June 29, 2022

Better User Awareness Training with Tim Silverline

by Cyber Ranch

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Show Notes

Tim Silverline, VP of Security at Gluware, joins host Allan Alford on the Ranch this week for a discussion about user awareness training and the latest and greatest (as well as not the greatest) methods around phishing simulations. Tim and Allan get into the nitty gritty of how your company can improve user awareness results through avoiding basic click-through models, considering advanced warning for certain training exercises, and understanding risk quantification when evaluating employee metrics.


Timecoded Guide:

[04:30] Running the right phishing simulation for your user base and gauging your results appropriately

[10:08] Pushing boundaries in the tactics used in phishing exercises and making employees pay attention more closely to their everyday emails 

[15:10] Calling out unlikely and unhelpful phishing strategies and simulations, including the harm of impersonating employees without any warning

[21:04] Realizing which methods of user awareness are no longer effective and shifting away from the mindset of just “checking the box” in these training exercises

[25:54] Changing security for the better with increased awareness and a better understanding around the value of risk exposure amongst employees


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What, to you, are the biggest highlights, the high points, the critical bits of user awareness training?

Tim has seen the good and the bad of user awareness training, and has found the best results for his users in interactive training sessions, especially when paired with gamification. Allan compares this method and approach to modern virtual escape room sessions, and Tim agrees that the more interactive and hands-on a training can be, the better the learning experience will be. Instead of framing our user awareness and phishing exercises around checking boxes for cyber insurance companies, we should be striving for active learning engagements that demonstrate the value of security to our users.

“After those trainings, users have come up to me and talked to me about how they weren't aware of this particular risk and hearing about it in a real-world use-case was very effective for them to really understand why it's important and why they should be behaving in a slightly different manner.”


If the users never fall prey to attacks, is there a reason to continue performing them? 

Hearing Tim talk about his success, Allan was curious about how he chooses to approach successful user bases. If someone isn’t falling for Tim’s phish, does he still see the need to perform these exercises? The short answer was yes, but Tim explains that user awareness training should be customized to the needs of a user base. Testing new employees is a must, along with refreshing successful users on their skills a few times a year. Additionally, scheduling out different exercises that hone in on different phishing simulations exposes employees to a variety of learning opportunities and encourages them to see this beyond just a yearly test where they might as well “get it over with.”

“If you've tested all your existing employees, and they haven't fallen or been susceptible to it, that doesn't mean that the next employee you hire is also going to be of that same mindset.”


What ineffective methods are there in security awareness?

Throughout the episode, Tim and Allan keep coming back to the simple fact that checking boxes no longer works. Having employees read or watch through videos and take “common sense” knowledge tests makes user awareness training a distracting activity that feels more like grunt work than a learning experience. While you never want to disrupt the workflow of your employees, stepping outside of the box with interactive activities that are explained in advance shows the value of these exercises to your users instead of making them feel that you’re yet again wasting their time with another gift card scam.

“I find that there's the typical thing a lot of people do to hit compliance, which is having their users watch videos, and answer questionnaires. My feeling is that most people just try to get that done. Their goal is really to get it completed, so they can check the box and their company stops bothering them to complete it.”


You are given a magic wand and you are told you can wave it and change any one thing in cybersecurity you want to change. What do you change?

There’s so much in cybersecurity that Tim and Allan would love to change, especially when we look at cutting edge approaches to user awareness training. However, Tim makes one thing clear: if he could change anything, he would change our mindset. Instead of seeing security as just someone’s job, we should encourage our users to see themselves as an instrumental part of their company’s security. When everyone concerns themselves with following the right protocols and caring about security beyond simulations, companies will find themselves in a much stronger, less vulnerable place.

“I think ultimately, a lot of the weaknesses inside of our organization are our users. If I could just increase the level of carefulness, or the level of interest that everybody has in keeping their own companies secure, I think we would overall improve the posture of all companies.”



Learn more about Tim Silverline on LinkedIn and the Gluware website

Follow Allan Alford on LinkedIn and Twitter

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