IT Leaders

My name is Jay Stanley, good morning. I, just had ACL surgery two weeks ago, so I may or may not use a crutch. I don't normally fall over. If I do, you can laugh and I'll just get back up. You will laugh, I know.

Alright. So that's my talk. IT IT team culture, a road trip, bumpy but worth the ride. So I was thinking somewhere and I thought, okay, what what should my theme be? And so the first thing I wanna know is how many you have been on a road trip?

Oh, lots of hands. Give me characteristics of a road trip. What do you think about when you think about a road trip? The rush of trying to get on the road. The rush of trying to get on the road.

Kids seat. Fighting in the Yes. Place is unknown. Planning. Yeah.

The accidental side adventures. The accidental side adventures. That's a good one, right? The balance between getting there and enjoying the journey. Okay.

Yeah, I think my first road trip we took right when I graduated from high school. There were five of us guys, we wanted to go somewhere and I was the guy with no money. And so we decided to drive to Lake Barkley down in Kentucky. Five Five guys in a car about the size of a Pinto. How did we pack?

We didn't pack much, did we? What kind of food do we take? Junk food, totally. We didn't have any groceries. We didn't have anything.

And we really didn't have much of a plan or agenda. So when I think about some of my things, the first thing, emphasis on the journey. I think about that when I think about road trips. You know, we drive because we want to maintain control of the journey. You can fly somewhere and jump in an Uber and go somewhere, but I wanted to have control over that.

Just take the basic needs, you pick a distance, a duration, a location and you go. And you enjoy the things along the way. The second thing I think about is flexibility. Open ended itinerary. When you go on a road trip a lot of times, you're really not trying to plan everything out.

I don't. Some people do, but I don't call that a road trip. Because I think I want the flexibility in being able to do the kinds of things that might just pop up. Adventure and exploration. Getting off the beaten path, right?

I mean, sometimes you're driving along and you see a sign and you're like, hey, I think I'm gonna stop out of town. It's lunchtime, I'm gonna go find a restaurant there. You know? And then, the other thing I think about social experience. When you go, especially when you go with a group of people, it could be with your family and your kids, it can be friends, but you're really, I think the most important part of it is the social experience.

The time you spend together. The memories that you have aren't thinking, I ate to that diner that had a tenderloin as big as my head. You know, I might remember that. Okay. But a lot of it is the people side, right?

And that piece. So you're thinking, alright, road trip, what the heck does that have to do with culture? You know, and I kinda thought about this, the culture you create as a leader is deeply tied to your personal experiences. Is that true? Yes.

Do you believe that? I believe it. I mean, I think about, you know, your personal experience as you're developing your values and your beliefs. You know, as you're growing up, whether it's religious or things from your parents. It could be your work ethic, those kinds of things.

Leadership style, you may associate very closely with a particular leadership style, or you might disassociate from one. If someone micromanages you when you're working at McDonald's when you're a kid, you might hate it. And you think, I have never managed people like that when I grow up and get into a professional career. You know, biases and blind spots, you develop these things. It's all part of what happens in your leadership style and how you think about your culture, recognizing these things.

You go out and hire 10 people that are just like you, think you have a great team? Probably not. You're to be sadly disappointed. Blind spots, I know one of my blind spots tends to be that I trust that people are going to do what they say they're going to do. And I don't follow-up like I should.

I've been burned by that a couple times in my career. And resilience and risk tolerance. If you've had many failures early in life, then you might be a lot more risk averse. If you work in the financial world, you might be more risk averse, you know, things like that. So all these things play into it and so that's why I was thinking road trip.

It's like, you know, I think about my career and where I've gone, you know, as a road trip. And so I come back to this slide and I think, okay, in my career, what are the kinds of things that have happened to me? And and these things all became a part of the culture that I developed. You know, emphasis on the journey, drive to maintain full control over the journey. You know, my first job, I was in it for eighteen years.

It was with utility. Where I grew up, in a small town in Illinois, you know, you got hired at a utility and you were set for life. You're gonna retire from there. You know, sixteen, seventeen years into it, I had a blast and I thought I was gonna retire. I had to make pension decisions at some point.

And I chose the pension, you know, the old defined pension because I was gonna be there till I retired. I didn't take the cash stuff thinking that I was gonna leave soon. At year 17, a CIO walks in that I couldn't stand. And I couldn't ethically work for the man. And so I chose to leave.

