IT Leaders

00;00;00;10 - 00;00;22;04
Deanna Durrett
Good morning everybody. I am going to be echoing a lot of what Olivia talked about, which is the power that you all wield as managers. My name is Deanna Jarrett. I'm CEO and general counsel at El Toro. We are in ad tech and data analytics company located in New Lu. And, I'm an attorney by trade.

00;00;22;07 - 00;00;47;02
Deanna Durrett
And in case any of you were wondering, no, they do not teach people management as part of the standard curriculum at law school. It's more contracts and property. But they should, And that will be my pitch today. So it was not until I was several years into my career. That I discovered firsthand the power of good people management.

00;00;47;05 - 00;01;09;14
Deanna Durrett
In 2012, I'd been practicing for several years. I decided to go in-house at an organization called Success Academy Charter School. Sorry, I don't know why. My slides are a little messed up now. Success Academy charter schools started in 2006. They are free public schools in New York City, and they started with their single school in Harlem.

00;01;09;14 - 00;01;36;07
Deanna Durrett
And she started the school of the founder as just a K to one. And then by the time I got there in 2012, so six years later, they were already at 14 schools. And then I was there for about almost seven years. So in the next seven years, I served as assistant general counsel, but then I took some non legal roles and ultimately was chief of staff to the CEO.

00;01;36;09 - 00;02;01;12
Deanna Durrett
And seven years later, we had 47 schools in four of the five boroughs of New York City. And not only did we, in my seven years, add 33 schools, but we were experiencing exponential growth. And that is because children tend to get older. And so we would open a school as a K to one. But every year we had to grade grow that school to add second grade.

00;02;01;12 - 00;02;37;09
Deanna Durrett
Third grade. You get the idea. And as we were growing, everyone, both honestly critics and supporters, we heard constantly there is no way you can grow that fast and maintain, educate educational quality. It's impossible. The wheels are going to start coming off the bus. But they didn't. So the year I left actually was 2018. And you can see here that, we had 47 schools, 17,000 scholars.

00;02;37;11 - 00;02;58;08
Deanna Durrett
And we were if you considered all of our schools kind of a network or a district, we were the number one district in the state of New York. You can see our household income. The average was $43,000. We were in some of the toughest, the poorest neighborhoods in New York City. And again, we were a free public school.

00;02;58;09 - 00;03;28;12
Deanna Durrett
You lived around the school. You got in. If you if you won the lottery. And we did. We actually had a lottery because we have more kids that wanted in. We were outperforming Jericho and Scarsdale and you probably can't see this, but the average household income at Scarsdale was 291,000 compared to our 43,000. And I'm very proud to say, because I still my heart is still with this group, that their results have continued.

00;03;28;12 - 00;03;51;24
Deanna Durrett
So again, children get older. We had to open high schools. So the year I left, we actually graduated our first high school class. And now you can see for the seventh year in a row, 100% of our graduates are accepted to four year universities, and we remain leading the state in, math and reading. How did they do it?

00;03;51;25 - 00;04;24;22
Deanna Durrett
How did this founder or the CEO do it growing that quickly? Well, I'm not I don't want to oversimplify it. There are a lot of things that go into great schooling. As our friends at JC know very well. But one of the things that, was foundational at success Academy was, oops, people, managements. We had a language that we talked about all of the time.

00;04;24;22 - 00;05;01;16
Deanna Durrett
It started with zip codes should not determine one's destiny. So we knew that, all kids could achieve if given the right environment. And, other tools at school. And we would never say, well, they came from a tough background or they don't have the right family situation at home. So they're not going to make it. Instead, we had a language about adult accountability, and we shared this definition, a very simple definition of what a manager's job is.

00;05;01;18 - 00;05;38;28
Deanna Durrett
A manager's job is to get great results through others. So at success, we talked all the time about holding the mirror up to ourselves and asking, what could we do differently about our practice that would get those better results through others? And the unique thing about schooling and about this organization that I was at, is, if you think about it, almost every single adult that we employed was a manager.

