Bryon Kroger

I am Bryon Kroger, founder and CEO of Rise8. We enable large enterprises to continuously deliver valuable software that people love. And welcome to part three of my enterprise comedy. Don't worry, I'll recap if you weren't here for parts one and two — but this is my take on Dante's Paradiso. I'm gonna explore the promised land of enterprise technology. You'll have to stick around to find out what that means.

Quick note, same as last time: if you're not religious, don't worry. Neither am I. I still think you'll enjoy this. If you are religious, also don't worry — you won't be offended. I have a deep respect for religion and theology. I'm especially a fan of St. Thomas Aquinas. Fun little Easter egg — that's why I love Dante's Divine Comedy. It's often referred to as "the Summa in verse," which he wrote. As you'll see, I get a bit too much into symbolism — so much so that I've matched my outfit color each year to the theme of the talk. This year, people looked at me like I was very crazy, especially after I found out it's spaghetti night. A bad, bad mix. So I will be changing in a minute here.

Now, part one involved a lot of external reflections. Part two was a lot more internal reflection. For part three, we're actually gonna explore the kind of leaders that we need to be in order to get to a divine state of DevOps. What does that even mean? You'll have to wait until Dante takes us to the Empyrean at the end.

But who the heck am I and why am I talking to you about this? Prior to Rise8, I spent 10 years in the Air Force using really terrible software to do critical missions. It's not funny. I saw missions fail, and I actually saw people die because of bad software. So I led a very successful DevOps transformation in the Air Force called Kessel Run — you might have heard about it at past conferences. And my goal was to fix this problem, this issue of bad things happening because of bad software. We established continuous delivery of valuable software all the way out to our end users — straight to the battlefield in countries around the world. And now at Rise8 I've helped several other organizations embark on similar transformations — some of the largest bureaucracies in the world — and they've achieved similar outcomes. So this three-part series draws on those experiences.

If you missed part one, Inferno, we talked about the 12 paradises — sorry, the 12 circles — of bureaucratic hell. So much symbolism wrapped up in that one. Who's been there, by the way? Eminem made a weird entrance, and we learned that Divine Comedy is not the only "Summa in verse" — it turns out he has Summa in Verse Two. And there's even a Dante Inferno Easter egg in the music video. Bizarre finding — so had to put it in there.

But as we navigated the sins of bureaucracy, we explored tools to deal with them. And at the end of Kessel Run, we found another Summa — Summa Verman, off of Star Wars fame — and we escaped hell to purgatory. And we started our journey to overcome the seven deadly transformation vices to get to the Garden of Eden, which we discovered represented the state of innocence that existed before Dev, Adam, and SRE fell from grace. Before — that — a SAFe consultant convinced them to eat some well-marketed bureaucracy. But we made it in the end. I think that violence is justified, by the way. We found Borg in the Garden of Eden, and we prayed for the return of Cloud Foundry, and then we found elite software delivery performance — which was the DevOps Garden of Eden. So now we're here.

And the important thing is that DORA elite software delivery performance doesn't guarantee us outcomes, let alone the ability to scale them. But Dante's Paradiso will offer us some insights into what it takes to lead enterprise technology to greatness.

Before we dive into that though, Dante is gonna take us through the first three rings of Paradiso, where we actually see deficiencies that keep us from ascending as leaders. And it'll help put all of this into perspective.

So the first sphere is the Moon. It's where Dante finds the inconstant — the people who couldn't keep their vows because they lacked the resolve or the strength to see them through. They're deficient in courage. Similarly, enterprise technology leaders and their teams — all of us — we often fail to keep our commitments to our fellow team members and to the mission. And it rarely ever comes down to ability. This is a hard pill to swallow, but like Dante observed, we actually just lack courage. It always comes down to courage.

What about circumstances beyond our control though? What about that leader over there that's in charge of everything and we can't get through them, or all the bureaucracy, or in some of the cases I deal with, literal acts of Congress? That's a slippery slope, because when we lack courage, we'll always rationalize it. And then we cast our power onto those externalizations, and we end up losing our power. And so courage has to be absolute. We have to own it in every sense. If we give into fear, we cast away our power. So the first lesson from Dante is that fear is the mind killer. That's a Dune reference. I'm just swapping up all kinds of sci-fi here.

