5 IT Director Skills Every Leader Should Know

Jay: What is going on? It is Jay and Michael here on the IT Directors Podcast. Hello. Michael, how you doing today, bud?

Michael: I’m having an awesome day. We’re having some fun this morning.

Jay: How are you? It’s always a great day in the Clear Winds IT Directors Podcast studio. We’ve had a blast already today preparing for the show.

Michael: Yes, we have. We’ll have some bloopers all ready to show later.

Jay: We’re gonna have a lot of blooper reels for you guys, for our listeners and followers. So we’re excited about this episode. I think this episode is really good. I’m excited about how our team and we put this together. So today, we’re gonna kinda ask ourselves questions and describe these for our listeners and viewers. Kind of what IT directors deal with, how they handle ’em, and how they face it. We got about five questions.

Michael: I love it. We’ve got about five questions from our followers, and I feel like this side is more the human side of being in that role and that position. So I love this aspect of it.

Jay: I’m gonna kick us off, Michael. So this one right here, this question that we got from all of our listeners and viewers across the country is one that I really have lived. I have been in it. I have been on both sides of it. It’s pretty exciting. So how do you get a seat at the table with the executive cabinet instead of just being the IT guy? Wow, that’s a great question from our listeners.

Michael: Well, I think it’s easy to get pigeonholed into your field. You can get so focused on what you’re doing that if you do that long enough, that becomes your seat, and you might find yourself losing a voice on the big picture of the organization.

Jay: 100%. All the time in my previous role as the IT director, COO, data center director guy, across the organization, all these business units would order software and solutions and different things. Guess what? IT was not at the executive cabinet table making the decisions, but we were tasked with trying to implement them. So it’s really exciting that our listeners and viewers are thinking that, ’cause I think this is something that IT directors face all across the board, in every vertical. K-12, government sector, healthcare, private, SMB space. I think they face this a lot, and I think it’s really interesting when you think about how do you get at the table? How do you get, instead of just being the IT guy to implement it, how do you get a voice? How do you get a voice to say, “Hey, you know what, Michael? That’s a great idea, but we don’t have the infrastructure to do that. We don’t have the hardware that’ll support what you’re trying to do.” Or, “We haven’t thought about the three-year roadmap, like, what happens after we implement this. How can we sustain it?” These are things that we think about.

Michael: So practically, even from your vantage point, from all of your experience at Birmingham City Schools, you’re in that role for, what is it, 25 years. So how did you find yourself in that position where you maintain what is your department’s responsibility, but also speaking to the organization as a whole?

Jay: I’ll tell you how we did it. We created a data governance policy and an IT procurement policy that forced business units to have us at the table to discuss. So anything that was procured, anything that wanted to be district-wide, they had to come before our… We had a governing body that was made up… It wasn’t just IT people. It was academic officers. It was teachers. It was people in technology. It was people in transportation. So we had a lot of various business units represented, but we had a board, a procurement board in terms of IT, where they would come to us, bring a solution, we would all agree upon it, and then we would go present it, and we would basically approve or deny. And hey, it got a little dicey sometimes when we had to deny things. But we didn’t deny them because we didn’t wanna do them. We didn’t wanna say no. But it was purely infrastructure or implementation or hardware, all these things played into it. So that’s kinda how we did it. We kinda created our seat at the table.

Michael: I think that’s really key, because it’s so easy to get siloed. When you’ve got an organization, whatever the industry is, you’ve got all the different business units that make it run and operate, and without having a board, some type of central team, you’re gonna be siloed. You’re gonna be working on separate things. There’s gonna be waste. You’re not gonna be as efficient. People are gonna be buying different things in different areas. But yeah, having that board positions you for success overall. When you say dicey, what do you mean? I can anticipate, but what would that be? If someone hears this and tries to say, “Okay, I’m gonna implement having a structure like that,” what are some things they could expect?

