Why the Military isn't Good for Technologists | The Cybrary Podcast Ep. 35
In this episode of the Cybrary Podcast we welcome back Josh Lospinoso, the CEO of Shift5. Speaking with Mike Gruen and Jonathan Meyers from Cybrary, Josh discusses an article he wrote about how the military is a bad place for hackers and what could be done about it.
Here is a link to his original article: https://warontherocks.com/2018/07/fish-out-of-water-how-the-military-is-an-impossible-place-for-hackers-and-what-to-do-about-it/
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The U.S. military built Cyber Command almost a decade ago, but it has disappointed to maximize its offerings to the national purpose. In this episode of the Cybrary Podcast, Mike Gruen and Jonathan Meyers from Cybrary are in conversation with Josh Lospinoso, the CEO of Shift5. They talk about Josh Lospinoso's article about why the military isn't good for technologists. They discuss how the military is a difficult place for hackers because of old-fashioned career management, overpowered time away from technical jobs, lack of goal, non-technical mid-, and senior-level management, and tremendous pay gaps, among other concerns.
Jonathan: Alright. So we want to welcome Josh back to the podcast. I think this is the second, third one we've done and then I think you did a 401 recently so I think we're gonna, we're gonna pick back up this time, kind of talking about, where we ended off and, I think the main thing we kind of ended on was why, why the military is not the greatest place for technologists and so you wrote an article on this?
Josh: I did and
Jonathan: Do you want to kind of give like a 30-second minute overview on kind of like how that went.
Josh: Totally. Yes. So, so I spent almost 10 years in the army. And as you know, Jonathan, there's this weird process of like, you just keep showing up for work, they keep paying you.
Josh: and that's about it so you have to like submit this paperwork. It takes about a year to get through. As part of this paperwork, you have to do a counselling with a very like senior officer. In my case, it was like a two star General. And he said, look like a lot of you are leaving, like tech, technologically proficient officers are leaving the service, like why? And I explained, he said, do you think you could write up like an article for me? And, and so that was the Genesis of fish out of water. Why the military is an impossible place for hackers.
Mike: Did you have any problems getting that published?
Josh: I did. So, so, the military has the army. I think every branch has something like this has an office called, public affairs, public affairs office, where you have to, anytime you want to do external kind of engagements or publish an article or whatever, you have to go through PAO. I won't say there were being obstructionists, but, they were, it was a really rigorous screening. We'll just put it that way. It took probably six months to get that article through PAO. Yeah.
Jonathan: Were they just ripping stuff out?
Josh: Yeah, there were some, you know, there were some, I mean, the, the primary thing is really for, for classification issues. But they went through like, a lot of passages that were not, it wasn't so much about classification. Let's just put it that way.
Josh: You know, yeah, I mean, the tough, the tough thing is, is, I mean, this is a, this is a really sore subject, you know, no one, no one wants cyber commands to fail, right and it's hard to get criticism like to be on the receiving end of criticism. Even when, you know, even when it's productive. So, you know, I think it was understandable, but honestly, like the PAO's job is to defend, you know, the interests and the image of, of, Cyber command and to their credit. I mean, once kind of like very senior officers got involved and there's one in particular who's pretty awesome. TJ White who's a three-star Admiral now in charge of, fleet cyber. He was like, look, this, we have to get this kind of discussion out there because while it's hard to hear, we're not going to get better unless we, we critically like inspect ourselves and try to, try to fix it.
Jonathan: So yeah. So what was in that decision in the article.Yeah like what was the sort of crux of it?
Josh: Yeah. So I mean, the, the biggest issue, in my opinion is the antiquated promotion system. That's just, you know, the essence of it. So basically, this is, you know, Jonathan, you know, a lot about this, obviously. You're, you're kind of like once you get stamped with the group, you start on this conveyor belt where basically there's this 25 year career that's laid out in like exquisite detail. And you're supposed to hit all of these key jobs that you have to do. You have to go to certain schools. You get rated by someone who only sees you a couple of times a year. And it's, it's designed basically, so that you're this like replaceable cog in a machine, that makes sense. Which makes a ton, I mean like, you know, if it's an infantry unit and you're, you know, you have a platoon leader that gets hurt in combat or rotates out or whatever, you want to be able to plug a new person into that role and they're just like off to the races right away, right.
