Using Outside IT Experience to Become a Better IT Professional with Chavarous Kennebrew

Guest: Chavarous Kennebrew, Senior System analyst, Irrimax Corporation

Episode Description

Despite his consistent passion for technology that started in kindergarten, Chavarous didn’t always work in the IT field. In this episode, Chavarous stories his work experience – from sweeping floors as a janitor to managing stress in a call center – and how it’s prepared him for his career in IT. He and podcast host Ryan Bacon discuss different avenues for entering the IT field and skills that help IT professionals, no matter what field they’re coming from or which specialization they choose. 

For aspirational and storied IT professionals alike, this episode of Where’s the Any Key? offers relatable insights into the IT professional’s world and common threads that tie IT into the overarching career experience. 

Introducing Chavarous Kennebrew

Ryan Bacon: Welcome to Where’s The Any Key?, the podcast where talk shop about topics, tips and trends for the modern IT admin. I’m your host, Ryan Bacon, the IT support manager at JumpCloud.

All right, joining to me today is Chavarous Kennebrew. He is the senior system analyst at Irrimax Corporation. How are you doing, Chavarous?

Chavarous Kennebrew: I’m doing good, Ryan. Thank you for having me today.

Ryan: Yeah, thanks for coming on. To start with, why don’t you tell us a bit about yourself?

Chavarous: Yeah, most definitely. Man, where do I start? You know, as you said, my name is Chavarous Kennebrew, and I love everything IT related. I love it from the beginning of time to right now to the future. I’ve always loved IT from the beginning of my kindergarten year. My mom bought me a Whiz Kid back in like ’87. That was my first computer, and from then I have done everything I can do to learn about it, to tear it apart, and it’s just been my life’s passion. Although I’ve had several other careers, my life’s passion has always been related around IT. I’m a father, I’m a husband, but at my core, I’m a computer. That’s me.

Drawing on Previous Experience in an IT Role

Ryan: All right. That’s a great way of putting it, and actually you mentioning that you’ve had a lot of other careers and jobs leading up to your time in IT kind of really does lead into what we’re going to talk about, and that is not only being an IT generalist, but reaching out and using those outside experiences to help you in IT, because when we were first talking, we came to the conclusion that you and I have very similar experiences. You know, we worked in different places, but we both had long stints in things outside of IT before coming into IT, and view that as a benefit. So, to kick things off, why don’t you go ahead and start with: What are some of the key things that you learned in your previous jobs and previous careers that help you the most in IT?

Chavarous: Oh, dude, where do I start? Man. You know, one thing I was thinking about after you and I had the conversation last time is my first job – actually my first and my second job – I was in high school in Germany, and I was a janitor. I was first a janitor at a gym, and then I was a janitor at the PX, at the postal exchange. One thing that that taught me that I’ve taken from jobs after that to right now is you’re never too good to clean up someone else’s trash, and man if that hasn’t really helped me. And it doesn’t even have to be trash, you know – someone else’s mess.

In this profession, you’ll come across many things that you would have done a different way, and it doesn’t necessarily make it trash, but you do have to clean it up because positions change, people change, and you’ll always have someone who thinks it should have been done a different way. So you’ve just got to be prepared to take your broom out, sweep up that trash and lay down a new floor, or just lay down some new groundwork and move forward. And every time someone comes to change, you’ve got to be flexible and ready to perform whatever task it is that they’re looking for. I took all of that away from sweeping up garbage cans when I was working in the gym. I hated it, but you know, 20-something years later I’m still sweeping up trash. I’m still sweeping it up.

Ryan: Yeah, and it’s really interesting that you say that with the perspective that different people have different ways of doing things. So I had the really … what I seem to think of as a unique experience of, when I left my previous employer to come to JumpCloud, I actually had the opportunity to connect with the person who came after me there, and we talked a lot about stuff. It was a very interesting situation where we both had different ways of doing things, and it was a non-profit, a fairly small non-profit, and he came in from a more corporate background. And he told me, he was like, “Why the heck did the Ryan person do things this way?” And we started talking about it, when he actually started diving in he’s like, “Oh. That’s because this is what he had to work with.”

