(2024-04-20) Cutler Octopus Careers Throwaway Stickies With Chris Butler

John Cutler: Octopus Careers & Throwaway Stickies with Chris Butler. Chris embraces the mess like few people I’ve met. Defying categorization in his career path, inventing models and techniques for collaboration and sense-making, he’s well versed in engineering, design and product, and figuring out how to challenge the status quo in big companies.

I’m excited to say it depends as many times as possible during this podcast.

I try not to require my identity to become one thing. Rather than like a T shaped career or whatever those other things are, like an octopus career. And the reason why I like that is because, you know, the octopus is like a very interesting neural kind of, system where it has one brain, but it also has like brains in all of its arms.

The anarchist kind of thread in my background or the fact that I was building red boxes or doing warez boards kind of says to me a little bit that I also have a problem with doing things within the rules sometimes. (rebel)

How do you know that you found your tribe when you’re in a company?

Joining very large companies is interesting because I guess I see part of what my benefit is to people is building connections between maybe topics that don’t make sense together

For example, there’s a group called Flux and Gale, and it was started by someone internal to Google that was all about people that are model thinkers, system thinkers, like that type of stuff.

I’ve been doing a lot of stuff with something called design fiction, which is really about this idea of like prototyping some future artifact.

But me going into like an intranet site and looking up things like design fiction, I started to find groups of people that were, you know, interested in these topic areas.

it’s not always possible. The intranet site that runs something like GitHub is different than the intranet sites that were inside of Google.

I knew you do a fair amount of speaking external to the companies you work at. curious how the desire to express yourself externally from your companies Is that a balancing act

It’s more of like an escape valve because I think like whenever we’re at an organization, there are cultural expectations. There’s the Overton window of what is acceptable or not.

I think I’ve started to come to the conclusion, and I think a lot of people in the Wardley Mapping community also think about this, is that like, I can’t use the terminology, I can’t call it this thing anymore.

I need a place to be able to experiment with these concepts. And so I use the external speaking as a place to do that

I did a workshop as part of one of the Wardley Mapping online conferences about how you use Wardley Maps as a game board for doing strategic rehearsal or wargaming.

I did that inside of Google as part of our summit

We did scenario planning where we would create basically critical uncertainty—so a two by two of like two different uncertainties, and it creates four worlds that we want to like talk about.

And the people that were user researchers, designers, they really got that. They, they did a great job inside of Google to do that. The PMs inside of Google had a really hard time thinking about like uncertainty about the future

But then like we, we changed it around and I had people build their Wardley Maps and then we would have random events that would happen and then they would have to like figure out what does that mean.

Within my community, It was like a little bit like pulling teeth to get people to think about this, like uncertainty and have an imperfect map. Inside the Wardley Mapping community all these maps are disposable. You create a map and then you will throw it away essentially.

Every time that I’ve ever done a workshop inside of Google where there’s like post it notes, someone’s like, “Who’s going to write down all these post it notes?” And I’m like, no, we’re not. We’re just going to throw them all away, like, or recycle them ideally. But like, we don’t need to have every single idea captured. It was about the lived experience of everybody inside this workshop that was actually meaningful.

There’s a lot of smart people inside of Google, right? For a very long time, the culture was around academic excellence, right?

what that means is like, for people that are very smart in a particular domain, they tend to think that if they just think hard enough about something, they will come up with the perfect answer.
That’s not true in my opinion.

This also is then related to like consensus driven decision making, which I think Google suffers from an awful lot.

there are benefits to those types of cultures.

I would say that in the face of uncertainty, that’s why we have to write down and take notes about every idea that came up because we don’t want to miss a good idea that was there, when the reality is like, this was really just more of a workshop to get people to talk to each other in a particular way.

John Cutler: seems like it’s a honeypot for a certain type of thinking or need. what, what, what about that context sort of is the flip side for that?

DoubleLoop.com is a great example of that type of thing. They are actually trying to, in some way, mechanize these types of strategies. The honeypot of Wardley Mapping is trying to understand what is going on (sense-making) and then making choices about that.

The antithesis to that is that we actually have to make choices together and we want to make sure that everybody’s happy. How much of your organization needs to agree to a strategic direction or not?

And I used to think it was like high, like you want to get everybody to agree. Then I was kind of like, Oh, well, maybe it’s like 51%. You just need like most people. And then now I’m, now I’m actually of the mind that like, if you have a leader that you trust, it’s actually only one person needs to actually believe in that strategy.

Culture is another one. Like, yeah, you can try to change culture. It takes a lot of work to change culture, but if this culture is just not right for you, you just shouldn’t be there. (Change Your Organization)

We want to make hard decisions. And I think most of the time making hard decisions is a better strategic value, but that doesn’t work inside of consensus driven cultures.

