Hi, my name's John Smart. I'm here at the DevOps Enterprise Summit 2022 in Las Vegas, and I'm here with Ross Clanton. Hi, Ross. Hi.

Do you want to, uh, introduce yourself and, sure. Uh, I'm Ross Clanton. I, uh, I'm, uh, chief Architect and managing director at American Airlines. I lead our, our technology transformation there.

And I've done that at a few other companies too. Yeah. Yeah. Um, so a, uh, an often question that gets asked is how to get started.

Mm-hmm. So, how to get started on the journey for, uh, better ways of working or transformation. So, Ross, in your experience, um, you know, what, what are your learnings and insights around getting going? Yeah, actually, one of the very first talks I did here when I was still at Target, probably 2014 or 15, I addressed that question kind of directly and, and really was saying, just start.

Like, just do something. Like, you've gotta start going down a path and, you know, don't spend all this time trying to plan everything and figure out how to get everyone in line. Just start small, get teams starting to work differently, experiment with teams. Every company I've, I've done transformation at or, or in America, and I joined after we already started, but we, we followed a very similar pattern as well.

Usually these things start with a couple teams. It's, you know, focus in on how you prove the value and how you do it, how you can demonstrate how you can do this stuff kind of right before you start trying to scale it across the enterprise. Um, and at that stage, I wouldn't, um, you know, I would try to actually give the team space to go and figure things out. I think as you start to wanna scale things and have more teams doing it, you do, uh, you do get into a lot more challenges.

'cause now you're talking about bringing more management and you're talking about different parts of your business getting more involved. You're talking about, um, finance potentially getting involved based on how you want to go after funding models. Uh, and all of those things add a lot more complication and, um, and it takes a lot more work to drive change and, and org change management through those types of situations. But, uh, you can't get there until you start to prove value and you gotta start small to prove value.

Yeah. And, and when you're starting small and you're starting with a first couple of teams, how do you, how do you figure out, identify which teams to start with? Hmm, good question. We, I've done it a few times.

So one approach was we picked, uh, teams that represented very different patterns in terms of like their technology stack, their architecture, the makeup of the team, um, so that we could prove. And we, we started with like three teams. Um, like one of them was mainframe based. One of them was more kind of modern development.

Um, I think one of 'em was cots and off shelf based. And we focused on, uh, this is before we were even getting big in product in the industry, but even from a, an agility perspective, we really focused on, all right, how do we get these practices to work in this type of an environment? And so we had three very localized experiments to demonstrate that you can get better outcomes in all of those patterns. And the reason we did it that way was so that when we did want to go and scale, we could demonstrate that we've, we've actually solved problems similar to what these different teams are experiencing.

So it, it helped us down the road when we were tr trying to figure out how to do the change management on scaling it. Um, you know, at American, the company I'm at now, uh, we started there. It was there, I would say it was a little different because we had a, actually my co-presenters at the conference here today, uh, Julie Wrath and Steven Leis, who are two executives, uh, at, at American that were kind of the early champions of this really, we started in their organization because they were the leaders that leaned in at the time and said, we gotta do something different. And, um, so even there, they picked two or three products, but it was, I don't know that they picked them because of different patterns.

They just wanted to just show their own organization that they could do this before they scaled it to everyone. Um, so, you know, I think the selection criteria and how you choose the few teams you start with could be based on a number of different things. Um, but you do gotta start small. You know, the target example was three teams, three different parts of the org, different patterns.

The American Airlines example was more same org. Um, but because of the leader involvement at that time, those were the leaders that wanted to drive change that really kind of dictated where we started. Yeah, I like that. So picking different contexts.

So you've got a broader range of proof points. Mm-hmm. Um, and I like the, the, the, uh, invitation over infliction of the leaders who, who basically the impression I get is they put their hands up. Yeah.

And they said, me, us, yes. We want to do this. Yes. That's, uh, um, one of the reasons I, I was so excited that Julie Wrath came and spoke with us, with Steven and I this year.