Josh: So it makes, it makes a lot of sense at an organizational level but
Jonathan: Ginger, you're rotating, you're rotating a lot. So like they're rotating people like very regularly, like you had the military moves so like in the army and that's every, like two to three years, you move on to another job cause they're trying to get you this like general like knowledge and experience in a bunch of different roles so that as you work your way up and you're making decisions like you have that kind of knowledge,
Mike: context, yeah.
Jonathan: you can make decisions like in smart and smart decisions. So yeah.
Josh: Totally, I mean, the way I've heard it explained is you basically, like every Lieutenant in the army is being groomed to be the next joint chief of staff. Right? Like they're trying to give you those experiences so that when you make it to the tippy top, like you've seen all the different parts of the organization. Yeah. So it, it might be fairly obvious why that wouldn't be conducive to like people that are either really high performers. Or, have a career that by its nature is much more like individual contributor, or leading like a small team of individual contributors and so this is kind of the crux of the article is explaining, I mean, A lot of it was what I felt, but it was really a composite opinion of so much of the conversations that I'd had with technical people, especially in cyber command, but also in other fields like Jonathan, you know, is a super technical guy and like the army, certainly wasn't gonna keep him in. And you know people in military intelligence or signal core, they feel that, that very, very similar kind of, just stifling environment. It's very difficult to, to excel in.
Mike: So in the private world
Mike: as you there's, I mean, this is more true a long time ago and things have changed a lot, especially on the technology side, but it used to be this idea that the only way to advance was to begin managing people, right, that like you couldn't stay super technical on a super technical track and, and either be team lead or whatever it was independent contributor. And I think that's changed a lot in the last, you know, 10 years plus, and a lot of places, but there is still some companies that probably still have that more like oh if you're not moving up in management you're not moving up in a way. Is it sort of similar to that in a lot of regards where
Josh: Very similar.
Jonathan: Yeah, I think the easiest comparison is if you think about like pilots, like as you start getting higher and higher in rank, like you fly less and less and less and so there's just not that path to kind of, especially like as an officer, you can't really say like, no, I just want to keep flying. Like, I don't want to manage people. It's like, you're lumped into the whole group cause all officers are like generalists. And so you're just lumped into this big old group and so you can't keep flying unless you resign your commission and go be a warrant officer, and then it's like this whole other like, path that you've now taken on your life and it's, it's very, like, that's not the easiest thing to do and not many people like, successfully do that. It is common but not and so I'd say that's probably the easiest way to kind of draw that conclusion. Or that similarity, I guess. So but yeah, I think that's, I think they're trying to change it, but it's still, it's still like difficult because it's such a large organization and so how do you give everybody kind of like that fighting chance to be able to succeed and like, how do you make these broad brush strokes? Telling people like what their career is? Right. Cause a lot of people going in, they go into the military because they want that structure. That's like, Oh, do step A, B and C, you will be promoted and I think in the private life, that's not always the case, especially in technical roles. I think it's very difficult to tell people kind of how to become security analysts 2 versus security analyst 3 and things like that and so I think it's like this weird balancing act, but the military does, I guess, differentiate between like technical roles and not technical roles. They don't have this idea of like the officer. They have the idea of like the warrant officers, but it's just not to the scale. I would say Cybrary has made it very apparent that it's just not to the scale and it kind of needs to be it's like, I guess it would make sense if cyber command was all warrant officers and everybody can just be technical experts in their field and never have to worry about anything else.
Mike: Can you take a step back and just explain to me, like, what a warrant officer is cause not military.
Mike: Yeah. Josh, go ahead.
Josh: Yeah. So I think they have, I don't know when warrant officers began. I think it might've been either Vietnam or like they've been around for awhile but essentially, the path is, is generally that you spend some time enlisted. So if you go to like a recruiting center and you're like, I want to join the army and then they like send you to bootcamp, so you'd spend some time enlisted and then you pass certain qualifications that are like pretty tough, you know, you have to do pretty well and like your physical exams have good reviews, I believe that there are college requirements now maybe like an Associates degree or something like that. You go through this, you go through this selection process and you can become a warrant officer, which like rankwise is like somewhere between being enlisted and being an officer. And the original intent of warrant officers is that you can be an individual contributor, that is like somewhat elevated over your, you know, former enlisted peers. And that you can focus on being like really good at one thing and so you see it very often, for example, in the aviation community, and cybrary you'll see it sometimes, but like, in military intelligence, like certain kinds of analysts who will spend 15 years focusing on a particular region or something could, could be, like a warrant officer.
