. So, Head on over there. You can join my newsletter and see what I’m doing.

You can have a look at some of my well, the book I wrote with Jeffrey Fredericks and lots of other exciting things that I have free videos. I do an event every week that’s free and Jeffrey and I are on episode 320 or something of our podcast. So, loads and loads of things there, and I’d love to hear from listeners.

Andy: Excellent. And we would love to hear from them as well. If anyone out there has any questions or comments or requests of us, that’s hosts at thettlpodcast. com. And thank you for listening. Until next time, be kind and stay curious.


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