Adrienne Shulman

Okay, everybody. We're short on time, so I'm going to get started.

Thanks for spending time with me. I'm giving a talk on leading with heart. I'm going to share some leadership lessons I've learned over the years, particularly around a thesis I have: that as technology professionals, we've all been trained to use our brains. But if we want to be effective leaders, it's the heart muscle we need to develop.

I am Adrienne Shulman. I've been building enterprise SaaS since the early 2000s. I started as an engineer and have had all sorts of management up to senior leadership roles.

Why am I here today? It's because I'm really passionate about DevOps. Anyone else in this room? I think that's probably what we have a lot in common. I've been introducing DevOps mindset and practices with all of the teams I've been working with over the last few years. In 100% of the time, team performance has gone up.

As a result, I was promoted two times in two years. That's not what I'm passionate about. So I think DevOps is good for our careers. But where the passion comes from is because in all of those times as well, I've seen employee happiness go up. I've seen stress go down. And that's what really got me weirdly passionate and super motivated for this movement we're part of.

I want to give a really big shout out to Gene Kim, all of the IT Revolution authors. I've learned so much from this community, but also the community. It's not just the ivory tower, the authors. I've met so many people even in this room over the years, and I've learned much from all of you. I think this community is some of the smartest people, but genuinely just genuine people, helpful. Everyone wants to help each other. So just a round of applause for you guys.

So I'll tell you my story. I was working at an enterprise tech company. It was a $5 billion global company, and I had a new leadership opportunity come to take over IT. I'd been in the engineering world. I got to pivot over to the enterprise IT world. So it was a 100-person department overseeing IT business applications. Think your low-code/no-code apps, like your Salesforce, NetSuite. I call it the tech stack that runs the business, data and analytics, and all that. It seemed like a good opportunity, but here's the context.

Growth had been slowing at my company for a few years. I know you can't read that, so I'll just say growth had been slowing at my company for a few years. We had acquired our biggest competitor about a year and a half before, and we integrated people and teams. So we were one company, except we didn't integrate systems and technology. So we were really two companies. Everybody in the company blamed IT for making their jobs hard.

And as a result, the CEO really said systems integration is the number one priority for this company.

So why me? I was chosen for this role because I had a reputation for getting things done, for being technical. This is a quote from our CEO: I was put in charge of this at an executive level because of my technical background and my expertise. And I had a very simple mandate: Adrienne, get the systems integration work done.

And my boss, who I was reporting now to the chief administration officer, I think he thought he was doing me a favor, but he handed me a Gantt chart. There was already a plan. So all they needed was someone to execute. Just get it done. So if there are any fans of Sooner Safer Happier in the audience, you know there are a few red flags, but I'm always up for a challenge.

So what's the first thing you do? You got to talk to people. So I was going to talk to key stakeholders, see what I could learn. I had previously been over on the right hand side of this org chart in product and engineering, and our organization, much to my chagrin, was organized in functional silos.

So I was going to talk to my team, the three key stakeholders, and talk to my team. I was going to talk to all of the functional department heads over our marketing department, sales, professional services, customer support, and finance. If I think about my team as owning that technology, these were the people using the technology. So whether you want to call them our customers or our users, they were the ones who I had to make happy. And then of course you talk to your executive team.

So I did my meetings, and here's what I heard. When I first spoke to the department heads, these are kind of my peers at the VP/SVP level, and I said, hey, what's going on with this project? Very hard. Same variation of the same thing: it sucks. You don't understand what we do in my department. You don't understand marketing. You don't know what we're doing here in sales.

I heard about recent projects that did not go well: Adrienne, pretty much every project we had to roll back. It keeps getting delayed. Quality is low. So just very little trust in IT.

When I spoke to my team, I said, what's going on? I heard a different story. Adrienne, we're the real heroes. We're really good at what we do. We're super technical. We know what we're doing. Our business doesn't know what they're doing. They're dysfunctional. They don't appreciate how great we are. So, not a lot of accountability.

And then when I spoke to the executive team, nice enough, but they didn't have a lot of patience, and they said, Adrienne, it's not your fault you weren't here. But guess what? You got to get this done. They showed me the plans and those dates that they were promised. So they're like, just get it done.

I diagnosed it as drama, dysfunction, and deadlock.

This is a quote from Chris, who is the senior vice president over our sales operations team. He described it as, when I took over, the functional and technical teams were at each other's throats. What I saw here was, yeah, it was deadlocked. Nothing was actually getting done. So it didn't matter that there was a plan. People were really not in a good place.

So what do you do as a leader? I'm reminded: the job of a leader is not to do work. You don't do the thing. And when you get your first job as a manager, the first thing they tell you is you don't have to do work anymore, you delegate. But leaders don't delegate. So a job of leader is actually not to tell people what to do. The job of a modern leader is to create the environment where work can get done. And create the environment is code word for create the culture.

And a lot of talk in technology these days is all about, you got to have the right culture. Luckily for us, we know exactly what that culture looks like. We have the great Ron Westrum in the audience here today. This is from the book Accelerate. If you're new and you haven't read this, highly, highly recommend. It was very much life-changing for me.