Next, Dante came to the second sphere, Mercury, where he found the ambitious — those who did the right thing, but they did it in pursuit of their own glory at the expense of devotion to what was really important. And as technology leaders, it's easy for us to get caught up in our egos and our own aims and lose sight of the team, the mission, the ecosystem. And without those, we might become good, but we'll never become truly great organizations. So the second lesson is that ego is the enemy.

The third sphere is Venus. This is where Dante finds the lovers — those whose earthly love sometimes overshadowed their devotion to God. They were deficient in temperance. And as enterprise technical leaders, we can get distracted by some shiny objects. By the way, today was AI day — so I asked AI to portray business leaders getting distracted by shiny objects. And like 10 prompts later, I ended up here. I used Grok on Fun mode. So I kind of like it — it speaks to my inner child.

So at least on AI: yes, that passion that we have for innovation and creativity is vital — but it can distract us from what's really important, which are the actual business results that we're chasing. And the third lesson is that we observe that indulgence is a negligence to our organization.

So how many of you have seen technical leaders get taken over by fear, ego, or indulgence? It was those other technical leaders, though, right? How many of you, if you're being honest, have given in to them yourself? I know I certainly have — each and every one of them, way too many times. And I'm gonna give you the most important tool — and it seems like you're all very reflective individuals already — but it's the most important tool that you could ever need in your journey as an enterprise technical leader. And that tool is a mirror.

Now, when I look in this mirror, I see many times when I gave into fear, ego, indulgence. And every single time I can see how it hurt my team and my mission. Every one of you in this room, regardless of where you sit in your organization, is a technical leader of some sort — formal or informal, at every level. Enterprise transformation starts with you — like, quite literally with you. When we're deficient in courage, justice, and temperance, we can't get to where we're going, let alone lead others there. And so this mirror is important because it's really easy, like I said, to give away your power with an excuse — "that other person, those circumstances." Don't do that. Instead, look in the mirror, find the deficiency, and grow.

And with that perspective, I'd encourage you to think about self first versus others, which is the easy part, as we go through the rest of this talk and explore: what are the virtues that we need according to Dante?

So the fourth sphere is the Sun — this is where Dante found the wise. This is where Dante found my man St. Thomas Aquinas, and other philosophers who illuminated the world with their knowledge and their teachings. They represent the virtue of wisdom.

Now, you have to be careful here. My friend Paul Gaffney, who's actually right over there, gives a talk called "Leadership Black Holes," and black hole number seven is "believing we know." And it's a big black hole. It sucks you in and it keeps you from learning, and it keeps you from moving towards success. What makes Dante's philosophers wise isn't what they know — it's that they learn. The truly wise never stop learning. And the goal of learning is to do what works. Not just to learn what works, but to do what works. And I'll get into that in a minute.

But I've found that successful technology leaders create environments where knowledge is not just held by a few but shared freely throughout the entire organization — sometimes even opening up corporate documents while they're in draft to the entire company to see. That allows the entire team to benefit from collective expertise and insight, and it enables an environment where people can be led by context instead of control.

And we only learn what works by doing it in production and measuring it. Everything up until then is just an assumption. You're building up risk. And you could do some risk reductions before you get to prod, but prod is the final validation. And that's why I propose that we change the dollar bills that our businesses generate to read "in prod we trust." That probably won't fly. Maybe we'll put it on crypto. I don't know.

Now, next, Dante comes to the fifth sphere, which is Mars, where he finds the warriors of faith — who fought and sacrificed for their beliefs. They represent the virtue of courage.

Now did you know that the phrase "do not be afraid" appears in the Christian Bible 365 times in various forms? That's once for every day. That's a lot. It's the most repeated phrase. Now, I know not everybody in here is Christian or even religious, but think about that. The Christian culture, the Christian faith, decided it was so important that followers needed to be reminded of courage the most. And I think that's a really powerful thing for us to keep in mind.

