Las Vegas 2023

Happier Leaders — A How-To Guide

Paul and Courtney will share leadership stories and experiences they’ve had throughout their careers. This talk will include actions you can take to be a happier leader regardless of your role/level in your organization.


Courtney Kissler

SVP, Customer and Retail Technology, Starbucks


Paul Gaffney

Chief Digital Officer, Omni Logistics



The next speakers are Paul Gaffney. He's currently Chief Digital Officer for Omni Logistics, and previously he was the head of software for the Home Depot. He was CTO of Dick's Sporting Goods, and then CTO and Head of Supply Chain at Kohl's. You'll be co-presenting with Courtney Kissler, currently SVP of Customer and Retail Technology at Starbucks. Uh, who has been part of this conference from the very beginning. And as a part of the programming committee, uh, she's helped, uh, shape everything that you're experiencing, uh, here this week. And so she's been a tireless advocate of getting more representation from business leaders, uh, in these talks. And so one of the things that Courtney and I have been talking a lot over the last year is how much we love talking with Paul Gaffney. Uh, he's someone whose achievements I admire as well as his incredible ability to understand the intricacies of a business model, to enable technology to help create outstanding business advantage. And so they will be presenting on something they're both very passionate about. Uh, here's Courtney and Paul.


How y'all doing?


It's time for something completely different. We're not gonna talk about engineering at all. Sorry. I mean, I was reading the, the chat. Uh, I mean, I love engineers, but we want everybody to be happy. Um, and I'm happy to be here today with Courtney. Jean gave us a great introduction. We have a couple problems, right? Like Jean laid out the kind of talks at the beginning, and I'm sitting there saying, we're not giving any of those kinds of talks. We're giving a different kind of talk. And, and Courtney actually likes unicorns. I do. Um, so I do


This is, uh, this is a fun, uh, story from the very first DevOps Enterprise Summit. So Gene mentioned yesterday that, you know, this conference was really for horses and for me, I was like, I'm gonna be a unicorn in a sea of horses. And so that became kind of my unicorn thing. And then I love the Seahawks, so just go hawks and Right? Yeah. So


<laugh>, despite that, I still


Love her.


Um, you are going to hear, you have already heard at this conference an awful lot about efficiency. Um, we're not here to talk about efficiency. We're here to talk about effectiveness. And the difference is, you know, efficiency is doing things without a lot of waste. Getting rid of waste, uh, doing things faster, doing things for less cost. In some ways, efficiency is doing things right. Effectiveness is choosing what those things are, choosing what to work on, trying to figure out are we working on the right things. Um, to me, the, the folks that we encounter who are truly happy, um, and, and when I've been my happiest is when I know that I'm being effective and I'm helping an organization be effective. Um, a lot of folks that we run into when they're unhappy and when I'm unhappy, it's feeling like, well, you know, the pipeline might be working well, but we're not putting out anything of value, and that's kind of demoralizing. And so we're here today to talk about how can you all be happier leaders by focusing on effectiveness and focusing on the things that swamp your effectiveness and how you might push through those things gracefully.


Yeah, I mean, one of my favorite examples from yesterday morning was the John Deere talk. I feel like Matt and Amy really drove home effectiveness and how critical that is to, I mean, we talk a lot about developer happiness and experience, and I am a big believer in that. I'm sponsoring that at Starbucks. I believe though the happiness it's all about are we working on the right things? And it really is a broader thing and not just about the developer side of happiness. And I'll tell you, a lot of the developers I talk to care a lot about effectiveness. Even if they can get code shipped faster, they wanna know it's actually making a difference, that it's actually value for customers. So it can feel really challenging, and I would probably even say overwhelming to really understand. And I think this community understands what it means to be part of a value based outcome driven culture. So you can know what that looks like and what good looks like, but be stuck in a power driven, uh, task oriented organization. So we're here to talk a little bit about what you can do to help with that.


And it turns out that, at least in, in my observation, and I've observed this across, uh, you know, I've had the privilege to spend early parts of my career, uh, at Office Depot, at Staples at Schwab, the last decade at Home Depot, Dick's, and Kohl's. Um, you know, it's great to have worked in an environment where I can just tell you if you want to see what, what my work was, go into the Home Depot. Uh, most people end up having a good experience there, but I have found that people choose to take two paths and one of them is easier. And that's the path of capitulation. So people find themselves in these situations that Courtney described, where you want to be, uh, outcomes based, you want to be collaborative, but you find yourself bumping up against power driven political feature factory type decisions. And a lot of folks just decide, I'm not gonna say anything.


I'm gonna simply capitulate. I'm gonna give up on working on effectiveness. 'cause I can go work on efficiency without bumping into any of those problems. Uh, there's that really demoralizing, uh, post out on Reddit by some product managers. And, you know, for about a year I tried this, like try to figure out what the users really want. It was really hard. So I just decided I'd give my sponsors what they want. Um, and I feel a lot better now, but that's really not the path to genuine happiness, even though it might lead to a little bit of happiness in the moment. Um, the other path though is the path we'd like to inspire at least one of you to go on, right? If we help one person today, I think we feel like we've been effective, of course we hope we'll help more. But that's the path of gracious perseverance.


