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
Chapters
Full transcript
The complete talk, organized by section.
Paul Gaffney
How y'all doing? It's time for something completely different. We're not going to talk about engineering at all. Sorry. I mean, I was reading the chat. I love engineers, but we want everybody to be happy.
And I'm happy to be here today with Courtney. Gene gave us a great introduction. We have a couple problems, right? Gene 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 Courtney actually likes unicorns.
Courtney Kissler
I do. I do.
This is a fun story from the very first DevOps Enterprise Summit. So Gene mentioned yesterday that this conference was really for horses. And for me, I was like, "I'm going to 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. Right? Yeah.
Paul Gaffney
Despite that, I still love her.
You are going to hear, you have already heard at this conference, an awful lot about efficiency. We're not here to talk about efficiency. We're here to talk about effectiveness.
And the difference is, efficiency is doing things without a lot of waste, getting rid of waste, 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?
To me, the folks that we encounter who are truly happy, and when I've been my happiest, is when I know that I'm being effective and I'm helping an organization be effective.
A lot of folks that we run into, when they're unhappy, and when I'm unhappy, it's feeling like, well, 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.
Courtney Kissler
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.
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 want to 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, task-oriented organization. So we're here to talk a little bit about what you can do to help with that.
Paul Gaffney
And it turns out that, at least in my observation, and I've observed this across, you know, I've had the privilege to spend early parts of my career at Office Depot, at Staples, at Schwab, the last decade at Home Depot, Dick's, and Kohl's. It's great to have worked in an environment where I can just tell you, if you want to see what my work was, go into the Home Depot. 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 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 going to say anything. I'm going to simply capitulate. I'm going to give up on working on effectiveness, because I can go work on efficiency without bumping into any of those problems."
There's that really demoralizing post out on Reddit by some product manager. 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. 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.
The other path, though, is the path we'd like to inspire at least one of you to go on. 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.
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 giving into politics or giving into power-based 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 going to help either. They're going to hunker down. They're going to stay in capitulation mode.
I've had the privilege of encountering dozens, if not hundreds, of people, 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?
Folks at Home Depot, Dick's, and Kohl's, many of them came into work and just hated being there, because they felt they were just in a factory not producing stuff that mattered. They now feel like they're actually working on value creation.
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 summit.
This path, 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. This can be summarized in kind of four forces that are going to put this choice right in front of you: are you going to capitulate, or are you going to graciously persevere?
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 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 been made, now let me tell you for a half an hour how we execute those well-made decisions.
We want to inspire more of you. When you see that power dynamic, 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 don't know if anyone else has seen this, but advocating for decisions based on opinions. They're often, I mean, we all work with very smart people, and their opinions are dressed up to sound really, really good. PowerPoint, effectively done PowerPoints, the number one delivery mechanism for someone's opinion.
Courtney Kissler
You've seen this, yeah.
Paul Gaffney
It's like the second most destructive tool on the planet. Excel being the first.
I didn't expect that.
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 very attached to it. You want to just get along. They've got a great PowerPoint. You're not so good at PowerPoint because you actually deal in facts. You'd rather be looking at code.
So, what do you do? Don't capitulate. Don't give in. Now, don't piss the person off. Don't be an ass. 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.
Courtney Kissler
And I'm going to 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 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 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.
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, 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 going to land the message?
But 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 ends up building that confidence over time.
Paul Gaffney
And that introduces the sort of fundamental paradox here. If you don't want to, and 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 that courage actually has to come before you become a senior executive.
A lot of folks say, "Yeah, well, it's easy for you senior executives 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 we've each had to do that. Correct?
Courtney Kissler
Yeah. I mean, find us later. We can share stories. 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 in facts is a really great way to build up that courage over time.
Paul Gaffney
And the thing 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?
I reflected as Courtney and I were talking about this. We get this feedback all the time about, "Well, you're already a CTO, so you can make these changes."
The first time this showed up for me, I was 26 years old, in 1993, at Schwab. It's my first day on the job. I had absolutely no idea what I was doing. And I was in this welcome new people class. It was like 40 people. I was the only technology person in there.
And they got to a Q&A, and someone says, "Hey, I've heard that Schwab has just decided that the standard desktop for everyone in Schwab is going to be a Sun SPARCstation."
And the person running the class said, "Well, I have no idea about that. Let's ask Paul. He's from technology."
And those of you who know me know I don't have much of a filter. And it's 1993. And I said, "Well, that can't possibly be true, because that would be a really stupid decision."
I would learn on my second day we had actually made that decision.
I came to realize it was wrapped up in a whole huge CIO transition political battle. And there was a small cabal of folks who were kind of Unix purists. And the prize to them for getting second place, of their leader not winning the CIO battle, was Scott McNealy convinced them that he was going to beat Microsoft, which even then was objectively stupid.
And what I had to do is I had to decide, like, this is day two. And I'm like, this is going to be a miserable job if we're going to try to build this company in 1993 on SPARCstation desktops while Windows is ascendant all around us.
And, you know, Schwab's a retail customer organization at the time, almost primarily. We're going to have people coming into branches and people trying to do things with X Windows.
So I decided I wasn't going to capitulate. I was going to speak up. 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 the people who were going to get pissed off, I found agents to piss them off for me.
But I just consistently talked about some principles around why we needed to undo this compelling decision. This was an embarrassing decision to undo. Thankfully, we undid it.
Bob DeSay, who was my partner, and 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."
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 sometimes when you think you're right, that path is easy to fall into.
So we share all of this because Gene 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. 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.
Courtney Kissler
Agree.
Paul Gaffney
Gene and I were talking, and this is, we're not actually going to ask for help. We're going to offer some help.
Gene 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 data support this, seem to be hitting a ceiling. 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 they have a good career progression, then as they get near the top, they stall.
I have a suspicion, and I think Courtney shares that suspicion, it's because they haven't fully developed the skills needed to persevere on effectiveness. Because 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.
We'd actually love to see if Gene's hypothesis here resonates with this crowd.
Courtney and I are going to host an AMA 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, to come to that.
I assume we'll post it on the Slack somewhere. We'll have it upstairs in the afternoon. And I would really look forward to, and I think you would as well.
Courtney Kissler
Yep.
Paul Gaffney
Hearing from as many of you as possible about how we can make this a more impactful part of everyone's toolkit.
Thank you all.
Courtney Kissler
Thanks.