Kevin Callahan is an Enterprise Agile Coach based in the United States and the program lead for our Enterprise Agile Coach Expert Cohort Program. Kevin was a member of the ICE-EC committee that co-created the competencies for ICAgile’s Enterprise Agile Coaching expert track. In this interview, Kevin discusses how he got started in agile coaching, what motivates him to work in this field, and how he facilitates transformation in the organisations he works with.

Hi Kevin – for those of us who don’t know you yet please tell me who you are and what you do?

Hi I’m Kevin Callahan and I bring people together to solve complex problems that looks like a variety of different things. Sometimes I work individually one-on-one with leaders, helping to coach them to be more effective in high complexity contexts and what that means. Sometimes I work with teams that could be software teams, it could be leadership teams around how they organize together to be more effective in what they’re needing to accomplish. And sometimes it’s working with entire organizational systems. That could be something as small as a program and it could be something altogether larger than that as well. So it’s all through those. It’s a complex adaptive response. Complexity informs everything I do. Working with people informs everything I do.

How did you first come to learn about agile coaching?

I started as a Scrum Master. I actually started as a developer on a Scrum team and that was back in 2007 or so. And my work before being a software developer as a professional outdoor guide so I knew quite a bit about leadership and leading people in uncertain environments and environments where they weren’t comfortable and in helping people feel safe in that discomfort. As we were organizing as a Scrum team, I was increasingly dissatisfied with how much leverage I had to really change things at that organization and change things on my team. So when a Scrum Master role opened up, I applied and was given that role. And as a good Scrum Master does, I worked to resolve impediments that my team had. And as we solved the easier ones that we had control over the impediments that then became visible more and more reached outside of the team to external dependencies or leadership or whatever. But the team couldn’t solve them. And I needed to reach out to build some relationships and bridges. And that path of working wider and wider in an organization ended up becoming an agile coaching role. And over time it started getting the attention of senior executives because they started seeing things were much different at the company and directly invited me to come work with them as well. Then I started down this path of enterprise agile coaching, which I discovered is actually really really different than working with teams and a couple of teams to help improve deliveries, for example.  It was very ad hoc and quite by accident, there was no intentional career path. I was just making one thing better at a time, the best I could.

What’s an interesting trend you have recently observed within the agile coaching world?

Well certainly one of the hot topics I could talk about is scaling. That’s been around for a while. It’s contentious and also quite loaded with conflict. I think one of the more interesting things besides scaling is there’s this relatively new idea of a project to product transformations of organizations that I work with and they’re realizing the paradigm of project management doesn’t really work in the kinds of high complexity knowledge work that we’re faced with today.  Looking at their offerings more as products and organizing around them as products is a better, more sustainable approach. For example, I was interviewing a video game company about a possible engagement. And I asked, What’s changed? Why are you wanting to do this work? Why does it matter? And they said,

“well several years ago when we released a game, the game would be in the market for some amount of time, people would play it. You could watch the adoption of it go up, and then it would peak, and then people would get bored of it and something else would come out and then they would stop playing it. And so we would discontinue it. And the lifespan of a game was maybe a year or two. Well, now we’re seeing that the games, the most popular games, like world of Warcraft, for example, or Assassin’s creed.”

I play Overwatch myself, which was released five years ago.

These are all still very well-played games. They’re profitable. They are, in some cases, continuing to grow and the organizations aren’t set up for that, they’re not set up for these open-ended games. How do you continue to improve things? How do you continue to make trade-off decisions? How do you continue to fund them? When there’s not really the kind of end date that you used to have, what about that? And so it calls into question just everything, everything that all the assumptions that have been put into place around How do you create value in the world? It’s a different conversation. So I think that’s a really cool trend. I’m hoping to see more of it. And I think it has a lot to offer us as change agents.

What can you tell me about the impact that coaching has on agile transformations?

