Whenever a cybersecurity failure happens, sophisticated hackers are automatically the suspects. But they’re actually getting more credit than they’re due. More often than not, security failures actually begin with ordinary people making ordinary decisions, which is why conducting a cybersecurity risk assessment is so important for identifying potential weaknesses before they lead to a serious incident.
An employee clicks an ordinary-looking email.
A manager shares a password because it’s faster than creating another account.
A former contractor still has access months after finishing a project.
It all seems harmless and unimportant. But it’s these small things that create the kind of security loopholes attackers are always on the lookout for.
For this reason, a cybersecurity risk assessment shouldn’t just focus on technology. Firewalls, antivirus software, and security tools should all be part of the evaluation, sure. But it should also examine how people work every day. Habits, assumptions, and unclear processes… these often expose a business long before technology does.
Many Nashville organizations are beginning to recognize this shift. Instead of asking, “Do we have the right security tools?” they’re now asking, “Where are our people unintentionally creating risk?”
This marks a huge turning point toward uncovering weaknesses that have been there all this time.
But how much is this going to cost? Surprisingly enough, reducing human cyber risk doesn’t always require major investments. It starts with very simple things:
- asking better questions
- identifying patterns
- giving employees the knowledge and support they need to make safer decisions
This employee cybersecurity risk assessment checklist is designed to help you do exactly that.
As you work through each section, don’t worry about achieving a perfect score – that’s not the goal at all. Instead, answer honestly. And pay attention to the questions that make you hesitate. Those moments often reveal the biggest opportunities to strengthen your business.
Along the way, you’ll also find reflection points that connect to the IT Readiness & Planning Workbook, helping you turn observations into a practical action plan.
Why Does Every Cybersecurity Risk Assessment Need to Include People?
Imagine installing professional-grade deadbolts on every door of your office to ensure security. Then someone opens a window and forgets to close it. That’s what happens when businesses invest heavily in cybersecurity technology but overlook the people using it every day.
A cybersecurity risk assessment that focuses on technology and produces a list of technical findings – but doesn’t evaluate the people – won’t really explain why security incidents happen in the first place.
Technology doesn’t act on its own. It’s the people who decide who gets access to sensitive information. They approve payments, open attachments, respond to emails, install new apps, and determine whether something unusual is worth reporting. Every one of those decisions can either strengthen your security, or weaken it.
What Does a Human-Focused Assessment Look For?
A comprehensive cybersecurity risk assessment still looks at technology, but beyond that, it also takes a close look at the environment employees work in. It asks questions that the old-school technical audits rarely address:
- Are employees given more access than they actually need?
- Do managers regularly review user permissions?
- Would someone feel comfortable reporting a suspicious email if they weren’t sure it was malicious?
- Are security policies practical enough that people actually follow them?
- Have new AI tools introduced workflows the business hasn’t evaluated yet?
None of these questions are accusatory. They’re not pointing fingers at employees at all. Instead, they’re designed to help you understand…has your business created conditions that allow people to make safe decisions easily? Or does it unintentionally encourage risky shortcuts?
Think of it this way: if several employees bypass a security process again and again, the issue probably isn’t the employees themselves. Maybe the process is confusing. Maybe it takes too long, or no longer fits the way people actually work. Whatever it is, a human-focused assessment helps uncover those disconnects before they blow up into incidents.
This broader perspective also gives leaders something a lot more valuable than just a list of technical fixes. It highlights opportunities to:
- Improve communication
- Clarify responsibilities
- Simplify workflows
- Build a stronger security culture
In addition to reducing the current risks, those changes make the business more resilient as new threats emerge.
And with that mindset, let’s move from theory to practice. The checklist that follows is designed to help you identify the everyday habits, processes, and decisions that often reveal people-based security gaps long before an attacker does.
The Employee Cybersecurity Risk Assessment Checklist
Every business operates differently, so there isn’t a one-size-fits-all checklist that guarantees security. Instead, use the questions below as conversation starters for your leadership team. Answer them honestly, and don’t be surprised if they reveal areas that have never been formally discussed.
Some questions may have a clear “yes” or “no.” Others might spark debate or uncover different perspectives across departments. That’s a valuable outcome. It often highlights where expectations, responsibilities, or processes aren’t as well defined as they should be.
There’s no score at the end of this checklist. Its purpose is simply to help you identify areas that deserve a closer look so you can decide where to focus your efforts first.
Let’s begin with one of the most common – and most overlooked – sources of human cyber risk.
Could Someone Access Systems They No Longer Need?
Access permissions aren’t meant to be permanent. They’re supposed to be given only as needed, and revoked when no longer appropriate. But in reality, this rarely happens. Employees change roles, contractors finish projects, and vendors complete work… and they still have the access that should already have been cancelled.