But even that being said, going back to that different people have different ways of doing things, he found different ways to do things like that I didn’t even think of. So it was good; it was a really interesting experience going in there and how he came in to clean up my trash.

Chavarous: I totally agree.

Ryan: And you’re right. You’re never too good for it, and you should never feel that you’re too… it’s humility. You should always be approaching your job with humility. And yeah, that’s a good thing to learn.

Chavarous Kennebrew: I agree with you.

Working Alongside Non-IT Professionals

Ryan: Yeah, so I’m going to pitch in with one thing that I learned on one of my back jobs. So, I had several sales jobs before coming into IT, and I will be the first person to admit that I am not wired for sales. I am, at best, an average salesperson. So, I’m glad to be out of that role. But learning the sales skills, all those soft skills and communication skills have really helped me a lot.

But something that’s helped me more is I deal with a lot of vendors. I deal with a lot of salespeople outside of the salespeople within JumpCloud, so I deal with a lot of people trying to sell to me, and knowing how salespeople think and knowing the practices and knowing how to interact with them has helped me so much. And not just figuring out when they’re just blowing smoke, but also building good relationships with my vendors, being able to talk the same language with them – that has been critical to making that aspect of my job bearable.

Chavarous: Yes. You know what, it’s the jargon. It’s knowing the jargon and knowing how to talk and communicate effectively with someone – with another vendor. That does go a very long way because it builds trust, it builds respect, and then they do sometimes tend to go out a little bit extra for you, because they see that you respect their craft, because sales is nothing but a craft. It is a really big craft.

Ryan: It really is.

Chavarous: You bring up a very valid point in that Ryan. Yeah, I don’t think … I thought about becoming an IT salesman at one point, and I am with you wholeheartedly. That is … no, that’s not for me. That’s a completely different set of skills, man.

Ryan: Yeah, and I will say this – I have said this, and I’ll keep saying this – that I feel that the sales team that we have here at JumpCloud is one of the best that I’ve ever dealt with. I give them all credit where credit’s due, because selling to IT people is … we’re probably one of the most difficult customers and prospects to deal with because we are ornery, we are opinionated, and we want to do stuff our way, so.

Chavarous: Yes. You’ve got salesmen, very great, some of the ones that I’ve had an opportunity to deal with. They’re extremely personable, and that’s what I appreciate most from dealing with IT vendors, are those that don’t necessarily try to sell you the product, they want to talk to you about the product, let the product sell itself. I don’t want to push it on you. I want to demonstrate to you what it is, how it can help you achieve whatever goal or goals your company wants, let you use it as a trial, and then I’ll talk to you. Ask me if you have any questions. But those that continuously push and prod and want to tell you about the benefits of it, and … that doesn’t make a great salesman for me. So I have thoroughly enjoyed working with JumpCloud, and it was a non-brainer when we decided to use … that’s not a plug or anything, but it was just a non-brainer. It’s a good product. The product sold itself, so here we are.

Ryan: Yeah. And there are plenty of other vendors that I have relationships with where we’re not active customers for them, but I stay in contact on a regular cadence because, who knows, in the future, their product and our needs will align and I already have a good relationship with them. So I think that understanding that sort of thing has been really helpful, and because they’ve come back and been really great resources as well, just with information and that sort of thing. That goes on to the soft skills side of things, where – any career where you have to heavily rely on the soft skills, whether you’re in sales, whether you’re in customer service, whether you’re a server at a restaurant – when I’m looking at prospects and that sort of thing, yes, there’s a need for a good technical foundation, but looking at people who have that experience with dealing with people is a huge plus, and I can’t overstate that enough.

Chavarous: Agreed, agreed, and that brings me to one of my other careers, you and I talked about it briefly, I was a claims adjuster, and I had done non-standard insurance. I’ve worked with some reputable insurance companies and I’ve worked with some that had a horrible reputation. But the soft skills that you speak of that I gained from working in that profession, it has helped me tremendously to deal with people in other professions.

