This is a transcript of episode 177 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

Our old friend Chris Clearfield explains how he helps leaders identify and fix overwhelmingly complicated organisational problems.

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Listen to this section at 00:14

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi Squirrel.

Squirrel: So this week we’re revisiting an old friend, Chris Clearfield from Seattle, Washington, is with us. Now, Chris, you were on with us a while ago talking about how accidents happen and meltdowns and other exciting things and you were looking at chaos and destruction. What have you been doing since then? Have you been melting anything else down?

Chris: I’ve stuck my hand in a little chaos and destruction. So Meltdown is the book that I co-wrote with András Tilcsik. And it’s all about complexity and how complex systems fail and sort of more importantly, how we can build teams, organisations that are resilient to that failure. And the book came out in 2018. I’ve been doing lots of different kinds of work with organisations. And one of the things that I-organisations, what a stupid word that is to use there. I’ve been working a lot with leaders who are trying to kind of create transformational change in their organisations. Which I know is something that you all think a lot about also. And one of the things I realised is that the gap between what we wrote about as a set of practises in Meltdown that you can use to build a team that’s resilient and robust and really manages complexity well, and the kind of state of the art of the practise where where so many leaders and organisations are. And so really, for the last year or so, I have been really intentionally focussing on helping leaders, particularly left brain leaders, guide their organisations through transformational change. And my observation is that this represents what I think of as sort of an impossible problem, which sounds a little bit silly and a little bit cheeky. But I think it’s an interesting way of of framing this kind of work. And, yeah, I thought it would be interesting to chat with you a little bit about it and to share how my thinking has evolved and what I’m working on these days.

Jeffrey: That’s fantastic. And the transforming organisations is one certainly that comes up a lot. And I think it’s the kind of thing where someone reads a book like Meltdown and they have the idea of how they can have their organisation be more resilient and then there’s the work of getting from here to there. Is that the scenario that you’re encountering when you’re talking to these leaders?

Chris: Yeah, well, that’s exactly it. First of all, let me say, you guys know that I’m just a huge fan of your work and Conversational Transformations is such a good a good book and a good, very practical way to approach that. And I actually see that there’s the level of the conversation, there’s the level of the team, and then there’s the bigger level of the of the organisation, and I think these things kind of slot together in a really interesting and nice way. But, I’m going to say I feel like when we wrote Meltdown, we rested comfortably in a little bit of of idealism and naivete and I think that’s fine. But I think kind of translating what we did in the book to making it really effective for leaders in a typical modern organisation, there was definitely a gap there. And so it was very humbling to kind of go from writing the book where we have these solutions that, on the surface seem, they’re not easy, but they’re relatively simple, like, write down mistakes and openly discuss them. Well, you know, for some organisations, like when I suggest that to a leader, like I can see their head kind of explode, like openly discuss mistakes, that’s just very far from where they are.

Chris: And that’s OK, because where they are works for them on some deep level. Right? I work with organisations that are that are big and successful. And so they have this whole activity system that supports where they are. But what I think is happening these days is that the complexity of the modern world means that those activity systems are no longer as adaptive as they once were. And so for me, the work now and kind of again, it’s been pretty humbling is to say, ‘OK, well, how can I help leaders build a bridge? How can I help leaders go from where they are right now, which is often a little bit siloed, a little bit procedural, a little bit project plan driven to being a leader that leads an organisation that’s dynamic and cooperative and collaborative and creative?’ And I think for me, that’s one of the biggest challenges of leadership, and that’s part of why I think about it as an impossible problem. But I also have some more specific ways that I think about what kind of makes a problem impossible.

Identifying Symptoms

Listen to this section at 05:29

Jeffrey: I’m curious, as I was going to describe this, I was thinking, ‘okay, look, this is Troubleshooting Agile, one of the things that we often talk about are the symptoms that people see. And I think may be a lead in here to possible problems. If I’m one of the leaders and I want to make this transmission, what would be a symptom I would see in my organisation? What would I be seeing or feeling or sensing that tells me that, ‘oh, actually I’m facing an impossible problem or I’m having that sense.’ What’s the kind of symptom that someone might have?

