How to Become an IT Director: 5 Skills You Need

Jay:  What is going on? It’s Jay and Michael here. Michael, how are you doing?

Michael:  I’m having an awesome day so far. It’s a good day. We’re transitioning into fall, and I am falling for it. Oh man, it is good.

Jay:  We’ve got the fall in the air, and we are here on The IT Director’s Podcast.

Our last episode, we covered a lot of questions from our listeners and viewers. This episode is a transition in that same vein, with some questions and answers that are great for our listeners and viewers about, “Hey, if I want to become an IT director, what skills, what traits, what do I need to do?”

Michael:  I love it. It’s the overall concept. You’ve got the hard skills, you’ve got the expertise, but what about the back side of it, to actually grow as a leader and manager, past being an individual contributor? What’s the other side of this?

Jay:  Look, for someone out there who’s aspiring, you’re working in IT, in development, in AI, you’re a network engineer, you’re a PC tech, and you’re thinking, “Hey, I want to be the IT director one day. I want to be the CEO. I want to be the AI officer,” or whatever. We’re going to give you some great skills that will help get you there.

So Michael, I’ll kick us off and let you answer this first one. How do you delegate without micromanaging? That’s a great question from our audience.

Michael:  That’s a tough one. I think we’ve all been under leaders, most of us probably, where you’ve been micromanaged. From the other side of the table, as a leader, it’s tempting to over-invest yourself in whatever task or responsibility you’ve given to your team, and then you continue to manage it through the person you’re supposed to be trusting to own it.

So with delegation, I feel like the underlying concept is, can I trust these people to handle what I’ve given them? You’ve got to have that trust established. If someone’s on your team, hopefully by this point you have invested in them, helped them grow and develop, and helped them get to a place where they can take that ownership, because that’s part of it. You limit your own ability to lead your entire team and the organization if you’re truly still maintaining ownership of all these individual tasks.

So you’ve got to trust that you’ve helped them grow and develop up to that point. Give them some room, give them some tasks and functions where, if they flounder a little bit, let them feel the tension of it. Use any type of shortcoming as a growth experience. Give them a chance to succeed or fail. They’re never going to be able to flap their wings if you’re always owning it. Give them a chance in a good environment, and then circle back and lead them. Give them teaching lessons along the way. That’s what I’ve seen, but what have you seen in your journey?

Jay:  That is fantastic. I love that. Leadership is influence, right? If you’re not influencing anyone, you’re really not leading them.

We have all worked for managers, because we were not managers and directors at the start of our careers, right? So we’ve all worked for people, like you said, who micromanage. That is not fun. No one wants to work for someone who micromanages, because you just feel like, “What am I doing here?”

I think you explained it fabulously, that whole idea of not giving people leeway to succeed or fail and grow, because a lot of times that’s where you get growth, in failure. You know me very well, and my philosophy is totally not micromanaging. That is not my personality. My philosophy is, if you can’t do these tasks, then why do I need you if I have to do them myself? So I try to build them up and help them grow and develop. But I thought you explained it great, because micromanaging is so prevalent. What is crazy is that so many leaders do it unknowingly.

Michael:  I think that’s the big thing. People don’t realize they’re doing it. If we’re talking to people who want to grow from being an individual contributor on a team to learning how to lead the team, you’ve been in the weeds. You’ve been doing the task yourself, so once you get some type of promotion, the temptation is to continue. If you weren’t taught how to empower and trust, then the temptation is to still hold on to it.

Jay:  Correct.

Michael:  And we’ve worked together for a while now, and I know you and your journey. What I’ve seen you do well is help prepare your own team, help with that succession plan, and even help people develop so that it’s not intimidating to know that I’m training somebody who could eventually replace me.

Jay:  Oh, yeah. Look, we always want to be looking for a successor, right? If you’re out there and you want to become a leader, that is phenomenal. These are going to give you some skills and some maturation and some tools to do that. But once you become a leader, we need to be looking for our successor, because we want to be pouring into the next people, and we never want to be a bottleneck. In IT, I see these bottlenecks a lot, and they happen unknowingly, right? You explained it great.

Michael:  Yeah, and I’d say one more thing with that. As you grow in your journey of leadership, you transition to thinking more and more big picture. As an individual contributor, this one task is what’s most important. As a manager, you might have a few people that you’re leading and managing, and they all have different tasks. So to lead them well, you have to put some things in place that help you understand whether your team is hitting the measurements they need to. Then as a director, at the senior level, you learn how to see more and more of the big picture and have different types of measurements to see if the big picture as a whole is moving in the right direction.

