Building Bridges (Colleen Esposito)

Ben is joined by Colleen Esposito, an agile coach and self-described bridge-builder with an incredible set of unique experiences spanning finance, software development, project management, and even home renovation. She and Ben explore the complexity of engaging with organizations as an outsider and what it really means to change the way we work.

Colleen Recommends: From Chaos to Successful Distributed Agile Teams

Follow Colleen on Twitter!

Intro / Outro Music by DJ Quads


Ben: [00:00:00] Hello everyone, and welcome to episode five of The Hired Thought Podcast. I am so pleased today to be joined by Colleen Esposito. She is an agile coach who loves launching new teams. She has a deep root in the tech industry. She was a developer. She, even became PMP certified getting into the product management field and made her way all the way to agile.

It’s just an awesome. I think to have you here today, Coleen, could you say a little bit about yourself and introduce yourself to our audience?

Colleen: [00:00:28] Yeah, absolutely. Hi, I’m calling Esposito. You kind of summed it up pretty well. Um, I’ve had this meandering career that ended up in the agile space and I don’t want to go anywhere else.

Um, so I’m happy to share my perspective today.

Ben: [00:00:42] That’s awesome. One of the things that when we first spoke, you pointed out to me immediately was how much you loved helping teams get started. Could you tell me a little bit about what that’s like for you and kind of how that shows up.

Colleen: [00:00:55] Yeah, absolutely. So yeah, I think that’s where my passion lies right now. Although I think there’s an, there’s another thing that’s right on the cusp of that. Um, but one of the things I love is when you bring this thing that we call agile to a brand new team and how all of a sudden they start to realize how it’s going to really change the way they work together for the better.

And how it’s going to be about, you know exactly what the manifesto was, which was uncovering better ways of developing software, and helping them not only understand that and really grasp that, but I’ll still identify what that means for them. That’s for me, my biggest passion right now and my second passion right now.

That’s something that’s just starting to really come up, is to help the people who are kind of. Helping these teams in a traditional sense, like the managers and the directors and the VPs, helping them get this thing and what it really means, not only for the teams and how they’re going to work together, but also their interactions with the teams and how that could evolve.

Right. And perhaps even needs to evolve so that the team can truly become empowered.  self organizing.

Ben: [00:02:01] So, so coaching kind of in both directions, from the standpoint of the hierarchy, coaching up to the people in management and leadership who are maybe a little uncertain about what this means for them, but also

Colleen: [00:02:12] Absolutely

Ben: [00:02:12] coaching with the people on the ground who are doing the work everyday, who probably are a little bit confused, maybe scared.

Tell me a little bit about what it’s like navigating that transition. Cause launching, launching things is great. Where did we come from and where are we going? What does that look like on the ground?

Colleen: [00:02:30] So I can speak from personal experience, having been, you know, eons ago, right? I’m not that young, but a long time ago I was a developer and I, I kind of left that field for a couple of different reasons, but one of the ones that I left for is because I had some ideas and I would, I would, I’m a, I’m a frequent, “I have an idea”-er.

Is what I call myself. I’m always like, Hey, I have this idea. Now that doesn’t mean it’s the best idea in the world, but at least I have one. And I would bring up these ideas and would be told essentially, and I hate to paraphrase, but it’s pretty true. Don’t worry your pretty little head about that, Colleen.

We’ve already thought through all of those things and you don’t even need to think about them. Just go sit and code. And, that’s one of the reasons I actually left the tech field.

So I love bringing that back to these teams who maybe they have had some ideas and maybe their ideas weren’t necessarily welcomed and, or they just weren’t encouraged. Maybe they were welcomed, but they weren’t necessarily encouraged to have new ideas to approach that same old problem. Uh, and so that’s what I love the most, is helping them get this and bring their best.

Ben: [00:03:37] Adopting agile is such a kind of difficult shift in expectations and understandings. I’m reminded of a recent experience I had where, uh, in Pittsburgh we have a pretty strong agile community, lots of interesting folks working in this space. And there was, kind of this moment, I think I was giving a talk at one of the local tech conferences and I just kind of like asked to see how many people in the room had been using agile methods.