00;05;39;00 - 00;06;09;03
Deanna Durrett
And that is because at the central office, we were managing the principals of the 47 schools. The principals were the bosses of all of the teachers on their staff and all of the operations staff. And a teacher really is a boss of their classroom. They are the manager, they are the boss. And it's their job to get great results through the students in the classroom.

00;06;09;06 - 00;06;37;25
Deanna Durrett
So this this management and adult accountability, it really changed my whole career because it made me realize that it was the lifeblood of this place, and it made me realize the power that it holds to produce results like this. I didn't realize then, but now I understand that what I was living is very well studied, and this echoes much of what Olivia was talking about earlier.

00;06;37;27 - 00;07;06;01
Deanna Durrett
We know that engaged employees deliver better results, and my stats, come from Bain and Company and Gallup, but they reflect the same thing, right? Companies with highly engaged employees grow revenue two and a half times more than companies with lower engagement levels. Me and my slides are not doing well today. Sorry about this. What affects engagements?

00;07;06;03 - 00;07;42;09
Deanna Durrett
The manager is the single biggest driver of engagement. The manager explains 70% of engagement. So what's cut off here is, an author rustler away. He sums it up. What I think is really well affect the manager, affect the enterprise. Companies should be spending more time focusing on the development of their managers in order to produce company results.

00;07;42;11 - 00;08;05;02
Deanna Durrett
But I think many of us realize now that we're in manager positions, it is a really, really hard job. And many of us, as we've come up through our career, have, at least at some point been under a manager that we would say has been less than stellar. Why is it so hard?

00;08;05;04 - 00;08;33;26
Deanna Durrett
In here's more stats. Actually, I'll add one thing before I go to why is so hard? This is just from February of 2025, a Fast Company article and a new study that's out that basically says managers are not okay, given the increase in remote work and hybrid situations. Given layoffs that have affected the middle management, managers are feeling isolated.

00;08;33;28 - 00;09;01;21
Deanna Durrett
They're feeling stressed and overburdened. They are not okay. And so more now than ever, we need to be addressing that. But why is it hard? Why do we see challenges with new managers? Anyone, whether. Yes. You're dealing with people. And people are difficult. Yes. I don't have a slide for that. But that's I would agree with that. Anyone else?

00;09;01;23 - 00;09;28;11
Deanna Durrett
Yes. There's absolutely no training for. Yes. They just get thrown into the fire. Absolutely thrown into the fire. If you are trying somehow to fire people, managers and yes, I agree with that. A lot of times managers are you first managers. You're going to hear individual contributor job and it's totally different skills. That's right. Yes. Bingo. 100%. So I think for all of these reasons, there's many reasons.

00;09;28;11 - 00;09;56;16
Deanna Durrett
I'll sum them up quickly. It is a totally different skill set. Right. You many new managers have been exceptional at the individual contributor skill set. And now they are asked to to have all of these other skills. You know, maybe they do have some of them, but they spent years focused on other skills training. Success is a first time manager, requires a major transition.

00;09;56;18 - 00;10;33;08
Deanna Durrett
While most organizations have onboarding programs for new hires, few offer similar supports to employees navigating leadership positions. So you get promoted. You are in this new role that requires a new set of skills. And many of us, maybe we get 1 to 2 trainings and if that. Right. And finally, I really think that, our instincts, our sort of natural tendencies, things we've been taught for years and years.

00;10;33;10 - 00;11;01;01
Deanna Durrett
I do not know why. I'm really sorry. But it is directly counter to, the skill set that you need as a manager. So this is supposed to go to. Let's see, delegation. So delegation is very important as a manager, right? But as an individual contributor, we know that if you want something done, you do it yourself.

00;11;01;04 - 00;11;23;23
Deanna Durrett
We also are trained via TV and the. So social image of what a good boss is to believe that bosses make all of the decisions, when in fact, when a boss makes all of the decisions, they are doing nothing to empower their people to make the decisions. This goes to conflict resolution. We're taught very early.

