Changing the Perspective on IT with Stephen Malone

Guest: Stephen Malone, Head of IT Operations, Built Technologies

Episode description

Stephen Malone is the head of IT Operations at Built, a construction finance software firm based out of Tennessee. Over the course of his career, Malone noticed that IT professionals like himself receive a bad rap, associated with the problems they are tasked to fix. Since IT is so critical to modern organizations, Malone wanted to turn this perception on its head, establishing IT as a trusted source of knowledge for all things technology in an organization. 

Listen to this episode of Where’s the Any Key? to hear what techniques and tactics Malone uses in his organization to provide the best experience for his end users, while also keeping his team moving and communicating effectively.

The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Ryan Bacon: Welcome to Where’s the Any Key? The podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud®.

Introducing Stephen Malone

Ryan: So, our guest today is Stephen Malone. He works IT operations at Built Technologies. Welcome, Stephen; thanks for coming on.

Stephen Malone: Dude. Thanks so much for having me. I’m really excited about this.

Ryan: Yeah, I’m excited to have you, why don’t you tell us a little bit about yourself?

Stephen: Well, like you mentioned, I work in what we call IT operations at Built, which IT Operations just means IT plus whatever else they can get us to do to fit within the bandwidth of whatever else we have going on. I have been in Nashville for about 10 years, a little over 10 years. I’m originally from Mississippi and moved to Nashville to play music like everyone else that lives in Nashville that’s not from here. And, I was doing that for almost 15 years. So the IT career path is relatively new to me. I worked at Apple for six years while also playing music and touring. And I just started working for Built a year ago. 

Ryan: Awesome, well, welcome to the IT club.

Stephen: Thank you. Thank you. I’m enjoying it. I’m enjoying the club so far.

Breaking Stereotypes and Rebranding IT

Ryan: Yeah, it’s definitely a good place to be in my opinion. And speaking of the it club kind of what we’re, what we’re going to be talking about today is,, when we first talked, I really see IT and moving away from that stereotypical, you know, anti-social, you know, just put your head down and do your work kind of, IT professional. I mean, I don’t want to put words in your mouth, so why don’t you go ahead and why don’t you describe what you, what you envision when you talk about rebranding IT?

Stephen: Yeah, absolutely. So, like I said, I mean, and we talked about this the other day, but there’s still this lingering, like perception and underlying connotation of when you just hear the word IT, I think most people have the picture of, I don’t know if you remember, but when Jimmy Fallon was on Saturday Night Live, they had a skit where he was like, they call it, he’s the IT guy he’d come in and be like, you know, it would just huff and had like a pocket protector… 

Ryan: “Move!” 

Stephen: Yeah, “move!” and just come in and fix it, like super condescending… you know, no interpersonal skills, no empathy, that kind of thing. And, like many stereotypes, they exist for a reason and somebody put forth those stereotypes. But yeah, like one of my missions, especially since I, you know, while I worked at Apple and now that I’ve transitioned to, to Built is like, we talked about rebranding it and helping people not only keep their technology and their tools like up and running and working properly, but also empowering people to use their tools most efficiently and how also, how they can use them to improve their personal lives as well as something that I’m super passionate about, like educating people. 

Something I didn’t mention is I used to be a teacher. So prior to starting to play music professionally, I taught band in public school for a couple of years. So, I have a passion for teaching people. And so that’s something that I’ve done at Built as well, partnered with the training team and done a lot with helping people learn how to better use their technology and how to level up, as it were, you know, get some XP and level up. So that’s something that I’ve really been passionate about. And also just like having a really, for lack of a better term, like a customer service sort of approach to the way that we deal with our team. And I have found that seems to be not the case at a lot of places. I get positive feedback from team members across the organization all the time about how, “Oh, I’ve never been at a company where like, the IT guy was super cool and you could just come and sit in his office and talk with him about music or star Wars or, you know, whatever.”

So yeah, like I really liked that and it makes people more comfortable coming to you with problems. Or if, you know, God forbid, if they’ve broken something or screw something up, you know, they feel more comfortable coming to you with that. And they feel empowered to also learn how to, to fix things. So, yeah, that’s, that’s my mission.

