Hiring a Head of Security Doesn't Solve the Translation Problem

Hiring a head of security is the right move. It doesn't solve the translation problem.

Six months in, you have a 40-page roadmap, three new vendor contracts, and a budget request. Your head of security is competent. The recommendations are probably sound.

But you have no way to evaluate any of it. Every question gets answered with more technical detail. Every pushback requires expertise you don't have. You are fully dependent on someone you hired to be independent.

That is not a failure of trust. It is a structural problem.

The Security Diagnosis is not a check on your hire. It is how you show up to that conversation as an informed decision-maker. It gives you the questions to ask, the benchmarks to use, and a clear picture of what is appropriate for your stage.

So when your head of security comes to you with a budget request, you can evaluate it yourself.