Jay: Well, you have to get buy-in, right? So when I say dicey, I mean it’s kind of uncharted territory for some IT directors and some CIOs. A lot of organizations have an executive cabinet where the CIO is already on it. But some organizations don’t. They have an IT director, or she, who isn’t really viewed as leadership, as true leadership making strategic decisions. So we kind of got buy-in from all the other business units and kind of showed the value of, “Hey, here’s what we can do. We wanna support you. We wanna support the math department in their new math initiative.” “But, hey, here’s what we need in return. We kind of need to know what you’re buying before you buy it.” Right? So we kind of evangelized and added value in the different business units within our organization, which led to us having the board and getting that. But, hey, when the superintendent wants something and we have to tell him, “No, that’s not gonna work,” sometimes that can be a little bit uncomfortable. But because we have a strategic policy in place, and we have a lot of voices, it’s not just the IT person, it’s not just one person’s voice, it’s a committee. I think you get buy-in. Right now, as I sit here recording this episode, that CIO is in every cabinet meeting on Monday morning for three hours. They’re at the table making those decisions. They still have these policies in place, and they’ve added more since I’ve left. So that’s kind of how we did it. We kind of evangelized and got buy-in.

Michael: Yeah, I think that’s key. I think for those who are thinking about implementing something like that, but still don’t see why they should invite the IT person, they’re trying to figure out what direction this company’s going. Why should I invite IT in that? They don’t care about what’s in the future. What would you say?

Jay: No, I’ll give you a great example. At Birmingham Schools, that’s where I was, in my previous role, we had 43 schools. So for our HVAC, we had a facilities and maintenance department. We had a director of operations, and then we had a facilities director, so it was really laid out well, a lot of organization. But with 43 schools, we had to update the HVAC system. What does that have to do with IT? Well, I’ll tell you what it has to do with IT. So all of those HVACs have controllers that talk to servers that we monitor that the HVACs turn on and off at the schools. Well, they had this multimillion-dollar project that IT wasn’t involved in at first. The servers were too old. They were end of life, running the current HVAC system. The HVAC team had been presenting it to the board for years and years, but no one really gave it validity. They thought, “Well, they just want to get new HVAC units.” But it really was more than that. The controllers that ran the HVACs, that controlled the air for the kids, were end of life and unsupported. So IT stepped in. We got a seat at the table, and we laid out a plan: these ACs will not work anymore if we don’t do X, Y, Z. Not only will they not work, if they break, you can’t even get these controllers. And so we gave them a great plan, and that one just came to mind because it was a multimillion-dollar project. But having these procedures in place, we were able to help and do that. So it was pretty interesting.

Michael: That is awesome. It reminds me, we had a meeting not too long ago. There was someone who came to us at Clear Winds and said, “Hey, we’ve had this multimillion-dollar facility, and we’re having some problems with what to do next.” And we’re like, “Well, hey, we’re here to help. What do you mean?” “Well, our leadership team wanted to have a completely wireless building, and a wireless infrastructure. No cables. And now we’ve got finished ceilings, we’ve got finished walls. Building looks great, yet there’s no cables, there’s no Cat 6, there’s nothing in there. What do we do?” So, this was a prime example, and I don’t know how it got to that level, it was actually a building that was ready to go into production, but there’s no infrastructure backbone to make it work. Yes, we think wireless, but—

Jay: There’s wires that drive the wireless.

Michael: And so it got to that stage because IT didn’t have a voice in the big picture as a whole.

Jay: No, and that’s why you need to be at the table. So, great question from our listeners and followers. Hey, second question from our viewers across the country here is, how do you say no to a CEO’s personal driven project without burning political capital? That’s a great question, Michael.

