Winning Friends and Influencing Employees: The Challenges of Hiring and Retaining Top Cybersecurity Talent

In a tribute to Dale Carnegie, let’s explore how we can build better relationships with and keep our high-performing cybersecurity employees.

Perhaps the most challenging day in an executive’s life isn’t the missed sales forecast or the angry customer call, but it’s the trusted employee that comes into your Zoom session on a Friday afternoon telling you that they have found other employment.

Attrition is always a business challenge, but losing a high performer with specialized cybersecurity skills could mean an open seat for a very long time.

It’s always a possibility that the demands of the job were disrupting their sense of work/life balance (and cybersecurity is certainly a high-pressure job – the responsibilities can never be ‘shut off’). That said, work/life balance is an elusive thing to delineate through policy, as some people like to work every moment of the day, while others consider their livelihood an interruption to their real life. Considering this, it’s not unreasonable to wonder if it’s truly possible for a company, through policy alone, to create an environment conducive to optimal work/life balance when that balance is established by the individual. It’s a conundrum many businesses face every day.

Finding skilled cybersecurity talent is difficult, so it’s hard not to think of them as irreplaceable, but generally there is always someone out there who can replace them, but it is painful. Very painful! Countless Zoom calls, predatory retained search practices, long timelines — all of which detract from the collective goal of growing the business. Especially at a time when the demand for talented cybersecurity professionals is fiercely competitive. Taking time now to nurture and improve relationships within your team will pay dividends, and may keep them from looking for an exit.

Over the years there have been various fads in the corporate world that try to transform human interest in the workplace as a retention mechanism: Trust falls, Outward Bound programs and others—some people love them, others go through the motions. Inevitably, these efforts are a surface-level solution to a deeper challenge, and people still leave.

Instead of one-off team building days, there are various cultural values and behavioral changes an organization can and should implement in everything they do to make sure that employees are better heard and valued.

If your cybersecurity company is trying to improve employee morale and retention, these are some basic corporate-culture questions to explore:

  • How well do you know the people that are supporting your business?
  • When is the last time you called — not via Zoom, but picked up the phone and chatted to one of your direct reports?
  • When there is a win, is the success shared?
  • Do you reach deep into your organization, across generations, into the 20/30-year-old demographic for ideas and opinions?
  • Are you too busy for the human side of business?
  • Is the compensation and benefits aligned with industry standards? Though important, in technical environments, compensation and benefits are not always the most important retention issue.

The list above can be found in any business book. But perhaps more important than any of the items above is this:

  • Do your employees believe that they are part of something meaningful and enriching?

Getting your employees to understand that they are part of a mission can be more engaging and can do more to cement relationships between your people and your organization — more than cash, more than trust-falls, and a lot more than a team building day at the beach.

As cybersecurity managed services professionals, our customers need us to help them stave off attacks against their businesses. The very early days of cybersecurity may have been mainly about protecting customer websites against vandalism and foolishness, but now the daily mission is defense against major material losses from global adversaries. This is a global critical mission! Cybersecurity professional need to not just feel, but also to truly know that they are part of this immensely important mission. They need to know that their company can’t succeed without their input, ideas, and opinions. Everyone wants to be part of a winning team, and a team that thwarts the internet’s worst actors is a winning team every day.

We are all competing for cybersecurity professionals to come and work for us every day. Here at SilverSky, we pay well, we have a great work environment, competitive benefits, and many other things that we can present to a candidate; however, the most powerful thing we can do to entice and retain talented cybersecurity employees is to develop our organization’s mission and goals, and to make certain everyone knows their part. While we’re always looking for new people to join our team, we also work hard to make sure our existing employees know that they are heard and valued, and that we give them the space and support for creative solutions to the complex problems that challenge us every day.


We’re always looking for amazing people to help us fight cybercrime – you can see all our open job postings here.