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

Chris: So Meltdown is the book that I co-wrote with András Tilcsik about complexity, and how complex systems fail and sort of more importantly, how we can build teams and organisations that are resilient to that failure. The book came out in 2018 and since then I’ve been working a lot with leaders who are trying to create transformational change in their organisations, something I know you think a lot about also. One of the things I recognized is the gap between what we wrote in Meltdown—a set of practises you can use to build a team that manages complexity well—and where so many leaders and organisations are. Really, for the last year or so I have been intentionally focussing on helping particularly left brain leaders guide their organisations through transformational change. My observation is that this represents what I think of an impossible problem, which sounds a little bit cheeky, but I think it’s an interesting way of framing this kind of work. I thought it would be interesting to chat with you about this and to share how my thinking has evolved and what I’m working on these days.

Jeffrey: That’s fantastic, transforming organisations certainly comes up a lot. When someone reads a book like Meltdown they gain an idea of how they can have their organisation be more resilient, but then there’s the work of getting from here to there.

Chris: Yeah, that’s exactly it. First of all, Conversational Transformations is a good, very practical way to approach that. I actually see that there’s the level of the conversation, the level of the team, and then there’s the level of the of the organisation. I think these things slot together in a really interesting and nice way. But I feel when we wrote Meltdown we rested comfortably in a bit of idealism and naivete. And that’s fine, but I think in translating what we did in the book to make it effective for leaders in a typical modern organisation, there remained a gap there. It has been humbling to go from writing the book where we have solutions that are not easy, but are relatively simple, like ‘write down mistakes and openly discuss them.’ Well, for some organisations when I suggest that to a leader I can see their head kind of explode. That’s just very far from where they are. And that’s OK, because where they are works for them on some deep level. For example, I work with organisations that are big and successful, so they have this whole activity system that supports where they are. But these days the complexity of the modern world means those activity systems are no longer as adaptive as they once were. So for me the work is to say, ‘how can I help leaders build a bridge 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 of an organisation that’s dynamic, cooperative, collaborative, and creative?’ For me that’s one of the biggest challenges of leadership, which is part of why I think this is an impossible problem. But I also have more specific ways that I think makes a problem impossible.

Identifying Symptoms

Listen to this section at 05:29

Jeffrey: As you were describing this I was thinking, one of the things that we often talk about are the symptoms that people see. If I’m one of the leaders and I want to make this transition, what would be a symptom I would see in my organisation? What might indicate, ‘oh, actually I’m facing an impossible problem.’

Chris: 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 experience of a leader and their team as they try to make this kind of transformation. If they are too reliant on going out and imposing change on the organisation, these leaders and their teams often feel really frustrated and isolated. You can see this dynamic emerge: ‘we know there is this new way to do things, but people aren’t getting on board with it, they don’t get it. They’re not willing to change.’ So you see a leader who’s frustrated, trying to move things forward, who knows that they’re going after something big and important. But as they push on the organisation, they get more and more resistance and push-back. That to me is one of the symptoms. It can make people cynical, too. Good leaders want the actual result, they don’t just want the theatre of the result. So if they are trying their hardest and getting frustrated and seeing the theatre but not the result, that’s often a place where I will connect with somebody.

Jeffrey: I really like that. What immediately came to mind with people who want the real result and not just the check box, was more recent discussions where we had Vasco on talking about the role of scrum masters and how, so often there are goals like, ‘let’s make sure we’ve got the right book and the right framework. We hired a bunch of scrum masters, so we can check the Agile checkbox.’

Squirrel: Yep. In lots of cases that’s the model that works for the organisation. The problem is it’s not going to let the organisation adapt. But it’s pretty darn adaptive where the organisation is right now. ‘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. That sounds like a company that doesn’t have an impossible problem. They have a possible problem: look Agile. The people who have the impossible problem are the ones who want to actually be Agile.

Chris: Yes! I use this phrase a lot, ‘supporting leaders,’ because I think that it’s really important to acknowledge how hard this work is, how hard undertaking any kind of transformation is. It really requires a leader and leadership team that is willing to marinate in uncertainty because 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. Given that you are where you are, you actually don’t know how to do what you will have to do. So to your point, I get a lot of questions especially early on in my work with leaders that are like, ‘what have other organisations done to cross this bridge, to cross this threshold?’ My response is often, ‘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 challenge your organisation are different than what challenges another organisation.’

Finding Your Organisation’s Superpowers

Listen to this section at 10:34

Chris: Kind of ironically, the challenges often coincide with that organization’s strengths, their superpowers. So the work really is to help leaders get more comfortable with the unknown. I do that by coaching and providing interpersonal support, but also by providing a real structure for thinking about what an impossible problem is and how to have structure to go on the journey in such a way to really get a result out at the end of the day that works for you and specifically for your organisation. Your organization which, by the way, you and your team are experts 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 hear in that approach is that this kind of transformation is not a recipie, it’s not one size fits all, it’s very different from that earlier ‘look Agile’ checkbox which you can apply universally, which requires no sensing of the conditions. You’re saying the path is going to be very different based on the specifics of the situation, and therefore one of the things you’re doing with people is helping them understand what’s different about their environment. I love this phrase, ‘superpower.’ What’s an example of a superpower an organisation might have, and how could that also be the source of their problem?