And then I did the same poll, but how many of you have actually like seen the manifesto and kind of read through the principles and, and thought about, uh, what the origins of this, these ideas were. And it, I was surprised how few had had that opportunity. And so that makes me wonder about a bunch of things right.

How do companies come about deciding to go agile and if that is the way that they’re viewing things, is making a switch from what was happening before to this new thing. Are the employees just along for the ride or are they aware of everything that’s about to change? How does it work for them?

Colleen: [00:04:41] So it’s interesting that you say that because I’ve just moved away from forced coaching cause I never, never been much of a forcer but.

Uh, or at least not in the last 10 years. I can’t speak about before then. Matter of fact, I probably was quite a forcer 10 years ago. Um, but this idea of invitation based coaching and inviting people into the solution, making sure that they understand what this thing is all about, the why’s behind everything that we do.

And then what does that look like for you? What does that look like from a very. Far in advance future future spective. What would that end state really be? And then what steps could you as a team, as a team member, actually take to move towards the vision that you’ve already identified?

Ben: [00:05:26] Yeah, that sounds awesome.

And part of this is like, it seems like it’s about giving people on the ground who are doing the work instead of just making them the order takers, be people who are making decisions and having agency in the process of the direction of the software.

Now that has to be counterbalanced though with the strategic direction of the organization. And I think this might have to do a little bit with what you were describing with coaching up, but I’m kind of curious what that looks like.

Colleen: [00:05:54] Absolutely. So the first thing I do when I come into a brand new organization is to try to understand the why’s behind their decisions, first of all. And then, you know, why did you choose to use agile? And if I, what I hear is twice to work and half the time, then I know that I might have to reset expectations.

Right? So, so I mean, but it’s good and it informs that. And the other thing I asked everyone is, what does success look like for you? , what do you envision there? What does that look like? What does that actually feel like? And then as a result of that, we design the coaching plan and the coaching engagement around that.

So that’s that strategic piece of it. I also have to understand the goals of the organization and the values behind that organization because agile is very value based. Very principle based, and if the values of the organization do not align with the values of agile, then we have to have a conversation.

It doesn’t mean agile will never be a fit. It just means we need to talk a little bit more. We need to think a little bit deeper. We need to really figure out what the path forward looks like for you. And it’s not going to be the same path as it is for any other company or any other team even. But once I understand the answers to those questions, then we can start to cocreate together.

Ben: [00:07:08] You drew an interesting distinction between forced coaching and invitation based coaching, and I’m really curious what invitation based coaching looks like.

Colleen: [00:07:19] Me too. No, I know. I have some idea what it is. Um, but, you know, keep in mind, I’m really early in this journey myself. So I think it’s bringing in, um, structures that actually allow the teams to make the right set of decisions for them.

And you know, uh, whether that be, you know, some of the liberating structures, which is something that I’m literally just getting exposure to attend my very first, very first liberating structure, a workshop last week. It was more of an exploration of liberating structures than anything else and having a lot of conversations around that.

But, you know, maybe that’s the thing. The other thing I’ve done, and at Assurant, this is a, it was an experiment that myself as a member of the agile center of excellence, there actually started to run is before we start any sort of adoption, let’s figure out the answers to some common questions.

And the questions are, why are we doing this in the first place? What’s in our way, right? What? What is kind of opposed to this agile thing? What’s in our favor? What are we going to do when, and there were specific ones. What are we going to do when we face anybody who has questions about what we’re going to do?

All right, what are we going to do when there are people who don’t want to work in this new way? What am I going to do then? And what I’ve seen in the past is often what happens is the, the leadership of the company says, well, we’re on this bus and if you’re not on this bus with us, well then you are going to have to decide when you get off.

And if you don’t decide to get off, we’re going to have to decide for you. And that’s a sad place to be because when you think about empowerment, doesn’t that mean empowering to also say, no, I don’t want this. And so what does that mean as an agile coach? Um, and, and I think that’s when I started that experiment, which was a few years ago, where not only did I bring the leaders into this conversation, but I invited them to bring their people into the conversation and to have some real honest conversation around what we’re really facing as an organization, even if it’s not pretty.

