Please join us on Friday October 31, 2025 for Super Cyber Friday.
Our topic of discussion will be “Hacking CISO Self-Interest: An hour of critical thinking about how security leaders actually make decisions.”
REGISTER FOR 10-31-25 Super Cyber Friday
Joining David Spark (@dspark), producer of CISO Series for this discussion will be:
- Howard Holton, CEO, GigaOm
- Angela Williams, svp and CISO, UL Solutions
Got feedback? Join the conversation on LinkedIn.
In preparation for our discussion, think about the following:
- What’s a security decision where the “safe choice” and the “best technical choice” weren’t the same thing
- When you’re evaluating vendors, what percentage of your mental calculus is about the technology versus implementability and organizational fit?
- What’s the security tool in your stack that’s more about defensibility than effectiveness, and is that actually irrational?
- If we’re honest about the 76% personal risk mitigation stat Howard mentioned in his post, what does that reveal about how security maturity actually works in organizations?
- What’s the difference between a CISO who manages risk and one who manages career risk? Are those actually the same job?
- How do you think about the tradeoff between “this will make us more secure” and “this has a realistic chance of successful deployment with my current team and budget”?
- What’s a vendor conversation where their honesty about implementation challenges actually won them the deal instead of losing it?
- How do you mentor younger security leaders about the gap between “what the tool does” and “what matters for getting it approved and deployed”?
- What’s the insight about how CISOs really make decisions that you wish vendors understood better?
- What’s the reality of CISO buying behavior that sounds cynical but is actually just organizational pragmatism?
- If you could redesign how security vendors sell to better match how CISOs actually evaluate and decide, what would change?
It all starts at 1 PM Eastern/10 AM Pacific. At the end of the hour [2 PM Eastern/11 AM Pacific] we’ll switch gears to our meetup where everyone will get a chance to chat face to face.
ALSO…
- We play games during the show, and some players can win prizes! Players in the US can receive prizes as gifts; those outside the US can win gift cards.
Super Cyber Fridays are open discussions where all viewers and listeners are welcome to become participants. Before the scheduled event, connect your webcam and microphone (avoid Bluetooth). During the discussion, if you have a question or comment, let it be known in the chat room and our producer will do his best to get as many of you into the conversation. We look forward to you joining us.