When you see people forming strategies do you have any example of of some contextual factor that they tend to think that matters that doesn’t really matter in the grand scheme?

One of the things I see pretty often is that people think about the plan, not about the strategy. And so we end up getting tied around the axle on like the stack ranking priority of this thing over this thing, rather than what are the rules that we’re actually trying to kind of think about from this?

I don’t want to create this false dichotomy between strategy and execution. Like every execution includes a strategy of some type. But what I really get annoyed with is like, your job is actually to build culture now or to build the team or to create incentives for practicing in a way that you want people to practice. And that to me is less about like you’re helping make these little tiny decisions and it’s more about like broader things.

why you should have a great strategy is because you should make the really hard decisions that people are constantly struggling with very easy. (strategic context)

When we have things like escalations happening from the people that are at the ground level or at like the practicing level where they’re talking with customers and they’re building things for customers.

It should be that probably those five different things that are in the same theme, that’s a strategy. And that’s actually something that’s really pertinent to today in making decision making, in doing decisions. We don’t have enough where people are looking at the escalations to see how that modifies the strategy.

And then the third kind of last thing I think happens a lot for leaders is that they don’t provide the context to their organization as often as they should.

When you think about the last couple of years why are we seeing this increase in people saying leaders should get into the details. Why are we saying this so often? Why is Brian Chesky saying this on an interview and, and every day on LinkedIn, someone’s saying or have to be more hands on than you thought you were like, what’s going on.

I’m sure that there are leaders that are domain experts, right? Like I, I don’t, I, I totally believe that’s true. Right. And, and I’ve, I’ve often gotten in trouble both internally with my teams or externally on Tik ToK about saying, I don’t think product managers should be very technical.

if you’re not actually building teams that are able to be the domain experts. Right. I think that’s a failure of leadership.

That’s why, like when, when managers complain that they don’t get any like feedback from people, it’s because that’s the way that they usually are interacted with is like, you’re there to make the most perfect presentation possible.

and any, any failure, like, you know, I’ve, I’ve heard about certain leaders that if anybody ever fails for any reason, they’re suddenly unlucky and they should not be trusted with anything else. And that just sounds insane to me. You’ve got to be incredibly lucky. And that’s like survivorship bias.

The last thing is to actually believe in the systems that allow for that type of peer feedback. PMs can learn an awful lot from the way that like does great design critiques work or great code reviews happen. (Pair-Product-Managing)

From those kinds of practices, you end up actually learning something much more from each other. And because there’s other people there, you accelerate the learning because other people are dealing with other problems.

I think that is what great leaders should do is they want to create as many opportunities for feedback, between their team members as possible. And they’re not always going to be the right ones to do the feedback because again, there’s power dynamics.

this is why leaders, what they should be doing more of, is actually telling people on their team why they made a particular decision. And what was the process by which they did that

this is why like things like forward looking case studies, like decision forcing cases I think are so interesting is that you get everybody in a room from both junior to senior people and I would run these inside of Google. (case study)

that’s why, I tend to want to have these types of containers for conversations that rather than the weekly, you know hand down of here’s what’s going to happen. I want the leader to be part of a game that talks about different decisions and see how different people in that room would do it because you learn about everybody’s decision making capability.

I’ve been starting to read this, this book about LARPing live action role playing, but there’s this idea of a conceit where I’m going to play this role. It’s not really who I am. Right. But I may be a jerk right now or like six thinking hats is a great example of that, right? Like one of those hats is a jerk and it’s okay because that’s just the way six hats work.

John Cutler: Back in the beginning of the podcast you talked about how you were okay with the flexibility in these particular environments. Right? Now I understand better about how you might be okay with like, we’re going to throw it all away afterwards.

Dave Snowden. We call it acceptation. I think it’s this idea of like meta or interdisciplinary thinking.

John Cutler: One thing I like about how you’re describing this though, is that you seem. to like the theory side of it, but then you seem to like manifesting it in an actually very visceral, hands on, out in the world type way.

Chris Butler: I’ve been definitely called very academic, like very theoretical. But what’s funny too is that like with a lot of the people that if I like be coaching someone or trying to mentor them, you know, I’m asking a lot of questions because I’m trying to understand what is the context of what’s going on.

And, and people have said like, you know, I’ll have a conversation with Chris and it’s like the first 55 minutes are just like meandering. I have no idea where they’re going. And then he gives me like three things to do with the 55 minute work. And it’s like exactly what I needed, basically.

I think like part of the product manager’s job is to be a toolbox of like methodologies and frameworks, right? It’s like shu ha ri from the agile world is

another kind of like honeypot name is probably Christopher Alexander and pattern libraries and stuff like that.

if it’s going to be for people, you have to build things in a very special way. And that’s why I think like. We need all these tools and then we have like a team, which is a bunch of just people together and we need to figure out how they work and what they, what they want to work like.