You’ve got to learn how to negotiate and how to talk to people and how to be talked to, or how to be talked at, you know? You got to deal with thousands – hundreds of thousands – of different people from all across the country who are in very stressful situations. So when a VP comes up to you and asks you why your server went down, it doesn’t make it as bad; it’s okay to deal with. It’s easier to deal with, or you can deal with it, because I had a customer once call in when I worked for an insurance company, and yell at me for something that I could not control. The same with this: I could not control it. But, because I had been yelled at all my 20s at a call center, I was ready. I was ready, and I was able to articulate myself and say what the issue was, how we come to a resolution and move forward.

And like you said, man it’s those soft skills that you gain from all these other careers or professions, and you just don’t realize how they come in handy. But when they do come in handy, you’re ready to use them, you know? It’s just an arsenal of soft skills that you keep at your disposal.

Managing Stress in the Workplace

Ryan: Yeah, definitely. And you mentioned being able to deal with people yelling at you, and dealing with stress and pressure and stuff like that. That’s another thing that I took away from one of my non-IT careers. So before I was in IT, I was in printing.

Chavarous: I’m sorry. I’m sorry.

Ryan: It was both an amazing experience, and horrendous at the same time. So I did everything in there, from production work to account management to design and print. I had my fingers in every single bit, and that’s where also I got my first professional IT gig. I convinced the owners, I’m like, “Hey, let me be your IT guy,” and make it part of my official job description. They’re like, “Go for it.”

So I will always be thankful for them because it was that that really got me started in getting that critical first few years of IT experience. But I will say this. It’s amazing, the amount of value that people put onto some ink on some paper. Like, when they want that birthday invitation out, if it’s not ready in three hours, it is going to be the end of the world. So that means our sales team there was just trying to make the customer happy any way they possibly can, which meant production deadlines were super tight. And if something slipped, it was all hands, everybody scrambling to get stuff done, insanely stressful.

But when I actually started … when I got into corporate IT, when I had moved on from there – while I was working on my graduate degree, I interned at Google on their physical security team. We did access control, security cameras, guest kiosk, all that sort of thing. So I went through my first bit of training within my first or second day, like actually taking tickets and stuff like that. A standard ticket came in that this badge reader wasn’t working. So I’m like, “Okay, I’ll take it and start going through the process there.”

And then all of a sudden, somebody would ping me and be like, “Hey, I see you’re working on this ticket. What’s the status?” Then another person’s like, “Hey, what’s the status on this ticket, and what’s going on?” And the TPM, the technical project manager on the team, came over and he was like, “Hey, I’m getting a lot of people asking me about this ticket,” and I’m like, “Okay I’m going through here working.” And it turns out that that badge reader was for the main access point for Google’s New York Chelsea office. So they had security there having to check people’s IDs and let them in one at a time.

So if you can imagine the amount of productivity loss just from there – the people were going crazy because it was going down. But it’s like, “Okay,” my whole train of thought is like, “I’m working on it.” From the very beginning, it had my full attention, and that’s what I was working on until we get through. So it’s like, “Okay,” you know, “all this stuff going on,” and it’s like, “Okay, we got it. We’ll go through.” It got taken care of. People were happy.

And there were comments afterward – they were like, “I’m surprised you weren’t freaking out with all these people coming at you and being like, ‘Hey, what’s the status? What’s going on? When is this going to get fixed?'” At that point, I thought back to all those times when it’s like, “Why aren’t those birthday invitations done?” And like, everybody’s scrambling, and years of dealing with that made this whole thing, which was a huge issue – I don’t want to underplay the fact that it was a massive problem – a lot bigger of a problem than, like I said, ink on paper -but dealing with all of those tight deadlines and all that stress in printing really prepared me for dealing with stressful situations in IT. That’s my biggest takeaway from my time in printing.

Chavarous: Man. You know, you brought back some really bad memories. You’re in the thick of it, and you’re on the cusp of figuring it out, and now you’ve got instant messenger, you’ve got Cisco pinging, you’ve got Microsoft Teams, all these different avenues of people trying to reach you, and just like, “I can’t do it, I can’t fix it and tell you how I’m fixing it while I’m fixing it.” Like man, you really brought it home on that one, because that is near and dear to my heart. It’s near and dear to my heart, man. I don’t think anyone who’s been with this profession long enough doesn’t have a horror story about having to deal with that, so kudos to you for keeping your head attached.

Ryan: Yeah, and really, when it comes down to it, it’s our job in IT to take care of problems and to fix problems, and, you know, you can’t fix a problem if you don’t keep a level head.