Jay:  No, 100%. I think you nailed it on that one, to be honest with you.

Michael:  Another question that came in was, what does it look like to translate tech into business language?

Jay:  That’s a great skill set for anyone aspiring to be in leadership in IT. When you’re in tech, you know the tech, you know the tech language. But to translate it to business language, to meet with the CEOs, to sit at the table with the CFO, to talk to the owner and all these executive team members, you’ve got to translate it into ROI. You’ve got to take your ticket data and turn it into KPIs, because that’s what they understand, right?

They don’t really care how many tickets you’re closing. They don’t know about that. But they want to know how the ticket closure rate affects overall business growth, or succession planning, or your KPIs. Are we meeting KPIs as an organization? So you have to learn how to translate that and turn it into data to make data-driven decisions. I think that’s where a lot of IT people really struggle, taking that tech language and translating it into business language. That’s a great question and a great skill.

Michael:  So what does that look like? I know this aspect of making dashboards. I mentioned it, and I know you’re talking about it. If somebody hasn’t really done that yet, what does that look like? What details are you putting into those dashboards you’re managing? How do you make that? What do you measure?

Jay:  That’s a great question. At Clear Winds, we have a whole practice around AI consulting and creating dashboards for organizations for this very thing. You take all these data sources. You have a bunch of databases, different web applications, reporting, CSVs, spreadsheets. You tie all those data sources into a dashboard where you can have an executive summary that provides this information on the business side and speaks to them, but the back end is the tech that’s driving it, right?

So that’s what it looks like. You’re tying all these data points together in a dashboard and correlating that data, and then you let that dashboard do the talking. Let it be the language for you. Give them a login, boom, they can see it. And they’re not calling Michael, “Michael, what servers are up and down today?” or “How many tickets has our tech department closed?”

Michael:  That’s good. I think if you can do that well, you really can get your eyes on the big picture. You increase your impact, and you can help the organization grow as a whole.

Jay:  No, 100%. So what about managing people across the organization? This is a great skill for all of the aspiring IT directors and leaders. That’s the hardest thing. Look, you never have problems, you have people. So managing…

Michael:  People are everywhere.

Jay:  People are everywhere.

Michael:  Hey, we’ve got our own quirks as well.

Jay:  Yeah, look, we’re all unique individuals. So just understanding different personalities, Michael, different age groups, different demographics, all these things. How do you deal with that?

Michael:  That can be the challenging part, based on your perspective. As an individual contributor, you’ve got functions and tasks you’re working through. As someone now managing all these different individual contributors, you’ve got different demographics and different personality types, literally everything. People who are hands-on learners, people all across the spectrum. Your role as a leader is to help move the organization forward and lead your team.

We were talking about micromanaging earlier. With all those different personalities, ways of learning, and even values, it’s easy to just get in there and tell them, “Hey, do this. I want you to do it this way. Now I’m going to make sure you’re crossing all the Ts and dotting all the Is.” But to manage well, I think it’s really about getting to know your people. You have to get to know them. You have to care about your team and be authentic and genuine about it, because if you do, you’ll make a big impact.

If you do, you can transition to helping your team take ownership and move things forward, rather than trying to white-knuckle it and drive it and push it and wear your people out. So I feel like part of it is actually learning how to care and be empathetic toward your people, because you don’t know how your team member is doing that day.

Jay:  That is such a great point. As you were answering this question, I was thinking about the prep the marketing team and I did to get ready for this, in terms of the skill sets IT directors need to possess. This is one of them, and as you were answering, I’m thinking, you do it phenomenally. I get to spend every day with you in the office, from marketing, from sales, and you do a great job with this.

I think you said something that I wanted to pause and take time on, and that’s getting to know your people. I think this is where people miss it, because when you get into leadership, sometimes you get disconnected. I saw it. I was sitting at the executive cabinet table. I’ve been across the spectrum of all these different roles, and one thing I prided myself on is that I always try to get to know the people I’m working with.

When you get to know them and build the relationships like you’re talking about, like what you have done, Michael, and what we do as an organization, then you can get things done, and it makes managing people much easier. Because if I like Michael and I feel like Michael’s for me, and he asks me to do something at 8:00 at night, and says, “Hey, I know this is nighttime, but J Berg, can you move this along for blah, blah, blah,” I’m going to be more apt to do it because I know you care and value me, right?

I think that’s a people soft skill that IT people really miss. They look at the CEO, the CFO, the COO, the VP of engineering, whatever that title is, and they think, “I want to get that title.” But you never lose the people soft skills, because you’ll never be successful without them.

