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Transitioning from the Military to Private Sector Security Careers (podcast transcript)

Greipp: Welcome to Security Career Cast from ASIS International and University of Phoenix. Career Cast features security industry leaders addressing the latest risks, trends, and demands that face today’s security professionals. I’m your host, Jeff Greipp, Vice President of Apollo Education Group.

And I’m speaking today with Lieutenant Colonel Jim Reese, Founder and CEO of TigerSwan, a major security services company, and Major General Spider Marks, Executive Dean of the College of Security and Criminal Justice at University of Phoenix.

Our discussion today is on transitioning from the military to private sector security careers. Thank you both for joining security Career Cast.

Greipp: Gentlemen, welcome. Today we're gonna be talking about transitioning from military to careers in security. And both of you had distinguished careers in the military and successfully transitioned into business and in security. So I wanted to talk to you both a little bit about your career pathways and recommendations you'd have for individuals that are making the same transition.

So I wanted to start with you, actually, Jim. You've had a successful career in the military, very successful business in private industry security, and I wanted to find out a little bit more about your career pathway.

Reese: Well, Jeff, you know, I'm probably a little bit outside the norm. You know, I went to college, and I dropped out of school, to kind of find my way, which most people have these things these days.

I enlisted in the army, and I thought I was only gonna do that for four years and then go out and go to law school and go to Wall Street. And that just turned into 25 years of just an incredible —you know, an incredible time.

I was a noncommissioned officer. Then I became an officer. The army sent me back to school, but then as my career started winding down, I knew that—okay, what am I gonna do next?—cuz I was still a young man, and I had a—I had a good way to go. And, what I did is I took a lot of the skills that I learned in the military—and I just started building a business plan on: what could I do on the outside world based on what I know? And at the end of the day, it really is helping people and secure people's places and things, that I was doin' all those years in the military, and I bring that to the commercial world.

Greipp: General Marks, did you have a similar experience when you were making this transition?

Marks: Yeah, absolutely, and I think the key thing in what Jim described is fundamental to success in any type of a transition like that. I think it's important that you reach out and you touch mentors. Those that you've served with before.

I did the same thing when I was departing the service. I reached out to those that were very, very helpful for me when I was in uniform and helped me guide a path and kinda create a path. Now realizing that as you build that path, you're building it as you're walking along it, and there will be cul-de-sacs, there will be adjustments, and there will be paths that you didn't anticipate. And that's what's happened—in your life and in my life as well. So I think the key thing is you remain incredibly intellectually flexible, but move along a path that you have confidence in and you know you can immediately make some adjustments, and you can immediately make a difference along that particular avenue, and then play it from there. But I think it's important to have folks around you that can help you along that journey.

Reese: But then a caveat to that, too: you can also have too many advisors or conseillers that are out there. And what you have to do is you have to really start asking yourself as you're gettin' ready to transition, you know, "What is my plan?" And I have former soldiers, sailors, and marines in my office at least a couple of times a week, and the first thing I say to them is, "What do you want to do? You know? Not what, you know, the army wants to you do. Not what the navy wants you to do. What do you wanna do now for you and your family?"

Marks: And also all those people that are whispering in your ear. You know? That might be a lot of noise. So really narrow that down and focus in on those that you really wanna listen to. You're exactly right. You could have—it could be a cacophonous kind of a crazy amount of input you're getting, and you've gotta be able to focus that in, and define what is core to you and what motivates you and what you're passionate about, and then step confidently in that direction. But you've always got your hand on somebody who's been there before and can help you.

Reese: Right. Yep.

Greipp: You know, the whole security industry started—it was after World War II. It was really actually returning veterans from World War II who really started private industry security, and that whole transition—career changes remains today. What is it about the skills that you pick up in the military that's still relevant to private industry today?

Reese: The bottom line is folks coming out of the military have an operational skill. I mean that's the bottom line. They—you come in the military, whatever service it is, and there is a need for security. You gotta secure yourself. You gotta secure your teammates. You gotta secure your ship. You have to secure your base. So there's that fundamental aspect of operational security, what we call, in TigerSwan, brilliance in the basics. Okay, so what are the basics? We have these, and once you have those basics—and that's what all, you know, military veterans have. They have good basics of study of an operational security background.