Sharing Knowledge and Building Relationships with Your End Users Through Trust

Ryan: Yeah. You mentioned something in there that I think is a good gauge to like how well the relationship between IT and their customers or their coworkers, you know, their end users. And that’s personal growth, you know, helping them in their personal life. I feel that when somebody comes to me and says, “can I ask you a non-work-related question?” Or “can I ask you about something for my personal setup?” I see that as like an immense step of trust, and I will never tell someone, “you know, I know I don’t have time for this” or, “go look it up” or something like I will make the effort to engage with them on that, because it’s just… first off the big thing is that just shows them that you view them as just a, you know, a person. They’re more than just that end-user, that PEBCAK error waiting to happen, you know? I really enjoy the conversations that stem from helping people with talking about their home network setup or what gaming laptop should I get? You know, stuff like that.

Stephen: Well, and too, just from a personal standpoint, you get to know things about people that you wouldn’t have known, and you also like you gain insight to people and you learn people, you learn how they work. And I mean, when I was a teacher, one of the things that was really important to me was getting to know students and understanding how they function and how they learn best. And I found that that approach translates super well into information technology because everyone learns differently. Everyone learns at a different rate and people apply things differently. So taking the time to get to know people personally and being approachable and having somewhat of a, like a personal relationship with them also improves your ability to do your job well, because you know how to communicate things to them and something that I’m super passionate about.

And like my coworker, Dylan, and I are both very passionate about not just helping people fix things and keep things up and running, but helping them understand what happened and how to resolve it in the future and not so that they don’t have to come to us with it, but that they feel empowered. And that’s a term that I use a lot is empowering because while I always want people to have the level of comfort with me and with our department to come to us with any problem I also want them to feel confident and empowered to take a stab at it first. And I found that people really appreciate that. And once you empower them with that knowledge, they also want to go share it with other people.

Ryan: Exactly. It’s the complete opposite of condescension, you’re telling them, “Hey, you can do this. This is not some obscure arcane thing that only those of us in IT have the power to fix.” I mean, it’s just common know-how. So I that’s, I completely agree with that.

Stephen: Yeah. I don’t, you know, I’ve never in my whole life wanted to be like a gatekeeper of knowledge. I found that, I mean, that’s a great way of isolating yourself. But I don’t know. And, you know, from a leadership standpoint too, if you want to be taken seriously as a leader and seen as a leader, like you don’t gatekeep because, A. that that’s not a way of earning people’s trust, but when you have a team of people and you’re giving constantly giving them knowledge, you’re not taking power away from yourself, per se, by giving other people power, you’re earning trust and earning respect and things like that. And that just, it makes for a much more comfortable environment. And it, in a way, a lot of people think gatekeeping is a way of, I don’t know, like maintaining status or something like that, or, you know, maintaining worth, you know what I mean?

Like if I don’t educate people about things, or if I just keep all this knowledge for myself, you know, some people think, “Oh, well, then that I’m making myself valuable because I know all these things that nobody else knows,” but you’re really not. And you’re putting yourself and other people in a scenario where like, if you go to another team or go to another job or something like that, you really haven’t made much of a mark there. That’s, that’s a little bit of a tangent, but, you know, that’s something that I really care about is making a difference. Not just going in and doing a job and fixing things and all that kind of stuff, but you know, at the end of my day, like I look back on my day on, like, who did I, not who did I help from a technology standpoint, but who did I have an impact on today? 

Ryan: Yeah, that’s a good way of looking at it. 

Stephen: Yeah. I think that’s important. 

Ryan: Yeah. And I think that, I’m glad you brought that side of stuff up because I think that an important part of, of rebranding it is, you know, these different elements that we’re talking about looking at the root cause. Like, why did these behaviors start? So like you were saying, the gatekeeping and, you know, maintaining status and all that sort of stuff, you know, leading to the hoarding of knowledge. And I think there’s another aspect of it too, that’s fear. If I give someone the knowledge to do something, or if I point them in a direction to something, what if they either misunderstood or did something where it’s like, I gave them enough knowledge to be dangerous, and they go break it and that falls back onto me. And I think that it does come back to trust. When you’re sharing this knowledge and you’re trusting in yourself to convey the information properly and you’re trusting them to receive it properly, and you have to believe that that sharing is, you know, and that, you know, whatever risk you’re taking by giving that knowledge is overshadowed by the benefit that it’s going to give to not only the person that you’re sharing it with, but to the organization as a whole.