And let’s talk about that. And let’s say, okay, we acknowledge this is not where we want to be. This is where we’ve. Become, this is what we’ve become as an organization, but that’s not a place that’s going to be sustainable long time. It’s not a healthy place to stay, and if we want this organization to really be around in 20 years, in 40 years, in a hundred years, we might have to make some changes right now.

As a matter of fact, I would say, given what we’ve seen in the industry, they have to make those changes, but just to make them on their own without any involvement of the people, they’re going to lose their perspective that’s really valuable. That’s why they bring their people into the conversation, for perspective.

And also that’s that first invitation. This is where we’re going. This is why we want to go there. Here’s what we see is in our way and in our favor. Tell us if we’re right. Tell us if there’s something that we missed. Tell us if the approach that we’re about to take is not going to align to how you want to work as a team.

Ben: [00:10:24] It takes a lot, a lot of humility from the standpoint of leadership to be able to entertain that conversation. And I was just struck by what you just said about. Being able to say, no, this reminds me so much of the common kinds of problems that come up with ideas like culture change and culture is, it’s funny, um, is kind of like this ingrained aspect of almost everything that we’re doing.

And it seems kind of interesting to try to like point at it and go like, we should change that, but in any major disruptive. Shift in any major disruptive transition culture is part of that. And I’m curious with that question of whether or not, you know, people who are participating can say no, what does that look like, that cultural aspect of changing the way that the work is done ?

Colleen: [00:11:12] That’s a big question. So, you know, and I’m not sure that I have a complete answer for that. I know, I just know what I’ve seen and what I’ve seen work and. Um, so you’ve got to think of culture. Culture is something more than just the organization.

Of course. It’s more than even just how they interact together. It’s this system of relationships. And I had the  pleasure and also the confusion of going to organizational relationship system coaching last year, which took everything that I knew and like kind of threw it on its head. I mean, some of this was instinctive for me, but other pieces of it, the fact that when you have an organization, an organization is built on relationships, makes absolute sense and always has.

But then what about the fact that these relationships actually create entities between the relationships. That is, every relationship is an entity and each person in the relationship is also an entity, and then the organization as a whole is an entity. So you have all of these entities interacting with each other and that big organization system is complex. It is constantly evolving in response to whatever stimulus or whatever change it goes through. So you have to consider what are the possible outcomes of whatever change we’re trying to introduce? What could happen to this system? Not only how can we make it happen, but what could happen? What are the possibilities?

What could go right? What can go wrong. Really wrong and how do we need to consider those things in whatever we decide to do next. The other thing I do is very, very, very small experiments and see what happens as a result of that experiment. And I think that makes a big difference too, to help that organization move to where they want to move.

Because if they think this thing is going to get them there and then they find that it doesn’t. Well then they’re going to have to make a decision about what to do next. It’s different than what they originally planned. How to adapt to change, something like that.

Ben: [00:13:24] Yeah. If they don’t have that presence of mind to recognize the underlying ideas that are driving them, the goals that they have, the hopes that they have about the outcomes.

Then if this one change doesn’t result in what they were expecting. There’s almost like a collapse. And so I always find it’s really helpful to go in, dig in for something deeper. And let’s, what I heard in what you were describing, always going for the underlying kind of, uh, motivations and understandings of what’s going on in the organization and really approaching it from that standpoint.

Addressing complexity like that is, you know, what can go right? What can go wrong? We are speaking the same language. Like, this is just so useful for thinking about these really messy kind of places to, to think about.

Um, one of the things that comes to mind is the notion of being almost a free agent inside these organizations

When someone hires you. Brings you into the organization you are one, constantly trying to understand what the current state is and orient to it and going again, going back to the motivations and underlying kind of mechanisms of how it’s working, but you’re also trying to interact meaningfully with it and intervene in ways that enable a higher state, a better way of working.

I sometimes wonder if roles like that exist and succeed. If only for being able to connect people together and be a line of communication between them. Is that theory close or is it wrong?

