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BerryDunn’s Cybersecurity Playbook for Management: The Workflow

Any sports team can pull off a random great play. Only the best sports teams, though, can pull off great plays consistently — and over time. The secret to this lies in the ability of the coaching staff to manage the team on a day-to-day basis, while also continually selling their vision to the team’s ownership. Chapter Six in BerryDunn’s Cybersecurity Playbook for Management looks at how managers can achieve similar success through similar actions.

The title of this chapter is “The Workflow.” What are we talking about today?
RG: In previous chapters, we’ve walked managers through cybersecurity concepts like maturity, capacity, and discovery. Today, we’re going to discuss how you can foster a consistent and repeatable cybersecurity program — the cybersecurity workflow, if you will. And for managers, this is where game planning begins. To achieve success, they need to effectively oversee their team on a day-to-day basis, and continually sell the cybersecurity program to the business leadership for whom they work — the board or CEO.

Let’s dive right in. How exactly do managers oversee a cybersecurity program on a day-to-day basis?
RG: Get out of the way, and let your team do its work. By this point, you should know what your team is capable of. Therefore, you need to trust your team. Yet you should always verify. If your team recommends purchasing new software, have your team explain, in business terms, the reasons for the purchase. Then verify those reasons. Operationalizing tools, for example, can be difficult and costly, so make sure they put together a road map with measurable outcomes before you agree to buy any tools — even if they sound magical!

Second, empower your team by facilitating open dialogue. If your team brings you bad news, listen to the bad news — otherwise, you’ll end up alienating people. Know that your team is going to find things within your organization’s “auditable universe” that are going to make you uncomfortable from a cybersecurity point of view. Nevertheless, you need to encourage your team to share the information, so don’t overreact.

Third, give your team a communication structure that squelches a crisis-mode mentality — “Everything’s a disaster!” In order to do that, make sure your team gives every weakness or issue they discover a risk score, and log the score in a risk register. That way, you can prioritize what is truly important.

Fourth, resolve conflicts between different people or groups on your team. Take, for example, conflict between IT staff and security staff, (read more here). It is a common issue, as there is natural friction between these groups, so be ready to deal with it. IT is focused on running operations, while security is focused on protecting operations. Sometimes, protection mechanisms can disrupt operations. Therefore, managers need to act as peacemakers between the two groups. Don’t show favoritism toward one group or another, and don’t get involved in nebulous conversations regarding which group has “more skin in the game.” Instead, focus on what is best for your organization from a business perspective. The business perspective ultimately trumps either IT or security concerns.

Talk about communication for a moment. Managers often come from business backgrounds, while technical staff often come from IT backgrounds. How do you foster clear communication across this divide?
RG: Have people talk in simple terms. Require everyone on your team use plain language to describe what they know or think. I recommend using what I call the Colin Powell method of reporting:

1. Tell me what you know.
2. Tell me what you don’t know.
3. Tell me what you think.
4. Tell me what you recommend.

When you ask team members questions in personal terms — “Tell me what you know”—you tend to receive easy-to-understand, non-jargon answers.

Something that we really haven’t talked about in this series is cybersecurity training. Do you suggest managers implement regular cybersecurity training for their team?
RG: This is complicated, and my response will likely be be a little controversial to many. Yes, most organizations should require some sort of cybersecurity training. But I personally would not invest a lot of time or money into cybersecurity training beyond the basics for most users and specific training for technical staff. Instead, I would plan to spend more money on resiliency — responding to, and recovering from, a cybersecurity attack or incident. (We’ll talk about resiliency more in the next two chapters.) Why? Well, you can train people all day long, but it only takes one person to be malicious, or to make an innocent mistake, that leads to a cybersecurity attack or incident. Let’s look at my point from a different perspective. Pretend you’re the manager of a bank, and you have some money to spend on security. Are you going to spend that money on training your employees how to identify a robber? Or are you going to spend that money on a nice, state-of-the-art vault?

Let’s shift from talking about staff to talking about business leadership. How do managers sell the cybersecurity program to them?
RG: Use business language, not technical language. For instance, a CEO may not necessarily care much about the technical behavior of a specific malware, but they are going to really care about the negative effects that malware can have on the business.

Also, keep the conversation short, simple, and direct. Leadership doesn’t have time to hear about all you’re doing. Leadership wants progress updates and a clear sense of how the cybersecurity program is helping the business. I suggest discussing three to four high-priority security risks, and summarizing how you and your team are addressing those risks.

And always remember that in times of crisis, those who keep a cool head tend to gain the most support. Therefore, when talking to the board or CEO, don’t be the bearer of “doom and gloom.” Be calm, positive, empowering, and encouraging. Provide a solution. And make leadership part of the solution by reminding them that they, too, have cybersecurity responsibilities, such as communicating the value of the cybersecurity program to the organization — internal PR, in other words.

How exactly should a manager communicate this info to leadership? Do you suggest one-on-one chats, reports, or presentations?
RG: This all depends on leadership. You know, some people are verbal learners; some people are visual learners. It might take some trial and error to figure out the best medium for conveying your information, and that’s OK. Remember: cybersecurity is an ongoing process, not a one-and-done event. However, if you are going to pursue the one-on-one chat route, just be prepared, materials-wise. If leadership asks for a remediation plan, then you better have that remediation plan ready to present!

What is one of the biggest challenges that managers face when selling cybersecurity programs to leadership?RG: One of the biggest challenges is addressing questions about ROI, because there often are no quantifiable financial ROIs for cybersecurity. But organizations have to protect themselves. So the question is, how much money is your organization willing to spend to protect itself? Or, in other words, how much risk can your organization reduce — and does this reduction justify the cost?

One possible way to communicate the value of cybersecurity to leadership is to compare it to other necessary elements within the organization, such as HR. What is the ROI of HR? Who knows? But do you really want your organization to lack an HR department? Think of all the possible logistic and legal issues that could swamp your organization without an HR department. It’s terrifying to think about! And the same goes for cybersecurity.

We’ve talked about how managers should communicate with their team and with business leadership. What about the organization as a whole?
RG: Sure! Regular email updates are great, especially if you keep them “light,” so to speak. Don’t get into minutia. That said, I also think a little bit of secrecy goes a long way. Organizations need to be aware of, and vigilant toward, insider threats. Loose lips sink ships, you know? Gone are the days when a person works for an organization for 30+ years. Employees come and go pretty frequently. As a result, the concept of company loyalty has changed. So make sure your organization-wide updates don’t give away too much cybersecurity information.

So what’s next?
RG: Chapter 7 will focus on how managers can help their organizations respond to a cybersecurity attack or incident. 

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