Mike: Interesting. So I think there's also a base premise and maybe on what we're talking about, which is this idea, that. The army has to use military personnel to fill these roles as opposed to trying to come up with other ways to maybe do it.
Josh: Right. Right.
Josh: Yeah. This is a huge problem.
Jonathan: And it's, I think one of the bigger problems, I guess that's been highlighted recently is like, say take the signal Corps. So the Signal Corps is traditionally all the communications infrastructure that the army has like, it's all run by the Signal Corps and I think somewhere along the line in the last, like 10, 15 years with all the Wars and conflicts that are going on, they've kind of outsourced all of that technical ability to contractors and so you kind of lost a lot of that, like core technical knowledge, in that branch and so it kind of leaves like a bad taste in everybody's mouth these days, because you're just like, well, all these people that have gotten 10 years in the signal Corps don't really have any technical skills cause there was always a contractor that was basically given a document that's like, here's your contract. You can do this, this, this, this, this, and nothing else and so you don't really have that kind of like ingenuity or people like going the extra mile or like trying to learn on their own. You have people that are just doing exactly what's written on that piece of paper and those are the people, the active duty people are in charge of and so it's like a very different type of problem that I think has kind of highlighted some issues.
Josh: And, and not to mention, so it's, it's bad for the contributor because they are sort of like under these very rigid contractual engagements, but it's also really bad in my opinion for the person in charge, because like, yeah, we've talked a lot about individual contributors and how important it is to have them, and it certainly is like to have attracted people to, to get paid the same and, and, and have like increasing levels of of, prestige associated with their, with their expertise, but also it's important to have people that do decide to go into management. Like having been there, done that, or at least have a really strong intuition for what the technical nuances are, because otherwise it's just like, why are you in charge? Like, you know what I mean?
Mike: Right, absolutely.
Josh: Like I have to explain all this stuff to you. I have to give you my recommendation and then like, why are you in charge?
Mike: Right, what value are you bringing to the table?
Josh: What value are you bringing? You're just a middle man between like the ability to make a decision and the people that should be making the decision.
Josh: And so you ended up with a lot of that too, which is, which is super depressing, right?
Mike: That's the nice thing, I guess, going back to the sort of private industry, right, where you actually have that ability to branch off at those companies that do recognize that like, Hey, a super technical person, architect, whatever you want to call them gets, you know, that's the equivalent of manager, director, you know vice president is sort of from a pay scale responsibility, prestige, if you want to call it that, whatever it is, and that they're staying, they're not necessarily managing people, but there's also this other track of, Hey, you know, team lead, you know, and then going more down a management route, and being more of a technical manager.
Jonathan: I could see it would be very difficult in the army.
Jonathan: Or if you think about like, product management, right? Like a lot of the bigger tech companies
Jonathan: Require you to have a technical background to kind of do that and it's like, Oh, if you tried to do that in the army, there'd be nobody, there'd be nobody in charge and so now you get those weird giant disparities as you're getting promoted, which I think is probably another one of your bullet points is like, how do we get that kind of institutional knowledge up to the level of the people actually making the decisions?
Jonathan: And you can't do that overnight.
Mike: So, and you were talking about before, right? So you have generally, the idea is everybody is doing these sort of, tours through different roles. So that when they are joint the joint chief of staff or whatever, they have done everything, which also implies then that they're going through some of these more super technical places and have
Mike: really no business being, I mean, like whatever, like, I don't want to disparage anybody, but there's certain roles I would not be very good at and I assume there's some people that would not be very good at my job.
Josh: Being in charge of a hospital
Mike: Yes, that would be bad.
Josh: or a surgery clinic or something. Right?
Mike: Right or the army car or the Corps of engineers.
Mike: Like I would not be good at building actual things. They would fall over and we'd say, Oh, let's just iterate to success.