She's, uh, an SS S V P and, and, uh, she was in our kind of customer facing group, not in the technology organization. Uh, she was a VP back then. But, um, she immediately, when they did that experiment, um, like got hooked, right? They, she saw, and the reason she got hooked is she saw how the team pivoted, like how the energy in the team, how excited they were.

Um, and like it was one of the best things you could do at the early stages of a transformation. 'cause you just developed like a huge champion. Um, who over the years that the five years that American Airlines has been, been going through these cha this transformation since then, she's been a huge advocate and she's helped us scale it much broader in the organization. She's actually moved to a whole different part of the organization now, more on the air airline side of the airport side of our business.

So it's been really good. That's good. I was gonna ask about senior leadership and senior leadership support. Uh, in terms of, in terms of getting going, how important is it to have senior leadership support?

Uh, it is absolutely critical. I, I, you know, I've done, I've done a few of these now and I've seen a lot of different patterns both in the companies I've worked in and people I've collaborated with of varying levels of senior leader support. Uh, you know, when I first started at Target, we were so bottoms up when we started, and it did kind of work for a while, but then when we really did get top level support, we had a new C I O come in that was really championing this, it really accelerated things at a much faster pace than I could have ever imagined. And, and Target's had an amazing story in the industry as a result of that.

Uh, you know, Mya, Maya Liebman is the, has been the c I O at American Airlines. She, she's who hired me. And, um, one of the things that I was so excited to come and why, why I ultimately joined American Airlines was, you know, I had the C I O and the c e O of the company. Even Doug Parker called me a couple times before I joined to explain how important our delivery transformation was to the entire company.

It wasn't an IT thing, um, why this was critical to how American Airlines was evolving, how bought in they were, you know, as much success as I had at Target, I don't think I ever had the c e O of the company call me about our, our IT transformation as it was largely viewed at that time. And, um, when you have that support at the top, uh, it helps, it helps cut through a lot of the, the resistance to change that happens across the organization. And, uh, and it happens in every organization. I mean, human nature, there's natural change resistance there.

And if you, you don't have really good support, you're gonna be battling uphill on a lot of things that, uh, it just kind of makes it flow a lot easier when you get it. It's not always easy to get it. And it can change when leaders change. Um, you know, I actually, I'm having a c i O change at American Airlines right now.

I'm really excited that Ganesh Jairam, our new, new C I o is very bought into this stuff as well. But I can tell you, I've, I know all the horror stories and I've been involved with some of C I O or c T O level changes, and then suddenly the whole thing gets undone in weeks sometimes. Yeah. Yeah.

I've seen that as well. Yeah. Yeah, yeah. Kind of years to make forward progress and A month to undo it, month to do it.

Yeah. Um, and, um, so I think this comes to incentive. Mm-hmm. I think the, the, the more senior a leader you have who's supporting it that effectively is providing incentivization across the organization.

So, um, you know, I I find then when you go knocking on a door of finance or HR or another, or a support function, the door opens and there's a willingness to have a conversation. Yes. And sometimes, I mean, when you have a really engaged senior leader, they'll sometimes even go have that conversation for you, which makes it even easier. Yeah.

Yeah. Definitely. Definitely. Um, what would your advice be for anyone who is trying to enact change in their organization where that's not in place?

So it's not that there's resistance, but maybe there's just like a, just not knowing, you know, just not being aware of the potential benefits. Mm-hmm. You know, what would your advice be to anyone in that situation, in an organization? You know, either bottom up or kinda middle out.

You know, what, what could someone do? I mean, I think if it's a top level issue, you know, a lot of executive top level executives are wired to think about the return the business case, what's, you know, what's the value that you're gonna get out of it. Um, and that can be, I still believe you have to figure out how to experiment early before you try to solve all of that, because figuring out how to bake out the entire value of a entire enterprise transformation can be a long undertaking. Uh, but for some organizations, that's ultimately necessary.

I've, I've worked in somewhere I've, where that is kind of how you ultimately get it aligned. And I've worked with some that you get lucky when you work with some where they just intuitively get it. Um, they either, there's been disruption, you know, with retail, the level of disruption that happened when all this started at Target made it so obvious that as a retailer, we had to fundamentally change that. There wasn't a lot of, um, trying to make a case on why we had to change.