Michael: That’s a great question, and it’s one that I think if you are in leadership in IT or really any area, you are gonna find yourself with a project or with some type of initiative or directive where it may or may not be in line with what your department’s goals are, but it’s something that a leadership wants, a CEO wants, and you’ve got to be in a place where you can hear the big picture and hear what we’re ultimately trying to accomplish, bring a voice to what’s currently happening, and trust that you’ve got some experience and expertise that you can provide, and share. Ultimately, hey, it’s a CEO. They’re gonna do what they wanna do ’cause they can. They’re in that position for a reason, and sometimes, hey, you figure it out, you make it work. There are times, though, when you can try to understand the big picture and share based off of what you know and what you see in production, and give feedback along the way, and I think that’s what your voice pivots to, is say, ultimately, if they wanna do it, they’re gonna do it. Make it happen ’cause you’re in the seat. Well, that doesn’t make it easy, but it means, as long as I’m in my seat, I can understand what we’re trying to accomplish. If I can find a way that’s gonna help do that more efficiently or a way that’s gonna accomplish part of that goal in a way that might make some more sense overall, hey, go for it. But yeah, that—

Jay: That’s a tricky one. No, that’s great. You know, I had a policy for my staff. I was kind of the guy that never said no. And you might think, “Man, Jay, what do you mean? You gotta say no sometimes.” Yes, in life, certainly you gotta say no to some things, but as the IT director, the CIO, people always view IT, and especially in big organizations as kind of like the no people. They won’t let me do this. They won’t let me get more cloud credits. I can’t go to this website. They’re blocking YouTube. I use YouTube to do instruction. They’re blocking blah, blah, blah. So we’re always viewed as the no people in all this stuff. So I tried to flip that narrative with my team. I never said no, but just ’cause I didn’t say no, doesn’t mean I did everything. So what I would do when the superintendent came to me and was like, “Jay, I want Wi-Fi on all the buses.” Well, that sounds great in theory. Let’s look how we accomplish that. Now they do have Wi-Fi on all the buses, but it took us a little minute to get there. Always, instead of saying no, to your CEO, to the president, to the VP of a company, to the superintendent, to whatever your hierarchy is, don’t say no. Evaluate, listen give great feedback, and then give some different options if you know you can’t do this, right? Or you see some huge pitfalls that are like, “We’re gonna go in a dumpster fire here,” right? But that’s kind of how I did it.

Michael: I think that’s the big part, is hey, you have a listening ear. You’re trying to understand. If you do have that policy-driven nature where it’s just like, “No, no, no,” you’re gonna find yourself in a bad spot. And you’ve gotta be able to listen, ’cause if the organization is making some type of move towards the future or some type of transition, if there’s growth happening, whatever might be happening, you gotta have a listening ear to try to understand, and I think that’s the disposition to take, is try to understand. Try to get on the same page. Try to get some buy-in to what’s taking place, and if you can see the vision, you can give it a yes, but it might look different to what makes sense currently within the organization, ’cause you’re trying to get away from those silos. And I’m sure that company we gave as an example who had the wireless, wanted the wireless building, got a building, multimillion-dollar building ready, and now there’s… It’s useless ’cause you can’t do anything in it. I’m sure that was a higher level objective that got implemented, and now they’re in a spot where they’re gonna have to go put holes in the pretty walls to make wireless work.

Jay: And I think this is why it’s so great on our podcast, ’cause having Michael, and your perspective from a business growth, marketing, to being our sales director, you have a whole different lens than I do, ’cause I come from a CIO role, IT engineer background. So it’s so cool getting to hear your take on that, right? Your lens. And I thought about something when you were saying that, ’cause when you say no, when an IT guy or an engineer or whoever says no over and over, what you find is, we go back to the first question, you’re not at the table anymore. Because you keep saying no, people will just do what they wanna do, and they’ll go around you, and then you find yourself looking around like, “Okay, I’m not even involved in any discussions.” And I’ll give you a great example. I thought about it, Michael, as you were sharing about the wireless. For all of our listeners and viewers, everyone knows who Tim Cook is, CEO of Apple. He’s the new Steve Jobs, right? Steve Jobs was the innovator, he was… But Tim Cook is the new CEO of Apple. I sat in a leadership meeting. We went around the table. The superintendent at that time was bringing in Apple to the district, and she needed someone to support it. I didn’t have anyone on my staff to support Apple. No one on my team. Went around the table, it’s like, “Can you do this? Can you do…” And all she heard was no’s. She came to me, and they’re like, “Jay, can you support our iPads with the company XYZ?” I said, “Sure, we’ll figure it out.” Because I said yes, you fast-forward two years, I found myself riding around with Tim Cook with Fox News Global going all over Birmingham, spent a whole day with him, the governor, and seeing a $21 million grant brought to Birmingham, where we’re sitting in this building right here recording. And I thought, “Man, if I would’ve said no, at that moment, the great things never happen.” So just for our IT directors, don’t always say no.

