The email arrives on a Tuesday morning.
It looks like it’s from the CEO.
The name checks out. The tone feels right. Even the signature looks familiar.
“Hey, can you help me with something quickly? I’m in back-to-back meetings. I need you to handle a vendor payment. I’ll explain later.”
The new employee hesitates.
They’ve been on the job for four days. They’re still learning how things work. They don’t yet know what’s normal, what’s unusual, or when it’s appropriate to push back. And the last thing they want to do in their first week is question the CEO.
So, they help.
And just like that, the damage is done.
Why the First Week Is the Most Vulnerable Week
Every spring, businesses welcome a new wave of hires – recent graduates, interns, and first-time professionals – stepping into unfamiliar roles. For companies, it’s onboarding season.
For attackers, it’s opportunity.
According to Keepnet Lab’s 2025 New Hires Phishing Susceptibility Report, CEO-impersonation emails are 45% more likely to succeed with new employees than with experienced staff.
Attackers don’t focus on your most seasoned team members. They target the people still learning the rhythms of the organization because early on, everything feels uncertain.
A new hire doesn’t yet know:
- What a typical executive request looks like
- How payment approvals normally work
- Whether an email “feels off” or just unfamiliar
They haven’t had time to build instincts or confidence. And cybercriminals take advantage of that gap.
But here’s the important part: the employee isn’t the problem.
The most dangerous employee isn’t careless. It’s the one trying to be helpful.
If you run a business, you probably already know exactly who on your team would respond first.
The Gap Isn’t Training – It’s the System
Think back to that employee’s first day.
Their laptop wasn’t ready. Access wasn’t fully configured. Their email account was still being created.
So, they borrowed someone else’s login to check something quickly. They saved a file locally because they couldn’t access the shared drive. They used their personal phone to look up a client number because it was faster.
None of that felt reckless. It felt resourceful. Like doing what needed to get done during a busy first week.
But before everything is fully in place, quiet risks pile up:
- Shared credentials create accounts no one is tracking
- Files end up outside approved systems and backups
- Personal devices touch business data
- And no one clearly explains what to do when something feels off
The same Keepnet report found that new employees are 44% more susceptible to phishing than tenured staff. That gap doesn’t come from carelessness – it comes from chaos.
When onboarding is chaotic, security becomes optional. And that’s exactly the environment the phishing email walks into.
The attack didn’t create the vulnerability. The first day did.
What a Prepared First Day Actually Looks Like
Fixing this doesn’t require a long security presentation on Day One. It requires a few critical things to be ready before someone walks through the door.
- Access is configured – not improvised
Laptops are ready. Credentials are created. Permissions are clearly defined. No borrowed logins, no temporary workarounds, no “we’ll fix that later this week.” - New hires know what “normal” looks like
This can be a ten-minute conversation:
Does the CEO ever email about payments? Does anyone? What should they do if something doesn’t feel right?
This isn’t formal security training. It’s basic orientation.
- There’s a clear place to ask questions
The employee who paused before clicking that email probably would have asked someone – if they’d known who to ask. Most first-week mistakes happen quietly because no one wants to look inexperienced.
Give them a person. Give them a process.
Most security problems don’t happen when someone ignores the rules. They happen when someone hasn’t been shown the rules yet.
Maybe your onboarding process is already solid. Maybe your team is small enough that first days feel more personal than procedural. But if you’ve ever watched a new hire improvise their way through week one or if you’re about to bring someone on this spring, it’s worth having the conversation before that Tuesday email arrives.
Call us at 866-443-8238 or book a quick Teams call to see how we can help streamline your onboarding process.