Chavarous: Agreed. Agreed.

Ryan: So, I think of the meme of the dog sitting in the burning room where he’s like, “Everything is fine.” And that’s almost the mindset that you have to take, where the building may be burning down around you, but it’s just like, “Okay, I can’t let that freak me out.”

Chavarous: No, no, yeah. “It’s hot. But just give me some water, let me fix this. We’ll deal with it later. I’ll deal with the heat later.” Which is funny that that meme is near and dear to my heart because I won’t show it. I won’t show the stress. I’ll continue the task. But my body will melt. I will be pouring down sweat. I’m calm, cool as a cucumber, but the sweat on the surface of my face, it is just pouring down, man. So I think I’m going to put that as my screensaver from here on out.

Ryan Bacon: Yeah, I don’t know how many times when we’ve had that emergency situation and then it’s game time until it’s fixed, and then after it’s done – then you can just collapse on the couch.

Chavarous: Yes, yes. Man, we had a very massive – a few years ago, one of the companies I worked with – we had a massive outage, Ryan. Everything was out. And I mean, I’m talking about databases, I’m talking about AD, I’m talking about 100% of our IT was affected. And I handled our service desk solution for the hospital, so I was the admin for that, and I was responsible for making sure – we had about 40 servers on that particular application – I was responsible for them all. They were all down. So that was the main communication channel. That’s how we kept up, how we kept track of all the ticketing system and whatnot. It was our ITSM [IT service management], so that was down.

And this lasted us for about a month, where we kept having these outages, this up and down. And you know, I’m on call 24/7, 3:00 in the morning I have to run to the data center, work with the database team and everyone trying to bring these applications back up. So at the end of all this – we found out, I think a switch or something went bad, it was faulty – but at the end of all that, after this full week, this week was … this was a hell week, dude. I went to my mom’s house to decompress. My cousin called me at 2:00 in the morning, and I thought it was work. PTSD, dude. I thought it was work.

And I picked up and I was ready, I’m like, “Chavarous Kennebrew, what can we do?” And he’s like, “Hey man, what you doing?” I hung up. I couldn’t do it. I couldn’t talk to him. I had to call him later and apologize and explain to him, I had just been on high alert, because my application had been down for weeks on end, and I had been at a data center trying to grind and figure out why it kept failing. And he called me at 2:00 in the morning just to say hello. I wasn’t ready for that, right? I wasn’t ready for that.

Getting Started in IT

Ryan: Yeah, in all fairness, I don’t think I’m ever ready for a phone call at 2:00 in the morning, even if it is just to say hello. So I can only imagine getting that, which would annoy me normally, on top of that stressful week of burning the candle at both ends, so that’s … oh man, I feel for you. And that’s another thing, to bring it back around to a broad experience helping out IT, is that when you’re getting to that point where you’re trying to solve a problem, critical thinking and problem solving is not an exclusive domain of IT.

So, my undergrad degree is in accounting, and I was originally, well, planning to be an accountant. Never got there. I graduated school and realized that to get to the jobs that I wanted in accounting, which were the analysis and auditing and all of that stuff that involves the critical thinking and the problem solving and stuff like that, I’d have to go through at least a few years of bookkeeping-style stuff, working the general ledger, and that didn’t really interest me. Still, I was working in IT at the time, and so I decided to just stick with IT.

But the point is that, I’ve talked to people in the finance field who are looking to break into IT on multiple occasions, or people from other fields that involve a lot of analytics. So like mechanics, I’ve talked to them, looking to break in, and all of these things, all these fields and all of these industries, they involve a problem and figuring out what that problem is and how to solve that problem, and critical thinking and everything like that.

Really, doing that stuff trains your brain to approach situations in different ways, and having a team of people who all approach problems in different ways covers you in such a … it creates such a wonderful mosaic of talent and mentalities that you could approach any problem and be able to tackle it.