But Dr. Westrum talked about pathological cultures, ones where people are driven by power. So it's a little bit of me, me, me first. The bureaucratic organizations, where people are driven by rules, so it's stay in your lane. It doesn't matter what the outcome is. If I did my job and I checked my box, I'll be fine. Versus the generative organizations, which are the ones that are really mission-focused. These are the ones that outperform. Highly collaborative. No such thing as failure in these organizations, only learning.

Because of my experience leading DevOps transformations in the engineering org, it was very easy for me to identify pathological and bureaucratic aspects of both of those cultures in this situation. So even though I was on the hook for this IT project, I knew I had to lead a culture change before any work could get done.

And that is where my thesis about brain versus heart comes in. My definition of brain is this: if you lead with brain, you're putting the logical, analytical, most correct solution or technology solution above anything else. That's the first thing that's important. Other things come second.

If you lead with heart, people come first, and brain will come second. The reason this is important, I think, for us as technology leaders is we were trained to lead with our brain. And guess what? It made us really successful. All my past success is because of my analytical brain.

But we like to say what got you here won't get you there. So when you get into a leadership role, it doesn't matter how smart you are, because guess what? Everyone's pretty smart. And in these complex dynamic orgs, it doesn't really matter that you have the right technology if someone over here isn't ready to listen to it.

And that's actually what I saw. I was guilty of this because I came in, rolled up my sleeves, and I said, oh, this is actually a really hard problem. I've got two of everything: two Salesforces, two NetSuites. We had like a 20-application tech stack. How do you do this? This is a complex system, and we need to do a complex migration.

So I admit I got with my team, and I whiteboarded it, and I was only asking about, what's the strategy? How are we going to do this? This is going to be so fun. And then I realized that I had three different opinions on the right way to do it, and people had beef with each other.

The one person who proposed one solution, we were not really at the place where you could have this honest debate over what was right. It was just, my ego needs to win, so my solution. And because you're pissed at me, you're going to go tell someone down the hallway why mine doesn't work, and then you're going to whisper. Nothing was going to get done.

Are we back? Okay. So that's the heart. It was, how do you actually get people to a place where work can get done?

So this is what it looked like. I first worked with my peers, at the leadership level but not in my department. I recognized that they all saw this as something for me to do for them. They wanted to be treated like a customer: I'm going to sit back and you do all the work. So the first thing I did was change the perception from this is an IT project to, I called it, a business optimization initiative. All of a sudden, the senior leaders who were kind of waiting for me to do all the work, I said, get in the boat with me and solve problems together.

I used hashtag one team all the time. I think anyone who's done any sort of M&A-type work, I'm sure you've heard these and you kind of roll your eyes. I threw it all the time, and I just kept following up, kept following up.

I was really explicit. I got on the phone. You might think you're collaborative. So this is IT and business, but maybe it's product and engineering, maybe it's engineering and security. You might think you're being collaborative, but have you ever called someone up and said, hey, I want to help you. How can I help you? Or, what's going on? What is important to you? Just really being explicit and putting it out there. I found that really powerful, because I was warned when I took my job: Adrienne, so-and-so over here, they're hard to work with. And then when I went and said to them, hey, I want to help you, they weren't so hard to work with.

And we committed to bringing problems to each other. In the past, when we were very much in our silos, when you have a problem, what do you do? Complain to your boss. And then what do they do? They've got their own problems, so they just complain to their peer over here, saying, hey, you got a problem over here. Then it goes down, and it's drama.

So I just said, hey, guess what? Our bosses are C-suite-level executives. They don't want to hear drama. How about if you have a problem, you bring it to me, and if I have a problem, I'll bring it to you. We did it in a safe space, and everyone was really happy working in that way. This was all about modeling behavior. The reason I could do this is because I'd seen it work before.

Who am I? I was at a VP level, so there were SVPs, there were people senior to me. It's not about title. It's just, hey, let me offer a different way. I said to one of them, look, right now we're in this scarcity mindset. What if we're successful with this project? Promotions for everyone. So it's not about departments competing.

We heard, I think in the session this morning with Ron Westrum, one of the big takeaways I heard is you can choose your culture.

What do I do with my team now? My direct reports: it was all about changing incentives. In the past, it was incented to be technical. I had leaders of my team who, as long as they told up to their boss, I'm doing a good job because of this, we weren't really incentivized for outcomes. So I set a new vision.

I told them the only thing that matters is that you're creating value for our company. And I followed that up with, value is defined together with your business partner. The two things this does: one, generative organizations are mission-focused, so you get people to say, it's not about local optimization. You have to further the mission of our company. And it forces collaboration, because now you have to define what that is with someone that you previously weren't collaborating with.

I told them, it's not me. I may be your manager. I may determine your promotion, but I'm actually not going to decide. The people over here that we called the business before, when they say you suck, I need them not to say that. I need them to tell you what value you're creating together.

