cat ~/writing/measuring-security.md

Measuring Security

By Ken Connell · written 2019


From the archive. I published this on LinkedIn in May 2019, five years before I ever worked a SOC shift myself. It is republished here with its pyramid rebuilt to match the house style. A new afterword follows, because the question at the center of it aged into a bigger one.

Pallets of plain cardboard relief boxes stacked in rows in a staging area at dusk, a clipboard with a tally sheet resting on the nearest stack, amber floodlight from one side under a deep blue evening sky
> count what matters_

I was recently speaking with a team member of a Security Operations Center (SOC) discussing cyber security performance metrics. This individual made an interesting statement saying they were a lot more productive this week than last week because they'd closed more "tickets" from their workflow. My response was, "so if closing tickets equals productivity, how many tickets do you have to close to thwart a cyber-attack?"

That was obviously a trick question, but led to further discussion as to the value of productivity-based metrics and how they should be accurately leveraged to depict an organization's success rate for achieving their security goals. This starts with an accurate picture from leadership as to what their security goals and priorities are so team members can better report metrics that will accurately predict when teams will achieve key initiatives. If an organization is focused on the wrong security metrics, then it can lead to teams performing work that doesn't contribute to a successful security posture.

Leaders should clearly define expected security metrics to better measure a team's effectiveness, which will lead to a more accurate picture of performance. The metrics should be defined in a way that every team member can easily interpret their courses of action and the desired end state to work towards. Security metrics should measure progress towards a shared goal and never just focus on performance alone (which is different than effectiveness).

An example I can relate to is from my time serving in the U.S. Army in Bosnia and later Iraq. Commanders desire metrics to report both the effectiveness and performance of their missions. A common approach I witnessed was counting the number of boxes of food we'd successfully delivered during humanitarian assistance missions. The logic being that the "second and third order effects" would be that the population was less hungry and thirsty, happier, and would become friendlier to our presence (aka: "winning the hearts and minds"). However, tracking the number of boxes delivered provided an inaccurate picture of the population's sentiment towards us. They were less hungry and thirsty, but this performance metric didn't correlate with us getting shot at any less (which would've provided a more accurate metric of our effectiveness). Successful metrics should combine both measures of performance and effectiveness.

A better approach in that example to identify an accurate metric might have tied together with the goal (i.e., improved morale and happiness in area). Combining a calculated layered approach like this would've provided a better picture of mission success and the knowledge the commanders really needed to plan future courses of action.

Another key ingredient for effective metrics is to make sure that they can be easily interpreted across multiple teams. Given each team is operating from different "fields-of-fire," they each have a different focus and self-derived understanding of success based on their missions. To make metrics valuable for both teams and key stakeholders to consume, metrics must clearly illustrate when security operations are succeeding and when they're failing. Commonly this results in the stop-light color-coding approach using Green, Yellow, Red. However, I'd argue that approach is too simple on its own and requires additional context to show when things are good, bad, and worse. This metric should also be translatable across teams for them to see where they play a part in mission success and should not require having to correlate other metrics and data points for interpretation.

An example can be illustrated by a security operations team seeking to reduce the response time for false positives. By only measuring the number of false positives detected in each period, we're missing a key measure of effectiveness because it doesn't provide what number would show that operations are improving. Reporting the number of false positives alone does not provide data on the impact to the team's workload and ability to focus on other areas of security. A better approach might be to measure the time spent by the team on each false positive and then calculate it with a total percentage of working time available for a team (e.g., 8 hours x 10 personnel vs. 24-hour ops staffed by 5-person teams split across two 12-hour rotating shifts). If a resulting calculation indicates that a team is spending most of their time on false positives alone, then we have a clear picture of an ineffective security operation that a leader can better make course correction decisions from.

Once security metrics are interpreted in a way that defines the "So what" instead of a measure that doesn't tell a key stakeholder the importance of the data, leaders can shift their course of action to increase their security posture. Military commanders seek the same "So what" information from their staffs to base battlefield decisions on. When a new Lieutenant stands in front of a Commanding General for their first "BUB" (Battlefield Update Brief) and simply reports stats calculated from a spreadsheet of battlefield incidents for that day, they will be quickly "corrected" (and possibly dismissed completely), leading to a realization that they've overlooked key measures that would help the commander make informed decisions based on actionable intelligence. Just like military commanders, organizational leaders expect measures of effectiveness that provide more than just data points. They want to be able to make informed decisions that will make an organization more secure. This example is commonly referred to as the Data, Information, Knowledge, Wisdom Pyramid.

WISDOM
KNOWLEDGEactionable intelligence
INFORMATION
DATA
> data to decisions_

Metrics should effectively convert Data into Information that results in Knowledge (Actionable Intelligence) and Wiser visionary leaders. Once effective metrics are clearly defined, then teams can translate steps into courses of action (i.e., combining facts with the intended Second and Third-Order Effects).

The examples I outlined here are geared towards security teams, but the key takeaway is that quality measures of effectiveness can be applied across any situation. These metrics should measure the effectiveness of a team towards achieving an organization's goals, translated across different groups, resulting in a clear understanding of what steps should be taken to correct a lack of effectiveness. Organizations should consider this when reviewing current security metrics and identify those that are not effectively helping achieve established goals. Once impractical metrics are identified, they can be eliminated, and focus can then be shifted towards more effective measures that will lead towards a more successful security operation.

Seven years later

I found this piece again while writing Building a Seat at the Table, and it stopped me, because it is a timestamp. In 2019 I was the outsider asking a SOC hard questions about its metrics. I had theories about analyst workload, false positives, and what the numbers should mean. Five years later I volunteered onto a SOC floor, sat Tier 1, and got measured by the same kind of queue I had been theorizing about. The workload math in this article turned out to be roughly right. Living inside it taught me everything the math leaves out.

So this article is the pattern from the newer essay, caught mid-flight and date-stamped: assessing work I had not yet learned to do, then going and learning it. I could not fabricate better evidence if I tried, and I would not need to, because LinkedIn kept the receipt.

The other reason to republish it is that the trick question grew teeth. In 2019, "how many tickets do you have to close to thwart a cyber-attack" earned a pause and a good conversation. In 2026 the honest answer is that an AI agent can close tickets faster than any team I have ever worked with, and it will, because a machine optimizes exactly what you measure. There is a name for the failure this article kept circling without naming it: Goodhart's Law (opens in a new tab). When a measure becomes a target, it stops being a good measure. At human speed that failure is a drift you can catch in a quarterly review. At machine speed it is a flood.

Which is why this old piece belongs next to the new ones. Humans in Command has mostly meant direction, review, and the final word. This article adds the part I understood in Iraq before I understood it in security: command also owns the measures. The machines will saturate whatever number we hand them. Choosing the number is the job.

The boxes still get counted. The question is still the one from Iraq: are we getting shot at any less.

> EOF