Michael: And I get why we’re policy-driven because a lot of times, hey, we’re trying to make things work and keep things functioning. But then again, it is that person who has the ability to see past where we’re at and where we might be going. And I think you’re completely right. If someone in leadership is asking, “Hey, how can we facilitate this or make it happen?” They’re getting no’s from everywhere. Well, hey, it might not be something that looks great right now, and you’re gonna lose your seat at the table. But they’re trying to find a way to make it work. So sometimes those first feelings when you get those requests, it’s like, “I don’t know how to do this. No, I’m sticking to this.” Well, if you wanna grow with the organization and see the organization grow, sometimes you just gotta pause, get on the same page, have a listening ear, and then start to get strategic about how to make something like that happen.

Jay: I think you’re spot on, Michael. And let’s go to the third question from our listeners and viewers. How do you handle a high performer who refuses to document anything? That’s a great question.

Michael: I love that. I encounter that often. I have at different organizations I’ve been a part of. And hey, you gotta love your high performers because they help the organization move, they help it grow. A lot of times those high performers are focused on making an impact and the things that make an impact, and the things that they don’t believe make an impact, they could care less. And it’s hard to then crank down on that because that might not be in their wheelhouse, but making a big company impact is. So the temptation from leadership is, let them get away with it. They are making strides, bringing in millions doing these types of things. Well, you’re gonna find yourselves with holes and gaps that are eventually gonna surface and show themselves in some way, shape, form, or fashion. So what I’ve tried to do is you celebrate your people. You celebrate those who are knocking it out of the park. You call it out amongst the whole team, and then you try to help them grow. You try to help them see, “Hey, here’s what you’re doing. Here’s the impact you have. That’s awesome. Here are some of the gaps that focusing on this creates. I wanna help you grow. If you can help me with this, then hey, I think we’re gonna win, and I’ll help you.” I’ll try to find some way to get some equity in there. So I’m gonna pump them up ’cause they are doing awesome. I’m gonna try to help them grow and show them the full impact of what they’re doing and find a way to help ’cause I do wanna put them in their lane to run and succeed. But you do bring some accountability to that when you show them the big picture.

Jay: I think the way Michael described that is phenomenal for all of our listeners and viewers, especially for the IT directors. I think that’s so good. In my experience, the high performers are people, especially engineers, but high performers are really people that move rapidly. They think fast, and they’re rapidly moving, and sometimes they’re not documenting because they don’t want to. But they don’t see it as important, right? They see the end result as important, and more important. And so I thought how you explained that is really good. I think that’s good, just empowering them but also guide them a little bit along the way. So that’s a great answer. What about the next one? This one is great.

Michael: So tell me your perspective on that. How do you retain good engineers if you can’t compete on salary?

