Sam Fleming
Associate Consultant, Red Hat
Raleigh, North Carolina, United States
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Sam Fleming is an Associate Consultant at Red Hat, and independently consults on Multifactor Authentication and Conditional Access policies for Microsoft EntraID. He is responsible for engaging with stakeholders of all technical levels, and directly manages multiple cloud environments. Before beginning his career in IT, he worked as a Sales Innovation Specialist, helping craft sales strategies for clients including Google, T-Mobile, and Grubhub.
When he's not at his computer, Sam is a competitive West Coast Swing dancer. He has competed and taught across the country, and is an active member of the local Raleigh dance scene.
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Beyond AI Recommendations: Enhancing Human Learning in an Agent-Driven Landscape
# Abstract:
When AI makes every method sound equally valid, users can easily spend days pursuing the wrong path with total confidence. This presentation explores how impartial AI guidance sidesteps expert-defined boundaries and misleads learners. Drawing on real-world examples, this session highlights why visible bias (showing what to do and what not to do) is essential for real human learning, and how we can productively utilize the power of opinions.
# Description:
When learners turn to AI for guidance, they now receive polished, confident answers to nearly any question, including ones that seasoned experts would instantly flag as misguided. Drawing from the struggles of real users, "Beyond AI Recommendations" examines how this impartiality in AI responses erases important context and judgment, facilitating people pursuing flawed approaches with misplaced confidence. The core issue isn’t capability, but calibration: users can now do almost anything, but lack the expert signals that reveal what should be done.
This presentation challenges experts, educators, and communicators to counter that neutrality by being intentionally and visibly biased towards informed best practices. By clearly identifying recommended methods, discouraging shortcuts, and explaining the reasoning behind each, we can restore direction in a world of limitless but guidance-free possibilities. Attendees will learn ways to design presentations, training experiences, and communication styles that complement, rather than compete with, AI assistance, helping learners make better choices in an agent-driven landscape.
From Burden to Solution - Reframing Multifactor Authentication in Contemporary Cybersecurity
Ready to tackle the challenges of multi-factor authentication (MFA) adoption? Join us for a session that flips the script on how we talk about and promote MFA. This session unveils smart strategies to make MFA not just a necessity, but something people actually want to use. We'll break down the barriers of misunderstanding and sluggish rollouts, showing how a fresh approach can boost buy-in and elevate security practices.
Full outline link:
https://samplayskeys.com/shared/2025/Reframing_MFA.pdf
Simply Cyber Con 2025 Sessionize Event
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