Chris: That is an idea rooted in Buddhism, actually, I first heard framed this way by Pema Chodron who wrote—among others—a book called When Things Fall Apart. Here’s an example: I worked with a senior leadership team at a global oil company last summer, and they were trying to change their approach to maintenance. This is not code space, we’re in physical reality, how they take apart these big pieces of equipment, how they do turnarounds on these huge assets around the world. This team was basically charged with making this process better, faster, smarter, cheaper. As an organisation, they tended to be very interested in controlling risk: pretty risk averse, pretty procedural. Those are really useful ways to be, right? You run a huge global oil company, you want to be pretty sure that 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. So in some ways, you can see that as a superpower of the organisation. But the team I was working with was seeing that indeed they have this superpower, but it prevents them from moving as fast as they want to. So a lot of our work was figuring out how to find partners in the organisation that were at a high enough level that they could make decisions, but on a low enough level that they were close to operations, so the team could for example, run experiments about how they can do these turnarounds in a different way. In a nutshell, you can see what this organisation was really, really good at. What came really easy to them was building these big, elaborate procedures that were rolled out on a global scale, and you can see how that’s very, very useful. And you can also see how if that’s the only thing they can do, it’s limiting. In a sense, every organisation’s behaviour is adaptive for where it is right now.

Identifying and Solving Impossible Problems

Listen to this section at 15:12

Squirrel: I kind of understand what an impossible problem is, but how might you identify or address such? What would that oil company have had to do?

Chris: I have a three-part test of if you have an impossible problem. As a leader, it’s a problem where you have a vision for the end state or direction you want to go, but without a lot of specificity, and without a clear path. It’s a problem where you don’t control the people that are involved. And finally, you don’t control the overall system, the the organisational context, the incentives, the regulatory structure, the technology platforms. You might be able to influence some of these things, but you certainly don’t control them. I think all of these things are true in 99% of transformational changes we’re talking about, but that is a scenario where the old tools don’t work anymore. What I do is take leaders through a process that has four parts. The first part is being explicit about the network of people that need to be involved. Thinking about who they are, what roles they have, and how connected they are with your core team. Are there ambassadors that you can recruit from that network to be a champion? Are there people you know are going to be willing to collaborate with you on a solution, or even on a deeper understanding of the problem? The next step is to really think about where people are in Rick Maurer’s Cycle of Change model. It’s wrong like all models, but I find it very useful. The idea here is to make sure you’re bringing people along. If you try to roll out a solution to people that don’t even know there’s a problem, you’re going to get resistance. That’s true at every stage of the process. You’ve got to help them connect with the problem they’re facing before you can start them thinking about solutions before you can start to roll things out. The third step is about skilfully working with resistance and realising that resistance has different flavours. And particularly as engineers, as technical leaders, we often want to meet resistance by showing people data and showing them the way it should be, 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. The last thing is to think in terms of experiments instead of a monolithic solution. The goal is not to come up with a policy and roll it out across the organisation. It’s 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. Then all of a sudden you’ve created FOMO. You’ve got people excited about it and you rapidly can shift the adoption curve from this plodding climb to exponential adoption, and that’s a really cool aspect of this work.

Jeffrey: That sounds great! That brought to mind the Cynefin framework and helping people deal with complexity. Cynefin says you want to probe, sense, respond, it sounds like you’re guiding them there with the idea of experiments to trial solutions, so I can see where that be valuable. For people who would like to know more about your approach to solving impossible problems, how can they learn more?

Chris: 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 about is something that could be a fit for you, your team, and your organisation. But also, for the first time ever, I’m taking some of this work and offering a public course where people can learn about this which, of course, actually starts with a free webinar, which I guess marketing people call a masterclass these days.

Jeffrey: A masterclass on impossible problems sounds fantastic.

Chris: That’s on July 7th at 6:00 p.m. U.K. time, 1:00 p.m. Eastern time, 10:00 a.m. Pacific Time, which is where I am in Seattle. Link in the show notes for you to read a little bit more about it. I’m going to be talking about how to solve impossible problems and 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 a mix of content and group work, with one-on-one coaching as well. I’m really excited about it. I talk a lot about helping leaders sit with the unknown and embrace the unknown, and I try to do that myself. 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: 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. Thank you so much today for coming in and telling us about your approach to impossible problems.

Chris: You’re welcome. I quite enjoy chatting with you so I hope to continue this conversation.

Squirrel: Fantastic. We like having you on and we know our listeners always respond well, so thank you Chris, and thanks, Jeffrey.

Jeffrey: Thank you, Squirrel.