Adjust Your Expectations: Tough Truths About Cross-Sector Career Transfers

Approximately 200,000 U.S. service members leave the military every year, and many pursue additional education, new employment, and other civilian opportunities.

The private and corporate security field can feel like a natural fit for many veterans and former law enforcement personnel, since their existing crisis management, security, and investigative skills are highly transferrable.

But while there are many commonalities between public and private security, the transition can still be challenging.

The Job Hunt

Kathy Lavinder, a recruiter in the security and investigations space, regularly works with people who want to transition from a public-sector role, military job, or law enforcement position into private security.

“The thing I tell them is that there will be some bumps in the road and to be realistic and manage their expectations,” she says.

The hiring process itself is radically different, she notes. In the military, service members get to indicate their assignment preferences for the next rotation, and the path to advancement is clearly spelled out.

“The private sector is very different,” Lavinder says. “It’s bumpy, it’s volatile, it’s unpredictable, it’s opaque. It’s all of those things that make it very challenging. It’s like a big mystery, and [military and law enforcement professionals are] looking for a job while locked inside a worldview that is very different from the private sector.”

Those different expectations and viewpoints can make transitioning careers quite jarring. For instance, a servicemember might tell Lavinder that he or she is separating from the military on 30 June and wants to start a private-sector job on 15 July.

“That’s ludicrous,” she says. “That is impractical and unrealistic. The timeline is not yours—it’s the hiring organization’s. That’s the first thing that people really struggle with. They struggle with the idea that they have some input in timing, and they really don’t.”

Some public service personnel also have inaccurate expectations of what they are qualified for in the private sector, says Scott Wolford, CPP, security director for Nationwide Insurance and a former Ohio State Highway Patrol officer.

“A lot of the people I talk to have zero formal leadership experience, but they expect to come out of public service and become a CSO, or become a director,” he says. “I came in [to private security] as a second shift supervisor, with Tuesdays and Wednesdays off. It wasn’t, ‘Oh, I’m out of law enforcement, I get that sweet Monday through Friday gig, holidays off.’ No, you’re working the second shift, you’ve got days in the week off, and you need to learn.”

If applicants don’t take honest stock of their experience and capabilities, measuring those against private sector needs, they are unlikely to land many interviews, Wolford adds. Individuals can use free resources like ASIS International’s career maps to determine which private security positions align most closely with public sector roles to get a realistic picture of where their skills fit into the corporate world.

“My advice: read job descriptions,” he says. “Think about a job that you would like to have after you retire or after you leave public service, read that job description, look at what you’ve done, and see how your skills align with that. See what you’re missing, and then look for ways to fill in the white spaces and become a more well-rounded person.”

This is a particularly valuable use of time for people with a longer timeline before leaving the military or law enforcement, Lavinder says.

“Use that timeline to get smart about areas where you know you don’t have exposure or you know you have deficiencies,” she adds.

Incoming private security professionals should conduct a SWOT (strengths, weaknesses, opportunities, threats) analysis of themselves to determine what to emphasize in applications, what to bolster with extra education or training, and where job searches and subsequent employment could go awry.

“I suggest you talk to your peers and supervisors and have a really candid conversation with them,” Lavinder says. “It’s very hard to be completely honest with yourself. If you are looking at the arc of your career or where you’ve been, it’s very easy to get lost in the granular…This very serious, very thoughtful self-evaluation is even better when you can get other inputs.”

Consider leveraging a professional and personal network [and try] to connect with people who have already transitioned out of public service and into an industry of interest, advises Rachel Briggs, OBE, CEO of The Clarity Factory, which is currently researching the security skill sets that are most valued in corporate settings. By reaching out to the people whose path you are retreading, she notes, you can get a better picture of what the career switch entails and what skills are increasingly important to hiring managers and security teams.

But beware if somebody asks you to pay for this exploratory assistance, Lavinder cautions. Many career coaches and résumé builders exist who can help job hunters, but at the information-gathering stage, there are many more individuals who want to be generous with their time and help others succeed for free. In addition, pause before taking too much advice from people who keep jumping between jobs and have endless horror stories about their employers, she warns.

