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The key to all effective cybersecurity questions is framing the question in a manner that encourages participation and addresses the issues at hand.
What is Your Security Nightmare? – YouTube
Security Need:
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What area of security are you looking to evaluate/improve? (email, intrusion, internal access, firewalls)
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What led you to want to investigate new security solutions?
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How many users do you have?
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Do you have any compliance regulations that you have to adhere to? (HPAA, PCI)
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What security solutions do you have in place?