Leadership's Trolley Problem: Choices and Consequences

Balancing Accountability and Compassion in Moments of Crisis. This newsletter first appeared on the Duha One substack.

Leadership Moment: Don’t Re-Blame the Victims

As hostages are (finally) being released from Gaza, a friend noted the terms of the deal (30-50 convicted terrorists freed from prison for each hostage), and asked, “But won’t the hostages feel guilty about that exchange rate?” Let me first lay my bias out: I dislike almost everything about the deal, except that hostages are being freed. I will celebrate every one returning home, while also holding, in a separate piece of my mine, a distaste for the terms of the deal.

But the hostages are victims. What price is paid to free them is not a price that they chose, and they are the most blameless people. There is a long list of accountable people: the ones who made the deal, who advocated for the deal, who put pressure on others to make the deal, who held the hostages, who didn’t advocate for their release.

But don’t lay the blame at the feet of those who’ve already been victimized.

Appearances

Recent

Jan 22: RSAC Innovation Showcase Webinar: Don't Mess with AppSec, with Daniel Shechter , Jadee Hanson , Mandy Andress , Jenny Brock , and Roni Fuchs

Jan 30: Webinar, State of the Cyber Nation, with Or Salom and Eran Barak

Jan 31: Talent First Podcast, The Idealized CISO Role, with Michelle Edmondson

Feb 4: CISO Series Podcast, Our Developers’ New Motto is “LLM Take the Wheel”, with Deneen DeFiore

Upcoming

Feb 12-23: Tel Aviv

Mar 13, 1015: Secure World Boston, [Panel] Mental Health vs. Mental Wellbeing: How to Cultivate Resilient Security Teams, with Val Dobrushkin , Kayla Williams , and Ben R Howard

May 28, 0830: RSA Conference: Zero Trust To Give: What should have come next?

May 29, RSA Conference CISO Boot Camp: A Unicorn by Committee: The Idealized CISO, with Helen Patton

One Minute Pro-Tip: Drive the Trolley

Everyone, rightfully, should hate the trolley car problem. But sometimes, as an organizational leader, you face one. Imagine a mild* case of sexual harassment in your team. As a leader, you’re often faced with your own trolley problem, a choice between two uncomfortable paths: Do you let it slide with a minor penalty (send the offender to remedial training, risking folks feeling you don’t take this seriously, and possible re-offense), or do you respond with a strict punishment (possibly termination, but risking creating an environment where your team feels you overreact)?

Both have downsides. Many leaders consult with the victim, trying to place the trolley problem on them, and using their desires as a justification for their choice. A victim might choose lenience, because they don’t want to blow up the organization, and now you can blame them if that choice has a downside. Similarly, they might choose to be harsh, and you can similarly blame them for the downside.

But that’s not fair to the organization or to the victim. You, as the leader, must choose the path you’re going to take the organization through. You bear the responsibility for the choice you’re about to make, not them.

*Yes, sexual harassment has a wide range of issues. I’m defining mild here as “the offender deliberately crossed a line that they should not have, but did not go so far as to trigger a universal and unambiguous response.” I’m not going to try to give specific examples, I’m not arguing where that line is.