“Talk to the people who’ve come in and done very, very well at integrating and adapting and are excited about it,” Lavinder says. “It is daunting, I realize, but it’s absolutely doable.”

See what you’re missing, and then look for ways to fill in the white spaces and become a more well-rounded person.

One area that Briggs and Lavinder see emphasized by hiring managers today is cybersecurity and technology know-how.

“Survey after survey of C-suite members says, in a nutshell, technology is what’s driving growth and making us more productive,” Briggs says. “Certainly, the corporate security function of today and the future is one that has technology at its core.”

However, many CSOs put technology acumen squarely on the shoulders of their younger employees and security professionals, delegating responsibility for it.

“Your function needs a vision on this… You have to lead from the front on it, and you’re going to have to be making decisions fast,” she adds. “Going forward, it will be the functions that are tech-savvy and tech-native that will be doing the most interesting—and therefore the most helpful—service for their organizations.”

For public sector individuals considering making the jump to private security, investing in technical skills—including cybersecurity certificates, security certifications, and involvement in tech projects in their military or law enforcement branches—can pay off significantly. Not only does it fill some likely gaps in your SWOT analysis, but it helps to demonstrate to hiring managers and future employers that you’re paying attention to corporate trends and you took the initiative to advance your skills. 

Demonstrating Your Skills

An inevitable part of any job hunt or career change is writing an effective résumé. A list of past military or law enforcement positions is unlikely to make the cut, because those terms and responsibilities are difficult for a private sector hiring manager to understand, says Lida Citroën, CEO of personal branding and reputation management firm LIDA360. Citroën works regularly with veterans and private organizations to make military to civilian transitions more effective.

“The military résumé reads differently,” Citroën says. But that doesn’t mean one should get it translated by a third party without some clear input—at that point, the language might make more sense to the hiring manager but the veteran can’t understand or explain it.

For example, changing military logistics experience to project management terminology might connect better for the HR representative, but it doesn’t accurately explain the veteran’s work.

Part of the disconnect lies with the hiring manager. Even though veterans bring indelible value to the organization—especially given their trainability, loyalty, and adaptability, Citroën says—many employers don’t take the extra time to evaluate whether veteran candidates’ résumés show that they accelerated in their career path faster than normal, if they jumped rank quickly, or if they struggled in a position.

“You can tell some of that if you’re willing to take a little bit of extra time on a résumé,” she says.

Unfortunately, not all employers will, so military or law enforcement professionals will need to work harder to make their experience shine through in an accurate but applicable way.

“It’s about distilling what you’ve done,” Lavinder says. Some professional guidance can help when you get stuck, such as leveraging a career coach to talk with you and extract a compelling narrative from your personal history.

“Organizations don’t want to know what you have done,” she adds. “They don’t want to know what you want. They want to know what you can do for them.”

The in-demand skills will vary depending on the role, but there are definitely turn-offs, Lavinder says.

“People who have been in SWAT teams and counter-assault teams, K9 units, military communication systems, and things like that—that doesn’t have an immediate application to the private sector,” she explains. “Step back from it and look at what the military or your agency taught you about project management, resource management, people management, meeting deadlines, and being able to pivot—those are the skills that will really serve you well.”  

Overall, companies are looking to hire security professionals who are smart, versatile, understand the organization’s mission, and can help accomplish goals.

“They’re casting a wide net these days, and I’m very happy to say that there is truly an emphasis on bringing in different backgrounds, lived experiences, and personal histories, and that brings more people of color and women into the mix,” Lavinder says. “They’re looking for problem solvers at the end of the day. Whenever I’m talking with people about what their messaging should be, if you just keeping hammering on ‘problem solver’ and you can really give some good examples of how you problem-solved and they’re credible and relevant, then you’re going to do well in the interview process. You’re going to get traction because at the end of the day, managing risk is solving problems.”

The résumé is only one piece of information hiring managers can use to get to know candidates, too. Generic cover letters are a red flag for HR professionals, so seek to write thoughtful, specific cover letters to accompany resumes that address the particular needs of the organization and explain some of your problem-solving experience.