00;11;23;24 - 00;11;50;25
Deanna Durrett
Don't rock the boat, right? And many of us just by our nature, are conflict avoiders regarding performance management. We are taught, since we are tiny children. If you do not have something nice to say, do not say anything at all. And we carry that with us into the workplace. And finally, empathy again, going to what Olivia was talking about.

00;11;50;25 - 00;12;10;28
Deanna Durrett
Many of us believe that we're humans until we're 22 years old. But then we go into the workplace, and we're not supposed to be a human anymore. We're to be professional, and we are supposed to check all of our emotions at the door. And we believe that our employees check their emotions at the door, but we carry those with us.

00;12;11;01 - 00;12;40;19
Deanna Durrett
So our instincts are directly counter. Require, you know, making the need for training honestly even greater. So what can we do? And our companies, what can they do? In, 2020, I moved back, from New York to Louisville, and I joined an incredible company. What I'm at now with, Dustin and Matt and very grateful to have fantastic colleagues.

00;12;40;22 - 00;13;07;13
Deanna Durrett
El Toro, it is us. We sort of still call ourselves a startup, but at the point at which I arrived, they were about 7 or 8 years into their journey. I was the first lawyer that they brought in-house. And since I've added several, hats but incredible environment. The culture is fabulous. It's innovative, young, vibrant, entrepreneurial.

00;13;07;16 - 00;13;47;16
Deanna Durrett
And to its credit, El Toro has done an amazing job at really home growing its talent. So we take, individuals, whether they're career changers or fresh out of school, and develop them, into, their roles, such as, like a developer with our unique technologies and tool sets. But I recognized when I started that what was happening was we were growing very quickly, and we were starting to promote many of these individual contributors, these data scientists, these developers into the role as manager.

00;13;47;19 - 00;14;16;28
Deanna Durrett
And we had, and we still have, great ambitions for our growth and our expansion. But what we were not doing was providing any supports to those individuals that we were putting in these roles. So. I decided to think back to my time at Success Academy and kind of what were those elements that existed that I knew we needed to put in place at El Toro?

00;14;17;00 - 00;14;52;12
Deanna Durrett
Excuse me. One of them, again, was that shared understanding, that language that, you know, at success, we would say, hold up the mirror and everybody knew exactly what that meant. We did not have that at El Toro. In fact, no one was really talking about what a manager's job was at all. So it sounds very simple, but in year one, I just decided to start a book club and I chose, what is, to this day, still my favorite management book.

00;14;52;12 - 00;15;19;29
Deanna Durrett
Has anyone read, Radical Candor? A couple of you. If you take nothing else away from my talk, I highly encourage you to get Kim Scott's book. Or if, videos are your jam, pull up any of her Ted talks. She is terrific. And I think her book is incredibly powerful, as Kim says. And this is one of the reasons that I chose this book.

00;15;20;01 - 00;15;28;05
Deanna Durrett
It doesn't get easier than a two by two framework. And that is what she offers in this book.

00;15;28;07 - 00;15;56;24
Deanna Durrett
So to sum it up really quickly. Kim says that we want to be leading from a place of radical candor. So the first dimension is to care personally. And again, that's the sort of she calls it the give a damn, dimension. But again, bring yourself to work care what is going on in people's lives, care about their professional development.

00;15;56;26 - 00;16;31;14
Deanna Durrett
The second, dimension is the challenge directly. And she calls this dimension the willingness to piss people off, the willingness to say what needs to be said. And when you care personally and you're willing to challenge directly, you're operating from that place of radical candor. So you are, in fact, saying something that might be hard to say, but because you want to advance that person's practice, advance their career, make your team a better team.

00;16;31;17 - 00;16;58;14
Deanna Durrett
And we also know that the more that we really hash out ideas, that we create environments where people are comfortable objecting, opposing, stating the cons, we get to a better results. I love this two by two framework, and I thought it was particularly helpful for El Toro because not only does it show what good looks like, but it shows what it is not.