Colleen: [00:14:58] I would say that’s pretty valid. Um, relationships do everything right. They, they’re what makes the change happen. Um, and, and I consider myself a connector actually, before I came up with my

Current, you know, kind of describing who Colleen is. I call myself a bridge builder. I am naturally a bridge builder. I try to build these connections between things and especially between people, and I think that’s a huge part of what I do. Um, I also think too, a lot of times organization bring someone like my myself in thinking that I’m going to make huge sweeping changes.

And eventually, maybe, but in the very beginning, it’s often connecting like what a development team is doing. With what an operations team is doing and the company that I’m just about to finish an engagement with had teams that were aligned around the departmental goals for each without a view and an insight into how each of them plays a part in the value stream that then, you know, produces value for their customer.

They had actually completely lost sight of who their customer was. Much less the fact that no matter how quickly development got because of this agile thing, if operations couldn’t deploy those things, just as quickly. We really weren’t going to have any gains at all within that company, so that’s another thing I brought to that organization.

Ben: [00:16:25] So taking a step back and thinking about this larger kind of scope of, of your career, like you, you’ve seen a lot, and so I was wondering, you said that you left tech because you had ideas and you had big thoughts about how to change the world. You entered project management and even got PMP certified, and that was sort of the path your life was taking. Could you connect the dots between there and here? How did you get to where you are?

Colleen: [00:16:53] Oh goodness. Okay. I have a full confession to make and I feel like I’m in church, so I was exhibiting behavior that I didn’t necessarily feel comfortable with, but I kept doing it because it was effective. Right. And by behavior, I mean things like manipulation. Right, and forcing and, and, and things like that.

And what happened? And I was very successful. I was able to deliver a whole bunch of stuff. And I love doing things. I’m a doer, right? But I also got to a point where I realized that the way that I was acting. Was doing harm. It was doing harm to others, right? Because I saw these people who are losing all this, you know, personal time with their family, and they were, their relationships were suffering and they were personally suffering.

I actually saw a team who went from very happy and smiley to completely morose working every night and every weekend, and just hopeless, almost apathetic after a while because they felt like they couldn’t make a difference no matter what they did. And then it started to impact me. And I realized that what was happening was being in that role and working in that way was eroding my soul.

And I was harming other people, so it was harming myself and harming others. And I had to stop. I actually left the profession for about three months, four months while I gathered my thoughts and tried to figure out what I wanted to do next. And what I decided to do was to move to another company.

Because I thought that it was the way that the company’s culture was, and it, it was a very toxic work culture. One of the most toxic I’ve ever been part of. And, um, and, and it was bad. But what happened as a result, as I ended up getting thrown into agile by accident, and thank God for that, because all of a sudden I went from, you know… Am I going to be a project manager? This is what I’m good at. This is what I know. I don’t know how to do anything else right now. What does that mean for me? Do I have to go back to school? … To, got thrown into this, this new team who was working in an agile way and went, Oh my gosh, this is what’s been missing the whole time.

This is the heart. This is the soul. These are the things that are really going to make a difference, not only in the company’s future, but also in the individuals’ future and in my own, and it certainly has.

Ben: [00:19:20] Wow. That is quite a transition. That is quite a story and it’s amazing to me that you were as sensitive to this question of, of suffering, frankly. I think a lot of corporations and large organizations tend to have a lot of like, effects that, you know, no one person is particularly responsible for, but that the structure and the incentives and the way that the entire thing is set up basically guarantees certain kinds of outcomes. Things like stripping people of agency, forcing them to sort of become individualists, or making local politics be the thing that’s most dominant and effective as a way to make decisions.

All these things are kind of, in some respect, right, they have value and they are useful, but to certain extremes and certain extents, they become actually detractive from people’s ability to survive and, and feel good about the work that they’re doing. But suffering is in systems, I think is one of those things that I’m in particularly, fascinated, and, and, and, you know, very like, curious kind of way because I’m so sensitive to it. When I notice something happening where there’s kind of like this wedge of someone being crushed against some system, some incentive, and I can see how they are actually being harmed by the system that they’re a part of.

