My Failure Made Me a Better CISO | Assaf Keren, former CISO, PayPal

Most leaders spend their careers trying to prove they're good at their jobs. But Assaf Keren does something different, he teaches his managers how he's failed. The current CSO of Qualtrics and former CISO of PayPal has spent more than two decades in security, but some of his strongest beliefs about leadership didn't come from the things he got right. They came from burnout, bad decisions, difficult feedback, and learning to let go of the need to be the smartest person in the room.

In this episode of RAM, Assaf joins Jake Bernardes to talk about the stories behind his book and the leadership philosophy they created. That includes asking employees to tell him when he's wrong, telling leadership what he intends to do instead of constantly asking permission, and an annual ritual his team has learned to dread: Assaf publicly grading his own performance. One year, he even went to his boss and asked to be rated lower. But some failures cost more than a performance review. Early in his PayPal career, Assaf was working across Israel and the United States, essentially working two shifts every day. Good nights ended around 1 a.m. Bad ones at 3 or 4. Then he'd wake up and do it again. He did that for a year. Eventually he was physically ill, emotionally reactive, unable to think clearly, taking 15-minute power naps between meetings—and closer than he realized to leaving cybersecurity altogether. Compounding that experience was something else he'd carried quietly for years: PTSD. During COVID, Assaf learned that an employee with PTSD was afraid to disclose what they were experiencing. So Assaf wrote a message to a PayPal Slack channel with roughly 40,000 people explaining his own experience. Then he stared at it, for three days. His extended family didn't know. His colleagues didn't know. He worried his leaders might see him differently.

Eventually, he pressed Enter, shut his laptop and walked away. Looking back, he says: “That was the moment I started healing.”

Memory 006 is a conversation about failure, burnout, vulnerability, mental health, ego and what it actually means to lead people through a profession built on uncertainty.

In this episode: Why Assaf calls English a low bandwidth language, and what it taught him about giving feedback The year he worked two full shifts a day, Tel Aviv mornings and US nights, until his body forced him to stop Why he asked his own boss to rate his performance lower than expected The Slack message to 40,000 people that he sat on for three days What a submarine commander's book taught him about intent based leadership Why he believes the entry level security career is disappearing, and what that means for the next generation of leaders