1. Do we provide executives, the board, and other stakeholders with meaningful metrics on a regular basis? Not how many tickets were opened or how many alerts fired, but how we are reducing risk and averting potential financial loss. Reporting may not seem important, but showing value, in the language of our stakeholders, on a regular basis goes a long way toward building relationships that we will need to accomplish our goals.
2. Do we regularly focus on building relationships and maintaining a dialogue with executives, the board, and other stakeholders? Meaningful metrics are a first step that can open the door, but we need to make sure that we walk through that door. We need to continually work to build the relationships that will help us achieve our desired results.
3. Do we regularly work to understand what vulnerabilities we have within our organization and what types of risks those vulnerabilities introduce into the organization? This is an important operational picture for us to understand continuously, and it is one that is extremely dynamic.
4. Do we understand where our most critical/sensitive data lies? We need to make sure that we always know the answer to this question, even as the environment changes, and that we take extra measures to safeguard that data.
5. Are we continually taking in new information, updating our operational understanding of the environment, and working to understand the risks and threats to it?
6. When looking to mitigate a risk, do we have organized, thought-out, and documented plans for implementing solutions that mitigate that risk?
7. When planning to request budget for a solution, do we map the desired solution to the risk it mitigates? This helps us show the immediate value and return on investment that the given solution (and its associated budget) will provide.
8. Do we have a staffing plan in place that includes resources for steps beyond implementation? In order to provide value in the boardroom, any solution requires people and process, in addition to technology.
9. Have we looked into closing holes and tightening security in areas where we might be able to leverage existing investments? For example, have we looked at segmenting different network segments that have no legitimate business need to communicate with each other but could be leveraged by attackers to move within the organization?
10. Have we ensured that we are following the principle of least privilege? For example, there is no reason that most users require administrator access, yet many have it.
11. Have we implemented two-factor authentication? Believe it or not, even in 2017, brute force password attacks are still a favorite attack vector. There are more organizations than I'd like to believe that still do not use two-factor authentication.
12. Have we limited remote access/Remote Desktop to only the instances in which it is needed for work-related functions? In many organizations, this is not the case. Sadly, in those situations, once an attacker is in, he or she can often move between different systems using legitimate remote access protocols and masquerading as a legitimate user.
13. Do we have visibility across endpoints, network, and the cloud? If not, we will not be able to put eyes on the enterprise to monitor continuously. It's particularly important to keep up with the environment as it changes, especially now as much infrastructure moves to the cloud.
14. Are we continuously monitoring the environment for malicious or suspicious activity, including exploitation of vulnerabilities that we have identified?
15. Do we have all the skills, expertise, and resources required to implement the solutions we've identified and planned for? If not, we should ensure we work with a trusted partner who does.
16. Do we know where our peer organizations stand and how we can look upon them as another data point and input to our standing? The goal here isn't perfection but rather a reasonable trade-off between cost and risk. Peer data points can be quite helpful.
17. Do we communicate our progress and expenditures vs. risk mitigated on a regular basis? We may not think that our stakeholders are all that interested in this information, but I would argue that they are.
18. Are we implementing and enforcing policies and procedures that will help us achieve our goals? As mentioned above, solutions require people, process, and technology to be effective.
19. Are we running security operations or working with a trusted partner who will run it for us? All the security investment in the world won't do us much good unless we continually keep an eye on things.
20. Are we prepared to perform incident response, or are we working with someone who can in the event of a serious incident? It would be a shame to focus so much on risk mitigation, only to forget one of the biggest risks of all — being caught with your pants down.

Security is a field where the to-do list never seems to end. While no list of actions would ever be complete, some actions have a greater impact and mitigate more risk than others. The choices we make in prioritizing investments in time and money can greatly affect how quickly we mature our respective security postures. It pays to plan strategically and act tactically.

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