Jonathan: It's agile, G.
Mike: It's agile, agile construction that's what we're doing. We're just, we'll get this bridge right eventually.
Jonathan: We'll fail fast, you know
Mike: So anyway, sorry. I sort of interrupted in there, so yeah. So I can also see why that would be problematic because you have these people going through who don't have the technical.
Josh: Yeah, I mean, the model works for certain kinds of fields, right? So like you think of, you know, I was in the infantry for a little while and like, most infantry officers go to razor school right and there's a reason for that. It's not because you need or how to like, you know, fire a machine gun or like rock with a hundred pounds on your back. Like those aren't management skills, but like, they give you, they give you an intuition for what the people that you're in charge of go through and like what the kind of associated problems are. It gives you like a visceral feel for it and like, I would argue, you know, mastering the nuances of software engineering is a lifetime endeavor, whereas like understanding generally how to do like dismounted platoon operations in the woods takes you like a couple of months and you've got it pretty much I mean, of course there's like, you know, a lot more nuance to learn, but for the most part, like you've got a pretty good intuition for it after
Mike: Are we still doing mounted or do we still have horses? Are we still
Josh: Yes. Well, they're vehicles which as I don't know if I've told you, but you can hack these things.
Mike: Yeah, I think we've talked about that before.
Josh: but a plugin. Yeah, so, so I mean, I think it's just, the system was designed for a different kind of technical expertise. You know, for, for, for combat arms and it just doesn't map well to, to the super technical jobs but somehow, I mean, I do, I do have to, there are some like real Patriots, some of our, our cohort, you know, Jonathan and me,that have decided despite all of these problems just kind of grin and bare it. And so I am hopeful that there will be some really technical people that somehow, you know, they, they latch on to the service aspect of, of what they're doing or are they, they see a deeply like flawed organization and they have just like this irresistible urge to stick it out and, and, and over the long term and fix it. I mean, I, there are, there are a lot of people working their way through the ranks now that are, you know, majors now in the Army's like, you know, kind of middle management
Jonathan: Middle management.
Josh: Yep, that are, that are, they're working their way through. So I'm, I'm hopeful that things will change.
Mike: Right and so also one of the other bullet points, before we shift off of talking about the military and one of the other bullet parts from the article, and I think we started touching on it last episode was what makes it good. You know, military, what infantry, whatever it doesn't necessarily translate to what makes a good technical person in terms of physical skills.
Josh: Yeah. I mean, the analogy I used in, in the, in the article was, you know, like the Venn diagram of people that can run a 15 minute, two mile and like dissect a Windows kernel memory dump is like, okay, it might be a couple of people, I don't know. It's like, it's like vanishingly small and so, you know, one of the questions we, we, we grazed on a little bit earlier was like, do these people, you know, the majority of this workforce even need to be in uniform and so, you know, for, for defensive cyber operations, I'm not even sure that there's any meat besides like deploying someone to a combat zone. Although we do that for contractors all the time now. There's this one little like bastion of holdout, where we're unwilling to like have non-uniform personnel operate the keyboard and that's like, whenever there's some sort of like destructive purpose to whatever we're doing in the cyber domain and everything else, though, pretty much we're comfortable with having civilians do and so there's, there's this really open question of besides making sure that you have a cadre of people that have a really strong understanding of who they're in charge of, like, why do we even need to be doing this AD under the auspices of the military anyway, is, I mean, it's an interesting question. I think there's, there's, there's points to both sides, but I don't know.
Mike: Is there anything to relaxing the rules for certain roles with regards to like the physical requirements?
Josh: There's a lot of discussion about it. There's a lot of discussion about it and, you know, the, the arguments around this, like order on like kind of religious
Josh: You know what I mean? Like people are there's every year there's like a state of the cyber forces. Where, I mean, I remember a couple of years ago the, the head of Marine, Mark Forsyther, the Marine general, you know, was reporting on some of the real difficulties they're having in retention and then, and one of the Congress people asked like, okay, well, what do you think about like re, you know, reducing some of the military requirements for like pull ups,
Josh: For example, or whatever and she just like, snapped to attention ever since, she's like, all Marines will do pull ups, you know, and I was like, okay. Alright. Well, you know, you're kind of bumping up against the physical issue, you know, like
Josh: laws of physics issue here. So, you know, you make your bed.