Um, I’m extraordinarily sensitive to that and I can always point at it. And that’s really hard to do when you’re someone working on the inside. As someone who’s part of this system that is essentially performing this behavior. But as an agile coach and as someone who has maybe a more, uh, not temporary, but less, uh, steeped kind of perspective.

You’re, you’re not the fish in water that can’t see the water so much, cause you still have the external perspective of all the other organizations you’ve been to. And generally being new to the organization generally, um, and how it works and learning how it works in its own ways. Um, how do you see your role as an agile coach in that reduction of suffering? Is it just the sort of helping individuals find agency and power at the ground, or is it also in that coaching above? How do you play that role in making that possible in an organization?

Colleen: [00:21:42] That’s actually a great question. I mean, I think what I, I think I focused on the customer period.

The customer could be that individual who’s in the system, who’s currently suffering. It could be the managers who are part of that system. It could be the executives who, and maybe even unknowingly are creating this system of suffering. They don’t even know. I don’t, I don’t consider that as an intended consequence, but it’s perhaps that they intend to do no harm, but they haven’t considered the entire system and how that actually can, can impact people.

Ben: [00:22:19] The executives don’t always mean to do certain things, right? It’s a large part because what can you fit inside your head, right?

You, you can only. Imagine the impacts of your actions to the extent that you’re actively exposed to the, the feedback, frankly, and thinking about like the iceberg effect, right. Where you only so much information…

Colleen: [00:22:43] …is visible to you. Well, let’s, let’s go even further. Think about this. We all think we can see everything, right?

But what we really can see is what’s just at the end of our thumb. That’s it. That’s all we can really focus on. That’s a really small area. And yet we think we see things. So, you know, there’s this, this, there’s all these things that are, um. Much more visible these days. The idea of you’ll have unconscious biases, you know, cognitive biases and bias is just a part of who we are.

But being aware of the fact that we do have a bias. Yeah. We can only see just at the end of our thumb. It gives us the permission to actually ask questions if we choose to. Now suffering as a whole. You brought it back. My visit to Menlo innovations in Ann Arbor and how their entire purpose in life is to end human suffering as it pertains to software development.

I cannot get out of my brain the image of the guy on the project that went well because I managed it from the very beginning. And how we got to the delivery point. We were ready to start UAT. We had done everything right, checked all the boxes, when there were scope changes we did a change request, and then we went to go deliver this thing and there was an interpretation issue, how the requirement was written and how it was delivered.

They exactly aligned. But the way that the person who wrote the requirement and the rate of the person delivered the requirement was different. And  basically our stakeholders at that time decided that they were going to dig their heels in and they were going to do whatever was necessary to win.

And the results  was the lead developer who had, by the way, lost his father during that year and still gave everything he had. Was forced to work nights and weekends. And that’s the one that made me leave the industry. Cause I said, I can’t do this to people anymore. So that’s the real impact of some of the decisions that are being made and the lack of perspective, um, awareness and the lack of asking questions.

Ben: [00:24:56] There’s a phrase that comes from lean manufacturing. Basically it’s, it’s go and see. Let’s go and walk the floor. Yes, exactly. And this idea that an executive or a manager. Should kind of have this humble observation, uh, show respect and kind of try to understand how things work and what the impacts of the decisions that are made often completely away from the work that’s actually happening, how those actually have much different and sometimes terrible, uh, effects. I think that kind of perspective is, is necessary, but it’s so often missing.

One thing that we talked about before the podcast started that I was really curious about getting your perspective on, was, I know that you survived as in lived in the moment during the 2008 financial crisis.

Colleen: [00:25:50] Yes, I did. Yes, I did.

Ben: [00:25:52] That is fascinating to me and want to learn, I want to know everything, but I was wondering if you could give me like the short version of the story of what that was like.

Colleen: [00:26:02] Yeah. So it was working for a really large financial institution. Um, one of the secondary mortgage market one of the players in there. And, uh, the project that I was managing could have limited the risk that that  institution had to the more the, the crisis. I don’t say that it could have prevented the crisis because there were just way too many factors going on, but what it was all about was taking a look at the derivatives that they were purchasing, basically the mortgage notes that they were purchasing and the risk that was inherent in the purchase of that portfolio of mortgage notes.