I've worked at other places where you do have to make more of a case because the burning platform maybe isn't there for that sector in the industry. Um, so, but ultimately you do have to figure out how to make a case. What I will say is one thing I've loved about DevOps more than any other space I've worked in, and, and I would say the product community follows a very similar suit, is like how much people want to share and help each other. Like, people that are driving these changes in companies want to help each other get better.

I'm a, I like the quote, uh, rising tides lifts to all ships. I use it all the time. And I think it describes this community really, really well, because when everyone's getting, when everyone's helping each other get better and everyone gets better, then it ultimately, it makes everything better for everyone. And, um, because there, and part of the reason it does is because you have more examples to show.

Like you can maybe talk to other companies in your, in your industry or, um, other companies that are maybe in an adjacent one where, where you could learn how they're doing it. Um, most people in this community are, are very, um, willing to give their time to go and have conversations and share what they've done. Maybe help talk to some of your executives, um, take advantage of the community. One, one thing I love about the DevOps Enterprise Summit is there's a reason, this is my favorite conference that I I go to every year, and I'm so thankful it's back in person, is the format of this is powerful because it's, it's mostly people working in companies trying to drive change, and they're all sharing their stories with each other.

And then you get an opportunity to come and connect and meet each other and do the hallway track and talk to each other, and, and you, you build these connections. And, you know, I mentioned on, on stage, uh, this morning at the, at the closing, every transformation I've done in any company, the inspiration that I got from it came from this community. It came from some hallway conversation or some bar conversation or some presentation where it was like, oh, they tried that pattern that looks like it worked for them. If I just tweak it this much, it's gonna work in my context, I think it'll work.

Like, we gotta go try that. And then they make themselves available to talk to you about it and even maybe talk to other leaders in your company about it. Uh, and it's, yeah, that was a long answer, but I would say take advantage of the community and the collaboration, the sharing that happens. Yeah.

I think that's a great answer. Yeah. The shared learning, um, and the social proof. Yeah.

And, and, uh, I've seen the same positive impact when you connect different organizations together. So there, there may be people in an organization who are not aware of the potential benefits of Yeah. Certain changes. Um, and then you, you, when they viscerally, viscerally see it in another organization and experience it and feel it, it's like, oh yeah, the light bulb's gone off.

Yeah. Like the light, well, the light bulb's come on. Like, we should be doing this too. Yeah.

The trick is how do you, how do you create excitement and energy for change? And I don't know that there's, I, I wish there was a silver bullet and there's a clear pattern for it. But I think when you can get there and, and it, I think you get there when enough leaders get aha moments. Uh, and whether it's aha moments for what they're seeing in their own comp company or what they learn at a conference like this or what they learn, because you set up some collaboration sessions or an expert like you comes in and you help, you know, know they've read your book or they, they, you've come in and you've helped illuminate some things for them.

Like, all of those different things can create aha moments for leaders. And I think you, you need to get a tipping point. You need to get enough of these aha moments that you get enough people excited about change that starts to build energy for it. Um, to me, like that's the trick culturally on how to drive a change in the company.

And I, and I, and I don't believe that it's the exact same pattern to get there in every company. And so that's a little bit of the trick with it. Yeah. Yeah.

Yeah. Great answer. Strongly agree. Um, something you said there about community as well, uh, creating the Rebel alliance in your organization.

Uh, yes. I find that works. Rebel Alliance. Rebel Alliance, Yeah.

So, or a, or a community of practice where basically you get the, you know Yeah. The people who will ask forgiveness rather than permission Yeah. To do the right thing in the company. Mm-hmm.

Um, yeah. I find that helps Too. And how do you empower those people? We actually use that term back at Target.

I think we called ourselves the Rebel Alliance for a while, and it wasn't like a team, it was a community of people that wanted to change. We've been using the term DevOps revolution at, uh, at American Airlines, very similar, right? Like, like, we wanna change, like we're, this is a revolution. We're gonna do it differently.