Professional coaching as a discipline, I believe is about unlocking potential and achieving high performance. And when I teach coaching fundamentals and I seek to help people understand in the organizational context, coaching is often a remediation and it’s often part of a performance improvement plan. When people are in trouble at a company with their employment, they get assigned a coach or they get sent to coaching. There’s this kind of negative connotation that coaching is about fixing people. And I’ve seen that, right? Like when I work in large transformations and I talked to a manager and they’re like, that team really needs to be coached. Which what they’re really saying is they’re not performing to expectations, or they’re not doing what we need them to do. Go fix them.

I think that’s tragic because one of the questions I asked when we started talking about what coaching really is, I say things like you show me the Olympic athlete that shows up without at least one coach, you show me the professional sports team that doesn’t have probably a whole suite of coaches that are very specialized in different disciplines of that team’s performance. You tell me how likely is it that they can perform at those levels of elite competition without that. And it starts showing people that coaching is an accelerator. Coaching is a way to unlock performance. Coaching is a way to find out what already works and amplify it, and intentionally design it into our systems in our organizations. It’s just a way to make things better in that way. From an agile coaching perspective, the critical importance of a competent, highly skilled agile coach is that we bring an enormous amount of content and expertise with us, and we can make informed suggestions.

I certainly don’t like to just say, here’s what you ought to do. I like to say here’s what you ought to consider. How does that sound? I’ve seen a lot of this stuff. This is maybe your first time running an agile transformation as an organization. Have you considered these things?

And usually they haven’t, which is why they’re calling me and the ones that don’t, don’t need our help. They’re great. That’s awesome for them. But the ones that need our help, they need that expertise. And so not only do we help them unlock and accelerate their improvement and their performance we just bring a tremendous wealth of knowledge. You know, personally, I’m walking around with over a decade of knowledge. I’ve had a master’s degree in advanced organizational development. There’s a lot in there that I can bring and provide to clients that need that.

What’s your favorite question to ask the leadership teams you coach?

There’s two one of them is what would it be if it were right? Tell me about if you pulled all of this off, what would be different than it is today? And help people really imagine very clearly based in reality. You know, I don’t want them to totally disconnect from what they’re doing, but, you know, what, what would your business be like if it were what it needed to be and have that rooted in some degree of reality. And the other thing I like to ask is, are you up for it?

This is not somebody else’s job, this is your job. And just as you see the teams that are changing around you struggling, are you ready to take that on yourself? And are you ready to find those edges because of the change that we need to make, that we are called to make it doesn’t leave anyone untouched and we all have to be willing to embrace that. And are you ready? Are you willing? Is that something that you, you can do? And that can be a very a very profound conversation for people as they realize what are they really signing up for?

What skills are essential for long lasting enterprise-wide agility?

I phrase this as you need to be really good at it not only solving problems, but you need to be really good at how you solve problems. Right?

So for example, if you are a financial services company, you’re really good at financial services. And if you’re an IT department within financial services, you’re really good at implementing those things. How good are you at creating products, value creating products that will build your business and build value in the world and enable you to fulfill your purpose?

When I get invited in, I will ask, are you asking me to help you solve a problem? Or are you asking me to help you get better at problem solving?  One is a very specific thing, and one thing is a very wide capability. So I think that the challenge of agility is that organizations used to be able to just be really good at whatever they did. Right. Typically we talk about the business part of an organization, which is maybe customer facing and product focused and sort of determines the strategic direction. And then at least in a technology context, sort of the IT group the implementation people.And those two kind of entities tend to have a hard time communicating and working together and collaborating and being really effective because they’re missing this piece of competence called product, product leadership, product management, whatever you want to call it which helps translate and align between those two things.

That’s usually a bigger question that organizations used to be able to figure out, but today, the competition is so fierce. Rates of change are so high. Customer expectations evolve so quickly. What are you going to do about that? Like how quickly can you respond? How, how many options can you keep open? And how much choice do you have?

If you are serious as an organization about long-lasting enterprise-wide agility you got to keep those choices open and how you do that is, well, you need to revisit everything. When I enter into a system, for example, I ask about how do you manage flow of value? How do you make your products and service decisions? How do you define and assess quality of your, your offerings? How do you set up your governance and your organizational structures? How do you approach teams and people, the human beings in your organization? Do you talk about them using words like resources, talent assets, which are very mechanistic, or do you talk about them as what they are?

