Trolley choices

Leadership Moment: Two Bad Choices

As you’ll see below, I’m in Tel Aviv right now. As the United flight was finishing up boarding in Newark, a flight attendant announced that they’d found a phone, and if it was someone’s on the plane, to claim it, or it would be left in Newark. A few minutes later, we pushed off from the jet bridge, and had made it about fifty feet when a passenger told a flight attendant they were missing their phone.

Talk about a hard choice. The flight crew (really, the captain) had to decide whether to part this passenger from their phone for at least a day (but, given the way separated items go wandering, maybe forever), or return to the gate to retrieve the phone. 300 passengers, delayed for an estimated half an hour, yields what might be a simple calculus: 150 person-hours against a phone. What would you do?

The captain chose to return to the gate. In making the announcement, he said something like, “I hope someone would do this for me, and you probably do too.” On the way back to the gate, the operations crew also spotted damage to the nosecone (which apparently had been missed in the earlier inspection), so the flight was delayed an additional hour while it was inspected. It’s not clear there is an easy “right call” here. Why you make a decision might be almost as important as the decision itself.

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One Minute Pro Tip: No Default Choices

Easy decisions, with one choice having significantly more positive outcomes at lower costs than other choices, are great … and uninteresting. Interesting decisions (at least to plan for) are ones where every choice is a mix of good and bad. It’s easy to get trapped by analysis paralysis, playing out every option in your head until you discover that you took too long, and now one of those paths has been taken. But not by you, at least. It’s not your fault.

As a leaders, you don’t really get to tell yourself that lie. The next time you’re presented with an interesting decision, first ask yourself, “What will happen if I don’t do anything? When do I have to do something to prevent that outcome?” Now you know what choice you’ve already made, and how long you have to change your mind. “Do Nothing” is a choice, so don’t pretend it isn’t.



May 7-12: Tel Aviv

May 16: panel moderator, What Security Leaders Are Doing Now to Keep Their Cloud Environments Safe, Cloud Security Live, with Justin Somaini, Unity CISO, Rich Friedberg, Live Oak Bank CISO, and Omer Singer, Snowflake Head of Cybersecurity Strategy

May 22: Jewish Book Council Network conference

May 31: Tufts radio

June 9: Talk, Building your leadership practice, RMISC, Denver, CO

June 14: Keynote & book signing, RVASec, Richmond, VA

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Chapter Cameo: Hard tradeoffs

The best available outcomes often involve finding hard compromises between groups you advocate for.

I almost cut chapter 25 from the book, because I didn’t feel like I could give clear advice; there is a challenge as a leader when you have to make tradeoffs that affect other people, and even if you can get their input, you can’t give them control over the decision (because it often involves yet more people). But it shows up over and over again (like in today’s Leadership Moment), and as a leader, it’s a place you need to prepare for. You need a level of firm empathy that is hard to achieve, and the serenity to accept that people will be upset with you, and you can neither tell them they are right, nor tell them they are wrong. They just … are.

The best advice I know how to give is to be willing to be wrong – to recognize that your first inclination might not be the right one, but to also recognize that making a decision and moving forward is probably better than seesawing between competing decisions.

Leadership Q&A

Leader B asks, I have experienced that founder/private company CEOs don’t understand the value CISOs can bring, and they aren’t ‘impressed’ with things they kind of should be. I’ve had some success with ‘borrowed credibility’ but very open to other ideas.

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