Now, where do you take that to the next step, getting to what we would call in the military kind of the operational or strategic phase? And that's what, dependent on what level you come out in the military—you know, if you come out as a sergeant or a staff sergeant or, you know, or a captain—a midgrade person, you're gonna have to take certain skills and move that to the next level. If you come out as a general officer, there might be some skills that you need to literally step down to, because you've been up at this level, but you're walkin' into somethin' brand-new, so you might have to step down a little bit until you start to understand the new operating environment that you're in.

Marks: There really is a handshake between what you see in the military and what you see in business in terms of what we call in the military forced protection, which is always job one. You can't do anything in the military if you don't have the capacity to execute those tasks. That means you have to preserve your ability to execute those tasks. And people are trying to get after you. People are trying to degrade your capacity. So that's what we call forced protection. That's always job number one for every military organization wherever you are. You must have an awareness of where you are, what you're doing, and what your threats and vulnerabilities are so you can address those as a first step—so that's the security part—before you then step off to do what it is your primary chore is. So fundamental, the basics, the foundation for everything you wanna try to accomplish, is what we call a form of security. And that's either physical security or that's information or intelligence security—all those kinds of aspects.

Just 10, 15 years ago, organizations had multiple security officers. You had a physical security officer. You might have an information security officer. You might even have a document security officer. All that has been conflated over the past number of years. We now have chief information and security officers in the form of an individual.

Years ago, that might have been three or four folks. So this has really grown. This market of security in industry has really grown and been incredibly relevant, and I would tell you the roots of those, as you've described, Jeff, go back to how we have evolved as a military as well. And, oh, by the way, we've had a pretty robust amount of experience over the course of the last 20-plus years—in terms of both conflict zones and combat zones. So we've been able to adjust how it is we go about the business of trying to define security in terms of executing our military tasks so there's immediate relevance into industry as well.

Reese: And, Jeff, I think the other thing that's important is every military, whether they're enlisted or officer, if they transitioned out, one thing we all know how to do is a risk assessment.

Where we have been drilled into us: what's the risks that are out there? What are the vulnerabilities? Assess those vulnerabilities and risks— and, you know, mitigate and manage those and lead your way through. Which, a lot of people, you know, in the security industry, you know, what I call the kind of the commercial or civilian side—they've never had that baseline. And, again, as a young soldier, seaman, marine, or airman, that's driven into you from day one. Look at the risks. You know, when you're comin' out of the barracks or PT in the morning, there's a risk. The weather. You—and you're forced early on, at a young age to make those assessments very quickly, which is what the commercial world is asking you to do—is make an assessment. How do we mitigate that risk to take away our exposure?

Marks: And the key to a risk assessment is you have to include your boss. If I'm going to assess risk and I'm gonna go to my boss and say, "Ma'am, I think we have some issues here. I can handle these numbers of issues. I have a couple of issues right here. I need your endorsement, and I need resources that you have access to."

So I can get about the business of mitigating. So risk is really a continuum of the acknowledgement of that risk from the lower individual to the top individual. Everybody's gotta sign off on that. So everybody who's in this organization has to be involved in what we call security. It's not simply the purview of the security officer.

He or she is responsible for what I call the functional requirements, the technical requirements. Whether you get about the business of really addressing those and mitigating those risks—that's a leadership challenge. So it really is a matter of being schooled in the nature of security and understanding the very broad and evolving nature of security but also having leadership involved in that discussion and in those decisions that are necessary to mitigate and get about the business of doing what you're really there to do.

Security is an enabler. It allows you to be more aggressive in terms of what you're trying to accomplish in business or in the military.

Greipp: Right.

Marks: If I've got a good security posture, it's almost limitless what I can try to do. I don't wanna just be secure and stagnant and achieve stasis. I wanna be secure. That allows me, with confidence, to move in a whole bunch of different directions and can bring value not only to my military organization but to the bottom line of this industry that I'm a part of.

Reese: And, Jeff, here's a great vignette. You know, I retired from Delta, and when we were in Baghdad in Iraq, we got to a point where we, the operators, got so busy that I had to turn to our support troops—okay?—our cooks, men and women that literally came in the army to be cooks. And I—but, here's the beauty, and this helps them in the transition to the civilian world, the commercial security world—is I turned to them and said, "Hey, I need you to secure yourself, secure your transportation. Alright?"

And they had to start making runs down the you know, Route Irish. They called it the most –the Highway of Death, the most dangerous highway in the world for a long period, and maybe even today still.