Um, I think figuring out how to empower those people and give them a voice and connect them is really, really powerful. Yeah. Uh, and when I look back over the last eight, 10 years, those have been like the biggest pivotal moments where step level change happened. Uh, and I didn't always know it was gonna happen.

It just, it got the right experiment of trying to pull the right things together and suddenly it clicked for people. Um, but when you get the opportunity to build more of those people, connect more of those people and empower 'em, you, you gotta jump on it every time you get it. Yeah. Yeah.

So making change sticky and sustainable and long lasting. Mm-hmm. So there's the, you know, the, the peak of excitement. There's lots of smet, you know, there's lots of excitement around we're doing this thing, especially when there's a senior leader who is, uh, verbally, vocally supporting change.

Mm-hmm. And, uh, as you said, uh, as you said earlier, you know, there might be a change in senior leadership at some point in the future, and, you know, it can go backwards very quickly. Yeah. So how do you, um, how do you make it sustainable and long lasting in your experience?

How do you make change sticky and durable? Uh, you, you have to be continuous about how you message it, iterate on it, bring people together. You know, one thing, uh, I was just having this conversation with some folks in the, in the hallway. One of the patterns I felt like has been the most powerful pattern in the companies I've worked is something as simple as creating, you know, we would model it after like a DevOps days conference, but creating a lightweight way to bring your people together on a very frequent basis, like quarterly, and get them in a, in a, in a fun environment where, where they're sharing, they're connecting, they're learning from each other.

You're infusing in maybe external thought leadership and other speakers. And, and, you know, I, I jokingly, I call it like our pep rally, because what, I mean, what happens is when people are trying to drive change and whatever, however big the group is that's trying to drive the change, usually there's some common characteristics about those types of people. They're usually really passionate, they're change oriented. Um, they're willing to, to be vocal and get out there and try to be leaders of change.

Um, but this stuff's hard. And there's always resistance, as I was saying earlier. And you do get worn down after a while. You, you need to recharge, you need to reenergize.

And, you know, I, we, American Airlines brought we 50 people to this conference this year, and I, I didn't even know all of them coming. I was just sitting there talking to a bunch of 'em, and they were talking about how energized they were at this conference. And I'm like, that's exactly what we need. Like, that's why we do this, because they're gonna go back to the company.

They're gonna have a, a renewed passion to push harder and change more. And if we have some way to connect, keep connecting with them, we can keep that, that flame lit. And if you don't, it can burn out. I can tell, even for myself, I get my, I recharge from being in this community and for, for a number of years.

I saw you and other, like friends of mine in this community that I've been close to 2, 3, 4 times a year at community focused events where we, you know, we, we kept moving these ideas forward and that kind of disappeared with covid. It, you know, the conference scene dried up, everything went virtual. We tried to do many things to recreate virtual experiences, but it's not the same. You don't, you know, it's good, but you don't, you can't connect, you can't have the hallway tracks the same way.

You can't get the deeper learning that happens outside of the presentation the same way, uh, and the energy isn't the same. And so I'm, I've been ecstatic that things are starting to get back in person. This is my second, uh, event that I've gone to in the last four months, and I hadn't gone to one in three years. Uh, so I, you know, I think there's a lot of ways to sustain change, but somehow you have to keep, obviously, support supported the tops key, but you've gotta figure out ways to keep the base engaged and keep the base excited about what's happening.

Mm-hmm. Yeah. I like that. Keeping people excited energy.

Mm-hmm. I can, can, I can totally see how 50 people from American Airlines are gonna be pumped Yeah. You know, from, from being here and energized to carry on. Yeah.

Um, and I'm excited about it. Yeah. Yeah. Uh, and a, a personal reflection also speaking at a conference mm-hmm.

Is a great thing, I think, to encourage, uh, people to do, because it makes, it makes you take a step back and reflect on the progress that you've actually made. Mm-hmm. When you're in the role, you know, when you are working hard, trying to improve things Yeah. In an organization, it feels like you're never making any progress.