Chris: Yeah, that’s a great question. So I think about it in two ways. Right. There’s the criteria of what is an impossible problem. And I’ll talk about that in a second. But then there’s the, if I can be a little bit woo woo like then there’s like what is the felt experience of a leader and their team as they try to make this kind of transformation. And if they are too reliant on kind of, I’ll say, old tools like thinking in terms of, you know, they often don’t put it this way, but I see it this way as a unilateral control model, kind of Top-Down leadership, sort of, you know, going out to people and telling them what, like imposing change on the organisation, the things that leaders and their teams often feel is really frustrated and, you know, like isolated. Also, like you can see this dynamic emerge. That’s like, gosh, like we know that there is this new way to do things, but people aren’t getting on board with it. And like, you know, they don’t get it. They don’t kind of you know, they don’t understand it. They’re not willing to change. So you can kind of see like a leader who’s frustrated, who is trying to move things forward who knows that they’re going after something that’s big and important. But sort of you know, as they push on the organisation, they get more and more resistance and the organisation kind of pushes back. And so that to me is kind of one of the like one of the symptoms. It’s frustrating and it’s like. You know, it can make people cynical, too, like good leaders, they want the actual result, they don’t just want the kind of theatre of the result. And so if they are trying their hardest and getting frustrated and they sort of seeing the theatre but not seeing the result, like, that’s often a place where I will connect with somebody.

Jeffrey: Oh, wow, I really like that. What immediately came to mind is the people who want the real result and not just the check box, and I think it made me think Squirrel of you. It was more recent discussions where we had Vasco on and we were talking about the role of scrum masters and how so often is sort of the check box of, you know, let’s make sure we’ve got the right book and we’ve got the right framework. And we hired a bunch of scrum masters well then then we can check the Agile checkbox.

Squirrel: Yep. And in lots of cases that’s successful, that’s the model that works for the organisation. The problem is it’s not going to work in the future. It’s not going to let the organisation adapt. But it’s pretty darn adaptive where the organisation is right now. But we need to be doing the latest things. We need to attract engineers and product owners and salespeople and others who want to be with an Agile organisation. So, look, we got our Agile certificate and we have our Agile hand stamps and we’re Agile, OK? Life is good. End of story. So that sounds like a company that doesn’t have an impossible problem. They have a possible problem. Their problem is: look Agile. The people who have the impossible problem are the ones who want to actually be Agile.

Chris: Yes, and I think, you know. I use this phrase a lot, supporting leaders, because I think that it’s really important to acknowledge how hard this work is and how hard undertaking any kind of transformation and Agile transformation included. It really requires a leader and a leadership team that is willing to kind of marinate in uncertainty because, you know, in some sense, when we’re talking about a transformation like this, if you knew how to behave under the transformed conditions, you would already be behaving that way. Right. There’s like- there’s kind of, you know, given that you are where you are, you actually don’t know how to do what you do. And where you are, again is very, very adaptive. So I think to your point, I get a lot of questions, especially early on in my work with leaders that are like, well, what have other organisations done to cross this bridge, to cross this threshold? And my response is often, well, I can tell you about that. But it’s not going to be as useful as you want it to be because your organisation is unique and the things that make- the things that challenge your organisation are different than what challenges another organisation.

Finding Your Organisation’s Superpowers

Listen to this section at 10:34

Chris: And your superpowers are different. And kind of ironically, the challenges in the superpowers are often the same thing. And so the work is really to like- is to kind of help leaders get comfort- get more comfortable with the unknown. And, you know, I do that by kind of coaching them and providing interpersonal support, but also by providing a real structure for how to think about what is an impossible problem and how to have some structure to go about… I don’t want to say solving it, but kind of taking the journey in a way that’s that’s structured and parameterise to help you really get a result ou at the end of the day, that works for you and work specifically for your organisation, which is something that, by the way, like you and your team are an expert in. You are an expert at how your organisation works because you’re part of it in a way that’s very different than me as an outsider coming in.

Jeffrey: What I heard in that approach is your idea is that it captures that, that making this kind of transformation is not a cookbook, it’s not one size fits all. And so it’s very different from that earlier sort of Look-Agile checkbox, which you can apply universally; requires no sensing of the conditions. And you’re saying something quite different, which is actually: what you do is- your path is going to be very different based on, you know, the specifics of your situation. And therefore that’s your one of things you’re doing with people, it sounds like, is helping them understand what’s different about their environment. Is that right? And you’re kind of casting that this idea. I love this phrase of superpower. Can you say a bit more? What’s an example of a superpower an organisation might have? And how could that also be the source of their problem? That sounds really interesting.

