It’s easy to complain about employees leaving the company for greener pastures. But it’s a little more challenging to find tangible solutions for retention problems.

4 Ways to Plan for Retention

At the 13th Annual Billington Cybersecurity Summit, key military and government leaders talked with the CyberWire editor, John Petrik about how to retain your workforce (especially in cybersecurity) after you hire them. Sometimes, the biggest issue isn’t just getting them in the door – it’s finding ways to keep them.

1. Manage Expectations

Managing Director at the Cyber Readiness Institute, Karen Evans said that it’s all about expectations. Her expectation has been for employees to stay about two years. She built a pipeline so that she could rotate people out and allow them to come back easily. Evans found that this built a workforce that was richer in their thought processes. With a two-year cycle, it helps maintain a highly skilled and flexible workforce.

But Evans pointed out that it’s important to keep your home base exciting – you want your talent to come back.

2. Transition Entry Level to Mid Level Better

Mark Montgomery, executive director for CSC 2.0 at the Foundation for Defense of Democracies agreed that two year assignments are often the sweet spot. But, he cautioned that we need to figure out how to get entry level employees to transition to mid-level – and stay with their employer. He noted that on occasion, poaching someone is the right move, but the vast majority of talent should be retained by actively growing them within the same company or in the federal government. Montgomery said that we need a cyber development program that works especially to get talent from entry to mid career.

3. Invest in People

Camille Stewart, deputy national cyber director, technology and ecosystem security at the Office of the National Cyber Director, said that retention is all about investing in your people. But a key component to making that investment, she says, is to understand their career trajectory. Stewart noted that your employees are all in different career phases, and different things motivate different people. So, when you recognize those factors, it will have a major impact on your retention. But according to Stewart, a key piece of this is offering managers the flexibility and support they need to come alongside their employees.

4. Continually Assess Skillsets

Colonel Candice Frost, USA Commander, Joint Intelligence Operations Center (JIOC) USCYBERCOM J2 pointed out the benefits that the military has to recruit talent. Frost said that the military recruits across the nation with a variety of skillsets. So, while this offers a variety of problems when you have to “create your own” people, Frost says that they have the “luxury” to assess and test who is the best fit. It may not make sense for every company to cast a broad net and pull in varying levels of talent, train them, and then move them around within the company. However, Frost noted that there are pieces of that strategy that are applicable for industry.

In the long term, Frost knows that military talent will be quick to snatch up competitive salaries from industry, she hopes to at least retain some in the Reserves or the National Guard.

Need to get Onboarding Right

Onboarding is all about getting a new recruit or candidate off on the right foot. And Frost said that the biggest lesson she has learned in onboarding in the military is the power of sponsorship. She said that the first 10 days and the last 10 days for your people are the most critical points in their career and impression of you. Frost noted that employees need to know where they fit in the overall organizational picture, and that has to be explained during the onboarding process.

She also noted that the military doesn’t usually throw new recruits into the fire right away. Instead, they give them incremental challenges over time. Organizations may not have the bandwidth to be able to do that, but it is a good reminder to manage the work thrown at newer employers.

Military doesn’t usually throw new employees into the fire right away. Smaller pieces and challenges thrown at an employee are helpful.

Montgomery talked to the power of paying for education in exchange for employment as a key way to onboard entry level candidates and retain them for a few years. He mentioned OPM’s CyberCorps: Scholarship for Service program as a great way for the federal government to attract and hire cybersecurity talent. Montgomery said that getting candidates invested into a workforce through internships and scholarships is one piece of the onboarding puzzle for those in their early career.

Evans agreed, saying that you have to educate and train employees. She said, “Help them know how they fit – right out of the gate.”

Institutionalize mentorship – It’s The Secret Ingredient

Mentoring is even more important in retaining a workforce today. Stewart said that the “Workforce today doesn’t want to follow a track and follow a linear career trajectory.” So, she says that mentorship is key because it helps employees know how their skills translate to other roles.

Stewart shared that “Flexibility is key…cybersecurity is an interdisciplinary space. There are a number of teams who need to be informed because what they do impacts your cyber posture.” Evans agreed, noting that cybersecurity is an organizational function, and it’s not just something for CIOs to figure out.

Frost added that mentoring helps people understand how they can move around based on their personal narrative. Frost commented that cybersecurity is a people problem, so leaders need to know the people they are leading and find ways to support them.

Montgomery leaned into attracting talent at a younger age, and offering more mentoring programs at the middle and high school levels. He noted that good cyber hygiene needs to be a part of their life. He said that the biggest problem in cyber is diversity, and tackling that begins in middle school.

Stewart noted that “Diversity is a force multiplier to understanding people – that’s the key to cybersecurity.” Evans agreed, saying that “No matter how technical we are, the soft skills are critical to success.”




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Jillian Hamilton has worked in a variety of Program Management roles for multiple Federal Government contractors. She has helped manage projects in training and IT. She received her Bachelors degree in Business with an emphasis in Marketing from Penn State University and her MBA from the University of Phoenix.