Don’t Be The Bear

Leadership Moment: Begging Forgiveness, or Planning Harm?

Two weeks ago, I wrote about the entertaining experience of watching a hotel clerk completely ignore me for ten minutes. To be clear, at any point I could have advocated for myself. I could have written my checkout note on a piece of paper, and then called my taxi. But my wait was somewhat performative – I knew what was likely to happen, and knew exactly how I’d use it to make a point about awareness. I wasn’t harmed, or stressed, or offended in any fashion. So I sent out the newsletter.

Shortly after I sent it, I received an email from a colleague – the one who handles our relationship with the hotel. The colleague wanted to know if I needed a followup. I read an undercurrent of stress (it might not have been there), because I’d surprised my colleague. It’s a trite saying in business that “It’s better to beg forgiveness than ask permission,” and in many ways it’s true. But you also need to recognize when the surprise isn’t providing value, and is just creating stress for your colleagues.

Subscribe now



Feb 28: Oped: The Death of the CIO

March 7: Blog: Decision Making at the Organizational Level (AI Part II)


March 19: Crestron Modern Work Summit, Orlando: AI-Driven Hospitality in the Modern Workplace

March 22: YL Ventures Breakfast Club, NYC: The Post-CISO Life

Apr 4: Webinar, CISO Fireside Chat: 2024 State of Public Cloud Security

May 8, 2:55 Pacific: You Can’t Measure Risk, RSAC (San Francisco)

September 24: HOU.SEC.CON

One Minute Pro Tip: Who Needs to Know? When?

When you’re about to do something noteworthy, pause for a moment and ask yourself, “Who needs to know about this? Who would like a heads-up that it’s coming?” Coordination and notification feels expensive, especially when colleagues who learn what you’re doing at the last minute demand more context and information (or, worse, input).

If you plan that coordination, it gets easier, especially if you’re clear. “I wanted to give you an early look at our new messaging; no action needed on your part, but I’d be happy to hear your feedback” is, surprisingly, less likely to elicit disruptive feedback than, “Here’s our new messaging effective tomorrow.” Why? Because the first sounds like you have everything under control, and are getting input from all the right stakeholders; the second doesn’t, which means people are likely to react to it by giving you the input you obviously missed.

Outrun the bear, not your friends.

Duha One: Leadership in minutes is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.