Over time, those unused accounts and unnecessary permissions become attack risks. Let’s say a dormant account is compromised. An attacker may gain access without raising immediate suspicion. And even when nothing malicious happens, excessive access increases the chance of accidental changes or exposure to sensitive information.
Ask yourself:
- Does every employee have access only to the systems and data they need today?
- Is there a documented process for removing access when employees, contractors, or vendors leave?
- Are user permissions reviewed regularly instead of only during major IT projects?
- Can someone clearly identify who has admin-level privileges across the business?
Not sure about any of these answers? It’s worth taking a closer look. Giving people only the access they need to do their jobs reduces unnecessary exposure. Not only that, it makes access management easier to maintain as your business grows.
Workbook Reflection: Document any roles or accounts that need an access review.
Would Your Employees Recognize a Modern Phishing Attempt?
Phishing emails used to be easy to spot. Common telltale signs were obvious spelling mistakes or ridiculously suspicious links. But now, the messages are very convincing, mostly thanks to AI. It’s very hard to tell fraudulent emails apart from real ones that actually come from colleagues, suppliers, or even banks.
Not even so much a question of whether your employees have attended cybersecurity training. It’s whether they can recognize today’s threats in the middle of a busy workday.
Consider these questions:
- Have employees received security awareness training within the past year?
- Does training cover newer threats like AI-generated emails, QR code scams, and business email compromise?
- Are employees encouraged to verify unexpected requests for payments, passwords, or sensitive information?
- Do you periodically test awareness with phishing simulations or other exercises?
Awareness isn’t something employees learn once and remember forever. Attack techniques keep evolving, so regular reinforcement is essential.
Businesses with a higher level of awareness maturity are better prepared because employees know when to pause, question unusual requests, and verify before taking action.
Workbook Reflection: Identify one awareness training improvement for the next 12 months.
Do Employees Know What to Do When Something Feels Wrong?
Cybersecurity training for employees is important, but does it guarantee that every threat will be caught? Not necessarily. What often makes the difference is how quickly they speak up after noticing something unusual.
Imagine an employee clicks a suspicious link. They might realize it, but they don’t speak up because they’re hoping nothing will happen. Or maybe they’re worried that they’ll get into trouble. The result? A problem that might have been contained in minutes can become a much larger incident, simply because no one knew about it.
Some questions to ponder:
- Do employees know exactly how to report a suspected security incident?
- Is there a clear process for escalating concerns?
- Do managers encourage reporting without assigning blame?
- Has the reporting process been reviewed or practiced recently?
If you’ve managed to create an effective security culture in the work environment, reporting is seen as a positive action. It’s not an admission of failure at all. When employees feel comfortable raising concerns early, your organization can look into potential issues before they become costly disruptions.
Workbook Reflection: Note one change that would make incident reporting easier.
Are Convenience Habits Creating Hidden Security Gaps?
With so many things on the to-do list, it’s natural for employees to look for ways to get their work done faster.
- A team shares passwords because logging into a shared account is faster.
- Someone uses a personal file-sharing app to send a large document because it’s more convenient than the approved system.
- An employee installs a free AI tool to speed up a task without realizing company information is being uploaded to a third-party service.
Sometimes shortcuts are fine, and the intentions behind them are innocent enough. But they could also open up security risks that no one wants.
To minimize such needless risks, ask yourself:
- Are employees using only approved apps and devices for work?
- Are there clear rules on the safe use of AI tools and cloud services?
- Are teams even aware that such security policies exist?
- Are secure processes practical enough that employees will actually follow them?
If good employees keep bending the rules, don’t just chalk it up to misbehavior. Ask why they’re doing it. You might discover opportunities to simplify workflows while strengthening security as well.
Workbook Reflection: Record any workflows that encourage risky shortcuts.
Can You See Risk Before It Becomes an Incident?
One of the biggest differences between reactive and proactive organizations is visibility. Businesses that regularly review user activity, access permissions, and unusual patterns are more likely to catch potential problems early. Meanwhile, those that don’t usually miss the small clues that indicate something isn’t right.
The key is knowing what to look out for. Ask yourself:
- Can you identify unusual account activity before it becomes a security incident?
- Are privileged accounts monitored more closely than standard user accounts?
- Do you review trends that could indicate insider risk, whether intentional or accidental?
- Is someone responsible for regularly reviewing security alerts and following up on them?
Modern security isn’t about going Big Brother and watching every action of every employee. It’s about spotting unusual activity early enough to ask the right questions. Reviewing patterns over time through user behavior analysis can help identify potential issues before they interrupt your business.
Workbook Reflection: Note one alert or activity log you don’t review today but should.
What Do Your Answers Say About Your Business?
Now that you’ve gone through all the questions in the checklist, it’s time to step back and look at the bigger picture.