And the path of gracious perseverance is not to shut your mouth, but to keep talking about the things that matter, to keep talking about improvements in effectiveness. Um, when you capitulate you make it really, really hard for anyone else to climb the value creation ladder when they see people that they admire, uh, giving into politics or giving into power-based, uh, activities or deciding to focus exclusively on things like the mechanical nuts and bolts of how we do work and leaving the decisions about what the company's working on to others. When people see you do that, they're not gonna help either. They're gonna hunker down, they're gonna stay in capitulation mode. Um, I've had the privilege of encountering dozens if not hundreds of people, uh, when I made it okay for folks to talk about, are we working on the right things? Do we understand what problems we're solving?


Uh, folks at Home Depot, Dick's and Kohl's, many of them came into work and like just hated being there. 'cause they felt they were just in a factory not producing stuff that mattered. They now feel like they're actually working on, on value creation. Um, uh, there's a longer story for another time about the various outcomes of those three orgs. So I promise I'll share that at a future, at a future summit, this path. If, if we can inspire you to be aware of capitulation, be aware of capitulation when it's on your own mind, be aware of capitulation when it's happening on your team. Um, there this can be summarized in kind of four forces that are gonna put this choice right in front of you. Are you gonna capitulate or are you gonna graciously persevere? The the first force is when you encounter decisions that are being driven primarily by power dynamics.


You're all here, I think, because you all believe that collaboration is more powerful than someone else decides. And you do. And that's what power is, right? Power is someone else decides, and you do. Someone else owns effectiveness, someone else owns the decisions about what we're working on, and you just figure out how to work on it efficiently. That's a non-collaborative environment that's, uh, power somewhere else. I get tasks and I do them. And we encounter that a lot. I've seen through presentations just over the past day and a half, people describing, well, once these decisions have made, now let me tell you for a half an hour how we execute those. Well-made decisions, uh, we wanna inspire more of you. When you see that power dynamic, uh, even if you can't completely overcome it, don't capitulate to it. Find a way to graciously and consistently question it. The second thing you'll find are, and I I don't know if anyone else has seen this, but, you know, advocating for decisions based on opinions. Um, they're often, I mean, we all work with very smart people and their opinions are dressed up to sound really, really good. Uh, PowerPoint, you know, effectively done PowerPoints, the number one delivery mechanism for someone's opinion. And you, so you've you've seen this, yeah, it's like the second most destructive tool on the planet. Excel being the first <laugh>.


I didn't expect that. When, um, when when you, when you encounter this force, when you find yourself in the middle of essentially an opinion battle, do you capitulate? Because the person voicing the opinion has built a lot of energy in it. They're, they're very attached to it. You wanna just get along. They got a great PowerPoint. You're not so good at PowerPoint. 'cause you actually deal in facts. You'd rather be looking at code <laugh>. Um, like, so, but what do you do? Don't capitulate, don't give in now don't piss the person off. Don't be an ass. Um, but lead with facts. Be the agent of facts. By doing that, you make it easier for all of your folks to do the same thing.


Um, and I'm gonna talk a little bit about expecting courage versus fostering a sense of safety. I mean, this community talks a lot about psychological safety. I believe in that as well. And I believe though, that there's this kind of expectation that if you declare that you believe in psychological safety as leaders, that just magic happens. And all of a sudden everybody's super comfortable speaking up. And so one thing that, um, I talk about a lot is honoring reality. Now, that used to be the only thing that I would say, and then I added honor surface and embrace reality. Because what I found was, as a leader, I could honor reality if people actually brought it to me. But if you don't create the right environment, people won't surface reality. And I talk, talk a lot about the verbs that I choose are very intentional because what I've seen happen is reality is surfaced and then it's judged.


And judging reality adds no value. Um, and so it's a flywheel. It's like the way that people react to reality will create the courage that you're looking for. And so I believe that that's a leadership challenge, but I also believe everyone can contribute to that because I've seen a lot of blame even amongst teams where it's like, well, we're having a problem, not mine. And so I just think it's super important to continue to create the right environment so people feel comfortable surfacing reality and then paranoid versus confident. So I will tell you that this is a struggle for me personally, and I do believe that some amount of healthy paranoia is healthy. Like always wondering like, am I focused on the right things? Am I doing the right things? But when it gets to, you're in your head and you're like, did I say the right thing? What's that person thinking? Did I make the beautiful PowerPoint? Is that gonna land the message? But like, figuring out how do you channel your confidence? And it comes through collaboration, using facts, being really intentional about what you're sharing. And I think that just that ends up building that confidence over time.