Chris: So I- it’s a it’s a great question and it’s actually an idea, really. I think, interestingly, actually rooted in Buddhism, which is kind of an interesting thing to bring. I first heard it framed in this way by this woman, Pema Chodron who wrote a book, has written a bunch of books, but wrote a book called I think it’s called Things Fall Apart. But it’s- here’s an example. I worked with a leadership, sort of senior, leadership team at a big, big oil company last summer, and they were basically trying to change their approach to how they did maintenance. So this is like we’re not in code space here. We’re in like physical space. Right. How they, like, take apart equipment and these big pieces of equipment, how they do turnarounds on their assets. And, you know, they have these huge assets around the world. And this team was basically charged with making this process… They didn’t really use this phrase, but really more Agile kind of better, faster, smarter, cheaper. And as an organisation, they tended to be very interested in controlling risk, pretty risk averse, pretty procedural. And so those are all really useful ways to be, right? I mean, you run a huge global oil company, like you want to be pretty sure that, you know, you’ve got a set of procedures that describes what you need to happen and that people are using it around the world and that they’re dialled in and all of this stuff.

Chris: Right. So in some ways, you can see that as a superpower of the organisation. But what the team I was working with was seeing and was finding was that indeed they have this superpower, but it prevents them from moving quickly. It prevents them from moving as fast as they want to. And so a lot of our work was figuring out how to go, how to find partners in the organisation that kind of we’re at a high enough level that they could make decisions about what to do, but on a low enough level that they were closest to the operations so that they could, for example, run experiments about how they can do these turnarounds in a different way. You know, and that’s kind of I feel like in a nutshell, you can see that like what this organisation was really, really good at. What came really easy to them was building these kind of big, elaborate procedures that were rolled out on a global scale. And you can see how that’s very, very useful. And you can see how if that’s the only thing they can do, it’s limiting. So that’s kind of- that’s sort of the way I see that kind of, every organisation’s behaviour is in some sense adaptive for for where it is right now.

Identifying and Solving Impossible Problems

Listen to this section at 15:12

Squirrel: And that’s the part that’s puzzling to me, because we’re coming to sort of toward the end of what we should be talking about in at least this episode, maybe we’ll have to go to multiple ones. But, Chris, I’m not quite hearing what they did to solve their impossible problem, whether it’s this one with the equipment being taken apart and maintained and put back together or in another case, what I kind of understand what an impossible problem is. And why you might not want to face it, if you’re a certain type of organisation, but how do you solve it?

Chris: Great. Well, let me let me say specifically what I think of as - the kind of - the three part test of if you have an impossible problem. So as a leader, it’s a problem where you kind of have a vision for the end state or the direction you want to go, but you don’t know the exact answer and you don’t know exactly how you’re going to get there. You don’t control the people that are involved. So you can’t sort of you know, I guess that’s just an easy way to say you don’t control the people that are involved and you don’t control the overall system, the kind of the organisational context, the organisational structure, the incentives, the regulatory structure, the kind of technology platforms. So you might be able to influence some of these things. But you certainly don’t control them. And I think those- that’s a sort of three part test that’s like, well, if all of these things are true, then you really- You’re really in a scenario where, and by the way, I think all of these things are true in 99 percent of the kind of transformational changes that we’re talking about, but you’re in a scenario where the kind of old tools don’t work anymore. And so you have to you have to push on it. Like if you push on the system, it’s going to push back. If that makes sense. And so, what I do is I take leaders through a process that basically has four parts to it. The first part is really being explicit about the network of people that need to be involved in getting to where you need to be.

Chris: So thinking about who they are, thinking about what roles they have and thinking about how connected they are with your core team, who’s trying to invite this change in the organisation and seeing, you know, are there ambassadors that you can recruit of that network to be a champion? Are there people that you know are going to be willing to collaborate with you on a solution or even on a more deep understanding of the problem? So one is just being explicit about that. The next step is to really think about where people are in- I use a model called the Cycle of Change, which this guy, Rick Maurer came up with. And it’s a really useful model. It’s wrong like all models, but it’s also useful. And the idea here is to just make sure you’re bringing people along. So if you try to roll out, if you try to push out a solution onto people that don’t even know that there’s a problem, then you’re going to get resistance. And that’s kind of true at sort of every stage of the process. If you move too fast, which you often do, as a leadership team because you’ve been thinking about this problem a lot. But you’ve got to bring people along. You’ve got to help them connect with the problem that they’re facing before you start to get them to thinking about solutions before you start to roll things out.

