What is expected of CISOs in 2021? The role has evolved in recent years, and, to be successful, a CISO now needs to be a risk manager and business enabler. In this article we distill advice from seasoned CISOs at First Ireland Risk Management, Kaplan International, Coosto and Transavia on the skills needed to succeed in the role, as well as strategies for sleeping at night, reporting to the board, educating on security hygiene and navigating the path to becoming CISO. The speakers discussed these issues on a panel during the recent PrivSec Global conference. See “How to Effectively Find, Compensate and Structure Cybersecurity Leadership (Part One of Two)” (Dec. 14, 2016); Part Two (Jan. 11, 2017).