Michael:  Well, you’re talking about the soft skills and the hard skills. Yes, you can have the expertise, you can have the knowledge. A lot of times you can be thinking about deliverables, what is the goal here, what is the goal here, and you miss along the way the people who are actually the key component to moving that forward. And hey, we’re getting into the whole aspect of leadership.

Jay:  You’ll look behind you, Michael, and think, “Oh crap, no one’s following me. I’m the CIO, but I have no one on my team.” And you’ll find yourself in an emergency, like the data centers shut down, and nobody shows up to help you. That’s a red flag. It means I probably don’t value my people, right?

I thought you explained that great, and you exemplified that, and so do other people in our organization. I think that’s what makes us at Clear Winds so unique for our customers and for the other IT directors that we serve, because we really want to have that partnership.

Michael:  I definitely agree. I think being under great leadership helps you learn how to do that. A lot of times you take whatever that culture is and you bring it downhill. Hopefully it’s a good, solid culture. And if it’s not, it sounds like you’re in a seat where you can build it and start making changes where you are.

Jay:  As you were answering that, and you answered it amazingly, by the way, you gave such great insight, it made me think about a story. In my previous role, I was an IT director at a big organization, and we had a mail room lady, okay? Not to diminish the mail room, right? She was awesome at her job. A dear friend of mine, I loved her to death. On the surface, when the CFO or whoever comes in, that’s the mail room lady. It’s a position that’s not in leadership, let’s just say that. But her role was so vital in the overall organizational structure. I had to work with her so much.

She helped me tremendously. I’d get shipments of pallets of computers, network gear, firewalls, and she would take care of all this for me. If I was in a meeting or at a conference, I remember getting a call one time. She said, “Jay, there’s an 18-wheeler out here, and they have 2,000 desktops. There’s no one here. What do you want me to do?” And I said, “Well, we’ve got to get them in the building somehow.” She said, “You know what? I think I’ll unload.” She unloaded the truck with the truck driver.

She wouldn’t do that for everyone. It was because I had that relationship with her. But it was pivotal to the success of our whole organization, you know what I mean? I thought about that as you were talking.

Michael:  I appreciate you sharing that, man. I think you walked that out well. You take time to get to know your people. Title is insignificant. You need to show the same level of respect to a CEO as you would a janitor, and that’s because people are people, and you’ve got to value who’s in front of you. When you do, it’s going to show. There’s going to be a situation, like yours with the whole shipping thing, where it comes back around.

Jay:  It comes back around, and that was not for any return. It was just what we were trying to practice as a whole company. I remember thinking, “Wow, our mail room was pivotal.” Those computers had to get installed the next day. It was a ripple effect, right? There were so many things going on, like opening a new building. But it made me think about that when you were talking.

Michael:  I could even think of stories, too, where you take time to get to know people. We had several painters at a place I used to work. We had a lot of buildings, a lot of areas. I’ll have a conversation with a brick wall, but this guy was always just a light wherever he went. He’d be singing a song, whistling a song. I’d get up there and sing with him, whistle with him.

I remember one day I’m struggling, about falling down the stairs trying to carry packages to a six floor area. Out of nowhere, his name was Nelson, Nelson was the man, he basically kept me from falling down the back of the stairs and then helped me carry the load up. I’m sure he would have helped somebody based on his demeanor, but it’s the people aspect. Care about people.

Jay:  That’s the whole thing. If you want to be in leadership, you can’t lead without people. If you’re leading alone, you’re not leading. So that sums that up. You answered that phenomenally.

Michael:  Another question that came in was this aspect of making decisions with incomplete information and having to act quickly. What does that look like? When you’re in the leadership role, something comes up and you’ve got to make a decision fast. You’ve got a split second to read the room and make a choice.

Jay:  Man, that’s a tough skill set to have. To be proficient in this skill, to make a decision when you don’t have all the information and you’ve got to make it fast, you’ve got to be very proficient in your skills and in your organization.

So you’ve got to be able to read the room, number one, and assess the situation. Is this mission critical? Is this DEFCON Level One? What’s going on here? Number two, you’ve got to know whether the information you’re being provided is accurate. As an IT leader, you’ve got to know what’s accurate and what’s inaccurate, and then you compile all that internally and think, “You know what? I’m going to make my best decision on what I have.” I’ve been in situations where I had to make decisions fast and I didn’t have all the information, and typically those turn out well if you can assess and do all these things mentally.

Michael:  Let’s even take a step back. You said, “Learn how to categorize what’s in front of you.” How did you develop that skill set? How do I categorize these things? What are the categories even? Mission critical, obviously, is one. I feel like a lot of times for our users or team members, everything can feel mission critical. But for you as a leader, how do you determine what’s mission critical?