Flexibility, and I think about adventure in that. You know, I am the type of person, I always have a bucket of money so I can leave my job. Honestly, that's how I think about it. I wanna be in control. When I left that job, had no other job.

But I made the choice, it was the right thing for me to do, and I was on to the next adventure. I went to the next job, and I was there for eight years. And about year five to six, there was a strategic decision made to outsource my entire group. And, you know, I wasn't in favor of it. And I was offered a position.

And I said, no, I don't want to be here anymore. And so I made the choice to go do something else. I made the choice to even try something different on the exploration side. I chose, I wanna be a CIO. And I wanna be a CIO at a mid market company.

I kinda chose what I wanted. It took me about a year. I sent out maybe a 125, a 130 resumes to CEOs around the city and other cities. I ended up getting one job offer out of it and I took the CIO position at Marsh Supermarkets. At that time, it was already going downhill.

That was four years before they went bankrupt. But what an adventure. I learned so much in that position. I don't know, I mean, you know, I just came out of a role where I just outsourced everything. I learned a lot there, if you've been through that.

I know many of you probably have. And then I walk into this role where we go bankrupt. Okay. Fabulous. But I learned a lot.

But, so I wanna go back and talk about the social side of this though. Because that is really where the culture came from. You Back when I was early in my career, I listened to my CIO, he wasn't called that, but that's the equivalent of what he was. He got up in front of the group and he could not read his slides. 300 IT people sitting there, and he couldn't do a presentation.

And I thought, I do not want to be that person. You know, that was kind of early in my career. A couple years later, Dale Carnegie came into the company I was at, and I went through the Dale Carnegie program. It was a fourteen week program at that point. And I thought it was a public speaking class.

But, and it is, but it's much more, you know. And every class is designed to stretch your comfort zone in some way. And so, I went through that program, and I remember lots of things about it, and I was asked to come back and be a graduate assistant, and talk again, mainly to help demonstrate techniques in the class. But what I really saw that stuck with me was, I saw these people. IT, you know, some were IT, some were in business, that were really introverts.

And I watched how they grew, you know, with expanding their comfort zone throughout that program. And what I saw toward the end of it, week 14, you bring in your boss for graduation, and we all got up and did a talk. Who were the first people to volunteer to get up and talk? It was the introverts. It was the people who had stretched their comfort zones and learned new things about themselves, and how they could impact, you know.

It was very cool. A couple years later, I ended up in a different role. I'm gonna just kind of walk through my career because it kind of, is where I got my culture. I'm gonna rip this microphone off. A couple years later, I ended up, I was an application development guy throughout the first part of my career.

And I got put in charge of an infrastructure group. And now, it was the support services organization, and it was desktop support, and help desk, and IT procurement. I had about 80 people in the group at the time. And many things, good things happened there, but the first thing I did was I really didn't know the area that well. I had three seasoned supervisors and we went to a Help Desk Institute conference down in New Orleans.

Familiar with HDI? Some of you maybe. At that conference, there was, we did all the bonding, you know, so we did the social bonding thing. But at that conference, there was a gentleman, his name was Kirk Weasler, who you probably haven't heard of. He was the chief morale officer at a data center company at that time.

And he did a Forrest Gump invitation at the beginning of the conference, and it was fabulous. And so he was doing a session, and of course his session was full, because everyone wanted to see Forrest Gump in person, right? And in the session, he did two things that I remember. And this was quite a while ago. First of all, he read to us.

He read to the class. And he wasn't just reading book, he was reading a children's book. And every, and you could hear a pin drop in that room when he was reading. He'd read it, just like you would your kids. And he'd turn it around, he'd show the pictures, and everybody's looking at the pictures trying to see what's in there.

And I was watching. I was towards the back of the room watching, thinking I cannot believe this, you know. And he was talking about how powerful it is to read and to read to your team. And I thought, okay, interesting. Second point, he talked about team building.

And he's like, you know team building is not an event. It's not that annual thing where you go off-site and people are falling and you're catching them, or you're building human pyramids, or I don't even know if you can do that anymore, honestly, there's probably something wrong with it. But that's not that. You know, team building is something that you do all the time. And you have to make it a part of your culture all the time.

And so, this percolated with me. I left that company and then I went to the next company and I had two teams of people. And I thought, okay, I'm gonna do an experiment. And on one team, I'm going to try and use some new techniques. For me, anyway.

And the other team, I'm not going to do it. And so, I actually met up with Kirk, and I talked to him a couple times. And he gave me something to try. He's like, try this to get the team building stuff going. It's called exercise.