Mike: Is it, I mean, maybe it's not, I mean, maybe it's just another branch, is that like, that doesn't have those physical.
Mike: I don't think that the Air Force has the same physical requirements that say the Marines.
Josh: Yeah, they don't, they don't. Yeah. So, I mean, there's, there are a lot, I mean, among, kind of our co cohort, a lot of people may think that that makes a ton of sense.
Mike: So we'll have the space force and we'll have the cyberspace force
Josh: That's right. Cyberspace for us and then the Cyber air force and then, I mean, there's just going to be so many
Mike: Just goes on from there.
Josh: Yeah, I've always just wanted to wear a star Trek uniform. So
Jonathan: I think if you've kind of made it it's own branch, then you can fill billets in the other services, by people that are able to fill
Jonathan: said, billet, right like, oh, there's three people that can do pull-ups, cool, send them to the Marines.
Jonathan: As their tour, like that's, you're the attache to whatever cyber in a Marine unit. Right? Like, it's just like. The air force sends their weather people out to all these different, like artillery units in the army.
Jonathan: Like the army doesn't concern themselves with whether the air force sends people that are then attached to that unit to do all the things. So I think that that's an interesting
Jonathan: way of kind of how to the force that
Mike: Cool, we've solved the problem.
Josh: Look at this, 30 minutes and we solved it. They should put us in charge.
Josh: Just have to wait 30 years. That's the problem.
Jonathan: Right. Yeah, our year group won't, won't be eligible.
Josh: Yeah, we won't be able to until like 20
Mike: Speak for yourselves, fellas.
Jonathan: Yeah and then I think, just to kind of wrap it up. I think they are kind of making strides in the whole, like how you apply for positions now. I think they finally started to get that under control cause I remember when I first got in. My undergrad was in Information Technology with like a very heavy emphasis on, Cyber Security coming out of West point. But the army didn't want to put me in that role. Cause I was, I was branched a logistician and so as the army cyber command got stood up and things like that, like I tried to transfer in and they were like, sorry, we don't have any spots for logistics officers and so I was like, well, my undergrad's in this like I had all my professors write letters of recommendation and everything, and they were just like, sorry, in the computer system, I can't put your logistics identifier in this spot and so, so you started going down a completely different path.
Mike: So I think you should have hacked that so that they could
Josh: That was a test actually.
Mike: I think that would have been your way.
Mike: Yeah. That was a test and you failed.
Josh: Yeah, you failed.
Jonathan: It would have been a very easy system, the encode system would have been very easy to break and so, but I don't think they would have taken it very lightly and it probably ruined my career and thrown me in Leavenworth.
Josh: I do have to say so I had recommendation, in the paper that the cyber force take like, some cues from military medicine. I think that was a bad recommendation actually, after some, after some like reflection on it. So
Mike: but you have no experience with the Medical Corps, right?
Josh: Yeah, Yes, Yeah, exactly.So, so my wife is, a physician, in the military she's still active duty and it's awful. It's just absolutely awful. The, the hospital doesn't, you know, military medicine is undergoing this like upheaval right now where they are essentially trying to assign all of the physicians to combat units so you'll have a cardiothoracic heart surgeon who will be assigned I'm, this is not an exaggeration. I will be assigned to like the 82nd airborne division. To go and report to like jump out of aircraft or go to jump school. Because the attitude is, if you can't deploy in service of the nation, why are you in uniform which there's like some merit to accept all these military treatment facilities are super underserved by, by physicians and so we can't have your cake and eat it too. You want someone to be a, you know, someone capable of doing a quadruple heart bypass? And also, you know, handout
Mike: To move and communicate.
Josh: You can move and communicate, you know, jump out of a C130. And you're stuck in a very corollary position to where most of the cyber force is today where, you know, Kernel Rppt Kit and two mile, or just kind of oil and water.
Mike: Not to mention, I think on the, not to go too far straight, but not to mention most doctors don't really like the idea of shooting people. I feel like that sort of goes against some of their principles.
