Who do you look up to within the field of Information Security? Why?
Where do you get your security news from?
If you had to both encrypt and compress data during transmission, which would you do first, and why?
What’s the difference between symmetric and public-key cryptography?
In public-key Cryptography you have a public and a private key, and you often perform both encryption and signing functions. Which key is used for which function?
What kind of network do you have at home?
What are the advantages offered by bug bounty programs over normal testing practices?
What are your first three steps when securing a linux server?
What are your first three steps when securing a windows server?
Who’s more dangerous to an organization, insiders or outsiders?
Why is DNS monitoring important?
What port does ping work over? 
Do you prefer filtered ports or closed ports on your firewall?
How exactly does traceroute/tracert work at the protocol level?
What are Linux’s strengths and weaknesses vs. Windows?
Cryptographically speaking, what is the main method of building a shared secret over a public medium?
What’s the difference between diffie-hellman and RSA?
What kind of attack is a standard diffie-hellman exchange vulnerable to?