Host Intro (Gene Kim)

So, one of the things I enjoyed most about last year's conference was when Paul Gaffney — who's around here somewhere, he was formerly head of Technology and Supply Chain for The Home Depot, Dick's Sporting Goods, and Kohl's — presented. During his presentation, he made some observations about the presentations. He said: many leaders are focusing on like efficiency and DORA metrics, and by doing so, they may be doing their team's job instead of their boss's job. I thought it was such interesting advice to this community.

And so the goal of this last wrap-up session is to replicate that. Each day I'll be sitting down with a leader I admire, ask for their reflections on the day. And today that leader is Lauren Woods, SVP and CIO of Southwest Airlines. So please welcome back on stage, Lauren Woods.

Gene Kim & Lauren Woods (Day 1 Close conversation)

Gene Kim

Ah, Lauren, thank you so much for agreeing to do this. So like — question number one is: you and your team — I brought my notes, you can see I'm a little more low-tech than [Lauren] is right now. All right. So I'm dying to know — you and your teams have been here all day, sat through sessions. What were the, say, three top highlights for you?

Lauren Woods

Well, we had a couple of highlights. I took some notes here, so I'm gonna refer to them. I think there were things like measurement is key, clarity of focus. Everyone is, you know, pressured to go really fast — I felt like that one was often. And cultural changes.

But we also had a couple of speeches that I wanted to mention. Like, "the data, the land that DevOps forgot" — just even the title of that made me feel like I totally understood what he was going for. And data being a product, and really talking about cost attribution. I was in the back — you know, I had just given my talk and I was in the back — and he talked about how, you know, data — those who carry the data costs aren't the same people who create the data. And I was like, "yes, I understand that right there." So that was great.

I think the SiriusXM — Ben, Rachel, and Carol — were great. We learned a lot from them about strategic alignment. I talked about that a little bit earlier — strategic alignment being so important to align and to realign and communicate and recommunicate. So I think that's really important. And then they ended kind of about keeping it fun and light. And again, something I felt like Southwest could really relate to. Because we all spend a ton of time at work, and how much, you know, do you want to enjoy what you do or not? And so I love that comment from them.

What I learned from Vanguard is — you had the most fun at that conference.

Gene Kim

Oh, it was so much fun.

Lauren Woods

And then we heard from John Deere again, and really around transformation. Go ahead.

Gene Kim

Actually, if I can just make — yeah, go back. Two quick comments. One is — I wasn't kidding that one of the things that just delights me about this conference this week is there's going to be a bunch of conversations about batch jobs, you know, how to create and democratize data, and that someone seeks to change it. It's just a different view of like, who should own the data and who should pay for it. I just thought it was great.

And second, I wanted to highlight one thing that I just thought was so interesting about the Mike Carr CTO Vanguard presentation. I'm not sure if this was clear, but when he was talking about the three leaders — Greg [Davis], Amma [Boateng], Matt [Benchener] — they were the business leaders, the three primary business leaders of Vanguard. And so when I saw them talk, I asked the person next to me, "are they the technology leaders?" Because they just sounded like technology leaders I admire. And she laughed at me. She's like, "no, no, no. Those are the three business leaders heading up what drives Vanguard." And it was all reporting to the CEO. So it was just, you know, one of the things we talked about is like — what does it look like when business and technology co-create?

Lauren Woods

Absolutely. And one of the comments he made was, "my job is to make our awesome developers' job more awesome." And one of our coworkers texted that to me, and he goes, "that's my new title." So I was like, that's awesome.

So yeah. Sorry, I interrupted you.

And then John Deere — Amy Willard, Justin, and Adam all talked. And I think what again resonated with us was — um, transformation feels like there's an end to it, and that's not really true. Right? Especially in technology, it never ends. I always liken technology to painting the Golden Gate Bridge — the second you stop, you've got to go back and do it again. So it's that never-ending process. So they talked about it as evolution.

Gene Kim

Yeah.

Lauren Woods

And I thought that was really good. They talked about where to, how to focus, you know, what you're working on. And again, back to that alignment — problems to solve, value, determining how you measure — back to that idea of measurement and being so important. And I know we heard from the DORA Metric gentleman in one of the breakouts that measurements were so important.