The human beings, they’re people and people are relational, not just transactional things to move around. I ask, how are you leading? And then I ask, you know, the thing that binds all of those things together is how well do you understand complexity? I don’t know that every organization needs to answer every one of those things, but I have a sense that they are probably important.

In what ways are one-to-one coaching and systemic coaching different?

Primarily scale because you can definitely use a systemic coaching at an individual level. You can help people understand where they exist in a relationship system. I just had a conversation this morning with one of my key stakeholders at a client, and for the past close to a year it’s been really hard for us to find enough one-on-one time to stay aligned and synchronized about the respective work we’re doing. On the surface it just looks like maybe we haven’t prioritized it, or it hasn’t been important enough. And so the question of, well, why can’t you just put time on my calendar seems the obvious solution there. And as we dig into what’s causing that, it turns out that in time her responsibilities have totally changed. Her focus has moved. You know, we used to focus on the same thing together. Now she’s focusing out over here, I’m focusing out over here. We have a little bit of overlap, but very, very small amount. Maybe that’s why we’re having a hard time finding time, because we have so little attention on that shared thing anymore. And once we realize that it’s like, oh, we can accept. We deescalate that the emotional charge around why aren’t we able to get together. Why aren’t we able to find this time. Why aren’t we able to prioritize making the time. Well, because the way that the system that we’re now in is not conducive to that. It’s not supporting us in that effort. So once we have that understanding, then we can maybe flip to an individual question of like, well, what do we want to do about that?

And now we’re focused just on the people, me and her, but that’s different than the context that we’re operating in as individuals and together. And so that individual work can be really profound in that way, but it does break down at scale. As soon as you have more than two people, how do you do individual coaching right now, you’re working with a team now, you’re working with a program and to be effective, you have to be coaching those bigger dynamics in those bigger entities often which are invisible. Relationships tend to be invisible and power structures tend to be invisible. Lines of influence tend to be invisible. So how do we find out ways to sense those and make them explicit so that we can work with them? And that’s I believe what systemic coaching is.

You are the program lead for our Enterprise Agile Coaching Expert Program. Why is this program so important?

This program is important because achieving agility is extremely difficult and achieving agility at an organizational level requires a mastery of so many different domains. When I was an agile coach, it was, enough to know Scrum. It was enough to know technical practices. It was enough to know the basics of the business. And with that knowledge, I can bring the right people together and we can have the right conversations and we could make things a lot better, pretty easily. Once I started coaching at the enterprise level I quickly ran out of tools and I realized that if I was going to be operating there, I needed a lot more. And that’s why I went back to graduate school to get a master’s degree in organizational development, for example agility cuts across a lot of different areas of practice, right? So for Agilists who have come from a Scrum background, they are often really tied to that Scrum is the answer. Folks who have come from a Kanban background can feel like Kanban is the answer. People that have jumped right into SAFe, the scaled agile framework, think that’s the answer. And what we’re wanting to do with enterprise agility is say yes to all of it. At least the good parts of all of it, and have a more informed, critical conversation around what of those things might we suggest or investigate, and which of those things are too risky? You know, what about economics? What about flow? What about all these other things that if you’re operating at the enterprise level? I believe you need to have not just a little bit of knowledge about them. You need a lot of knowledge about them, all of it, product development, it’s just everything. And so that’s a big ask. That’s a high bar. As we wrote the competencies (for ICAgile’s Enterprise Agile Coach Expert Program), we struggled as a group of, are we setting the bar too high? Are we saying that in order to get this certification is anyone going to be able to achieve it or are we making it too hard? And if you make it too easy, is it relevant? Is it valuable? Because somewhere in the middle, there is a really powerful place for practitioners to make a really big impact. So this program seeks to find that sweet spot by assuming that people are going to need coaches, as human beings are going to need to be supported, mentored, coached by their peers, by us as leads to achieve that. So we have this cohort based program where we as, as an agilist perspective, as a complex adaptive response, help people step by step level up to where we think they need to be. And at the end of that, you get you one of the core artifacts we have which is a case study. The case study is an artifact, but the cohort is not about creating the case study. The cohort is about developing you as a coach to the point where you can write it. And I think that’s really different. I think that’s really important.

