First up, you need someone on the inside with the skills and mindset of those you're trying to keep out. "Organizations should look to hire a security professional with the skillset to conduct comprehensive penetration testing and put your security measures, procedures, and processes through the wringer," says Destiny Bertucci, head geek at SolarWinds. "This person should have a healthy curiosity and is probably the first to attempt hacker challenges at DEFCON."
Greg Hoffer, vice president of engineering at Globalscape, calls this person "the white hat wonder" and says "they're the team’s sidekick, performing security assessments of information management systems in a mock combative manner. Their antics help build the security team's overall performance."