Chavarous: Agreed. I mean I’ve had cops on my team, I’ve had guys that have worked for the Department of Homeland Security. You know, critical thinking, as you said, is not exclusive to our profession. But, can you think? Have you ever had a problem that you’ve had to solve? Did you ever have to create some sort of logic to that problem to fix that problem? If you have, then you can do it. You can do what we do, you know? Are you curious? Do you enjoy knowing how things work? And if you don’t know how they work, are you okay with trying to figure it out? Can you sit there and try to figure it out? Can you do it by yourself? Can you do it with a team?

That, again, is not exclusive to our profession, but it’s necessary. It’s a necessary component of what I think it requires to be good at this job, is can you apply that? Can you think critically? Can you listen? Can you hear what the other person is saying, and can you apply it? And can you Google it? When all this fails, can you jump on Google and figure out what someone else did, because when you think you are at the end of your rope and you’ve done everything you can do, someone else has also had that same problem. So, can you apply that? Can you see what they’ve done, and try to utilize the same methods that they’ve done, or get creative and do your own? But can you go that one step further? When you think it’s done, can you go one step further in finalizing it – just finish it? Man, I … this is a great profession Ryan.

Ryan: It really is, and the surprising thing is that I’ve, like you, I’ve been a computer nerd ever since I was little. I grew up with a Commodore 64, with an Amiga 500, like with all of these things, because my dad was a big nerd with this stuff, too, and had these … I grew up with computers all around me, but it never occurred to me that I could make working on and with computers my career. I knew about software development and all that stuff, and there’s a little bit of interest there, but that’s not what I … I didn’t want to go that way. I wanted to get my hands dirty on … in the guts of a burnt out PC, that sort of stuff. It never occurred to me that you could do that outside of a hobby. When I made that realization, it was like just … it was magic, and I’m like, this is what I want to do.

Chavarous: Oh, man. You said you can do it outside of a hobby, you’re right. You can. And the thing about it, I don’t know about you, but even working in IT, my hobby is still IT. I love reading about it. Right now I’ve got 50 note cards, right? I’ve got thousands of note cards, I’m studying for AWS certification, and you could just … I’ve got eight IT books all around me. I’m trying to surround myself with it.

I try not to become infatuated with it, but it’s hard not to, right? It’s hard not to wonder, why is a Mac different from a PC? Why is someone who knows Linux, why are they better than me? It’s questions like that that I need to have an answer to.

Ryan: Well, I would like to say that just because someone knows Linux doesn’t mean they’re better than you. But in all honesty, I ask myself the same question a lot. And that’s one of my goals, yeah, I’ve always … one of the pieces of advice that my intern host gave me that has stuck with me … he gave me a lot of advice that really stuck with me. So, Jeff, this is a shout out to you.

So, he gave me two pieces of advice that really stuck with me. The first one is … it seems so simple. When I was trying to pick out what OS I wanted on my work laptop or on my work systems, he said, “Pick the one that you’re least comfortable with.” And that you way, you use it as your daily driver, and you’ll become comfortable with it. So like my main desktop PC that I had there was a Linux machine. And then coming to JumpCloud, I did the same thing. At that point I was least comfortable with Macs. And so I’ve been using a Mac constantly for almost three years now, and now I dare say that the OS that I’m least comfortable with is probably Windows.

Chavarous: I just made the transition in November to a Mac from Windows, and I don’t know if I can go back. It hasn’t been that long. I don’t know if I can make that transition back. I understand. I agree with you, man. But you’re three years in the game, so I’m going to have to reach out to you to get some pointers and see what I’m missing out, a lot more in that aspect.

Ryan: Yeah, don’t get me wrong. I still have a lot to learn, and the guys who run the front line here at our IT department here at JumpCloud, they already surpassed me in some ways, and they’re going to surpass me in more ways as I stepped back into a managerial role – which is a whole new challenge – it’s a whole new set of skills. But you know, one of the challenges is trying to keep my technical aptitude sharp, so I’m looking forward to that.

Managing and Motivating Teams

Chavarous: We talked about that last time, about that transition from being a front-line worker to a manager and trying to keep your skills sharp, and not wanting to be in the weeds. So like it’s … let me ask you, what’s been the most challenging thing that you’ve had to face as a manager?