Candidates should also be ready for hiring managers to review their LinkedIn profile, any letters of recommendation, and other aspects of their personal brand, Citroën says. In many cases, this extra digging can benefit the candidate, especially if his or her résumé doesn’t match up exactly with the job opening.

For example, if someone was a cook in the Navy, they might not have a clear transition path to private security. But if he or she decided on their security career goal two years before separation and started taking courses or pursuing educational programs through professional associations, those additional credentials and efforts illustrate the candidate’s commitment to his or her future profession, she says.

Going forward, it will be the functions that are tech-savvy and tech-native that will be doing the most interesting—and therefore the most helpful—service for their organizations.

Remember that the hiring process is as much about vetting the employer as vetting the candidate, says Anders Noyes, CPP, head of security and safety at Honolulu Museum of Art and a former municipal police officer.

Job interviews should be a two-way conversation, he explains, and candidates should have questions ready to help them determine if the organization is a good cultural fit for what they need. For instance, ask about policies and expectations around taking time off to care for a sick child or to go on vacation, using all of the allotted paid time off.

“Some organizations, depending on your level, expect you to be available all the time,” he says. “I think that applicants really should remember to ask the questions about things that are important to them. If it turns out that the answers are not what they want to hear, then that’s probably not the right job—it’s not going to change when they get there. Hoping for the best is not the best strategy. Corporate culture is something that is long in place before you get there and will remain in place after you get there. You can influence it, but you’re not going to change it—not immediately, anyway.”

Culture Shock

Once a veteran or former law enforcement officer lands a corporate security job, the transition process has only just begun. Now, it’s a matter of keeping up with the dramatic pace and radically different culture in private industry.

“The CSOs I speak to say it is the cultural shift from being in the public sector moving into the private sector—it’s difficult to see it before you get there,” Briggs says. “You definitely feel it when you get there, and then it’s very challenging to reorient yourself.”

Citroën adds that there are often many unwritten rules and implicit guidelines that are simply understood in a private sector environment.

“That’s really hard for someone who has had the playbook and knows every step,” she says. “It’s also hard for the employer who is looking at the team, the culture, and the personality of the organization and saying ‘How do I help someone come into this culture when they’ve had everything spelled out for them? How is that person going to fit in?’”

Both employers and candidates can benefit from studying some of the common pitfalls that veterans entering the security industry often face.

Hierarchies. “The military is a very structured organization,” Citroën says. “Things are predictable. Standards are written, understood, sworn by. Everything is spelled out.”

That goes double for the chain of command—it is incredibly clear who reports to whom, and circumventing the chain of command is typically a serious misstep.

In the private sector, though, hierarchies and influence are radically different and will vary from organization to organization.

“In a private sector environment, it might be appropriate to talk to your boss’s boss, and that doesn’t mean your boss is going to get mad,” Citroën explains. “A lot of that has to do with the company culture. Early onboarding, spelling that out, can help the veteran understand that we recognize in the military this might not be appropriate but in our company, this is how it’s done.

“The military teaches you that you get influence with rank, just like old school corporate taught that you got influence when you have the job title or authority,” she continues. “But we’ve seen a lot of that shift… Now we see people in the organization who have influence but who don’t have the title and rank. They have more influence than the CEO over how an idea gets sold, the collaboration, and the alignment with mission.”

Security leaders will also have to excel in wielding influence to succeed in risk advisory roles. While military and law enforcement officials are used to an “Ask, Tell, Make” model of issuing orders, security teams in corporate or civilian settings will need to convince rather than issue orders, explaining the why behind an action.

“It’s a negotiation,” Briggs says. “It’s about influence and building teams in very, very different ways.”

Tempo. The pace of work at private corporations often takes public sector individuals by surprise, according to Lavinder.

“The tempo in the private sector is ‘get it done now,’” she says. “The tempo in the military or policing and law enforcement might be, ‘This is a group effort; this is a long-term objective; this is a reach; this is something that we’re going to plan for.’ In the private sector, it’s ‘let’s get it done starting now.’ Some people struggle with that.”