What does it mean to be an expert?

So I think it means a knowing of your limitations. For me it is where do I need to help? Either from someone in my client or from another coach or from a group of coaches? I can certainly bring a tremendous amount of expertise. That expert-NES shall we say at this level is about being very clear on the limitations of that expertise and that I can’t do it all. I can do a lot, depending on where things go, I’ll probably need help. And that’s a different paradigm of expert than somebody who can do it all. An expert mechanic can fix anything in my car. That’s awesome. An expert, organizational agility practitioner cannot address everything that would happen in an organization. We know what we can do. We know what we can’t do. We know what we need help with, and we can pull those people in. [it takes a lot of] vulnerability, courage, self-awareness self-knowledge. We believe in this certification program, at least, you know, from the authors that built this, that self as instrument of change, that the agile coach themselves are the primary instrument of that change. And, how are we under stress? How are we under duress? How are we in ambiguity? How can we hold space, even in profound conflict? You know, we’re talking about the future of entire organizations and the future of careers and livelihoods and how much empathy and compassion can we bring to that while standing for, and asserting just the hard realities of business. How do we hold space for those multiple truths all at once. Sort of a weird version of expert, but I think it’s important.

This program sets a high bar. Why should I learn about this topic from you?

I am a practitioner first and foremost. I’m living this stuff every single day. I have an active portfolio of clients that are undergoing these kinds of changes. Some of them I’ve been involved with for years, some of them are much either shorter or briefer, or I’ve entered and left. This is not an academic pursuit for me. This is a pragmatic approach to making the world a better place. And I’m here to learn as much as I am to share and teach and to be coached as much as I can coach. And I would like to think at least that I’ve wrapped my head around some pretty big topics. People have told me I’m a good teacher, a powerful teacher. I can help them make sense of things that they couldn’t make sense of on their own.

And I feel like I can demonstrate competency in all of the required areas of an enterprise agilist, and I think that’s still a relatively rare thing. The whole purpose of this program is to change that and grow the number of us that can do that. But right now, today at this point in time in the world, I think it’s still a relatively small number. I take this really, really seriously. I’m really passionate about it, very purposeful about it. And it probably helps a little bit that I helped write the competencies as one of the track authors. So I have a lot of context about why those competencies exist and how they relate to each other from an intent perspective.

What does it mean to you to make a difference in the world?

Well, I think it means it means a lot of things. It means being a person of honor and integrity that I can be proud of and that my family can be proud of. I think it means being able to say with honesty and conviction, that every day I try to make a measurable impact, even if it’s very small. And it means that I still get calls from people that I worked with years ago. Sometimes I haven’t spoken with them for years and they share with me how impactful it was to work with me. And so they tell me that I’ve made a difference in their world. And I tell me that I made a difference in the organization’s world and that’s just profoundly moving and it’s profoundly motivating. We’ve got a lot of differences that need to be made right now in our crazy world of today. We got some big, big problems that we need to take a hard look at, and I think complexity and options. What we’ve learned about agility in the organizational space has a lot to contribute to those conversations and a lot to contribute to the possible solutions. So I’m hoping that what we’ve learned and through practice and application to refract out into the greater world certainly outside of software and definitely outside of the corporate organizational sphere.

If you enjoyed reading this interview and want to learn more from Kevin, you can enrol in one of the following amazing courses that he will be leading beginning next month:

Check out our public schedule or course pages for more info and to book your place.

I work at AWA HQ looking after day-to-day operations, speaking with people, organising events and training, and thinking up the next cool thing we can do. Outside of work I’m having fun with my family, usually walking our whippet, Luna or playing games with our daughter, Scarlett.