Stephen: Yeah. That’s always been funny to me because in all of my past lives, I’ve encountered people who, like you just said, they feel like they’re risking something by letting people in, on certain things or giving people a certain amount of knowledge. They fear that they’ll be unnecessary or something like that. But it’s like, I don’t know. I just, I just never have enjoyed that approach. And I think for some people it’s there, like you mentioned, there’s a fear or risk of maybe not being as important or letting people know enough to be dangerous, that kind of stuff. But I think it also, there’s also some need to feel important or need to feel special with some people too. 

This was kind of related, but when I was young, like, you know, 14, 15, I really got into punk rock, like underground punk rock. And, you know, I had a lot of friends that were. This term that people used to throw around all the time called “poser”, like anybody that was into anything that wasn’t like super obscure was like a poser. And people were really bad about, you know, the whole gatekeeping thing. Like they would never talk about bands that they liked or where they got certain things. And they, you know, they wanted to keep that stuff private because if you, if other people know about it, then it’s not special anymore. And I think that that’s a similar thing with people that, you know, to kind of take it back around to rebranding IT, you probably have a lot of it guys who feel as though they have something special that is unique to them. And they feel if other people know it, it’s like, well, “Oh, well, I’m not special anymore.” Or, “Oh, I don’t have this knowledge anymore. And I’m a I’m irrelevant now,” et cetera, et cetera. And I just, I don’t know, maybe there’s truth to that, but I don’t, I just have never felt that way.

Ryan: Yeah. And I think that, I think part of it is that you need to have an understanding of IT’s role in an organization. I mean, your knowledge is part of it. But knowledge without experience is so much weaker. Also I think we kind of mentioned this about how IT draws a certain type of person, when we first talked, and that mindset, that looking to solve problems that, you know, create, you know, thinking outside of the box, all that sort of stuff that, you know, this type of thinking is drawn to the IT field. That is probably the most valuable thing the IT pro brings to the table. It’s not just what you know, it’s how you think. And you can’t really give that… you don’t lose that. Yeah.

Empowering End Users to Help Themselves

Stephen: Well, yeah. And there’s a certain level of creativity involved with that level of problem solving and looking at a cluster of issues and being able to compartmentalize it and then take all these different things and piece together a solution. Yeah. I mean, I think that a lot of people in the IT field don’t see themselves as contributors to the business, because they’re not bringing in revenue. You know what I mean, but part of an organization, not even an organization, but a team’s ability to be successful is the ability to get rid of as many hurdles and roadblocks as possible. And that’s, you know, part of the job of an IT team is removing hurdles, and not just technologically, but, you know, removing hurdles from people as well. And if it’s, you know, removing a hurdle from someone who just doesn’t grasp a concept, like to me, that’s part of my responsibility. Like I see, I see myself, like not only, as like a troubleshooter, but as a person who educates and a person who, again, the term empower, you know, I, I like to empower people to not just be like, “Oh, well, if I have a problem, Steven can fix it,” which yes, I can, and you can depend on me for that. But don’t, you want to grow a little bit and, you know, learn some new skills and then feel empowered yourself with whatever it is, whether it’s using your computer or you know, setting up things on your network, et cetera, et cetera?

Ryan: Yeah, and actually in a way it’s know, I was thinking about times when I’ve had, well, I’ve had interactions like that, where I’ve shown someone how to do something once, and then they’ve come back later being like, “Hey, I did this and it works.” So, you know, we’re mainly a Mac shop and, you know, one of the go-to, early steps in troubleshooting and Mac is, you know, you do an SMC reset. When we were in the office, it was commonly something that, you know, we would just do in person and not a problem, but in this remote world, you have to lean on that education part of it, like, “Hey, here’s, Apple’s article on how to go ahead and do an SMC reset. Let me know if you run into problems,” that sort of stuff. And I had one person who, who we went through that process with, and they pinged me on Slack later. And they’re like, “Hey, I ran into this issue, like sound or something was weird. And like, I did an SMC reset and it fixed it!” And it was like, so they were so proud of themselves, justifiably so, and then those moments where you get to celebrate that growth and that accomplishment on their end is just, it’s just amazing. It’s a great feeling.

Stephen: Yeah. And, you know, back to like the educational aspect of it, that’s something that was very fulfilling for me being a teacher is like seeing the light bulb go off in someone’s mind. That’s something that I carry with me to this day. And just like you were mentioning, you’re talking about SMC resets or PRM resets. Like not just teaching people that, “Oh, this will fix certain things,” but helping them think about why that fixes the thing, and the light bulb goes off. And then when somebody, you teach somebody that, and then they reach out to you and they’re like, “Oh I just wanted to let you know, my, you know, my computer, wasn’t sending out a video signal to my monitor. So I did an SMC reset and it fixed it. And I thought, because I thought about what you told me about how that works. And I thought, ‘Oh, well, maybe that’ll fix it.’” You know what I mean? Like, not just teaching people the things to do, but like, why that thing does the other thing and seeing that light bulb go off… that’s a fulfilling aspect of it for me.

