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# Your organizational culture may be your biggest security vulnerability.
- URL: https://www.danreshef.com/your-organizational-culture-may-be-your-biggest-security-vulnerability/
- Published: 2026-08-28T13:11:35.000Z
- Updated: 2026-08-28T13:11:35.000Z
- Description: It’s your organizational culture that determines whether someone feels comfortable raising the red flag when an executive says: “We’re running behind schedule.”
- Author: Dan Reshef
- Tags: Technology & Judgment, Cybersecurity, The Odyssey

In my previous posts I’ve argued that the Greeks didn’t defeat Troy’s walls. They defeated the rationale for deciding what was allowed to cross them.  
  
But it wasn’t just that Sinon lied his pants off so that King Priam would say yes to the horse. It’s that two people spoke out and King Priam still said yes.  
  
One was Laocoön. He was a Trojan priest and explicitly warned against bringing the horse into the city. Then he tried to make the point more explicit by throwing a spear into the horse. Sadly, he and his sons were killed by sea serpents shortly after he threw the spear. The Trojans interpreted the deaths as divine punishment for attacking Athena’s offering. And, using logic similar to trial by combat, his death is proof that his warning was wrong. QED.  
  
The other was Cassandra. She was King Priam’s daughter, had the power of prophecy, and forecasted a 100% chance of disaster for Troy regarding betting on this particular horse. Sadly, she was also cursed by the god Apollo that no one would believe her prophecies. Including her dad. Cassandra knew the truth, was about as close as anyone can get to leadership, but was still disbelieved.  
  
Two people raised the red flag that something was up with the horse.  
  
But some very compelling signals said otherwise.  
  
The competing reality was that the Greeks were gone, the war was over, and Troy just needed to break their own walls to put that horse near the temple of Athena. This way they would have Athena’s divine protection and turn the tables on the Greeks. Even King Priam couldn’t resist a BOGO…  
  
Laocoön had role power, Cassandra had proximity to power and the truth, but neither had enough influence.  
  
And the person asking those uncomfortable questions? Yeah, they just don’t get the work… Maybe they’re no longer a cultural fit?  
  
This is why organizational culture matters to cybersecurity.  
  
Your policies can say: “All requests need to be verified.”  
  
But it’s your organizational culture that determines whether someone feels comfortable raising the red flag when an executive says: “We’re running behind schedule.”  
  
Security controls don’t operate outside the organization. They operate through its hierarchy, incentives, deadlines, relationships, and norms.  
  
Troy had excellent walls. It lacked a culture capable of slowing things down when leadership wanted to move forward.  
  
A warning is not a control unless the organization is capable of acting on it.  
  
Next: What can we do to make it safer to slow things down or even say “no.”