I could write a long paper on this, and I would have if I thought it would've made a difference... But some highlights:
- Stovepiped organisations: stick in your own lane. But security is cross cutting.
- Security orgs want to stick to what they know about, not what the threat scope is.
- Security unwilling to own risk, fall back on ass-covering checklists and mandatory processes. This leads to them being an obstacle, a cost rather than a benefit.
- True lack of expertise at stakeholder level. Particularly in the US, the experts are contracted, and never speak out of turn.
- Staying quiet. Americans are extremely conscious of organisational (rather than technical) status and embarassment, and it isn't career enhancing to identify naked emperors.
- Good security costs money upfront, and pays back over time. Bad security is free at the beginning, and costs massive amounts to fix, but: (a) fixing is someone else's problem, (b) fixing is new contracts and more work, (c) systems might not be noticeably hacked.
Large companies (e.g. Lockheed Martin) are often very adversarial, and deny fault with lawyers. I've often wondered if places like Japan, with more cooperative cultures, can address this differently.