And that introduces the sort of fundamental, uh, paradox here is if you don't want to, and we, we want you not to rely on the courage of others, that to a certain extent leads to the paradox that you've got to have your own leadership courage. This path of gracious perseverance requires your personal leadership courage. And that courage and demonstrations of those courage, that courage actually has to come before you become a senior executive. Um, a lot of folks say, yeah, well it's, it's easy for you senior executives to to have courage. Well, yeah, but that's not when you actually start building your courage. You start building that before you're a senior executive. And, and we've each had to do that, correct?


Yeah, I mean, find us later, we can share stories. Um, but I definitely can share a lot around leadership courage. Before I had a senior leadership title, and again, I go back to grounding conversation and facts is like a really great way to, um, build up that courage over time.


And the the thing, um, to be on the lookout for is when will your moments to display your courage present themselves? When will moments to display courage present themselves to folks on your team? And have you created the conditions where they will act on those moments? Uh, I reflected as Courtney and I were talking about this, um, we get this feedback all the time about, well, you know, you're already a CTO so you can make these changes. The first time this showed up for me, I was, uh, 26 years old in 1993, uh, at Schwab. It's my first day on the job. I had absolutely no idea what I was doing. And I was in this, um, uh, you know, welcome new people class. It was like 40 people. I was the only technology person in there. And they got to a q and a and someone says, Hey, I've heard that Schwab has just decided that the standard desktop for everyone in Schwab is gonna be a sun spark station.


And, um, the, the person running the class said, well, I, I have no idea about that. Let's ask Paul. He's from Technology <laugh>. And you know, I, I, those of you who know me, know me, know I don't have much of a filter. Um, and it's 1993. And I said, well, that can't possibly be true because that would be a really stupid decision. Um, I would learn on my second day. We had actually made that decision. <laugh>, um, uh, I came to realize it was wrapped up in a whole huge CIO transition political battle. And, and there was a small cabal of folks who were kind of Unix purists. And the, the prize to them for getting second place of their leader not winning the CIO battle was, you know, Scott McNeely convinced them that he was gonna beat Microsoft. Um, which even then was objectively stupid.


Um, and what what I had to do is I had to decide like, this is day two, right? And I'm like, this is gonna be a miserable job if we're gonna try to build this company in 1993 on Spark Station desktops while Windows is ascendant all around us. And, you know, Schwab's a customer of retail customer organization at the time, almost primarily we're gonna have people coming into branches and like people trying to do things with X windows. Um, so I decided I wasn't gonna capitulate, I was gonna speak up. Um, I haven't always been good at not pissing people off. I think somehow I managed not to piss a lot of people off and, and the people who are gonna get pissed off, I found agents to piss them off for me, <laugh>. Um, but I, I just consistently talked about some principles around why we needed to undo this, this compelling decision.


This was an embarrassing decision to undo. Uh, thankfully we, we undid it. Um, uh, Bob DeSay, who was my partner and I, he went on to be CEO of Schwab Europe. Later, Bob and I became known as, hey, those are the two guys that put out the sun. Um, <laugh>. But the important thing here is it was on everyone's mind, it was on thousands of people's minds. If one person doesn't speak up, thousands of people remain unhappy. Most will capitulate. Your job is to lead, lead graciously, graciously persevere through these difficult moments. You know, there's a third path, right? Capitulation, gracious perseverance, bullheaded pain in the butt, making people mad. Don't pick that path. And, and sometimes when you think you're right, that path is easy to fall into. So we share all of this because Jean has asked us to try and help elevate the leadership talent that comes to this conference.


And leaders delegate efficiency leaders focus on effectiveness. This conference has demonstrated year in and year out that you're all actually really good at efficiency. We've seen all the presentations, they're fabulous. The content is excellent. That is content that is delegated by most CTOs and CIOs. And if you aspire to be the one doing the delegating versus the person to whom these things are delegated, twist a little of your own. Like, look at your calendar. What percentage of your calendar is focused on efficiency? What percentage is focused on effectiveness? Change the ratio. If you do that, I'm pretty certain you'll be a happy leader. Agree.


Um, Jean and I were talking and this is, um, we're not actually gonna ask for help. We're gonna offer some help. Jean noted to me a couple times over the last few days and leading up to the conference, that many leaders in this community and the, and the data support this seem to be hitting a ceiling. They, they can't get their boss's job or they're blocked by their boss, or maybe some of their peers have it out for them and, and they have a good career progression, then as they get near the top they stall. Um, I have a suspicion, and I think Courtney shares that suspicions because they haven't fully developed the skills needed to persevere on effectiveness. 'cause the things that get people into those jobs, no one gets those jobs because they made something more efficient. They get those jobs because they helped make the company more effective.


Um, we'd actually love to see if Jean's hypothesis here resonates with this crowd. Um, Courtney and I are gonna host an a MA session tomorrow, and we'd love for any of you who are struggling with this or want some help with this or have some answers to this, uh, to come to that. I assume we'll, we'll post it on the slack somewhere. We'll have it upstairs in the, in the afternoon. And I would really look forward to, and I think you would as well, yep. Hearing from as many of you as possible about how we can make this a more impactful part of everyone's toolkit.


Thanks you all. Thanks.