Marks: Sure.

Reese: And—

Marks: Unfortunately.

Reese: - because we didn't have the assets, and so we had our cooks. But they understood the fundamentals of security, safety, risk mitigation. And then, a couple of days later, here's our cooks goin' out with their gun trucks, movin' food to other places, and they're doin' that operational security job.

Marks: They're doin' their jobs.

Reese: Right.

Marks: Fundamentally, they're doin' their jobs. But they're adjusting to their environment.

Reese: Right.

Marks: And that's what Jimmy's sayin'.

Reese: Yep.

Marks: It's an assessment of that environment. I've had—I now have increased risks. I acknowledge what that risk is. I can delineate what those elements of risk are, and I can go back to my commanders. I can go back to my brothers and sisters in this organization and say, "Here's my recommendation in terms of how to adjust." What you just described is a perfect example of "I fundamentally must continue to be able to do my job—irrespective of this environment."

Greipp: Exactly. Let's talk about that adjustment. You know, both of you have been very successful in business and security and education, and you talked about that conversation you'd have with the soldier.

What would that conversation look like today with the gaps we often see in security professionals and making that transition? Are there common gaps? And what would that advice be to that soldier today?

Reese: There's three things that I talk to everyone. We're gettin' ready to hire a brand-new former Green Beret lieutenant colonel comin' in, and we just hired a couple of former NCOs, and there's three things I’d tell all of 'em.

First and foremost, number one, is they have to learn now a new culture. Right? They're coming from a culture in the military that is driven. It's all about success, it's all about mission, and it's all about gettin' the things done, and it's getting it if you have to work 24 hours straight. There are some places in the commercial world that can be a little intimidated by that. So just like us goin' to Afghanistan and Iraq, we had to start to integrate with the Arab culture and the Afghan and the Pashtuns. And we weren't very good at that—when we first got there. And we had to learn, and we had to un—because we're walkin' into their field of dreams, per se. So that's what I tell 'em. I say, "You need to sit back, you have to make an assessment, and you have to now learn to integrate into their culture a little bit. You're gonna bring your post—your former culture, but you need to also to integrate into that." That's number one.

Number two is you have to be a good written communicator. People don't write well these days, and it drives me crazy. And I tell people, "Take a class. Go back to school. Go to creative writing."

Marks: Composition 101.

Reese: Composition 101. I mean it drives me nuts. I mean just talkin' in that active voice and literally—I literally, when people come in to hire—or to come in with, interviews at TigerSwan, we ask them to bring a documentation, some type of example of a written—what they've done—so we can look at it. And that's part of our coaching and mentoring at TigerSwan, is we really start working because it's very important in today's Information Age. There's so much information out there, and some time you can't get face-to-face with the boss and/or the client. And so you need to get that out. Something needs to be written. That's number two.

Number three is leave your ego at the door. Okay? Like General Marks said, the military has been in conflict and war zones now—and the conflict we're talkin' about is really Bosnia, like Balkans, and some other little, small things there, but 20 years now. There's some great operational experience out there, but that operational experience is just—it just cuts a very small slice of what the commercial world is, is understanding budgets and cultures and technology and the asymmetric approach the commercial world has to take at security. So I tell people, "Just leave your ego at the door. Don't be afraid to just kind of step down a little bit so you can understand this whole new world you're about to get into because, of your skills, you will immediately jump in, but if you walk in and say, 'Hey, you know, I'm Jim Reese, and I retired from the Delta Force, so I demand this,' you're gonna have a lotta people say, 'Have a good one.'"

Marks: You know, we spend our life in uniform adjusting to a whole bunch of different environments. That was mission number one wherever you had to go. What we saw in Haiti, what we saw in Central America, what we saw in the Horn of Africa, what we saw, in the Balkans, what we saw in the Korean Peninsula, etcetera, and what we saw in the Mideast and in the Levant—those are strikingly different environments. Yet you can serve and you can excel in each one of those environments, which means when you plop yourself down, what does this environment demand of you but won't fundamentally change you? So what are the gifts that you bring to the table that can be modified and adjusted so that you can be successful in this environment. And that really is a skill set that, in the military, I think every soldier, irrespective of rank, has that capability to an incredibly high, very well refined level. As they make the transition into the civilian world, into the private sector, sometimes they lose that. I mean that's my observation. It's very difficult—to your very last point—it's very difficult in many cases, Jim, for folks to, acknowledge that their contribution in this new world that they are—their new world—a world that's been in existence forever and ever and ever. You're the stranger in this new world.