Emphasize progress over perfection. When you're dealing with these massive, big-stakes projects, like, hey, we need all of our systems integrated, there was so much fear that it wasn't going to get done, and everyone was trying to come up with this perfect solution. It just would never get done. So I just had them focus on the small. I said, what business value can you create in this month? Not next year, not next quarter even, because that actually would never happen. And then I told everyone, everyone has to be willing to try.

So if you're completely stuck in, I'm doing my job but it's everyone else's fault, it wasn't going to work out.

And this does take patience. When you're leading with heart, you have to give it time, because people have heard words before. So you have to say the words, and then you have to follow up with actions, and you've really just need to consistently give people time. There were some managers and leaders on my team who told me, Adrienne, you're the leader we needed a year ago, but I'm exhausted. I can't do this. And it was okay, and they left. There were other people who couldn't help but give excuses. It was just excuse after excuse about why things weren't getting done. So ultimately, as a leader, you do need to find the right people with the right mindset.

With the executive leadership team, I'm not going to talk too long about this, but I just want to say the importance of telling your story when you're doing these culture changes. I like to also say, if you don't tell your story, someone else will.

Luckily, I did not tell the story on my own. So I used IT Revolution and the DevOps Enterprise Summit community. It was really, really helpful for me, because so many of us are going through similar challenges. I'd met people through book clubs, through previous conferences, through Slack. So for me to tell the leaders in my company, hey, we're not unique. Other people are going through these challenges too. And then following up with information I learned from books. I was able to say, for this scenario I particularly pulled from Accelerate and Sooner Safer Happier. To be able to say, hey, there are practices, there are patterns.

What this does is it helps with my credibility, because it's not my ego saying it, which eventually leads to trust. Because I focused on that, my peers across the aisle were all telling the same story too. So instead of complaining about IT, they would say, you know what, we're working together. I feel more optimistic about where we're going. When the drama gets cut, we're not fighting about people. All of a sudden, we're in a place where work can get done.

So here's what happened. Over about a three-month period, my one team went from a corny slogan to reality. As a one-team group of executives united, we asked for help. That's unheard of, right? We're so bad at asking for help. One of the things the DevOps community taught me is I can say I don't know how to do something or I need help. We asked for help. By the way, help is code word for budget. There was no money to be found when everyone's fighting, but when you come together and tell a story and agree, all of a sudden we got help, aka money. Ultimately, we started working small.

And we broke deadlock. We were actually shipping little small things that were needed today. And people were happier.

So this is all to say: because I led with heart and I put away the brain, we got to a place, and it took time, where we could follow up with brain work. It's not that brain doesn't matter. It just means you have to start with heart.

The end of the quote I had started with from my CEO: he said I might have been chosen for technical expertise, but he recognized it was my ability to influence stakeholders from different departments that becomes a superpower.

So for us as technology leaders, unless you live in some place that doesn't exist where you can just do your work on your own and not worry about other departments, maybe you don't need that. But this is reality. And the end of the quote from Chris, who is the SVP of global field operations: he talked about us being at each other's throats. He finished up, and he said he understood I was asking for time to build the relationships and trust, to create a single-team view, so that now you could follow up and roll out a plan to get work done.

This was probably the hardest work I've ever done. I would come home from work exhausted at the end of the day, just completely depleted. It was also the most proud I've ever been.

I think this is important. Gene Kim loves to end talks with, how can you help? I had to think about this. Here's what I'm going to say. I think we all know the value of DevOps. DevOps allows us to safely deploy code quickly so that we can get faster feedback and ultimately solve customer problems better. But a lot of the DevOps stuff that I've been reading focuses on technical constraints.

But clogged flow is clogged flow, and deadlock is deadlock. My story is just one where it was very obvious that culture was contributing to a blockage. So I just ask you, can we further explore as a community how culture contributes to flow and what that looks like? Ultimately, my biggest wish is we take these soft skills and actually turn them into hard skills. When we think about, if you close your eyes and picture what a leader looks like, what do you picture? Don't picture the person barking orders. Picture someone who's coming up alongside you and saying, I don't know, but let's find out together. How do we normalize this behavior and make it so that it becomes just what leadership is?

Just the start of a conversation. And actually a lot of the talks this whole week have been about heart, have been about leadership, have been about culture. So, not necessarily new.

I will try to finish up with two quotes. I was traveling in Mongolia a few years ago, and I visited the oldest Buddhist temple in Mongolia at the Erdene Zuu Monastery. We met with the head lama there. It's a very remote place, took about 10 hours overland to get to, and we asked for advice: what advice do you have? This is a spiritual guide. What advice do you have for Westerners? And he talked about Western culture and how smart we are and productive and busy and we're inventive. But then he paused and he pointed to his head. He said, don't forget, your brain is useful, but your heart is important.

And he was urging us to really lean into your heart and connect with humanity. I think about this quote because I think it really resonates with what we're doing as technology leaders. We need our brains at work, and it is very useful. But at least for me, where I find the most gratifying is really leaning into the heart muscle and understanding people, and figuring out how do we work together to make better software and happier people.

That's my talk. Thanks for listening.