00;16;58;17 - 00;17;27;05
Deanna Durrett
So when you are challenging directly but you fail to care personally, you get into obnoxious aggression territory. Frankly, you are seen as just a jerk. Like no one, really wants to deal with you. You're just obnoxious. Even worse is when you fail to challenge directly. You don't care personally, and then you're in the land of manipulative insincerity.

00;17;27;07 - 00;17;58;18
Deanna Durrett
So if obnoxious aggression is front stabbing manipulative, since insincerity is backstabbing, you are now talking behind people's back. You're not saying things to them directly, and you really don't give a damn at all. Most of us, however, and I think if we think about bosses that we have had that have been challenging to us, and even mistakes that we make and, and I'll be honest, I sometimes still make them.

00;17;58;20 - 00;18;24;29
Deanna Durrett
Most of us live in this land of ruinous empathy. And this is we actually do care. We're good people, right? I care what Matt is going through at work, whether that's challenged with a project or something going on at home. It matters to me. But it's really hard that sort of, again, if you don't have something nice to say, don't say anything at all.

00;18;25;02 - 00;19;07;12
Deanna Durrett
So we live here in ruinous empathy, and we let poor performance continue and continue and continue. And it hurts that person. It hurts the team. And it's certainly again, because you do care. It's giving you tremendous angst. Right. So no one is benefiting from ruinous empathy. So the reason, again, why I love it is because radical candor, I believe, and this is a quote from the book, Radical Candor builds trust and opens the door for the kind of communication that helps you achieve the results that you are aiming for.

00;19;07;14 - 00;19;29;18
Deanna Durrett
So for me and for El Toro, I felt if it established a really good foundation and after a year of kind of just slicing up the chapters and going through it together, I did notice people's language start to change. So before people would come to me and say, I have a problem, it's Tim. Tim is late for work.

00;19;29;24 - 00;19;55;01
Deanna Durrett
I constantly see him on his phone, and he's he's not carrying his weight with the tickets. And I would say, okay. Yeah, that sounds like a problem. Let me, when's the last time you've talked to Tim about this? Well, I mean, I did tell him he was late the other day, and I'm like, that's it. And then I pull up Tim's performance review from three months ago.

00;19;55;04 - 00;20;30;18
Deanna Durrett
It is glowing. Tim gets a four out of five. Tim. The tickets that Tim does answer are exceptional, right? But after the book club, again, the language started to change. And so people would come to me and say, I have a problem. Okay, what is your problem? It's me, it's me. I have not I have let Tim proceed for three months now without addressing the fact that he is constantly looking at his phone and he is not carrying his weight.

00;20;30;20 - 00;20;57;04
Deanna Durrett
So now we had a name for the problem, and the name was not Tim. That I knew was a big step forward. So then it was time to really unpack those skills. What do you then do about Tim, and how do you do it right? Wrestled away who's kind of a contemporary of Kim Scott? This is another excellent book.

00;20;57;06 - 00;21;34;06
Deanna Durrett
He says focus on a small number of leadership behaviors that, when practiced, measurably deliver happy results. Again, the engagement, right? The radical candor. And so I went back to the most simple setting I could think of, the classroom and what that teacher is doing as he or she manages those 20 something second graders. And it's the same that we need to be doing as people managers in the professional workplace.

00;21;34;08 - 00;22;00;29
Deanna Durrett
They are building trust. That is someone the kids trust, right? They go there and want to feel safe every day. That teacher has strong communication. And if any of you have kindergartners like I do, you know it is very strong. They are very clear in their instructions. They provide direction. They set really clear expectations. Where are we going to sit?

00;22;01;01 - 00;22;26;05
Deanna Durrett
We're going to sit exactly here on the rug. Right. There's no room for interpretation until they want there to be. Right. They coach along the way. They're giving real time feedback. That red pen is out there marking up that essay. And then ultimately they're responsible for promotion. Just like I believe every manager in this room is you have achieved when your individuals get promoted.