Reese: Right.

Marks: But it's so different to you. Often, folks look in the rearview mirror and kind of imagine what they were before and how they're now going to fit. You've gotta leave that, but hubris must be completely washed away so you can get in there and say, "Look, I wanna make a contribution. How can I best make that contribution? It may not be exactly what it looked like when I was in uniform.

Reese: You might be comin' from some of the greatest military organizations in the world. You might have, you know, been the command master chief of a nuclear sub, you know? But now you're walkin' into somethin' else. Just understand that—just kinda back and start workin' your way into this new environment you're in.

Marks: You know that really is a really good point because it acknowledges if a service member can really take that next step and be successful. But I go back to, fundamentally, everybody has gifts, and those gifts have to be realized irrespective of where you are. They're not necessarily—those gifts are not tied to a title. If you leave your title at the door—to your point—

Reese: Right.

Marks: - you're gonna be far better off.

Reese: Absolutely.

Marks: That command master chief in that nuclear submarine had gifts that he was able to galvanize this crew for incredible amounts of time underwater, close quarters, immensely tough mission sets. So what does that mean? It has nothin' to do with bein' a command master chief. It has to do with being a good leader, understanding human nature, being able to carry on a private conversation, being able to do the heavy lifting when somebody else should be doing it but they're incapacitated for some reason. "I can lend a hand, and I can do the jobs that must be done."

Again, you leave your title at the door. It doesn't matter. It's amazing. And that's what you see. You see that in business a lot, too. You know, you see late nights where the CFO herself is there helping with the proposal. You see the general counsel—who's there ensuring that this bid is going to fairly be represented and is not going to put the firm at any kind of risk. It's not based on a title. It's based on a skill set, and they realize, "I must contribute in this way."

Reese: And you know—and the other thing, too, is people from the military have to realize is the private security industry has a large number of workers out there that have never spent any time in the military—or the law enforcement. They go to college. They get a degree, and then they walk out and they—they work an internship somewhere. And then they might go work for the federal government or—and all of a sudden they might be director of security, chief security officer for X-billion-dollar corporation. So they have just taken a different route.

Marks: So what you're really saying is that the security business, not unlike a number of different verticals, is there is a real requirement to address skills and gaps—

Reese: Absolutely.

Marks: —as you progress through the professional development requirements, the continuing education requirements, the personal requirements to go get that next degree to ensure that you are not only broad and have a very strong foundation as an educated professional, confident in what you're doing, but also the very specifics within the field. The security field is growing.

I mean as we were talking just a few minutes ago, who would've guessed ten years ago that there would be this immense—growth and demand for these chief information security officers in these monster corporations, single point of contact to protect every security issue that exists in that organization? Didn't exist.

The security world right now is not a whiteboard, but it's a whiteboard that's filling up. We still don't know what these job positions are gonna look like, what the demands are gonna look like. So you have to understand what are the competencies that are required, what are the specific skill sets that are required, and acknowledging "I need to stay current. I need to develop myself, and I need to be better prepared for the unknown"—which is you know, when you talk about a volatile, uncertain—complex, and ambiguous world—

Reese: Absolutely.

Marks: —we are constantly in a world of chaos and transition. You need to embrace that and accept it. So if I'm in this very chaotic world and I'm in a security space, what am I doing to make sure that around the corner, I am better prepared for that eventuality that I haven't even really thought about yet?

Greipp: Right. And General, I have this question for you as well. So your mission now is to prepare tomorrow's security professionals for that career pathway to be a chief security officer in a major corporation, and we've been mentioning associations like ASIS International. You've made a huge investment in your relationship with ASIS. Why?

Marks: ASIS represents the security industry in a very robust and cutting-edge way. The fact that the security industry is so ill defined, and it should probably remain that way because it's so vibrant. It's changing. You have to have professionals that can acknowledge that that change is a norm. It's a new norm.

