Question 1

Our cyber insurance premium just doubled. Is that about us or about everyone?

Accepted Answer

Usually some of both. Part of it is the market. The rest is your application: insurers price what you tell them about MFA, backups and incident planning. I'll read it with you and tell you which answers are costing you money, and what it takes to change them.

Question 2

We've got two technical recommendations and can't tell which is right. How do you decide?

Accepted Answer

I start with the decision, not the technology: what it has to do, what it costs to run for the life of the contract, who owns it when the person who proposed it leaves, and what it changes about your security. Usually one option falls out quickly. Sometimes the answer is neither.

Question 3

We already have an IT provider. Why would we need you?

Accepted Answer

Keep them. They run your systems; I make the calls they're waiting on someone to make: what to buy, what to stop, what "secure enough" means for a company like yours, and whether the contract covers what you think it covers. The good ones are glad to have someone on your side who speaks both languages.

Question 4

Someone we answer to asked what we're doing about cybersecurity. What do I tell them on Monday?

Accepted Answer

Three things, in plain language: what's protected and what isn't, what you've decided to accept and why, and what happens next, with dates. That fits on one page. They aren't asking for a list of tools; they're asking whether anyone owns the risk. If the honest answer is "not yet," say so and show them the plan. That beats a page full of logos.

Question 5

Be honest: will you tell me if we don't actually need you yet?

Accepted Answer

Yes. If a good IT provider and a few decisions will cover you for now, I'll say so on the first call and point you to who can help. That's better for both of us than paying for work you don't need.

Question 6

Are you a CTO or a CISO?

Accepted Answer

Both. At a company your size the questions overlap: the app, the IT contract and the insurance form are one conversation. Splitting them across two part-time people is how gaps happen. When a question needs a deep specialist, a pen tester or a senior developer, I'll say so and help you find the right one.

Question 7

Why "Nightglass"?

Accepted Answer

A night glass is a telescope built for seeing in the dark: a wide field of view at low magnification. That's the job. Look across the whole company, find what's hard to see, and tell you what to fix first.

Bring the question. We’ll find the answer.