Ryan: Honestly, delegation. I mean part of it … in a way it’s easy because I just don’t, you don’t … there’s only so much time in the day, and one person can only do so much. So, just out of necessity, I’ve had to offload things from my plate onto the other team members’ plates. But sometimes it’s … so, one of my pet projects from when I started here, when I was like the only IT person here at JumpCloud, is working on a script for automating our onboarding process, and that was my baby. It started off as a little next-to-useless thing, and became the primary way that we got people added into our system and provisioned and everything like that.

So, the second IT hire that we had, he is … this is his first IT job, but he was wanting to grow into more of an engineering role, and so he wants to develop his skills with automation and tooling and everything like that. So I have all these other responsibilities now, so I didn’t necessarily have time to sit there and develop this script and keep it up to date, because as features come out in our platform, and as new technology comes out, you have to adapt the script. It’s a living thing. I had to hand that off to him, and it’s now his baby. He owns that.

That was really hard for me, and I still have to keep from being like, “Here, I wrote this; you should implement that.” I’m trying to step back and my involvement with it as support, so we can brainstorm and spitball together, and also just providing guidance as to, you know, we should look into adding these features and everything like that. But yeah, handing that off and no longer having ownership of that tool was probably one of the most difficult things that I’ve had to do.

Chavarous: Man, you’re speaking to my heart yet again. I get it, man. I understand. That’s been the same with me. I haven’t achieved a managerial status, but I’ve had to build something up and then hand it off to someone when I had an internal promotion. And every now and then I’d peek up, pop my head up over the cubicle, “Hey, how’s it going? How’s this going? Is there anything I can help with?”

It’s your child, it’s your baby, and you put so much blood, sweat, and tears, and it’s … you just want, more than anything, you want to see it continue to be successful because you know the type of groundwork that you’ve done in order to bring it to where it is. You just want to see it continue to be successful, you want people to use it, you want it to be of use. I think that’s more of a testament to your character, though, honestly, that you’re proud of what you built and you just want to see it, and you want to see it thrive, man. There’s nothing wrong with that.

Ryan: Yeah, exactly.

Chavarous: Nothing wrong at all, right?

Ryan: Yeah. And also on the flip side of it, I’d be overjoyed to see him take that and turn it into something that’s a hundred times better than anything I ever made. So I am looking forward to that, and I’ll be jumping for joy, and I’m cheering him on on the sidelines to reach that goal. So, and that’s … bringing it back around to the original topic, that teamwork, that right there, again, is another thing. Even when I was working as the only IT person in an organization, I still had to work with other people. I still had to collaborate with other departments and all that stuff. So anything, any kind of job, any kind of experience that builds on the ability for teamwork is huge, is a game changer – and again, should never be looked down on when you’re looking at someone trying to break into the IT field.

Chavarous: No, no, no, not at all. People, on a piece of paper, they’re resources. But you and I know they’re critical parts of an organization. You need people in order to make your organization thrive, and you’ve got to have people that can interact with others, and work together to have a shared goal achieved. You need that.

In order to do that, it may require what I like to call currency, you know? You need the right currency. You need to know how to motivate people, what they like. Different things motivate different people. I was a claims trainer there so I had to learn how to help these adjusters get what we would call “A” calls. And you have Adjuster A over here who, she had a family, so you had to know how to motivate her because she’s had a long day, she’s got to go back home with kids. So how do you motivate her to do her best, which is going to be different than the recent grad over here who’s just more concerned about the party tonight. And you take those same skills and translate them into IT and now you’re working with people with a completely different set of skills, but they’ve got the same exact needs. They’ve got families at home, and they may have had a bad day, but still, what can you do to motivate them, especially when you’re working on a team project?

You know, chocolate motivates everyone. Chocolate and candy is a great motivator. Conversation is the great motivator. And it’s only through those that you can achieve a goal. I don’t think you can be successful even if the project is achieved, you know, I think there are different levels of success when it comes to achieving a project. I think if you bring it to fruition of course, which is the main goal of any project is to complete it successfully, complete it on budget, complete it on time, but I measure my success on projects on … if I work with this person on another project, are we going to have the same problems? Did I learn anything about them that could potentially help us on the next set?

What can I do to motivate this person differently next time? What can I do to motivate myself differently next time? What type of currency can I bring so that way our interactions with each other is just a lot better than it was this time around? Everyone doesn’t have currency, but the vast majority of people do, and at the end of the day, I’ve learned that people just want to be heard. They just want to be heard.

