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The one question to ask a security team that will tell you if their company is secure

Well, okay, it won't actually tell you whether they are secure or not and there are other questions you could ask, but the point is you can tell a lot about a company's security by how they answer security questions. I was recently at a security round table and the conversation turned to third parties and how you can assure yourself of their security. Some advocated scoring companies or certifications, while others advocated sending questionnaires. The argument against questionnaires is that they are a point in time view of the organisation. However, you can ask process and policy based questions and you can tell a lot from how they answer.

So, what is the question that will reveal all? Well, as I said it's not one question as such, more a type of question. It should be about something basic, some security control you're sure they have because everyone does. For example:

Why do you have a firewall?

Probable answers:
  • "because everyone has one"/"because the course I went on said I should have one"/"because my last organisation has one and they are very secure" - bad answer, you're not thinking about controls or security, but instead just buying popular products or whatever the vendor sells you and undoubtedly have a false sense of security
  • "because our PCI/ISO/HIPAA/Other certification says we have to" - bad answer, you're ticking boxes and chasing compliance rather than actually trying to be secure
  • "well, a firewall is part of a secure layered architecture and enables segregation at the network level, restricting the ingress and egress... etc." - okay answer, at least you know what it does and may understand its limitations
  • "our threat modelling has identified threat actors and attack scenarios that can be mitigated, in part, by introducing a firewall at this location in our network" - good answer, you understand the technology, you are thinking how to deploy it, what technologies could help you secure your assets and what are the best projects/controls you can spend your limited budget on to reduce risk

I have done (and still do) many third party assessments and I do advocate asking them questions rather than just trusting someone else's word or a rating/certification of some sort, but I'm mostly interested in how they answer questions. I've seen too many 'compliant' companies say "We're secure, the U.S. Government uses us!" or "All the high street banks use our service!", yet fail close inspection and have glaring weaknesses or vulnerabilities.

Trust your own judgement; ask them a question. And if you're a third party, ask yourself the question... with all your controls.
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