A Cascade of Avoidable Errors: The Microsoft Breach & Human Risk in Modern Security Practice
Key Considerations for CISO’s in the wake of the CRSB’s Report on the MSFT Breach As we all know, the need for cybersecurity is still on the rise,...
Team CM
Dec 9, 2023 6:17:49 AM
A practical guide for CISOs who are done pretending awareness equals resilience
Let’s start with the uncomfortable truth:
Most cybersecurity incidents don’t happen because someone didn’t know the rules. They happen because someone was human — rushed, overloaded, trusting, tired, improvising, or trying to get their job done.
Yet for years, organizations have treated human risk like a training problem instead of what it actually is:
An operational, cultural, and systemic risk that needs to be managed — not just explained.
That’s where Human Risk Management (HRM) comes in.
This guide breaks down what human risk management really means in modern cybersecurity, why traditional approaches fall short, and how leading organizations are shifting from awareness theater to real-world risk reduction.

Human Risk Management (HRM) is a structured, programmatic approach to identifying, prioritizing, reducing, and measuring the risks introduced by human behavior within digital systems.
Unlike traditional security awareness training, HRM focuses on:
How people actually behave under pressure
The systems, incentives, and cultures that shape decisions
Reducing risk through design, enablement, and feedback — not fear or blame
Think of HRM as the difference between telling people not to crash and designing roads that prevent accidents.
Human risk isn’t about careless employees or “weakest links.” That narrative is as outdated as perms, acid-wash jeans, and thinking shoulder pads were a good idea.
Your people aren’t risky. You’ve put people in risky situations.
We’ll happily die on this hill: expecting humans to behave like machines is what got us into this mess in the first place. If security only works when people are perfect, calm, uninterrupted, and never under pressure — it doesn’t work.
The answer isn’t to lecture people harder. It’s to design security with people in mind.
Human risk shows up when:
Cognitive overload leads to shortcuts
Conflicting incentives encourage workarounds
Trust is exploited through social engineering
Fatigue, stress, or urgency override policy
People compensate for broken systems just to keep work moving
In other words:
Human risk is not a people problem — it’s a system problem that shows up in people.
Most organizations still rely on a familiar playbook:
Annual awareness training
Phishing simulations
Policy acknowledgements
Compliance checklists
These activities create documentation — not resilience.
They measure exposure, not decision-making. They track completion, not capability. They tell you someone sat through a course — not whether they can apply judgment under pressure.
A user completing a phishing course tells you very little if you don’t unpack what they were meant to learn, which behaviors should change, and how those behaviors show up in real work. Without clear learning objectives, a competency model, and a behavioral lens, you’re missing the forest (and it’s a very big forest) for the trees.
Worse, you’re sitting on a goldmine of signals and treating it like noise.
Courses and compliance that aren’t designed for measurement are effectively dumb by default — not because the people are, but because the system is. It’s like running a marathon barefoot and then blaming the runner. Or having a full church organ in front of you… and only ever playing “Chopsticks.”
And in the moments that matter most — when something unexpected happens — those gaps show up fast.
This is how organizations end up “compliant” — and still breached.
Read More: Why Cyber Awareness Programs Get Stuck—and How to Break Through
Security awareness asks:
“Do people know the rules?”
Human Risk Management asks:
“How do people behave when the rules collide with reality?”
| Awareness Training | Human Risk Management |
|---|---|
| One-size-fits-all content | Risk-based prioritization |
| Knowledge-focused | Behavior-focused |
| Periodic | Continuous |
| Compliance-driven | Outcome-driven |
Awareness isn’t useless — it’s just incomplete. HRM builds on it and makes it operational.

Effective HRM isn’t a single initiative. It’s a lifecycle:
Understand where human risk actually exists — by role, behavior, context, and culture.
Not all risks are equal. Focus on the behaviors and moments that create the most exposure.
Design systems, nudges, and learning that support better decisions in the flow of work.
Track meaningful indicators — not vanity metrics. Look for behavior change, not box-ticking.
Provide leadership and boards with confidence that human risk is understood, improving, and governed.
If this sounds more like operations than training — that’s the point.
Read More: The Human Risk Management Blueprint: Turning Strategy into Action
Here’s where things get interesting.
Human risk doesn’t exist in a vacuum. It’s shaped by:
Leadership behavior
Psychological safety
How mistakes are handled
Whether people feel supported or surveilled
A strong security culture reduces human risk. A weak risk culture amplifies it.
Culture isn’t a vibe. It’s infrastructure. And like any infrastructure, if you don’t maintain it, it fails quietly — until it fails loudly.
Read More Here: Security Culture vs. Risk Culture
AI didn’t eliminate human risk — it supercharged it.
AI has fundamentally changed where decisions happen, how fast they happen, and who (or what) is involved in making them. Humans are no longer just users of systems — they are supervisors, trainers, validators, and escalation points inside increasingly autonomous and agentic AI workflows.
This is why conversations about AI workforce management, human-in-the-loop security, and AI oversight can’t be separated from human risk management. Every AI system still relies on human judgment at critical moments: approving outputs, trusting recommendations, overriding controls, or failing to notice when something feels "off." Those moments are now the new attack surface.
Add innovation pressure into the mix — move fast, ship faster, automate everything — and organizations find themselves trying to keep the car on the track while accelerating into corners. Innovation and responsibility are now in constant tension, and culture is the stabilizing force that determines whether teams slow down when they should… or drive straight off the edge.
In practice, today’s AI-driven human risks include:
Today’s risks include:
AI-enhanced phishing and impersonation
Over-trust in automated outputs
Shadow AI and unsanctioned tool use
Humans acting as “rubber stamps” in AI workflows
HRM is essential for securing the human-in-the-loop, where trust, judgment, and oversight now matter more than ever.
Read More: AI Workforce Risk: The Problem You’ll Only See When It’s Too Late
Organizations doing HRM well see:
Faster and earlier incident reporting
Fewer high-impact human-enabled breaches
Reduced training fatigue
Clearer board-level insight into people risk
Security that works with humans, not against them
In short: fewer surprises, better decisions, and more resilient outcomes.
We patch software weekly. We update infrastructure constantly. But humans? We expect them to run on outdated assumptions in a radically changed threat landscape.
Human Risk Management is how organizations finally close that gap.
If you’re ready to move beyond awareness and start managing human risk as the strategic capability it is — we should talk.
(Because attackers already understand human behavior. It’s time defenders did too.)

No. Awareness is one input. HRM is the operating model that turns knowledge into safer behavior.
Yes — but not with a single score. HRM uses behavioral indicators, cultural signals, and outcome-based metrics.
HRM typically sits at the intersection of security, risk, culture, and operations. Ownership matters — and ambiguity is a risk in itself.
No. Any organization with people, pressure, and digital systems has human risk. Scale changes the approach, not the need.
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