Looks like this. I sent it out to everyone in my group, and I said, I want you to take this, and in each box, I want you to draw something. And then bring it to the next team meeting. And so, that's what we did. And he told me this is how it would go, it went exactly the way he said.

First meeting I brought it up, you know, people brought their doodles and we talked about it. And for each one, so you have people draw something in the box. And then there's like a psychological thing. So like the first one. It's confidence.

The line at the middle of this block indicates your confidence with the world around you. Items drawn above the line are objects which you have a command over. Items drawn below the line are things which are generally out of your control. It's not the narrative that's important, honestly, here. And then there's a question.

Name one thing that you do really well. And you just go around the room and have everybody talk about one thing they do really well. And as a facilitator, when something interesting comes up, then you ask more questions. The purpose of it is to get people to talk about themselves, and so that other people can get to know them. Know?

The purpose is more in the conversation surrounding the evaluation of your doodles, than the actual evaluation itself. And so the second meeting, they, you know, always start the next team meeting. I'm like, know, pull out your doodle exercises. And some people are like, yeah, I didn't bring it. I'm like, yeah, go back to your desk and get it.

Or virtually I'd tell them pull it up. I won't, you know. And we do it again. Third meeting, it kind of, you know, I just started the meeting. I didn't even talk about it.

I just went into a different agenda. And they're, woah, woah, woah, woah. What about the doodle? And at that point, they're hooked. And that's that's where how I started doing the team building things at every team meeting that I did like that with the full IT group.

Along with that, I started reading to them. And the content was centered around team, the team focus, you know, roles within the team. I would talk about their role, you know, a help desk, my role, what's my role? My role is to set the target target for the group. And then, it's to take a step back and knock barriers down so that you can achieve what you need to do.

You know, some call it servant leadership, call it whatever you want. I mean, that's, I'm trying to make them successful. But I could talk through every role like that with them. And, but I would read about team stuff, I would read about leadership within your role. Because everyone has the ability to lead within their role, right?

And so what I noticed there was team that I did this with, they started becoming much more close with each other. Because they started getting to know each other. You know, when you know people better, are you more or less likely to talk behind their back? Less, right? Are you more or less likely to go ask them a question?

Yeah. I think you're more likely. You know, know, if you need help, if they need help, are they gonna come and ask you? It started breaking down barriers in the group. So the one team we saw, I saw big success with.

The other team, they were still a bunch of slobs, they still, know, they didn't get along well, you know. And it just, I was like, okay. Learning for me. I left this company, and I went to Marsh Okay, I mentioned that a minute ago. I decided I'm gonna do that with my whole group.

And so, the first meeting I called, the company wasn't in very good shape when I went there. The first meeting I called, they thought I was gonna lay them all off. They thought I was calling them to a room to lay them off. And then I have the doodle thing. Right?

And so we do the doodle. And it happened the same way. First meeting, second meeting, third meeting. And I'll tell you what I saw in that group. I saw a couple of really good examples.

I saw, one, I saw a parallel between that and the Dale Carnegie stuff. I saw my real introverted people over time come out of their shell because they got more and more comfortable. At first they thought, they were scared to death. They were terrified I would call on them. And then as we went, I just made a part of the, my meeting was an hour long, I'd spend forty five minutes doing this stuff.

Because we talked about it a little bit ago. I mean, are most most of the issues in IT, are they technical? Or are they people related? They're people related. And so we did this and a couple stories, you know, one, I had this one individual, the most introverted guy in the group.

I mean, he walked by himself. I think he talked to himself. He never went to anybody's desk to talk to him. And in one of these sessions, he talked, he spoke up and talked about how his house was haunted. I'm like, okay, you know, I'm facilitating this and I can't this is too good to pass up.

And so I started asking questions. I'm like, so does your wife think it's haunted also? And he's like, yes. And I said, do you know the people haunting it? And he's like, oh no, it's not people.

It's our former cats who have passed away. We both see them walking throughout the house. Some of the looks I'm getting are like. And you know, it was everything I could do to keep a straight face. I'll be honest with you.

But I kind of went with it because he was so passionate about it. And it was really meaningful to him. And a couple days later, there are guys sitting across him, the cube next to him. He says, hey, so and so. How are the ghost cats?

And the guy got up from his desk, and he walked around. He sat at this guy's desk for thirty minutes talking about that. He would have never done that in the past. The guy comes, the other guy comes to my office, he's like, Jay, you're never gonna believe what just happened. And it didn't have anything to do with the ghost cats.