Um, and it's feels like incredibly hard work. And then you, you come to, to a conference like the DevOps Enterprise Summit, and it's like, oh, well actually that's quite refreshing to just take a step back and realize actually we have achieved some stuff. Yeah. Yeah.

No, it's, sometimes I'm the most critical internal leader. 'cause I do, I do have really high expectations on what, what we can, what any company I would work in could get to and what we could achieve in terms of, of a transformation like this. And I've seen greatness in many different pockets in companies. I've worked collaborating with other companies, and so I know what's possible.

Uh, so you're right, sometimes you get really critical and, uh, you're thinking about how much progress have we really made? But yeah, when you come, when you come, when you take the time to actually think about the progress you made, and you package it up, and you come share it, and you get in these deeper conversations and you hear what people are taking away from it, even like what, what nuggets they're taking away from your story, uh, it's, it's motivating. It's re-energizing and Yeah. It's an awesome experience.

Yeah. And you know, I I, I always hope that there's, you know, all these talks, for instance, at the summit, you know, all these experienced talks from these companies, usually there's like a couple aha moments, like, oh, that company, you know, they're doing this pattern or they have this way of messaging things or, uh, and it's novel. It's new. It's maybe a little bit of a pivot on something before, but it's enough to like trigger a different way to think about and be like, I think something like that could work in my company.

Uh, so yeah, it's awesome. Nice. Nice. Um, and one final question.

Yeah. Uh, let's imagine your passionate senior leader who is advocating for change at the executive committee level, at the top table moves on, yeah. Goes to another organization. Let's imagine, hypothetically speaking that, uh, a new leader or leadership team come in who don't have the same mindset or belief system.

In your experience, have you seen any kind of tricks or tips, or do you have any advice or thoughts as to how, you know, assuming you are working in that organization, how might you prevent, as we were discussing earlier, you know, things can roll back very quickly. Yeah. Do you have any thoughts as to how you might, uh, prevent things from rolling back quickly? Yeah, I think, I think for a while, and even like this community, this conference, its origins are in DevOps.

And, you know, in the early days, a lot of these DevOps transformations were very, IT focused. And I think as you know, the product community and the DevOps community started to merge more. And, and a even agile and DevOps started to have convergence points, and these communities started to come together. And even the evolution of how we've thought about agile, I think even as like, you know, product mindset and product model have taken hold in the last five years or so, these transformations are increasingly being understood as business transformations, not, not technology transformations.

And what's important with that is that if it is just a technology transformation, at the end of the day, all your other executives of the company are not paying that much attention. 'cause it's like, oh, it's, you know, the technology team, they're doing what they're doing. Um, well then the, the, at the end of the day, whoever's leading that organization is ultimately the leader that's gonna make or break where you go when you start to have it be permeating across your business, and you actually get buy-in and stakeholders and champions that are in finance, and they're in different business groups. I know that, you know, business versus it, but they're in different parts of your company, and they're not just the technology organization.

It, I, it has staying power, then it can outlast a leader, uh, a, a, a functional leader that leaves. Um, so I think, I think that's key. And I think we're increasingly seeing with, with how much product has really taken off. And that's, that's not some niche thing that's happening.

That's just something many in the industry are going after now. I think that's actually helping propel this to a level where it's, it's harder to undo it. It, and then if that, and if it does happen and you get a whole new leadership team. Yeah.

If you're a passionate change agent that believes in this stuff, you're very hireable. So sometimes you just gotta make a decision to work elsewhere too. But change your, Change your org or change your org. That's right.

Yeah. Yeah. I like that. I like, I like your answer as about being, you know, uh, effectively, uh, business value make it about business value A hundred percent.

And if, and if you're focusing on the outcomes mm-hmm. Not on activity. Yeah. Not on the means to the end, but if you're actually focused on articulating and measuring and communicating the outcomes and the outcomes include business value outcomes mm-hmm.

You'd be crazy. Right. To, to undo anything and go, you know, so in my language, better value sooner, safer, happier. No, I want lower quality.