Developing a Culture of Trust in a Remote World

Ryan: Yeah. It really is. I definitely get that. And, actually speaking of, I’m gonna pivot a little bit on here. Speaking of, so in the remote world, if you’re not in an office, you know, you’re kind of, you know, separated from everybody else on your own, you’re isolated. And humans being social creatures, you know, any, any chance you get to have a connection, you know, to spend some time with another person to talk about, you know, to have a discussion, whether it’s work-related or whether it’s, you know, just talking about music or hobbies, something like that. It helps to either build a community, a culture, or maintain a culture that was already established pre-remote world that was established in the office. And I think that that’s, you know, that that’s not necessarily an it specific thing, but it’s something that everybody needs to consider when interacting with your, your remote coworkers.

Stephen: Yeah. Well, I think one thing that sets IT apart from other organizational groups in any type of company is that that department interacts with every organizational group, from, you know, your salespeople to your front desk people, your marketing team, your executive team, your engineering team. And that, like, that’s a lot of, in my opinion, the way that I think of it, like that, that’s a lot of responsibility to have that kind of influence. And I don’t think people realize how influential you can be on the culture of a company. And I’m glad that you brought up culture because that’s something that I’m super passionate about too, is having a culture of that interpersonal connectivity and a culture of open dialogue and a culture of like feedback and things like that.

It’s something that an IT department can have a huge impact on because you are talking to everyone, all the time. Another thing, and I don’t know how it is with you guys, but I know for us, like we, because of the nature of the business and the nature of what we do, a lot of times we learn about things that are going to happen before other people do. And there’s a lot of trust to be earned and a lot of respect to be earned in, to be had there. So, yeah, I think there’s so much responsibility and it goes outside of, you know, just being a sysadmin and sitting and writing in bash all day long and writing a bunch of automation, like that’s super important, but at the end of the day, like the only person that really is going to appreciate that as you, whereas, like we’ve talked about, if you’ve had a good conversation about something with someone, and you talked about your favorite album, or you talk about movies or books or something like that, and you make that human connection, you’re having so much more of an impact long-term and culturally than, you know, just sitting at your computer just like hacking away all day.

For me, on a personal level, like that’s important to me because otherwise, why am I doing what I’m doing? You know, if I’m just going into work, just to check off a list that I accomplished a task, I don’t know, that’s, for me, that’s not very fulfilling. I like knowing that, like, I actually accomplished something I guess, matters, you know, not that the technical stuff doesn’t matter because it does, but I guess it’s less it’s less far reaching.

Ryan: Yeah, exactly. And I, there’s two things I’d like to do. The first thing is, to go alongside with what you’re just saying, when we’re hiring people and we’re having these discussions about what we’re looking for in a candidate, we’re like, you know, you, you can teach technical skills. It’s a lot more difficult to teach personality and, you know, soft skills and that sort of thing are a lot more difficult to teach. And that becomes… the primary question becomes: is this a person that I want to interact with on a daily basis? And that’s also important, so there’s that. And then the other part that I want to bring up before we go too far off of what we were saying, with the whole conversation, you know, talking about non-work-related stuff and, you know, building rapport with people, you may get some, some managers or even some IT people who are like, well, if I’m just sitting there chatting with people all day about random stuff, you know, isn’t that gonna be a loss of productivity on my end, or a loss of productivity on their end?

You know, that sort of thing. I’m going to rebut that with saying that, having that rapport and establishing that trust, and those relationships will actually, will actually serve you better in the long run, because on their end, they’re going to come to you sooner. They’re not going to sit there and fight with problems and waste time and lose productivity in the long run. They’ll come to you earlier with problems. And also, on your side of things, you will find out about problems before they become like a bigger issue. So you’d get earlier access to, an earlier look into potential issues and can solve them when they’re, when they’re easy to solve and before they blow up in your face and, you know, bring down the entire company’s infrastructure, you know, stuff like that. 