Although there’s inevitably a learning curve to any new job, moving into corporate security requires candidates to be agile, open-minded, and flexible amid the fast pace of work and high demands, which isn’t a great fit for everyone, she notes.

Savvy employers will make the extra effort to onboard veterans and former law enforcement with extra training, guidance, and support to enable them to withstand the rapid change of tempo, Citroën says. Without that support, many veterans leave. In 2014, researchers found that 43 percent of veterans leave their first civilian job within a year, and 80 percent leave before the end of their second year, citing a lack of opportunity for career advancement or personal development.

“They struggled, and instead of drawing attention to themselves or looking inadequate they would just leave, which is a real problem for employers focused on retention,” Citroën adds.

This doesn’t mean slowing down the pace of operations to accommodate new employees. Instead, organizations can focus on setting expectations about asking for help. They can also designate a mentor or private sector “battle buddy” that can get a newly transitioned veteran up to speed and clarify any unspoken rules and business practices that could frustrate a new recruit.

Visibility. “There’s nowhere to hide in the private sector,” Lavinder says. “You’re going to be held to account for your performance and whether you’ve accomplished the mission and your tasks—which may not be clearly defined. One of the things I hear frequently is they were waiting for the directive to do X, Y, and Z. Sometimes that’s on you entirely. If you’re given the responsibility of managing some functional areas, then you’re going to have to figure out what—operationally, tactically—that means. Some people struggle at that.”

This is where influence comes into play again. Security directors need to be savvy at relationship development and stakeholder education, and they will need to communicate the benefit of any new initiatives in a way that will resonate with businesspeople, Lavinder says. Even when plans go awry, being able to explain the shortcoming or delay in relation to the organization’s mission can earn understanding and leeway to try alternatives to achieve a goal.

“You’ve got to be a really good storyteller,” Briggs says. “Remember that influencing is as much about the heart as it is the head. That is a challenge. I see people in our industry falling over themselves to find data and statistics, and my case will be made if I have this magic number or once the percentage gets to this point. That might get you though the door, but the thing that’s convincing is the human connection. It’s understanding what’s going to really influence that particular executive to say ‘yes’ at that moment in time.”

Those relationships are living things, too—they need to be nurtured in the long-term, especially because of the level of turnover across private organizations. Six months after a CSO develops a positive working relationship with the CFO, that executive may have moved on to a different organization and the CSO has to start over.

“It’s an absolutely critical skill, and it’s something that you have to do in the right way,” Briggs says. “You’ve got to be up for doing it and redoing it every single day that you go in to work. It’s a task that’s never completed.”

Resources. Military and law enforcement professionals are typically used to working as part of a large unit. But security departments are often a unit of one. While many responsibilities can then be outsourced to vendors and security partners, it will fall on the security director to take on both strategic and operational tasks, and any other duties as required.

“This is a real challenge for people transitioning from very senior roles in the government to a CSO role,” Briggs says. “They are used to doing 90 percent strategy, 10 percent tactics, and then they move into the corporate space expecting to keep that balance in their portfolio. But there’s only so much of your time that you can spend doing strategy, and then it’s time to get on with it.”

Although keeping a birds-eye view of organizational strategy and security’s role in enterprise risk management is valuable, security directors have to strike a balance between doing that and then leading and managing a team to get the day-to-day work done.

“The higher up you go [in government], the further you get away from the day-to-day operational action,” Lavinder says. “It’s hard to be thrown into the minute-by-minute action and have to roll up your sleeves and really be integrated into it. That’s the expectation… You can’t just sit back and look at it from a big-picture standpoint. It’s not realistic; it’s impractical. That’s not why they’re hiring you.

“Programs in the private sector run lean—I don’t know any organization that tells me they have too many people. They say everybody is operational, everyone is outward facing, and everyone has to be willing to really do the work that needs to be done at any given moment, in any given scenario.”

The hopeful message, though, is that security directors can make the business case for resources in the private sector.

“It has to be put through a business filter and using the language of the organization about return on investment, but you can get resources,” Lavinder says.

Claire Meyer is editor-in-chief of Security Management magazine. Connect with her on LinkedIn or email her directly at [email protected].