Jay: Man, I’ve been there. I’ve been in that exact situation. I’ve read this, when our team sent these questions to us, from our listeners, and you have to create an environment, and you have to have a culture and an environment where there’s more than just salary involved right? Fringe benefits, their work environment, flexibility. You’ve gotta have training. So high-performing engineers, and you know they might leave because they’re super talented, but you can’t pay them, but they really wanna stay. We can pay for training, right? We might not be able to give them 25 thousand more, or 70 thousand more, or whatever, but you can always keep good people if you have a great environment, to a certain point. That’s my experience. I had to do that for years because in public education, your salary is what your salary is. Whatever position you accept is what you make. You get raises from the state. I couldn’t come in and be like, “Michael, you’re one of my best senior engineers. I’m gonna give you a $10,000 raise.” You can do that in the private sector, but not in public, right? And so I had to create an environment where my employees like to come to work. Flexibility.

Michael: What does that look like?

Jay: Yeah, flexibility. If they’re on call, we’ll work and give you comp days. If we’re working over, I wanna make sure you get your overtime. Hey, new devices come out, I’m gonna make sure my team is outfitted with the greatest technology, because we’re supporting it. Training, involving them in meetings that they typically wouldn’t have been in just to let them see through a leadership lens, and involving them in discussions, being more team-oriented. So I’ve tried to just create and cultivate a culture that they wanted to be a part of, and at the end of the day, they knew that I would go to bat for them. If something went drastically bad, they knew I would be in the foxhole with them. So I think that’s kind of how you do it. There’s no one-two-three-four checklist. I think you have to know your team. That was my team, right? In the public sector, it might be something different. But ultimately, it’s creating that culture where your employees feel empowered and valued. And if they’re valued and empowered, they might overlook the salary a little bit. So that’s kind of what I have on that one.

Michael: I think it’s being authentic. If you can be an authentic leader, you can actually care about your people, and I think it comes across. There’s always gonna be somebody who’s willing to pay somebody more, but if I can show my people, hey, man, we really do value you, and these are things that I wanna see you grow. and develop, even if it means that a couple years from now you go and you do something else at another organization, do something that, at a higher level, whatever. Hey, I’ll also be your cheerleader on that point. I’ll champion you because I want our people to grow, and I want them to know it’s a safe place where, hey, you can grow, you can develop. Here’s the impact. I think another big thing I try to be strategic on is understanding what’s the organization as a whole. What’s our directive? What’s our goals? What are the things that the organization is trying to do? And what is our department? How does it inform that vision? Then individually, how do we each contribute to that? ‘Cause I think people can understand their own value as well, that they can provide. And when you can understand your own value, it’s rewarding ’cause I can see the impact. So I try to also help our people see the impact that we’re doing. And I think that plays into the culture of knowing, even getting to knowing your why, and knowing the organization’s why, and how does that all play into it.

Jay: That is spot on. That is so good. The last question from our listeners and viewers, this is a really good one. How do you actually unplug, Michael, when you’re the only one who understands the infrastructure?

Michael: Yeah, that’s tough, because a lot of times your people will also see you as the answer and the only one who knows your infrastructure. Your people will also, if you’re not careful to train and develop and empower them along the way, then you’re gonna be the Yoda for everything, and you can’t unplug. And I think that’s the way it’s gonna feel, that you can’t. But you have to be strategic in your day-to-day to develop people, to train them to help them grow along the way, ’cause if you can, you don’t wanna… Sometimes you might feel like you’ve got job security if the organization can’t run without you, and I see people create that environment all the time. And they’re creating it whether intentionally or unintentionally. The organization can’t run without you. Well, good luck taking a break, and when a crisis happens, it’s all, like, you’re gonna be carrying all of it. But if you can develop your people along the way then that’s something that you can either slowly turn the ship or you create a different type of culture.

Jay: Man, that is so good. I wanna just pause right here for a second. So if you are an IT director and you’re a COO and you’re the only one that understands your environment, you’re not a good leader. I’m just gonna say it. Because if you’re the only one that understands your environment, that means you’re not empowering your staff. Right? Now, look, if you’re the only IT guy in the whole company, that’s one thing. But if you have people that are around you that are helping and doing things, you never wanna be in that position where you’re the only guy. ‘Cause look, when I wanna go on vacation and I wanna detach, I wanna detach. You know? And I’ve been that guy. You see this in a lot of young leaders and IT directors. They wanna hold all the keys to the kingdom, right? And unknowingly, they kind of silo themselves. And then they’re the guy that everyone comes to, and then they start feeling important like, “Oh, man, this is great,” you know?