Investing in Culture from the Top Down to Promote Productivity

Stephen: Yeah. Well, I, man, that’s such a great point. And like, when you’re talking about, I don’t want to go too far off on a tangent on this ‘cause I could, but you know, when you’re talking about people who are focused on lack of productivity… I mean, I, I just have to call BS on that. And luckily like, there’s, I haven’t experienced any of that at Built, the culture there is so good and healthy, but like I’ve experienced it before in previous career paths. And I just, I just don’t agree with that. Like that whole approach of “you need to be constantly working on this certain set of things for eight hours straight and then go home and come back and do it again… we’re you to work” kind of thing. I understand the concept behind that, but I just don’t… that’s not contributing to the development of a healthy culture.

And I mean, there’s, so there’s so much evidence and research out there that just investing in people — yes on one side, like financially — but realistically investing in people personally, contribute so much more to productivity because when people feel comfortable and they feel valued and they feel trusted and they have trust of you I mean, productivity goes through the roof because they feel more invested in their job and in the company and what they’re doing. If you take someone who works for a company that really invests in their people and invest in and makes the type of culture they have a high priority, you’re going to get so much more value out of those people or more productivity out of those people in less amount of time, because they’re happy and they’re getting stuff done where if you go to a company — and I have experienced it firsthand — where the only value that a person has is what they call human capital, which is one of the most egregious like terms that I’ve ever heard in my life.

But, you go to companies where that’s the only value that people have is their human capital. Those people are getting enough done to keep their job. You know what I mean? They’re going to work; they’re getting enough done. They’re doing enough to get their job done, and then they’re going home. They don’t care about being productive because they don’t feel… they’re not invested in their job. They don’t feel invested in and they have no you know, desire to do more than they have to do. And I’m sure that’s not like a hundred percent true because there are plenty of people out there that are really motivated by metrics and numbers and things like that. But I mean, at the end of the day, we’re all humans and we all, when it comes down to it, we want to be happy and enjoy our lives and all that kind of stuff. And I know I’m getting on like a philosophical tangent here, but like, you know, just the whole productivity thing, it is important. And obviously for a company to stay at a company, they need to make money, but I have seen firsthand the difference between a company that invests in their culture and invests in their people and values their people as humans and as individuals versus a company that does not. And I mean, I can say that I feel that way about Built, it’s one of those things where I kind of want to say it starts at the top and it trickles down and it does, but you know, it radiates; it permeates.

Ryan: It’s diffused across the entire organization.

Stephen: You know, like in talking to…. when I spoke with Raj [CEO at JumpCloud], I got the same feeling that I get when I talked to our CEO, Chase. He’s super invested in his people and he cares. And he cares about the quality of the culture that we have. And I got that same vibe from Raj. Like he seems like he really cares a lot just about people. And I mean, if you just look at a company that has a CEO like that versus a company that has a CEO who only cares about productivity, I mean, you think you’re gonna be talking about two different businesses from a performance standpoint. And you know, I think that all the things that are happening at JumpCloud and for JumpCloud recently are proof of that. I mean, I have no idea about what you guys’ internal culture is like, but everyone that I’ve ever spoken with at JumpCloud always seems super happy and is outgoing and very personable and stuff like that. So, from a business relationship standpoint, those are the kind of companies that I want to be associated with and that I want to have, you know, business relationships with. End tangent.

Ryan: Oh, not yet, because I want to add it. So, you know, along those lines, I think back to… 2020 has been a horrendous year, it’s just been difficult across the board and it goes without saying, and transitioning to remote, you know, and adjusting and everything like that… until you find your groove, it can be really stressful. It can… I’m someone where I have, as I put it, I have workaholic tendencies. So when that clear dividing line between what’s home and what’s work kind of goes away, it was common for me to, you know, work 12+ hour days because it’s there.  I could just step right over here. No, while this is fresh on my mind, I should get this done sort of thing. 

It wears you down. It wears you down. It’s super stressful. But when you enjoy your work, when you believe in the organization, when you love your job… I love my job. And that helped me through that period and I feel really kept me from burning out and also having other people there that were looking out for me saying, “Hey, take a day off.” And that sort of thing, it really helps. Still learning little tips and tricks to help things, but, you know, I’m much better off now. And it took the culture at JumpCloud and the people here helping me get to that point. Yeah. So I try to help other people whenever I can, as well, because I know that we had some people who were… here’s an example:

So we have, you know, we have a policy in place where your screen locks after five minutes of inactivity, if you’re reading something, your screen can lock if you’re just sitting there reading there. And we had several people who, you know, were new, who came on after we went remote and they were like “can we do something about the screen lock? Because I don’t want people seeing that I’m inactive.” I tell them, “We’re all in the same boat. We know what it’s like to work from home. Nobody’s going to get on your case if they see you go from active to inactive and back and forth, and that sort of thing, because we know how it goes.”