It had everything to do with the change in the personality and the comfort zone of that gentleman coming over and talking to him. And we had an HR, a new HR person come into Marsh that, the last two years it was there. And he did focus groups with everybody in the corporate. Mixed groups of people. And when he got done, he went back to the CEO and the CFO and he said, I got, you know, he gave his observations about what's going on.

And then he said, one thing I gotta tell you, I wanna talk about. He's like, I do not know what's going on in IT and with Jay's group, but all the IT people were so upbeat and they got along so well. And he just talked about it and all I could think of was, what that's my grade card. Because if somebody outside IT can see how these people are behaving, what a positive thing. How do you think those people are treating their end users, their internal customers, their other customers, if they're doing, you know, they have that kind of, you know, behavior?

I just thought it was fabulous. So I thought that was very cool. And the other thing I would mention is, I think that when you think about, and so this is my culture, right? All of you are leaders, you're creating your culture. This is how I created my ideas on how to do some of it.

So another aspect of this that I want to talk about is that, you know, this is not a lip service type thing. You know, when you go down this path, this is something that you believe in, and that you live. I think that, you know, the old adage, if you're not growing, you're dying, is absolutely true. In religion, and physical health, and self care, and all those things, I think if you're not growing you're dying. Part of my culture is, is I want people to Not technically so much.

I'm not talking about certs and things like that. That's not what I'm talking about. I want them to personally grow. Because as they personally grow, their perspective changes. And how they look at things change.

How they look at people change. Change. So, you know, my challenge to leaders is, is that you have to demonstrate this. You know, I have lots of hobbies that I like. I have I I do woodworking.

I play an instrument. I sing. I, I like to play sports, that's why I got my ACL fixed because I ain't done yet. I might not be very fast, but I ain't done yet. And you know, a couple years ago, I chose, I thought, okay, I'm not doing enough.

And I auditioned for a musical. I'd never been in a play before. I'd never tried anything like that. I auditioned for the musical, didn't know a single person there, and I got in the show. You know, and I and I thought, you know, okay, I can sing and I'm comfortable in front of, relatively comfortable in front of people and all that.

Talking about comfort zone, you know, they got that singing thing, they got that memorizing lines thing, but they also had this choreography thing that those brain cells had never been activated. And so, I, it went well, you know. And then I auditioned for another show, and I got in on another show. And then I thought, I'm not very good at memorizing, and so I auditioned for a play. And I got a main part in a play.

And, you know, I mean, it just feels good to continue to expand. And it wasn't just the things I learned on the stage, it was the people. The people, the social side, the people that I I got to meet and hear perspectives that I probably hadn't heard before because I wasn't in those circles. That's that's the big thing. And so my challenge is as you come up with your culture and think about your culture, and you know we got the quick stuff, you know we want things quick, I know that.

Culture isn't that. Okay, it's the long game. It's like reading Atomic Habits. How many have read Atomic Habits in this room? A number of people.

And it's making small changes, you just keep going. Keep going. Keep going. Because they just keep compounding, right? And that's what this is.

It's compounding. So, summary, from my perspective, you know, embrace the journey. Go back to that road trip. I mean, career is kind of a road trip, man. You know, you never know where it's gonna go.

You gotta be flexible. You gotta be willing to change. We always talk about that. I don't wanna talk too much about change because we talk about that all the time. But you know, you just have to be willing, you know, the journey accommodate the flexibility.

Be willing to take the side step, be willing to take the project that you, you know, nobody else wants just to build the experience. Be willing to try something personally that's out there. Be adventurous and explore. I don't know how you're gonna find that tenderloin the size of your head if you're not gonna take that side road to go look for it. You know, when you're on your road trip, talk to people you don't normally talk to.

Ask them where they like to eat. You know, ask them what they like to do. Where are the good shows? What, you know, what sporting events should I go to? Ask questions.

Be adventurous. And then focus on the social. You know, and the things here, team building isn't just an event, it's constant. Create opportunities to build relationships on your team. I'm not talking about you with the people on your team.

I'm talking about the entire team getting opportunities to build relationships between the people on your team. I want the help desk to talk to the infrastructure people or the applications people to not get ticked off every time. Know, I want those I need those opportunities. Challenge them to lead within their role, to collaborate, and take accountability as a team member. All good aspects of a team that if you're looking at that, you'll you'll talk about.

Then challenge your team to grow. But remember, it starts with me and it starts with you. Thank you very much.