Ryan: Yes. Yeah, and that … I don’t think I’ve ever heard of it referred to that way, the using currency, but I like that. I’m going to steal that. It’s also one of the reasons why I really, really like internal-facing IT as opposed to external customer support and stuff like that. People who do that, they are amazing, talented, more power to them. But what I thrive on is, I thrive on those relationships and getting to know my coworkers, my colleagues, and finding out, like I said, what motivates different people. How to work best with different people, and being able to use that and build those relationships. To me, it’s a lot easier when you’re working essentially with the same pool of people day in and day out. For me, internal IT and corporate IT is where my heart lies because of that, and for all the reasons that you’ve said.

Chavarous: Yeah, yeah. I’ve done tech support as well with external customers, and I’m going to stick with this one. I’m going to stick with this one since man, you said it man. More power, and I salute everyone who has to deal with that. I know my strengths and I know my growth areas, and that is one of the growth areas is dealing with those external-facing customers with IT-related issues. That’s a completely different puzzle, man. Completely different puzzle.

Ryan: Yeah and frankly, here at JumpCloud, in a way I kind of get the best of both worlds, because … you’re a customer of ours, and I get to interact with you and other customers, but more on that peer level, and that is … I mean, in a way, that almost feels like cheating.

Chavarous: We can become difficult if you want, Ryan. I don’t want to cheat.

Ryan: No, I’ll take it. I’ll accept it with a heavy heart that I’m kind of cheating over what our customer support team has to do. But I’ve interacted with several of our customers, and it’s great that I get to do it because we can share best practices and commiserate as fellow admins and all that stuff, but at the end of the day, I don’t answer your support tickets.

Chavarous: That’s a good way to put it.

Leveraging Soft Skills in IT 

Ryan: And that’s … more skills. We mentioned customer service. I think that what I would like to see people get out of this episode is, are those people who are looking to get into IT, who are looking to make that change, or step out of the little small business – the one man shop, the little print shop – and move into corporate IT or larger roles is that you have so much more to offer than just what your checklist of accomplishments in IT are. So, you should remember that. You’re bringing a lot of value to the table, in addition to the technical stuff that’s running in your head.

Chavarous: Yes, that is right. You are a whole entire person, with skills, with memories, with things that you’ve consolidated from your entire life. You know, you are a package. I wish someone would have told me that starting out in IT, because I was super green, super green, dude. I started out, my first IT job straight out of college, I was a business/database analyst, super green, and I thought I just had to sit there and work with a database. I had so much more to offer the company, and I sort of pigeon-holed myself into thinking that they hired me to come here and be a database guy so let me just do the database guy. “Let me write a SELECT query, let me do this.” That was my only job that I took on.

It wasn’t until I moved to my second company where they said, “Hey, do you know how to do this? Do you know Excel? Do you know these other technologies?” I’m like, “Yeah, yeah.” “So, do them.” It was only two of us there that worked in IT, and I end up adminning at that point. You know, I told her I was a jack of all trades. That’s when I became a Webex admin, I became a SalesForce and a ClickView admin. I had worked with Microsoft RDS [remote desktop services], I worked with all these different technologies, and it’s because of all the skills that I’ve brought to the table from my previous jobs. I knew how to think, I knew how to sit still for an hour at a time and figure something out.

You’re more than just what you’re doing in that moment. You’re a culmination of your total life experiences. And you can take all of those life experiences and you can apply them to your IT career, and you can do wondrous things, and you can push companies forward. You can design, you can build, you can develop. You may not be able to learn Linux, but that’s okay, because you can do everything else. You can do so much, man.

Finding Career Direction: Should I Specialize? 

Ryan: Yeah, and taking the same philosophy and applying it to your actual technical skills, to your technical knowledge, also works out because I’ve made a career out of being a generalist, out of being the jack of all trades, and IT is one of those industries where you can thrive without having to specialize. There will always be a place for specialists, I mean, there is still a need out there for COBOL and Fortran operating, so, if you specialize, you can find a niche and you can be successful.