Instead of trying to calculate a score, look for patterns in your answers…
Did you answer most questions with ease and confidence? Or did you need to think long and hard for several of them? The questions that made you pause are likely the ones that deserve the most attention.
You’re in a Strong Position If…
Most of your answers were a clear and resounding “Yes.” They’re supported by documented processes, and are understood quite consistently throughout the business.
This doesn’t mean you’re risk-free, because no one absolutely is. But it does suggest your organization has a solid foundation for continued improvement. The focus now is maintaining that momentum as your business growsand new threats emerge.
You Have Blind Spots If…
Many of your answers were “I’m not sure,” or you suspect that different people in your organization would give you different answers to the same question.
That could be a sign that responsibilities, policies, or expectations aren’t as clear as they should be. It might not really be an urgent problem, but wouldn’t you rather address it now than wait for something to go wrong?
You Should Prioritize Action If…
You answered “No” to several questions, especially those involving access, employee awareness, reporting security concerns, or monitoring.
A “no” doesn’t always mean a security incident is going to happen. But it does tell you where some of your bigger issues may be. Start with those areas that could cause the most trouble if they’re left unaddressed. Then work through them one at a time.
From the start, we’ve emphasized that this checklist isn’t about getting a perfect score. It’s about getting a clearer picture of where your organization stands today. Once you’re aware of where the gaps lie, it’s much easier to decide on what to improve next.
Why Do MSPs Focus on Reducing Human Cyber Risk Instead of Eliminating It?
There’s no such thing as guaranteed zero human error. People get distracted. They make assumptions and take shortcuts from time to time. That’s just part of being human. But still, who wouldn’t want to make those mistakes less likely, and less damaging when they do occur?
That’s exactly why a good MSP doesn’t treat cybersecurity as something you set up once and then forget. Technology is a huge part of it, but so are the everyday things that help people work safely. That includes having clear processes, giving employees regular reminders and training, and checking from time to time to see what’s working and what needs to change.
An MSP can help your organization:
- Review who has access to what and remove permissions people no longer need.
- Keep security awareness training going throughout the year.
- Watch for unusual account activity that could signal a compromised account or insider risk.
- Create simple response procedures so employees know what to do when something doesn’t look right.
- Review security policies regularly and update them when the way your business works changes.
These actions aren’t meant to replace your team. Rather, they help employees make more secure decisions as part of their everyday work.
As your business grows, new employees are hired. Vendors come and go. And technology changes. Revisiting your cybersecurity risk assessment regularly helps ensure your security strategy keeps pace with those changes and continues to reduce human cyber risk as time goes by.
Reduce Human Cyber Risk with Small, Steady Changes
A cybersecurity risk assessment can help you find out what’s wrong. But more importantly, it shows you the things you can fix before they turn into bigger headaches for the business.
If this checklist raised questions or showed that people aren’t always following the same process, don’t treat that as a failure. It’s actually useful information. Maybe some user permissions need to be cleaned up. Employees need a refresher on what to do when something looks suspicious. Maybe a reporting process needs to be clearer.
Don’t feel pressured – you don’t need to fix everything at once. Start with the areas that need the most attention, and you’ll achieve your cyber risk reduction goals over time.
Continue the Conversation with the IT Readiness & Planning Workbook
This checklist is a starting point. The IT Readiness & Planning Workbook takes a closer look at the bigger picture, helping you assess where your business stands, work through important decisions, and figure out what to tackle next.
Access your copy of the IT Readiness & Planning Workbook and use it to turn what you found in this checklist into a practical plan.
Start with a Quick Risk Check
If this checklist raised more questions than answers, it’s worth understanding where the risk is actually coming from.
Calculate Your Risk. It takes less than 60 seconds and helps you identify where security, access, or awareness gaps could impact your business next.
Your results and the Cyber Incident Survival Guide for Business Leaders will be emailed to you, giving you a highly practical reference you can keep on hand if things don’t go according to plan.
Frequently Asked Questions
Q: What does a strong security culture look like?
A: A strong security culture makes secure behavior part of everyday work, encourages employees to ask questions, and treats reporting mistakes or suspicious activity as responsible behavior.
Q: How does security culture affect cybersecurity risk?
A: Employees who understand security expectations and feel comfortable reporting concerns are more likely to pause, verify unusual requests, and raise issues early.
Q: How can a business improve its security culture?
A: Provide regular training, clarify responsibilities, simplify security procedures, reinforce good decisions, and make it easy for employees to report concerns.
Q: Where can I find help improving security culture near me?
A: Alpha & Omega helps organizations in Nashville strengthen security practices through training, policies, monitoring, and ongoing guidance.
Q: Can Alpha & Omega help build a stronger cybersecurity culture?
A: Yes. Alpha & Omeg offers Managed IT Services that can support security awareness, employee practices, policies, monitoring, and ongoing improvement.