Chris: So that’s really all about engagement. The third step is about skilfully working with resistance and realising that resistance has different flavours. And I mean, particularly as engineers particularly, as kind of left brain technical leaders. We often want to meet resistance by showing people data and by showing them this is the way it should be. This is the ideal state. And, you know, that just doesn’t work. That just generates more resistance. So I help help teams that are undertaking change, work more skilfully with resistance. And then the last thing is to think in terms of experiments instead of monolithic solution. So, the goal is not to come up with a policy and roll it out across the organisation. It’s to find pockets where you can not just connect to as like a pilot, but really admitting that we don’t actually know how to do this. We don’t know how this is going to work in our organisation, but we have a place where we’re going to try it. And as we start to get momentum and it starts to get working, then other people are going to start to get interested in what we’re doing. And then all of a sudden you’ve created FOMO. You’ve got people excited about it and you sort of rapidly can you know, you can shift the adoption curve from this kind of like plodding climb to this, this exponential adoption. And that’s a really cool aspect of this work.

Jeffrey: That sounds great and when you’re describing that I was thinking in my head about the Cynefin framework and kind of helping people deal with the complexity and Cynefin says you want to probe sense, respond, it sounds like you’re kind of guiding them through that process of these experiments to probe, to find out what happens and then alter their path. So I can see where that be valuable. For people who have heard this description, Chris would like to know more about your approach to solving impossible problems. How can they learn more?

Chris: Well, I’m glad you asked Jeffrey. So, of course, if you’re a leader in an enterprise and this is something that is interesting to you, you can send me an email, and I’m happy to schedule a call and figure out whether the approach that I’m taking is something that could be a fit for you and your team, your organisation. But I’m also, for the first time ever, taking some of this work and offering it in a public way. So I usually do this with leadership teams within an enterprise. And, you know, like sometimes I can talk about that. Like I’ve done a bunch of work with Microsoft, helping them create a culture of innovation in their legal department, which is this really interesting, kind of like socio technical problem. And I get to talk about that work publicly sometimes. But for the first time, I’m actually doing a public course where people can learn about this. And that, of course, actually starts with a free webinar, which I guess we marketing people call a masterclass these days.

Jeffrey: That sounds great, a masterclass on impossible problems.

Chris: A masterclass on impossible impossible problems. Yeah. So it’s on July 7th at 6:00 p.m. U.K. time, 1:00 p.m. Eastern time. And that’s 10:00 a.m. Pacific Time, which is where I am in Seattle. And we’re going to put a link in the show notes for you to go and read a little bit more about it, register, it’s free. I’m going to be talking about how to solve impossible problems and kind of giving some practical tools and then also giving an overview of the course that I’m offering, which is going to start in mid-July and be this kind of mix of content and group work and one on one coaching as well. So I’m really excited about it. You know, for me, I talk a lot about helping leaders sit with the unknown and embrace the unknown. And I also kind of try to do that myself. This is the first time I- I’ve taught this material a bunch and a lot of different contexts. But this is the first time I’m doing a launch like this to a public community. So there’s a lot of sitting with the unknown for me right now. And I am really excited about it.

Jeffrey: Right, and I’m excited, too. I’ve been enjoying your work, not just the book, but your podcast. And I’m looking forward to the webinar and very happy to share with people. So thank you so much today for coming in and telling us about your approach to two impossible problems.

Chris: Well, you’re welcome. And I mean, you guys know how great I think your stuff is, how much I like talking with you about how much I like cooking stuff up with you. Yeah. So stay tuned. I hope to continue this conversation to continue this, this partnership. So I’m really excited.

Squirrel: Fantastic. And we like having Chris on it and we know that our listeners always respond really well, so do get in touch with Chris. All the information you’ll need is in the show notes. And of course, if you have questions and comments for us, you know where to find us. That’s at Videos and email and Twitter and you name it, it’s probably on there. So we’d love to hear from you there. And we’ll see you next Wednesday for something equally exciting and interesting as solving impossible problems. Thanks, Jeffrey.

Jeffrey: Thank you, Squirrel.