This week on The Awareness Angle: Interviews, Anthony is joined by Harley Sugarman, co-founder of Anagram Security, a company taking a fresh, no-nonsense approach to security awareness. Think short, sharp challenges, real behaviour change, and zero tolerance for checkbox compliance.
We talk about why so much training still misses the mark—and how Harley’s background (which involves a surprising early career twist we won’t spoil here) helps him see awareness through a very different lens.
🧯 Smoke, Mirrors & Metrics – “Most training is built to satisfy auditors, not change behaviour.”
📉 Bad Metrics, Bad Decisions – “Completion rates aren’t proof of learning. They’re proof someone clicked play.”
🧠 Nudges, Not Magic – Nudges are useful, but they’re not the main event—and people can smell the white noise.
🧍 Stop Calling People ‘Risks’ – “You can’t build trust while labelling people as the problem.”
📚 The Anagram Origin Story – From puzzle-based security training to bite-sized interactive learning—why they’re doing it differently.
🤖 The AI Bit – Why most “AI-powered training” isn’t as clever as it sounds, and what actually works.
🎩 The Secret Ingredient – Let’s just say Harley’s old job involved a bit of sleight of hand—and it explains a lot about how he thinks about engagement.
If you’re tired of awareness that ticks boxes but changes nothing, this one’s packed with ideas, honesty, and a few good laughs.
The Awareness Angle: Interviews is our ongoing series of honest, practical conversations with the people reshaping how we think about human risk, behaviour change, and learning that actually works.
🕒 Timestamps
00:00 Intro: Why Security Awareness Still Matters
00:35 How Awareness Training Has Evolved
03:52 Measuring Success: Metrics That Miss the Mark
09:58 Human Risk: What Are We Really Solving For?
15:34 Where AI Fits in Security Awareness
19:11 People Over Systems: A Needed Mindset Shift
25:05 Smarter, Fresher Training Approaches
30:41 What’s Next for Awareness Programs?
32:16 Compliance Isn’t Awareness (But It’s Changing)
34:54 Anagram’s Shift from Training to True Awareness
39:04 Standing Out in a Crowded Awareness Market
40:51 Reframing Human Risk Management
45:27 Real Change Requires behavioural Shifts
46:07 Diverse Paths into Security Awareness
50:34 Buzzwords We Need to Ditch
54:09 Human Risk + Communication = The Real Challenge
📩 For links, videos, and the newsletter – head to riskycreative.com
💬 Check Out This Episode's Discussion Points
📧 hello@riskycreative.com
🔗 riskycreative.com
🎵 Our Intro & Outro Song (© 16! by falling forever)
License: https://creativecommons.org/licenses/by/4.0