But at the end of the day, you’re not growing. You’re not developing your team, and then also you’re hindering business growth. So, especially in a private business and organization, there can’t be one guy responsible for everything because you can never grow. It’s the law of the lid. John Maxwell, we all have

Michael: I love that.

Jay: heard of him. You can’t go any higher than the person above you. So if the lid is here, you’re never gonna go beyond that. So I always took the mindset of empowering my staff, training them. I never wanted to be that guy. Hey, I was the guy because of circumstances. I didn’t have a team at first, right? But once I got a team, I was like, “I’m training these people.” I think that’s something that people get into, especially in the corporate environment. They wanna feel important. They wanna build these things. They wanna do stuff. But man, I’m all about empowering the people around me, and you summed it up, Michael, really good.

Michael: Well, one thing you said too, let’s address that, is those environments where it might be a smaller company and there might only be one person. Well, that can be tough because there’s not a lot of resources that you can lean upon. And specific to an IT director, like if you’re the only one manning that, it can be challenging, because there’s not gonna be others that have that mindset or experience or skill set in the organization. I’d say for those types of things, you can still find a company or someone that you can help learn part of your environment or to give some things to, ’cause we do that for some people. I can think of a handful of companies. And this isn’t necessarily a plug, but it kind of is. If you’re in that spot, find a company, find someone that you can teach part of your environment or train part of them, something that you can give them over, if a crisis happens and you’re out, give it to them, something that they can come in and plug in and learn and help. Because ultimately, you have to be able to unplug. Because if you don’t unplug, you’re gonna burn yourself out. And then don’t worry about not being able to solve a crisis, because you’re gonna be burnt out and you’re gone anyways.

Jay: And this is why it’s so good to do a podcast. This is natural conversation, right? I thought about that as you were speaking and as I was answering that question from our listeners. I’m like, that’s what we do at Clear Winds. We are an MSP. We’re a managed service provider. If you’re in that position and you’re the only guy, reach out to us. We can offer help. We partner with people. We help people, ’cause you never wanna be the guy that can’t go to the beach, or can’t go to the lake or can’t go to the mountains or can’t just watch Netflix on a Saturday and not be disturbed. You know what I mean? You

Michael: wanna be able to enjoy what you’re doing. And if you’re positioning yourself to be worn out by it, eventually you’re gonna get worn out by it. So if you can bring someone along the way who can help or help train and develop your people, you’re positioning the organization for success by doing that, and yourself, and you will increase your longevity there.

Jay: I agree. Michael, this was a great episode. I love just the conversation, and these are amazing questions from all of our listeners and viewers. And we hope everyone gleans something from this. I know you guys, if you go back and listen to some of these questions and some of these answers, I think you’re gonna really, really be impacted. Michael, I think it was good for our listeners and

Michael: viewers. Yeah, no, definitely. Hey, send some more. I like this side of the house. I know a lot of times we’re talking technical, but also what does it look like functioning in that role, and how do you go through some of these natural, the human side of it, so.

Jay: Yeah. Five things almost every IT director deals with, and we answered them for you guys today. So look, this is Jay and Michael. We’re signing off. We’re glad you joined us. Go follow us on all of our social media platforms. Go follow us on all the podcast platforms. Hit us up at IT Director Podcast. So we appreciate you guys, and we are out. Hey, thanks for joining us today on the IT Directors podcast. We’re so glad you joined us. Look, go follow us on all social media platforms, the IT Directors podcast, powered by Clear Winds, and look. If you want more information, check out our website, clearwinds.net. We’re gonna have show notes, special guest bios. We’re gonna have reels. Our marketing team has done a fantastic job. Go check this out, and we’re so thankful that you joined us today.