But the other thing that really stuck with me was: treat your employees like customers. And a lot of us, especially as technologists, our end customer isn't always the customer buying the product from the company, paying your paycheck. A lot of times it's another group you're doing work for, and/or even another set of developers. And so really that understanding that our employees are your customers, and having that mindset and switching it from "I'm creating a product because it's cool" to "I'm creating a product because I'm helping somebody do their job" — I just thought that was so cool.

Gene Kim

And by the way, that was actually part of your journey to become CIO — you were part of that cloud migration journey where you had similar challenges, right?

Lauren Woods

We did. We were part of that cloud migration, really kind of learning from our first iteration through it, and how we need to move from just doing something because it's important. We did a lot of tagging, we did a lot of things trying to make it very standard, to now understanding that we really need to look for ways — because adoption's so important. And I think that's another theme I really heard from all of the speakers today: we're all in it for us from a technology perspective, but people and culture really matter. And you don't get to get out of not having that people and culture being a part of what you're creating. And so I thought that was really cool.

Gene Kim

So thank you. And so maybe if you could summon your inner Paul Gaffney, and say — given the talks that you saw, what advice would you give to this community?

Lauren Woods

Okay. So I think measurement matters. And I think that's one that I heard in a lot of different speeches. But I do think we got to remember why it matters. I think you want to measure success along the way. I think it's really, again, back to that idea that transformation has an ending — and I think we want to wait till we get it all done. And that's not the story to tell. The story to tell is measurement, and small measurements, and those small wins along the way. I think that is crucially important. So that's one thing.

I think another thing I want to talk to you about is choosing effective over being [perfect]. Right? I think, again, as technologists, we have a tendency to want to get to the right answer — like in a math equation, there's a right answer at the end. And the truth is there's probably like 15 or 20 right answers, that we all could do things a certain way. And so yes, alignment is important, but also speed, and not getting stuck in only looking for what's perfect — but really working through that, and don't fall into that trap. But really working in that speed over perfection, that I think is another thing I would tell everybody.

Gene Kim

Yeah. By the way, I have to echo someone who noted that boy — there were a lot of data-driven projects.

Lauren Woods

Yeah.

Gene Kim

In the talks this year. In the effort today.

Lauren Woods

I don't think anybody gets out of that. Right.

Gene Kim

So you've mentioned that you've been talking with your team, that you have a large number of your team here. And I know that time is not free. So like — what is it that you want them to be doing? How do you expect them to spend their days here, and what would make you say at the end of the week that, "gosh, it was worth our while"? It was worth the time.

Lauren Woods

Yeah. We are lucky here. We have all different types of groups. We have product teams — some people representing product teams, representing our DevOps platform, our cloud engineering, and architecture.

One of the things is that I'm asking them all to be really curious, right? So all of them to really be curious to learn new things, but then also to bring back that info to the groups that didn't get to come. I know that it seems like we brought a lot of people, but we have 2,600 employees in the technology department at Southwest Airlines. There's a lot of people that didn't get to come that really wanted to come.

We want to bring back one or two ideas. I'm hoping that they each individually pick one or two ideas that they then go deep on later. And how do you go deep on that later?

I think it's really important. I think this is the most important thing I want them to do, is I want them to network. There are so many awesome people here. I know I'm really enjoying meeting so many new people. But then I'm enjoying these talks, and I'm also enjoying just hearing from other people who are going through similar problems that we're going through, and then being able to connect and getting those lessons learned — or talking about ideas, or different ways to do it, or, you know, even the ways don't do it. I mean, I had somebody behind stage that was talking to me, he was like, "yeah, don't do that." I was like, "oh, okay, I think we're doing that." You know, it's those types of talk. But those are great talks to have. And I think the network is one of the big value-adds you get out of a conference like this.

Gene Kim

So good. Well, thank you so much for sharing your experiences and wisdom with us. So everyone, please, a round of applause for Lauren.

Lauren Woods

Thank you.