Category: Leadership

Leadership Moment: Tipping Over The Edge A summer camp that hires mostly young adults (high school/college) as its camp counselors has what is probably a standard policy: its counselors do not accept tips (while an understandable choice, not one supported by an argument that the counselors are well-compensated, but that’s a conversation for a different…

Leadership Moment: Lessons from Underdogs The NFL season has resumed, in case you’d managed to miss that. This weekend, from both college and professional leagues, two underdogs lead the way. On Saturday, fifth-ranked Notre Dame took on Northern Illinois University. If you’re not familiar with college football, this is what’s often known as a “cupcake…

Leadership Moment: A Bedroom, or a Dorm Room? A weekend ago, I had the sad joy of dropping our eldest off at college. As we helped put together all of the furnishings and accessories to make it feel like home, the residence advisor (among many others!) kept checking in on us, making sure we were…

Leadership Moment: Throwing Shade at Representation At the recent Blackhat conference, Palo Alto Networks threw shade at women in the cybersecurity industry, as attendees at their party were greeted with this sight: It’s 2024, so you could be excused for wondering if that was an AI hallucination. Nope. Palo Alto was quick to apologize, and…

Leadership Moment: The Crowd Strikes Back In case you missed it, CrowdStrike had a small incident last month. As part of that incident, they communicated a lot. Incident reports. A $10 gift card for coffee for customer admins. Apologies. Full screen ads at BlackHat. Interviews with media from the Wall Street Journal to the Today…

Leadership Moment: Championship Football For the first time since 2018, the Boston Renegades are not the champions of the Women’s Football Alliance. Falling short 30-27 to the St. Louis Slam, the Renegades will start 2025 in a new position: trying to get back on top. It’s easy to denigrate sports teams when they don’t win…

Leadership Moment: Playing Your Cards Right Last week, I was in New York for a CISO dinner with two of our portfolio companies, Valence Security and Aim Security. Yoni Shohet (Valence CEO) pulls me aside before the dinner and says, “I brought you a gift.” Now, I often get a lot of swag from companies…

Leadership Moment: Shields Down Talking with a startup CEO recently, they shared the story of one of their principal software engineers who had just left to join an even earlier stage startup. On the surface, it seemed like a reasonable career choice: after learning that they had what it took to be a key contributor…

Leadership Moment: Choice isn’t Frozen There are times when an organization wants to demonstrate bold leadership on as issue, as the Paris Olympic Committee did when it decided to use geothermal cooling systems instead of more effective air conditioners. Unfortunately for the POC, they didn’t anticipate the entirely predictable consequence: that many countries would bring…

Leadership Moment: Asymmetric Communication Checking into hotels has become increasingly automated. For a recent hotel stay, I received a WhatsApp message from the hotel asking me to provide some pre-checkin information, to smooth the check-in process (reading between the lines: reduce the cost to the hotel to check me in with a human). After a…