Now, maybe it’s an issue if nobody hears from you and you don’t respond for a whole day. That might be a problem, but that’s something completely different. The little things like you need to, you want to run downstairs and grab something to drink or something like that… We’re all human. We’ve all been there. We all understand, and that kind of thinking and that mentality, I think is, you know, is important and helping to spread that is a good thing to do. So that’s my part of the tangent.

Taking Time to Interact While Working Remotely

Stephen: Yeah. No, I mean, that’s super spot on. And I mean, that goes back to the whole having a… I don’t want to say a defined culture, but like having a certain type of culture at a company where everybody is in it together, regardless of whether you are a front desk person or you’re the CTO or CEO or whatever… everybody is there to achieve the same end result, which is the success of the company on one hand. If the culture is right and everybody is on the same page and everybody’s there to support each other, you’re going to have that productivity, you know, and those results. 

And yeah, I mean, you, you know, you were talking about the transition to work from home. We’re very lucky. I mean, well, we’re lucky in general because we both work for companies that we’re able to transition to that, I mean, I’m assuming pretty seamlessly. For us, it was pretty seamless, but I know that, we were… there was some division in that, like some people, they’re mental health was really good because they’re not as outgoing, you know what I mean? So being home and being able to really focus on their work was really good for them. And then you have people who are, you know, kind of like me, who like to be going around and talking to everyone and having conversations and stuff like that who were struggling. 

So, certain people in our company recognized that and started implementing certain things. We were doing what we call Hallway Hangouts… scheduling people out actual time to just disconnect from work and just talk to each other, not about work, just to talk. ‘Cause you know, like, especially you, obviously you guys are, from an employee standpoint, have a lot more a lot bigger team than we do, but, we have a good amount of people who have never interacted before and don’t know who each other are. We’ve gotten to that point and that that’s been a really healthy thing for us to have that time to connect with people. And again, on the interpersonal thing and the like having conversations thing, I’ve had, I’ve talked to some people that I normally probably wouldn’t have had an extended personal conversation with. One, you get to learn so much about people and two, they get to learn about you. And it just, again, it adds to the culture, it adds to the… and it makes people human, too. Sometimes I just I’m like, “okay, it’s on my mind. I’m going to get this done.” And then like 10 hours later, I’m still like doing stuff, you know? And in some ways, I’ll feel very accomplished when I get something done, but then there’s the part of me that is lacking, because I didn’t have any human interaction that day. 

Ryan: Right. Yeah, and along with that, you brought up, kind of, the water cooler hangouts. Here at JumpCloud, we use a Slack app that’s called Donut. And what it is, you attach it to a channel and people join that channel. You set a period of time… so like every three Mondays, or, you know, every once a month or whatever. What it’ll do is it’ll pair people up. And I’ll be like, “Hey, go schedule a time to go chat about stuff, you know, chat about whatever you want. Doesn’t have to be work-related anything like that.” And I think just having, having something like that in play is a game changer. Because, you know, once a company gets past a certain size, there’s… gosh, I don’t know. There’s a term for it, but I don’t remember. Anyways, once a company gets past a certain size  —and I want to say, it’s about 150 people — you can’t maintain that many personal relationships. So when an organization gets larger than 150 people, you get to the point where you don’t… it’s no longer like, “okay, everybody knows everybody.” So you actually have to put effort in to keep everybody connected and understanding at least what other teams do and everything like that. 

Building IT as a Hub of Communication

Ryan: So, I think that’s an important part and circling back to IT on that in particular, where if IT is doing their job, you don’t hear from IT. If they’re doing their job well, they can be a very low visibility thing or low visibility company. I think it’s one of the responsibilities of a good IT team is to make yourself visible, you know, to go reach out, talk to people. 

Stephen: Preach.

Ryan: If everything’s going well, maybe you could put out a presentation. One of the things that I like that JumpCloud does is we regularly, at our all-company meetings, we’ll have a department or a team be like, “Hey, this is what we’ve been working on.” That sort of thing, having that visibility. Have the IT team go do that and be like, “Hey, everything’s going good. This is what we did to get to this point.” Or, you know, “These are some projects that we’re, that we have on the docket that we’re really excited about,” that sort of thing. Let people know what you’re doing. 