But also, you don’t have to do that. You don’t have to feel pressured to go in and be like, “Okay, I’m going to focus on network security, and that’s going to be what I do.” Now if that’s your passion, go for it. I’m not going to tell you not to. But again, when you’re coming into IT, it can be overwhelming because there are so many facets to it, and you may feel like you have to pick one. You don’t.

What interests me most about IT changes constantly. So I may be looking at AWS stuff today; I may be looking at Linux tomorrow. I may be going deep into G Suite administration, or just switch configuration. There’s so much stuff out there, and it may be that at times I have a hard time focusing on one simple thing, but you don’t have to feel pressured to go drive into that specialization at first, or ever. Just like all of your non-technical skills build you as a person, a wide variety of technical skills does the same.

Chavarous: You hit the proverbial nail on the head. You said it, man. You said a mouthful. It does, and I think about that, too. One of the tasks I had when I worked for a non-standard insurance company was to build a way to calculate total for salvaged vehicles, using KBB [Kelly Blue Book], using all these different ways of estimating values for vehicles. I had to build an Excel spreadsheet, and one of my Excel spreadsheets I would import to CSV, and I would always lose my trailing zeroes, and I could never figure it out. And this was before it was so easy to go on Google, I ultimately figured it out. I had to, you know, import it and then format the columns.

Move fast forward a few years later, I had another job where they kept dropping the leading zeroes from a process, and I said, “Hey, do you guys know how to import it using this tool?” And it worked. And minds were blown, and had I never become a salvage adjuster, I may have not known that you had to have that format that could keep those leading zeroes in Excel.

So even that technical aspect of a non-technical job was something that I was able to take and travel with me, and I’ve never forgotten that. I remember that to this day because Excel can and will drop those zeroes off, so you got to know how to keep them. They’re important.

Ryan: Yeah, my thing with that has to deal with the bane of pretty much every IT person out there, and that’s printers, being that I was an IT person in a print shop. But even before that when I was working in printing, knowing that a bad font in a PDF can cause printer errors, or if a printer’s putting out weird fade boxes, the design, knowing that the design of an image can impact the end result, even with things you can’t see – you know, transparency layers are a thing – and knowing that and being able, when somebody says, “Hey the printer is broken, I can’t print this thing out correct,” being able to say, “Hey what’s going on is, this is what’s wrong with the actual file, nothing is wrong with the printer, this is wrong with the file, this is how we fix it, and here we go.”

Chavarous: And bam, now you’re fixing printers for the entire company.

Ryan: So yeah, we could go on and on about this because I would imagine we both have a practically endless supply of examples that we could go through. But I think that we’re running up against our time here, and I think we have … I don’t want to beat a dead horse with all of this.

Chavarous: Agreed, agreed.

Wrapping Up

Ryan: But I think we made some really good points. Anthony, is there anything that you think we should expand on before we wrap things up?

Anthony: No, I think it was really good. It was kind of cool listening to everything.

Ryan: All right, well that’s what I like to hear. If we entertained Anthony, that means we’re doing our job. All right, so do you have anything else that you want to talk about before we wrap things up?

Chavarous: Ryan, don’t get me started. Outside of table tennis, bourbon, IT is my passion. So I’ll sit here and talk forever, man. I appreciate you for having me and wanting to hear what I had to say. Thank you very much for your time.

Ryan: Oh of course, it was a pleasure having you.

So that’s all we have for today. Again, my guest is Chavarous Kennebrew, senior system analyst at IrriMax Corporation. Chavarous, thank you very much again for coming on and chatting with me. It has been a pleasure.

Chavarous: My absolute pleasure, Ryan. Thank you guys very much for having me.

Ryan: Thank you for tuning in to Where’s The Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon. I lead IT at JumpCloud, where the team here is building a cloud-based directory platform that provides frictionless, secure access to virtually any IT resource from trusted devices anywhere. You can learn more and even set up a free account at

About JumpCloud

JumpCloud is a cloud-based directory platform that combines identity, access and device management to get your users the IT resources they need securely, no matter what operating system they use. It’s free to try – sign up today to make remote work happen in your organization. 

About JumpCloud

The JumpCloud Directory Platform provides secure, frictionless user access from any device to any resource, regardless of location. Get started, or contact us at 855.212.3122.