00;22;26;05 - 00;22;55;15
Deanna Durrett
Right. And so those teachers are promoted to the next grade. So I took these and I laid it out over the course of the year. And it's really nothing fancy. I decided to, select a different presenter for each one of these. Again, I grouped it into sort of foundations of establishing trust and good communication, then went into direction.

00;22;55;18 - 00;23;24;20
Deanna Durrett
How do you set the expectation? How do you give very clear direction then coaching, team building and finally career development? I did bring in leadership Louisville. Doug mentioned them. I think that they are fabulous. And so I brought, leadership Louisville, some outside voices to lead 1 or 2 of these sessions. But for the majority of them, I asked my colleagues, and sometimes I even asked fairly new managers.

00;23;24;20 - 00;23;52;10
Deanna Durrett
You want to ask someone that has a lot of credibility, a good reputation. But what I knew would happen when I ask someone, say, to lead a delegation is that person had to not only share the language and speak the same language that I was trying to get everyone at the company to speak, but they had to become they had to brush up their delegation knowledge and skills in order to teach it.

00;23;52;13 - 00;24;27;02
Deanna Durrett
And so it was sort of training the trainer at the same time. And what happened after we taught the skills is then we started to have a deeper conversation. Just naturally, I noticed about Tim. What was Tim what was the root cause of Tim's lackluster performance? Did that manager need to set clear expectations and do a bit more hand-holding for Tim than maybe that manager does?

00;24;27;02 - 00;25;02;06
Deanna Durrett
For some of the managers highest performers? Was the manager failing to give real time feedback, or did Tim actually have a will problem? Tim didn't really want to be there, and therefore the manager needed to do things like put Tim on a performance improvement plan and potentially even part ways with Tim, and those all require skills. But again, it was sort of the identification of what needed to happen and then building up those skills to do it.

00;25;02;08 - 00;25;28;14
Deanna Durrett
Russell Way, preaches this in his book very strongly. You cannot just train and walk away. And we know this again from students. We don't teach kids multiplication in one setting. And then we're like, you got it. You're good. It's worksheets after worksheets after worksheets. And so that is kind of the phase that we are in right now at El Toro.

00;25;28;16 - 00;26;03;11
Deanna Durrett
I think there are a couple different ways to practice. You can do it in the very obvious way through role play. So I give people scenarios and we just talk through them. I think it's also really important as managers that we practice what we preach. And so when I have to give my team members feedback or when I'm setting expectations, often I will do it in a very overt way, especially if I'm doing it to someone that is a new manager themselves.

00;26;03;13 - 00;26;34;15
Deanna Durrett
So I will start by saying we need to have a conversation. I'm going to give some radical candor here. And then they they see what I am doing and hopefully can start to again incorporate it into their own practice. And finally, I think it's really important that we assess and evaluate, we have now built into our performance management system or our performance review process, a question about how are you doing as a manager?

00;26;34;20 - 00;27;01;23
Deanna Durrett
Because frankly, it should be your number one objective to be, again, getting those great results through others. That is really it. I in this, Fast Company article, I would say this resonated with me, that we we are in a crisis right now more than ever for for managers. And the article talks about how Gen Z is looking at managers and they're saying, no, thank you.

00;27;01;23 - 00;27;35;09
Deanna Durrett
Like I don't need that pressure, I don't need that stress. I will go the individual contributor route. So it's really important that we start offering our managers those supports. And the key lies not in grand transformations, but in consistent, practical steps to embed the fundamental fundamental capabilities of resistance and support across the organization. The result will be a more stable, sustainable work faith workforce capable of handling change and ready to lead through it again.

00;27;35;09 - 00;27;51;00
Deanna Durrett
It's nothing fancy that we have done at El Toro, but hopefully, we are putting in those supports that are starting to move the needle and ultimately will contribute to the company's, growth and success. That's it.