As you mentioned before, IT is a cost center. Unless you’re a managed service provider and IT is your product, IT is a cost center. We’re not revenue generating, we’re just a bottomless pit that money gets dumped into, and so if you go and show what you’re doing, showing how you benefit the company. You’re gonna have a lot fewer of those conversations of “Why do we even have an IT team?”

Stephen: Man, what you said about how a lot of people think that if IT is performing, if IT is doing their job, you never hear from them…. It’s so funny because like, I have heard that from so many, like not people at Built, but previously have heard that comments like that before. Your IT team is doing their job if you never hear from them, but it’s like that, I don’t, that sounds, that’s like counterproductive. And I feel that’s the opposite of like, when we are being very productive,, we’re being communicative about what we’re doing. And you know, obviously just like every organization and every organizational unit, there’s a lot of stuff that goes on behind the scenes that no one will ever know about, or even maybe really doesn’t need to know about. But, we really do try to make an effort to be public facing and communicate, whether it’s on Slack or through email around the office. 

When we, prior to quarantine, we would every day, Dylan and I, would get up and go walk around the office and check back in with every department and check in with different people. Just under the guise of making sure everything is going okay. But, I don’t know if under the guise is like the right term. It wasn’t nefarious by any means, but we were both social people, but also we wanted to make our presence known, like, “Hey, we know we’re just checking in with you. How’s it going?” Kinda like having little water cooler chats around the office every day. And that, again, back to what we were talking about earlier, like that gives them visibility to you, like from a human standpoint, but also earns you some trust points with your team and they know who you are and you’re familiar and they can come to you with various things. And they’re not scared to… I’ve had a couple of people who spilled coffee on their computer and they came to me and they’re like, “Hey, so this happened.” And I’m like, “All right, sweet. Well, I’ll get you a new computer.” And they’re like, “Okay. I thought you were going to be mad.” I’m like, “Yeah, **** happens.” Sorry, I don’t know if I can say that on here, but yeah.

Ryan: Yeah. And to add to that point, I have in one of the places where I worked in the past, it was a single person IT shop and the person who was there before me was that very standoffish, condescending, unapproachable, kind of the person who just kept every, you know, hoarded all their knowledge and everything like that. And one of the things that I did when I got there that I think made the most progress towards, establishing that trust between everyone else in IT was just what you were saying. I got up and I made the rounds. I talked to people. And it took a while! Because at first, I would get a ticket being like “This printer hasn’t been working properly for two months.” So it was like, you could tell me right away when this stuff happens and I would go there. There are two parts of it. Part of it was making it known that I was there and I was available and getting to know the people. And another part was being flexible with my priorities. 

So if they’d be like, “Hey, the printer broke.” And like I was working on some sort of automation script or something like that, it’s not something that was like, you know, a P1 topic, but, you know, I was technically busy. You know, I could take a break from the script and go fix a printer. You know, I can shift my priorities and that lets them know that their problems mean something to me. What that helps with is the times when you really are doing something that you can’t stop… So if you’re trying to bring back up a server that’s down or something like that… when those things happen, if you’ve established that you will help them as soon as you possibly can in normal situations, when you’re like, “Hey, I’m working on a critical problem right now. I’ll get to you as soon as I’m done,” then they’re like, “Oh.” They don’t feel like you’re just blowing them off. They trust that you are being straightforward with them. And this also plays along with my thought that IT people should be as transparent as possible. As you said, there are some things that, we get advanced knowledge of… some things that we just honestly cannot share with other people. But there’s plenty of other things that, you know, we were rolling out this piece of software, we’re rolling it out for these reasons. Or we have this policy in place for these reasons. And if you, and part of that is like, if you can’t articulate why you made the decision… maybe you didn’t put enough thought into the decision that you made. That’s kind of my thinking on it.

Stephen: Spot on, dude. Yeah. In general, being a human, communication is so important, but specific to what we do, the amount of trust that you have from your team and your efficiency and ability to really be impactful. It is, well, communication and transparency is paramount to that because our primary job is to keep the ship afloat from a foundational standpoint, and your ability to do that hinges on more than how quickly you can write an automation script. Like that’s a huge, important factor, but how you communicate what you’re doing, but also how responsive you are to communication from your team plays an important role in how effective you’re going to be at your organization.