I want longer time to value, I want unhappy. Of course. No one's gonna say that. I think you, you bring up, you bring up a great point on that because if, if you're achieving the outcomes, if you're achieving better value sooner, safer or happier, who's gonna undo that?

Like, there's no executive anywhere in your business that's gonna be like, I don't want that. Um, now a lot of these transformations don't get to value either, often because there's challenges somewhere in, in the transformation itself. Uh, and that that absolutely can be a factor in things getting undone. But, uh, you know, part of the challenge is, uh, you know, a lot of executives, a lot of the things that, that are espoused in this community and that people are learning are very different ways to think about how you've traditionally delivered technology, discovered value, thought about your work across an organization.

And, uh, it's, you know, the one thing I guess, and this is maybe a detour, and I'm probably rambling a bit so you can cut this part for a second, but, um, the, the thing that I guess, I don't know a decade in on this stuff that still kinda gets at me is there still are a lot of leaders in a lot of companies that don't get the value of this stuff. Uh, and I think that number, I think that number's still very high. I think there's as many, if not more, that don't get it as than there are that do. And that's, that's I would say 10 years on this journey.

I could say 20 plus years. If you look at, look back to when agile really started to get big and it's getting better, like more leaders are getting it. But like, when, when does the tipping point happen? Maybe you got insight in this.

I'll ask you the question. When does the tipping point happen or when, when do you reach enough critical mass where the risk of senior leadership change isn't that big of a risk anymore? I feel like today it's still a very big risk for many companies when it happens. Mm-hmm.

Two couple of, as you're asking me the question, couple a couple of thoughts. The first one is, it all comes down to incentive. Mm-hmm. And so therefore, one way to mitigate the risk of new people leading the organization, potentially undoing good work is to have changed the reward system.

So there is a learning, there's a, something I've recently learned, um, a learning from a large financial services organization mm-hmm. Where they are currently seeing a, uh, a bit of a, an unwind, a bit of a retreat. And the learning there was the reward system wasn't changed. So because there was an individual keeping the elastic band stretched, there was, there was a sufficient incentive.

Mm-hmm. Take that in, take that individual out. Mm-hmm. The incentive goes with it.

That's right. Because the reward system, and I'm here, I'm talking about explicit rather than implicit mm-hmm. Incentive. I'm talking about the HR reward system.

Mm-hmm. I'm talking about, um, kind of, you know, priorities across the organization, how people get paid, promoted, what the definition of good is, what good values and behaviors are, with the absence of that being codified and kind of chiseled, you know, reach chiseled in stone, uh, for the reward system. We're seeing that, not surprisingly, the the incentives drive the behavior and if it isn't an incentive, it won't drive the behavior. I can see that.

So that, so that's a learning. That's a learning. And then another learning on this is, um, professor John Kotter's, eight steps to change. Step number eight, institutionalize the change.

Mm-hmm. Um, something that I found to work is again, to this point around chiseling things in stone. Uh, take the, and it depends on the culture of the organization. It depends on the industry sector, but take the change standard and the change controls mm-hmm.

And speak to the chief risk officer and speak to internal audit, re chisel your change standard and your change controls. I've seen that. Get a new stone tablet and a chisel and redo them. No one in their right mind is gonna go and undo your change standards.

And you don't, you don't have to. They don't, they don't have to kinda mandate, um, you know, agile or DevOps kind of ways of working, but they have to need just to not prevent. Mm-hmm. They need to not prevent continuous delivery.

Right. So start from the point of continuous delivery and work backwards. Everything we do, every single control has to support continuous delivery. Yeah.

That's not negotiable. Yeah. And then let's figure out what's our controls are. Yeah.

That's insightful. Actually. Think you're onto something there. Um, something I've done where, where it was Yeah, chiseled and then it's like, well, okay, there's nothing now to prevent it doesn't mandate it.

You could still work big batch if you really want to, but why would you? Yeah. Yeah. Awesome.

Yeah. Uh, great conversation. Thank you, Ross. Thank you Jen.

Appreciate it. You too.