Now, you might be thinking, "but I don't go into burning buildings or out onto battlefields. I sit behind a computer. Why do I need courage?" Remember we saw that fear is the mind killer. That phrase comes from Dune, of course, as I mentioned. It's the litany against fear. And it says: "Fear is the mind killer. Fear is the little death that brings total obliteration." Letting a little fear take hold — even just a little bit — does lead you to total obliteration. And it's really easy to see what you actually fear. The big fears that you have are right around the corner from a little fear that you give into. So an example: you might be afraid to give your team feedback, but the really big thing that you're afraid of is that your product's gonna fail because your team's on the wrong track. By giving into the first fear, you guarantee the second.

And so we have to focus on having that courage to never give in to even the little deaths. The goal of courage then is to be bold and to overcome that fear. Courage is a skill, though. It's a skill, and you have to build it by doing it. So I encourage everyone to start stepping into courage. Take small steps at first if you need to — but the thing that will help you take those steps, however small, is confidence.

Does anybody here deal with imposter syndrome, in yourselves, with people you lead and mentor? I think everybody — everybody's talking about imposter syndrome these days. I have some unpopular spicy takes on this — but one that I'll say is an unpopular take on confidence in our culture today. And that's that, sometimes — not all the time, but sometimes — affirmation is BS. You don't get confidence by shouting affirmations in the mirror every morning, okay? You get confidence by building an undeniable stack of proof that you are who you say you are. And so sometimes you might just be an imposter. You're not who you say you are, and you need to go do the thing, and do it again and again and again.

Imposter syndrome happens when you aren't who you say you are — not just when you don't recognize that you are. Now, sometimes when I feel like an imposter, it is because I have to build that stack of proof, one small step at a time. Now, if you do have a stack of proof but you still struggle, then absolutely — affirmation, reaffirmation, totally valid practice. Take stock of what you've accomplished, and what your team has too. But affirmations that are disconnected from proof are just delusions, right? They actually create proof-resistance for you. They create a wall for feedback, and they create a barrier to your self-improvement.

So the task here, the practical thing that we can do as technical leaders every day, is start building proof that we are who we say we are, and that our teams are who they say they are. We don't talk about it, we do it. And we do it over and over and over again.

There's also a meta-proof to build here. So when it comes to learning, no student ever feels like an imposter. It's only the students who pretend to be the expert that feel like the imposter. And so they say the truly educated never graduate. So be a lifelong student and embrace that in every single sense. Adopt the frame of a student always, in everything that you do, and then build an undeniable stack of proof — not that you know things, but that you're capable of learning new things, that you're a learner. That frame, combined with that proof, will give you the meta-confidence to do all things, even when you haven't done them yet.

The sixth sphere, Jupiter, is where Dante finds the leaders who governed with righteousness and fairness, and they represent the virtue of justice. Now, the goal of justice is to do the right thing. And I'm actually gonna lean on Gene a little bit for this one.

The best antidote to a genius-driven egosystem is to be a senius, right? — and to create an ecosystem. In his opening talk, Gene talked about this. The things that senius has: foster mutual appreciation, rapid exchange of tools and techniques, success being contagious, and a tolerance for new things.

And I think that sometimes these things can be interpreted as soft. So rather than rehash what Gene talked about, what I'll say is: when you talk about these things, especially with business leaders, you run the risk of being written off for being too soft. So I just wanna say that a senius can still have accountability. And in fact, it has to have it. And it can have better accountability than the traditional hierarchies that we're used to, which actually remove a lot of accountability by removing people from the problems.

Now, each one of these lines is actually a contract of sorts, right? So I would say: you need to embrace contracts with SLAs, not just for your technology but for your interactions as a team. And then you can use tools like growth boards, which I talked about in part two, to make sure that everyone's playing by the same rules, held to the same standard. There's no project pageants, as Paul Gaffney talked about last year — where the best-looking slides presented by the toxic back-channeling leaders win. Everybody gets the same scorecard, the same standards, and there's outcomes over outputs as a focus.

So next, Dante came to the seventh sphere, which is Saturn, where he found those whose lives were marked by moderation and inner peace. And they represent the virtue of temperance. So the goal of temperance is to do what's necessary. And this one might seem a little odd at first — like, how do we go from temperance to do what's necessary? Typically when we talk about temperance, we talk about avoiding excesses, right? Such as the example of those lovers from Venus — you know, the leaders that fall in love with all the trends and the processes and the buzzwords at the expense of actually getting things done. But temperance is also about avoiding insufficiency. And this is literally Aristotle's golden mean between extremes.