There's transition as a matter of routine in this particular vertical, in this space called security. What we're doing today might be fundamental to what we're gonna do tomorrow, or it might fundamentally change. So don't you want an organization of security professionals that are routinely thinking about the business and doing things about the business of security and representing those security professionals that are out there trying to make the best in terms of their professions in those industries? You want somebody who is there looking over your shoulder, taking from you—because those security experts at the edge of the organization. They're defining doctrine. They're finding out new techniques. They're implementing new ideas. They need to bring those back to this association and say, "Look. We're doing this in this industry. I would like you to kind of capture that and tell me if you think that makes you, ASIS International—do you think this makes sense?" And if it does, I would say this is a best practice that needs to be disseminated and made available to all members in this security. Don't we all wanna learn from the experiences of a few? Absolutely.

Reese: The key word there he used was—that you'll understand is "doctrine." And I learned this a long time ago as a brand-new second lieutenant. One of my biggest mistakes on an exercise for an evaluation—and I—you know, big gung ho Ranger, and I made a mistake. And after the mistake, my commander came up to me and said, "Hey, uh, Jim, you know, do you know what you did wrong here?" You know, I thought I had kicked butt on this thing. And he said, "Hey, I told you attack, not do a raid."

And the meaning is, I did this raid, and I'm startin' to pull everybody off the objective, and he goes, "No, no, no. I said attack. That means attack and hold the ground. You're not in the Rangers anymore." And he said something to me that I use throughout the day. He goes, "Before you can veer from doctrine, you must know doctrine."

This is where transitions happen, using terms like "best practices" that we don't use in the military. You know, we use SOP. You know, things like that. So best practices in the commercial world is—that you know, I'll have people tell me, "Well, Jim, what are the best practices that are being done in the industry?" And that's what ASIS does for us—for my company. We say, "Okay, let's make sure doctrinally we're right because if we're gonna bring something in this new asymmetric world of threat, we must know doctrine before we veer from doctrine."

Marks: And you're not hidebound by it. The point is, is that if you understand, as you've said so very well, brilliance in the basics, if you understand the doctrine, if you understand how this security world is evolving, that doesn't mean you're locked into that. And, in fact, I would suggest entrepreneurial—and you're an entrepreneur, Jimmy—entrepreneurial, you wanna get out there and be nimble and create new ideas and new tactics, techniques, and procedures, new standard operating procedures, best practices that can now migrate back in and made available to everybody else. I mean that's what you fundamentally wanna do. So doctrine is not inviolate. It's not locked, and it can be challenged.

Reese: Mm-hmm. Correct.

Marks: But you have to understand what you're challenging, or you're out there—

Reese: Right. You've gotta know it before you challenge it.

Marks: That's exactly—or you're out there makin' stuff up, and you may, sadly, in industry—you may—you've been through this. I've been through this. You might be putting somebody else's money at great risk.

Reese: Absolutely.

Marks: In the military, we put lives at risk, so it was sacred.

Reese: And it can be in the commercial world, too. Lives, infrastructure.

Marks: In the security world, absolutely correct, and fundamentally, you've got shareholders. You have advocates. You have constituents.

Reese: Reputations.

Marks: You have to be mindful of all of that, so you better understand how this world is evolving and what is happening out there on the edges of this organization and how that's brought in. That's the value of ASIS International, as they reach out into the industries, as they pulse what is taking place, they codify it. They share it. They distribute it. They disseminate it. They talk about it. They iterate it. I could go on and on. And they do a validation.

Reese: It's the parallel is the military has the army has its Army Center for Lessons Learned. That's was ASIS is and should continue to be, is "Hey, what are the lessons learned comin' from out there? Let's put it together." At the end of the day, what I really think it is. It's a—for transitioning military and for the security industry, it's an exciting time. And what you should be excited about is when you come out and you start lookin', you're gonna see things that you know. You know, that are very relevant to what you've been doin' in this fight over in the Middle East and other pla—over in the Pacific Rim. So it's out there, and it's tricklin' into the commercial world and the private industry, so you'll be excited.

Greipp: Gentlemen, on behalf of ASIS International and University of Phoenix, thank you so much for your time and sharing your thoughts with us.

Marks: Thanks, Jeff.

Reese: Thanks, Jeff.

Greipp: And thank you all for joining us at Security Career Casts. If you'd like more information, then join us at and visit the Career Center, or visit Above all, thank you for your time.

On behalf of ASIS International and University of Phoenix, I’d like to thank our listeners for tuning in to Career Cast today.

For more information about ASIS International and career information and tools, visit And for more information about University of Phoenix College of Criminal Justice and Security visit Again thank you for joining us today.

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