And I mean, obviously I am not saying by any means that we are the most effective or even knowledgeable IT team out there, probably the opposite of that. But we are very communicative and we try to make ourselves very public facing. And I mean, I feel super confident that we have the trust of our team. And that, I would say anyone like anyone at Built will come to us with anything. I mean, and even sometimes stuff that’s not IT related, you know, people come to us and ask for help with things because they know that you know, we have that far reaching… I don’t want to say influence, but we have communication with everybody across the team and it’s like you know, people will come to us with like, “Oh, I need help with this.” And I was like, “Well, okay, let me see what I can do here.” That kind of stuff. 

So, yeah, I mean, a good example of that was I had an engineering team that was really wanting to get a new tool to use and to integrate into our tech stack. And they hadn’t really been told no, per se, but it just wasn’t something that anybody had made a priority for. I had a bunch of people reaching out to me and being like, “Hey, we really want to get this tool. Here’s how it will help us.” And so I basically just put together a little presentation of what this tool does, how much it costs, how it can streamline processes and save time, by doing this, this, this, this, and this. And, I feel pretty confident that I won over some people by going to bat for them in that respect. And that’s not necessarily a part of my day-to-day job, but it’s like, “Okay here’s an opportunity for me to have an impact on a group of people in something that doesn’t really fall into my responsibilities.”

Proving Trust by Going to Bat for Technology on a Team’s Behalf

Ryan: See, here’s the thing: this is where I’m going to kind of disagree with part of what you said: “It doesn’t fall into part of your responsibilities.” I feel that one of the responsibilities that IT should have is understanding how different tools, different technology impacts the business and being able to write up a business plan that is, being able to write up a proposal. I think that is, that should be, a part of an IT pro’s responsibility. And granted, do you do it more to the team leader/manager’s role? In bigger teams that may be the case, but if you’re just one or two people, then both people should know how to take this request from engineering, look at the tool, and translate that into business speak. 

That’s how… that’s not only how can you get the stuff that you want to get, the stuff that you need, but also it shows the people on that side of the organization that, you’re willing to put forth this information, that you can speak their language as well. And that, again, that helps build trust. I would like to say that I have a good amount of trust with our financial team because I will put forth these proposals. I tried to put a lot of thought into a request before I made it. And that goes a long way. I try my best not to just make frivolous purchase requests.

Stephen: Yeah, dude, it’s funny that you say that because we both feel like, and not that we feel, but we are in a lot of ways, like an extension of our finance department and we have a great relationship with them and we’ve worked side-by-side with them constantly in helping make those decisions. So you’re spot on with that. And it’s like you said, because we should, and we do have an understanding of what every component —well, when I say component, I mean, like within our tech stack — like what everything does and how it functions and how it operates within that system,, we can help them make decisions about stuff like that. And we do all the time. I mean, we, Dylan and I, both are big contributors in our technology, or what we call our Technology Review Board which is part of our procurement process. That’s something that we take a lot of responsibility in, not only like assessing and helping make decisions about what will work well, but also from a financial standpoint, what direction we need to go, what pay, et cetera, et cetera. So, yeah, totally agree.

Ryan: Yeah. And yeah, to kind of take a step back and look at the bigger picture of it, when talking about rebranding IT with the understanding that IT’s purpose in an organization is to both keep the organization afloat and also to improve the processes of the organization. Really, when you look at anything we do, we are helping build the foundation of how the organization works, and also we are helping things to move smoother. So it’s kind of vague and kind of a higher level thing, but, or maybe I would say, really simplified. But, really that’s what we’re about. So what can you do to help achieve those goals? From as many angles as possible. And I think that’s how that’s how people should be, my opinion, is that’s how people should be approaching IT,

Stephen: Yeah. I am of the same opinion. So I’m going to say you’re right.

Closing Remarks

Ryan: All right. So our guest today has been Steven Malone. Stephen, thank you very much for coming on and chatting with me. It has been a pleasure.

Stephen: Yeah. Thank you. You guys probably all know by now that I love JumpCloud, I’m a huge fan. And everybody at JumpCloud that I get to interact with on the reg is amazing. Shout out to Aviv. He’s my boy. But yeah, this was really fun. I wish we could do it every week.

Ryan: Thank you for listening to Where’s the Any Key?. If you liked what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud, where the team here is building a cloud-based directory platform for system and identity management. You can learn more and even set up a free account at So until next time, keep looking for that any key. If you find it, please let us know.

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