Jay:  I think it comes with life experiences, right? Just being in that role and understanding your user groups and your different business units. So, say the payroll server’s down and no one can log into finance. That’s a mission critical system. People need to get paid. We’ve got to be able to invoice and pay bills. Susie, who can’t print in the math department, is not mission critical to the overall success of the organization. That doesn’t mean the issue is not important to her, but it doesn’t rise to that level when the whole fiber connection is down for the organization, right?

You’ve got to be able to assess these, because as an IT director, everybody’s issue is mission critical to them. So you’ve got to put some priority on different things. If you do the background work, like what you were talking about, the pre-work of having your SLAs defined really well and having processes in place, it’ll help you make those decisions quicker. Sometimes you’ve got to make decisions fast that are not the popular decisions. But you’ve got to trust your gut, and you’ve got to read and assess the situation, which really comes with experience.

Michael:  Sometimes you might find yourself in a tough spot where both of these are bad outcomes, and the question is which one is the worst.

Jay:  Yeah, which is the path of least resistance here?

Michael:  Yes. That part’s tough, but that’s real life. It’s going to happen.

Jay:  It’s going to happen. In IT, look, I used to tell my people all the time, “Michael, no one calls you to say hello.” If you’re wanting that, you probably don’t need to be in IT, right? Every time my phone rang or I got an email, it was because of an issue. No one ever called me to say, “Hey, Jay, how’s your day going today? The network is great today. My computer is amazing. How are you doing today? What are you eating for lunch?” No, it was always, “This doesn’t work, this doesn’t work, this doesn’t work.”

So you’ve got to have those mental expectations and know we’re here to serve, right? In IT, your whole role is service. Once you take that mindset, you can articulate and make these decisions a little faster, and it helps you prioritize what’s important and what’s not. But it comes, Michael, with just doing it. Reading the room is a great skill for any IT director, because you’ve got to be able to read the room and read your people. That’s a learned skill set too.

Michael:  We’ve got another one that’s a piggyback. This is kind of a manager-style question, a people question. Let’s say you’re having back-to-back mission critical issues, your team’s been going for a while, and people are wearing down. What do you do for your people to help them?

Jay:  Oh, 100%. I mean, common sense, right? Comp time, different things, remote working ability. You’ve got to create a culture and environment within your team that is conducive and where they feel appreciated. If we’re banging away on all these mission critical things, once we get through that, we’ve got to give them some time to detach. That’s being able to read the room as well, because you can only grind it out so long. We’re humans, right? They’ve got to feel like there’s some value on the other side.

Michael:  I think that value is what can help people weather storms. If they feel that value and feel that place, and you’ve helped them understand their position in the organization, and that you’re more than just a wheel in the whole system, that you matter for who you are and we want you on the team, we’re grateful for you. If you don’t, people will get worn out and burned out along the way.

Jay:  I did it numerous times throughout my career. I’ll just use Johnny. Johnny was not my real employee. I’m just using that name for illustration purposes. “Hey, Johnny, look, I know, dude, this was a terrible payroll issue. We got the server back up. Hey, man, take tomorrow off. Just work remote. I’ll send you some tickets.” You’ve got to be able to do these things for your people.

Michael:  That’s a good leader. A good leader recognizes where my people are, and if they have gone above and beyond and they’re starting to deplete themselves, you can say, “Hey, I see what you’ve done. Take a minute, because I want you to be refreshed, and I want you to know we care about who you are.”

I do see a lot of times the other aspect, where if we’re focused on those deliverables, you blow past it and keep plugging away, and fast-forward, you see where that team member slowly started to detach along the way.

Jay:  You can only maintain that for so long, right? That goes into the last skill set, one that would be very valuable for anyone who wants to get into leadership, period, but in particular as an IT director, because there’s going to be times where you’ve got to have hard conversations. I’m not talking about just personnel conversations or layoffs, but conversations with other leadership, where you say, “Hey, we can’t do X, Y, Z, what you’re requesting. Maybe we can do it this way.” How do you handle that, Michael, in leadership, having these hard conversations?

Michael:  Having hard conversations, I think you can look at it two different ways. You’ve got one person who says, “Hey, you’ve got to say what’s got to be said, and you just do it and let the chips fall where they may.” That’s some people’s approach. That’s not mine. I don’t think that’s going to work well to help build your team and the organization overall.