Josh: Yeah. It's certainly not part of the Hippocratic oath. Do you no harm, you know, I think, yeah, they're, they're a really bad place. Military medicine is in a really, really, really bad place. Like the, the survey, the annual survey that goes out is just like abysmal; their retention numbers are absolutely horrible. The only way that they manage to keep people in very similar to in the cyber branch is through these service obligations, which is. I mean, it sounds a little harsh, but it is the only legal indentured servitude that still exists in the United States. So every other contract that you make with anybody else in your life, you can basically pay your way out of, there's always like, like monetary kind of component that you can, you can get out of it. You can't get out of service obligations. So basically they, they view this as a retention tool, just basically locking people into their jobs and it has caused just abysmal. Abysmal. Morale.
Mike: I was gonna say, I'm sure it really helps with morale. I'm sure.
Josh: It's awful.
Mike: We're actually instituting it at Cybrary. I'm training people to death.
Josh: Yeah, you can. Right, exactly. Yeah. Yeah. So yeah,
Mike: COVID, Since it's, COVID, we're doing, I'm training them at home. They get chained to their desk at home. It's, it works out pretty well.
Josh: Right, right, right, right. Yeah. Yeah. so I mean if I had to change one thing about the article, it would, that would be, I tried to be constructive and like, think of, you know, a solution, and look, look to a model that that may maybe was working and, and I definitely picked the wrong one there, so I don't know. We'll have to rethink it.
Jonathan: Come on. I don't know what else you could pick?
Josh: I don't know what else you could pick.
Mike: What about Jag core or whatever? For lawyers? I feel like that's a very similar,
Josh: I think
Mike: I often think, I often think that lawyers and software engineering very, very similar
Mike: with esoteric language, both either trying to build a contract that can't be broken or trying to figure out how to break a thing that's already been written.
Mike: So I feel like there's a lot of overlap there. Yeah. I don't know what the retention numbers look like in JAG. I do know, like one of the positive things people say about that is, you get to practice a lot of criminal law. I don't know what that says about the army, or like, like trial law, you know, you get to do a lot of
Mike: Yeah, probably trial a law more than just
Josh: Both. So, so yeah, so, I mean, there are some unique experiences I think, and I've heard some generally good things. But I don't know what the retention numbers are. Jonathan, do you know?
Jonathan: Well, I mean, I know people that went in to be lawyers like a couple of years ago, but I'm so far removed now that,
Jonathan: I mean, I guess they're still in but like, it's, it's a lot different, I think for legal because every level of unit in the military has a legal team and so because like, say the lowest in the army, like company commander is like the legal guardian for all of those soldiers. Like you're legally responsible for all of them. Like you have lawyers at that level that are like your counsel.
Mike: Well, my brother in law, so, sorry to jump in, but my brother-in-law lawyer who was with the 82nd airborne. I don't know exactly the, you know, we've never really talked about his military experience as being a lawyer, but I know so clearly there's, there's a difference, right? He's actually part, you know, he was until he retired, part of the 82nd. So. Why?
Jonathan: Yeah, yeah and so you have them at that lowest level and they're being used.
Jonathan: Right and it's very, it's like, everybody knows what a lawyer does like nobody's trying to make them do other things like it's very accepted, but I think the problem with like cyber and some of these more like doctors and things, it's like, they don't, they don't live at that echelon of service. Like there there's so many levels up that it's like.
Mike: Right and they're not as embedded
Jonathan: Right, right because like I mean, the closest you have, I think would be in the medical is like your tiers of hospital but even then it's like, there's a line that's like, oh, if you need anything, that's like cutting you open, like they're flying you somewhere else. Like they're not
Jonathan: Doing certain things at certain levels.
Josh: Yeah you'll have like the flight surgeons and things or like flight docs in the air force. The problem is, is it's you're, they call them like general medical officers. So you're not required to have any advanced training beyond medical school to do that job and so for something like my wife is a dermatologist and for her, like that takes years and years and years of training, it's very specialized and she has to practice in the clinic a lot to keep up on her, on her skills and she's out like giving booboo, bandaids, you know, at, at JRTC or something like she's losing all of that training on the dermatology side and so there's this real schism or like dissonance between what she does most of her time at like the hospital running a dermatology clinic. And like what you would do out in the field with the 82nd airborne people like sprained ankles and stuff and just standing out Motrin.