And this particular project could have shown them how much risk they were about to take on before they purchased this portfolio of really, really bad loans. And it didn’t go well. Well, I hadn’t managed that project from the very beginning. They had run into a bunch of challenges and I had taken over when they were supposed to be coding and they hadn’t even finished requirements.

But I think often back to the fact that like had agile been mainstream, more mainstream than it was back then. You know, kind of like where it is now and the company moving towards agility at that point. What difference would that have made? Well. What we ended up doing to be successful was to work right alongside the customer because the customer had a lot more domain expertise than the team member would.

Matter of fact, the team never would have that kind of expertise and that knowledge of knowing when we bring this data in and there’s this translate layer that we’re interfacing with that isn’t ours that we’re not actually even building. And then we’d get numbers that are completely different than what we inputted, are they even right?

We had no way to know whether those numbers were right. We just knew the numbers we were receiving. And um, so had we been working alongside the customer, had we, um, build things in a more iterative and incremental fashion where we could show off what was actually ready to be shown off, and then we could have delivered value much quicker.

Could it have prevented the risk and the exposure that they were actually facing. And I believe the answer to that would have been yes, yes. Had we been able to deliver that in an incremental and iterative fashion, that project could have made a huge difference in the future of that company.

Ben: [00:28:25] Wow. That’s amazing.

Yeah. And my, uh, kind of knowledge and experience of having lived through that is, you know, I was only a kid and I, so I recently watched The Big Short, and I’m just like this whole dramatic like portrayal of everything that was going on and happening. But to think that. All, all it really could have come down to is the ability to, to see the risk, uh, with software that could have been delivered in a way that would enable that risk to be, uh, more readily available, maybe not perfect, maybe not feature complete, maybe not perfect requirements, comprehensively documented and very carefully artisanally crafted, um, and maybe delivered never.

But, but maybe just maybe if things had been delivered incrementally, we could have seen a difference in the way that that played out. That is a heartening thought to think, and I wanted to thank you so much for being here today and for sharing this time with me.

Is there anything that you’ve been reading lately or any books or articles that you would like to recommend for people to check out.

Colleen: [00:29:28] Um, let’s see. So I just finished From Chaos to Successful Distributed Agile Teams by Mark Kilby and Johanna Rothman. Now I’ve been working with distributed teams for a lot of my, my career. Um, surprisingly just because different locations, and even if they’re not sitting together, it’s kind of distributed, right.

Or really is distributed if we’re not right co located. So there’s different approaches that need to be taken.

There is one hidden tip in there that I just tweeted about… And I tweet, by the way,  @TheColleenE… that I’ve found in that book. This is almost a matrix of, Hey, is agile, right? For your team? Depending on what your context of work is and what domain you’re actually working in, it may be, but you know what, it may not be. And here are some alternative approaches that many people haven’t even heard about that you could use to weigh in your decision.

Ben: [00:30:24] Awesome. I’ll make sure to include it in the show notes and I’ll make sure that people can find your accounts and follow you on Twitter. And, uh, any final thoughts? Anything else you’d like to share.

Colleen: [00:30:34] So I, you know, agile is not a fit for everything, but agile can be a fit more than you realize.

So I personally have used agile to remodel seven houses. Matter of fact, it didn’t just help us remodel the houses, it helped us really think about the outcome that we wanted to achieve.

And the first outcome that we had, we achieved very quickly to live in a house that was better and nicer than we could normally afford. And then the second was this, getting a house for cash, no mortgage. And it’s been pretty awesome. You can also use agile to respond to crisis.

I’ve done that a couple of different times, so just imagine the possibilities. Yes. Don’t take agile in as something as a solution for everything, but do think about when you’re in the complex zone, when you’re in this complicated zone, where could agile actually fit? Well, it’s more than just software.

Ben: [00:31:25] That’s for sure. Thank you so much, Colleen. It’s been fantastic to have you.

Colleen: [00:31:29] Thank you so much. Take care, Ben.

Ben: [00:31:31] Take care.

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