I'll use a non-technical example. There's gotta be at least one sales guy in the room, or gal. So if your sales conversion rate is like 10%, right, and you need to close 10 customers, that means you need to make 100 calls. And you just have to do it. And if you suck compared to everybody else, you might have to make 500 calls. You just have to do the work. And sometimes we start talking about outcomes so much, we forget about all the activities that have to go into that.

An example in enterprise technology is toil, right? SRE accepts as a basic premise that there will be toil, and Google sets a standard of about 50% — about 50% of your work will be toil. And we don't talk about this a lot, because it's not the sexy DevOps stuff that we like to talk about. And sometimes, though, you just have to do what's necessary. You have to do the work. Sometimes it's toil, and that's what separates the good from the great.

And so this really embodies the principles that we know about — just-in-time and just-enough from Lean. The goal here, though, is just to apply it universally — not just to our products and the way that we operate, but also to our organizations. And, you know, especially our projects. I've seen too many gold-plated Kubernetes architectures to deploy static web apps. That might be excess. But do what is necessary. Temperance. Temperance is the last of the four cardinal virtues.

Now, Dante comes to the eighth sphere, which is the fixed stars. And this is where he finds the people who exemplified perfect faith, hope, and charity in their earthly lives. These are actually the theological virtues, if you're familiar with them. I'm gonna recast those today as belief, hope, and care.

Remember that DevOps organization that I mentioned, Kessel Run? My friend Josh Mark Hughes once gave a speech and he said the most important thing that Kessel Run ever delivered was hope. And it was something that hit me like a ton of bricks, especially because I really invested in those products. But he said it was because we never compromised on our culture, and we did what we set out to do — and that we should never stop doing that.

And that led me to this really simple framework. First is, clearly articulate your beliefs. Say what the team will do based on those beliefs. Do it. Say what the team did — and that's what will create hope. And then throughout each step of that, you have to show people that you care.

And for that, I will say, you need to attend Paul Gaffney's talk tomorrow. That's a big picture of you. That's great. Tomorrow at 5:00 PM in the Azure Ballroom. So stick around, don't leave early. I promise it will be worth it. But high-stakes communication — how do you get those points across? I'm not gonna go into that today, since he will cover it more brilliantly than I ever can. So I'm just gonna focus on a slightly different tool.

It might sound easy, but of course these things go really, really bad along the way, and we've all experienced that. And temperatures start to rise, and you have two choices. It's one of my favorite metaphors from MLK Junior — he said: you can be a thermometer or a thermostat. You have to set the temperature of your organization, instead of being a reflection of what's happening or an amplifier of all of the complaints and the problems and everything that's going wrong. You have to listen to those things, you have to show people you care — but then you have to drive the organization to what it needs to do, not what's currently happening. And you create that environment of belief, hope, and caring.

The ninth sphere is the Primum Mobile. It's the ultimate power that moves all of creation. And for us, the ultimate power that will move our organizations to action is a clear articulation of the gap between where you want to be and an honest assessment of where you are.

Humans have an intense desire for deficiency gratification. As soon as you create that deficiency — that gap between where you want to be and where you actually are, honest about where you are, which is really hard to do inside of enterprise — we all do it. We get up on these stages and we tell slight embellishments, and they grow each year. And we get into a point where we don't have the honest assessment of where we are. And we think that we're doing ourselves a service by promoting our organizations and getting leadership buy-in, but we're actually closing the gap along the rest of the organization that pushes them into action. That gap is really important.

And so I would say breaking the deficiency down into sequential target conditions is also really important to help the team stay aligned. And then empowering them to experiment towards those target conditions — that ensures that they can move autonomously without waiting for your instructions. That doesn't scale. Decentralized, autonomous teams require alignment to function — but once you get it, you get a flywheel effect that keeps going even without you.

And when you combine that with the cardinal virtues — of belief, hope, and caring — you have a foundation from which you can derive first principles. You have a manifesto. And I would encourage you to actually write that down. I don't wanna steal his thunder, but I'm pretty sure Paul's recommendations are gonna involve things that make you write a lot. And it's gonna be about these things.