You’re going to have to have conversations as an IT director, as a leader. It’s going to happen. You’re in leadership for a reason, and you work with people. Things change, and at that point you’ve got to rely on relationship. From my seat, what I’ve learned is that’s why I develop relationships along the way with my people. If I’m in a role where I’m leading leaders of departments, I’m trusting that I’ve built up the relationship along the way to where it can withstand some hard news or some direct news.

Sometimes I’ll try to give the big picture for whatever the situation is. Let’s say a project didn’t get funded, or a department is having to downsize, whatever. I’m trusting the relationship I’ve built along the way, because I have tried to mentor, develop, and coach my people, and they know and understand they’re valued in the role, yes, but as a person. Honestly, I’ll be transparent and give them the big picture. It’s not fun. It’s not easy. But you hope that relationship, human to human, can withstand some tough news.

Jay:  That’s great, Michael. I think your points there nailed it. Being open, honest, and transparent, right? In those hard conversations, honesty goes a long way, and not trying to just skirt around it. You’re able to be honest because of the relationships you’ve built up, right?

Michael:  Yeah. Sometimes you can’t give all the information. Sometimes it’s, “Hey, I want you to know I value you. I appreciate you. You are a rock star on this team. Here’s where we are, and that’s all the information I can share. Hopefully we can share more later, but this is what I can share right now.” It’s not fun, but you trust that equity you put in there. Genuine equity can go a long way.

Jay:  It can. Hey, building up that karma credit with your team, right? You’re putting that in there, and you’ve got to make a withdrawal every once in a while, because sometimes you’re going to have to have a tough conversation.

Michael:  That goes back to it’s not all micromanaging, it’s people. As an IT director, you’re leading people. Yes, you’ve got your goals, your outcomes, your deliverables, making sure you’ve got your uptime, all these different things you’re working on, but it’s the people who are making it happen. So learn how to lead the people, because if you lead the people well, the department will be successful.

Jay:  If you lead the people, everything else falls in line. You’re going to have to have these conversations. You’re going to have to say no sometimes. You’re going to have conversations where your team doesn’t agree, because they don’t know, like you said, part of the other situation you’re facing with upper management, right? You’re trying to do a project as an IT director, and your team’s like, “Hey, why can’t we just do X, Y, Z?” And you’re like, “Well, there’s more to it than what you guys know.”

I think you explained it greatly. These are amazing questions and amazing skills for anyone who wants to be an IT director. These skills are so valuable. I think you did a great job explaining that too, because with those performance issues, no one likes to be told they’re not doing well. But you can tell it in a way that is edifying and uplifting, and we can have constructive conversations that are difficult, right?

My wife always messes around with me. She says, “You never like to be told you’re not doing well.” As humans, we don’t, right? I’m more of the positive guy, and I’m like, “Well, you know.” But no one likes to hear that they’re not doing great. If you approach it in a way where you construct it, the other person can evaluate it based on the relationship and the trust and the value, and then you can say, “Okay, I accept what Michael’s saying.”

Michael:  That’s a good point, too, because it’s how you communicate. What I try to do is take into account how I’m communicating what I’m trying to communicate. If your goal is to help a team member improve in this area, one of my former leaders always said, “Hey, butter both sides of the bread.” So start with positive affirmation. Here’s what you’re doing well. You’re rocking this out. It’s going great. You’re doing awesome. Here’s where I need us to step up our game. I know you can do it because I’ve seen the work you’ve done, and I believe in you. Sometimes it’s more direct.

Jay:  And your tone, right? Your tone in these hard conversations. So being very mindful. People are unique individuals. We’re very unique creatures, right? So you’ve got to understand your people. We’ve got to be able to make decisions fast. We’ve got to translate all this stuff into tech. We’ve got to delegate without micromanaging. These are great skills. Awesome skills.

So, Michael, I loved talking through this with you. This was great.

Michael:  I did too, man. I love being able to talk about the other aspect of it. I love seeing these questions come in that are more about the human side. What does it mean to have the soft skills of an IT director as a leader in my organization, and how can I continue to grow and sharpen that?

Jay:  Look, our world is very competitive right now, and in IT it’s only going to get more competitive. With AI and all these tools, people are going to be sharper. They’re going to have more skill sets and be more well-rounded. But you’ve got to be competitive in all these areas, because if you don’t possess these skills, you’re probably not going to get into leadership. Or you might get into leadership, but you won’t last, to be honest with you.

So, look, we’re glad you joined us today. Go follow us on all of our social media platforms: YouTube, Instagram, Spotify. Go check us out on all of our platforms, The IT Director’s Podcast. This is Michael and Jay, and we are signing out.