Leadership Moment: Getting Caught
Every parent knows that there are two indicators that your child is doing something they shouldn’t. The first is when they go completely silent, to stop drawing your attention to them. The second? When you stumble across them, and they panic, trying to hide whatever they were up to. Your quick check-in is now confronted by a new reality: they’ve been caught, even if you didn’t know what they were doing.
The memes of the Coldplay concert have gone far and wide, and what stands out to me is just how much of the attention begins with the culprits, in their moment of panic, drawing the eye. Acting like they needed to hide guaranteed them becoming a meme; had they just relaxed in the moment, there is a chance they would have gone unnoticed by the Internet.
Workshop: Selling to CISOs
Next week, I’ll be doing a workshop with Blumberg Capital, aimed primarily for cyber founders, on Selling to CISOs. Those interested should apply to join us at https://lu.ma/s13u7q0c, for this closed door (but virtual) event Tuesday, July 29, at noon Eastern (7 pm Israel). I’ll cover how to reconstruct your pitch into the key truths that CISOs need to believe before they’ll buy, common faux pas that get in your way, and how to authentically market, and sell, to the security buyers. (If you’re interested in bringing this, or related workshops, to your company, let me know).
One Minute Pro-Tip: Prep Your Lying Truths
Executives often get blindsided by the employee question, “Are you planning a(nother) layoff?” Most of the time, your answer can be an unequivocal, “No.” A small part of the time, you’re caught between repeating that denial (which is now an untruth), being honest (which you can’t do, because it’s very confidential), or dissembling on the spot.
Instead, you should always dissemble. Being asked if you’re doing something confidential is an inappropriate question, and the problem isn’t what you say when you need to hide the answer–it’s that you didn’t hide the answer all the time. Prepare an answer that is always true. “We are always looking at the state of our business, and evaluating where we have opportunities to further invest or the need to conserve capital. Those might result in staffing changes, and we prefer not to be surprised by those moments, so yes, we are always evaluating both layoff and investment opportunities.” You could add a slight denial, “But nothing is currently written in stone,” which, especially for a public company, is basically true except for the few days before a layoff.
BlackHat Panel: From Security Alerts to Soccer Games
Okay, my kids only played soccer for one brief summer, but I’ve got a lot of experience juggling parenting and work (and managing parents), so I’m excited to participate in this community conversation on Wednesday, August 6th, at 2:30 pm. What else will I be doing at BlackHat? With enough interest expressed, I may do a livestream from the expo floor, commenting on the messages I see from various vendor booths. Otherwise, I’ll be engaging in Hallway Tracks.
AI-matched news items
ChatGPT suggests the following relevant news articles:
1. OpenAI’s Superalignment Team Implodes
Story: Jan Leike and Ilya Sutskever, the leaders of OpenAI’s “superalignment” safety initiative, both exited the company amid internal dissent over the direction of the company. Leike’s resignation was followed by a highly public critique of OpenAI’s leadership and priorities.
Leadership Lesson: When leadership stops listening internally, people go external. The instinct to hide or control dissent often backfires—drawing even more attention. Transparency and internal accountability matter more than crisis comms after the fact.
2. Samsung Bans Use of ChatGPT… After Employees Feed It Confidential Data
Story: Employees reportedly uploaded sensitive code to ChatGPT, triggering Samsung to ban AI use internally.
Leadership Lesson: This is classic “caught red-handed” behavior: users found a workaround to a gap in company enablement. Leaders who don’t provide secure, sanctioned tools should expect shadow tools—and when they crack down after exposure, it shows they weren’t thinking ahead.
3. Boeing’s CEO Resignation and the Panic Pivot
Story: Under intense scrutiny for 737 MAX safety failures and near-misses, Boeing’s CEO Dave Calhoun announced his resignation, part of a broader leadership shakeup.
Leadership Lesson: The company’s panicked reshuffle came after being caught trying to downplay recurring safety issues. The public’s trust eroded not from the incidents themselves, but from the sense of evasion and deflection.
4. TikTok Creators React to Ban Legislation—With Misinformation
Story: In the wake of potential bans, TikTok influencers were caught spreading misleading content about the bill’s implications—seemingly in panic or under pressure.
Leadership Lesson: Leaders (or influencers) under stress may mislead their audiences out of fear, but the truth almost always catches up. Being “caught” in a bad moment tests whether your instinct is honesty or obfuscation.
5. Harvard President Resigns Amid Plagiarism Scandal
Story: Claudine Gay stepped down after plagiarism accusations surfaced—compounded by awkward attempts to explain it away.
Leadership Lesson: The lesson isn’t just about plagiarism, but about how leaders respond when caught. The damage wasn’t the initial issue; it was the delay and defensiveness that undermined authority.