And I'll tell you, my biggest failure at Kessel Run was not writing these things down. Because as soon as a new swell of leadership came into the organization as we were scaling, it was all lost. It used to happen by osmosis. Osmosis was gone by proximity, right? Just wasn't close enough to people. And the organization suffered because of it. So write these things down.

If you want a copy of our manifesto, by the way, I'll share it to you — you can reach out. You might consider also filling in some of the scaffolding with Gene's work here. So the Three Ways, the Five Ideals, the Three Wirings of a Winning Organization are universal things — universal no matter what organization you work for — that can help fill in this manifesto and help you derive your first principles.

And the way that we framed the lessons from the four virtues is also a really important guide. I phrased it this way for a reason: be bold, do what works, do the right thing, do what is necessary. Doing takes courage. So it enables the other three. Be bold. And I really want to emphasize: do, do, do. Or, as they say in the military: execute, execute, execute.

I'm gonna play you a short clip that really hits this home for me.

[Video clip — Jocko Willink / military voice:] "And I would just see a bunch of sets of green eyes, right? It was my entire team was waiting for three words. And these three words ring through my head every single morning. And the three words are: execute, execute, execute. And on the third execute, I would put power to that charge, and all freaking hell would break loose and we would crush our enemy. And that's what people don't do. Yeah, they don't execute. And you have to understand: if you don't execute on the plan, if you don't get up in the morning when you're feeling tired, scared, you don't know what's gonna — if you don't execute, you're not just cheating yourself, dude. You're cheating your family, you're cheating your employees, you're cheating your team. Whatever you're a part of, it's bigger than you."

It is bigger than you. Much like the Empyrean, right? The Empyrean here represents the goal — the big thing that we're trying to accomplish. Has anybody read The Goal about Eli Goldratt, by the way? Fun fact: did you know that Gene actually modeled The Phoenix Project very closely on The Goal? He wrote a really great blog about it. Check it out. I geek out on this stuff — it's a great blog. And I took so much respect for Gene doing that.

Anyways, in The Goal, the protagonist is trying to save this manufacturing plant. And initially he engages in a lot of local optimizations that end up causing global de-optimizations, until — through his mentors and trial and error — he learns the theory of constraints, and then engages in improvement, but in the context of the larger goal.

And I think that that larger goal is what trips up a lot of the technologists. Now, hopefully — hopefully, I know this isn't gonna be true for everybody — but hopefully for most of you, it's true that your organization has a purpose that you can align to, right? Because the goal is business results. And that might not have been what you expected me to say. It doesn't sound nearly as inspirational as all the other talk.

And I just want you to remember that business results serve our organization's purpose. Without business results there's no business — meaning there's no path to our purpose. So if you're in an organization that has a purpose that you've gotten behind, you need to care about business results. Business results serve the purpose, not the other way around. We're not in the business of making money. We're in the business of a purpose, and we make revenues and profits and grow so we can have bigger impacts and serve those missions.

So we have to achieve business results. The goal isn't elite software delivery performance according to DORA, right? It's what comes next. It's that 2× that they talk about — the 2× increase in likelihood that you achieve your organizational outcomes, business results.

So stop talking about IT and "the business" — there's only the business. And for you to generate those business results, you're gonna need to focus on the missing focus area in most organizations — and that's actually outcomes. Senior leaders will talk all day about the impacts they want to achieve — the results for the business. And then most execution teams are talking about their activities and their outputs and their features and everything else that they're doing. The thing that bridges the gap between those is what people actually do with what you give them. Those are the outcomes.

And so DORA elite software delivery performance unlocks your ability to deliver fast — there's no doubt about it. But then you can deliver a ton of outputs at really high frequency that do absolutely nothing for your users except maybe piss them off. So you still have to learn what works for the customer, and then deliver business-aligned outcomes.

Your goal: business results. Your means of achieving that goal: delivering outcomes, by way of software delivery performance. So be bold. Do the right thing. Do what works. Do what is necessary. Be the thermostat that creates that environment of belief, hope, and caring — and then manifest action. And you'll start that flywheel that carries you to this divine destination of DevOps: divine business results.

That's the real goal. And now you have some of the leadership tools that will help you get there. Thank you.