Is this hypothetical (if-clause) question grammatically correct?

Question

I came across the following question at a chat room:

If I were an admin responsible for the security of an organization's network who were using X products in their network, how would I know for sure whether there were backdoors in them?

Is the above question grammatically correct?
And for the part in bold, is it a real question (as in asking for an answer) or is it rhetorical?

Answer 1

Just one small mistake, as I've highlighted. The word after "who" needs to be "was", because its singular and not subjunctive.

If I were an admin responsible for the security of an organisation's network who was using X products in their network, how would I know for sure whether there were backdoors in them?

It could be a real question or a rhetorical one. That is, I could be asking if there is a way to be sure that there are no backdoors in X products; or I could be asking rhetorically, because I know that there is no way to be sure.

Answer 2

The problem with the question is that there are two presumptions any listener is being asked to make as background for it:

1. That they are "an admin responsible for the security of an organization's network"
2. That the organization in question is "using X products in their network"

But the second one is presented as a extraposed relative clause modifying a distant noun (organization) instead of the one it follows (network), all of which makes it subordinate to the first one. So it's not clear whether it's an independent presumption or not.

Better would be something like

If I were an admin responsible for the security of an organization's network, and the organization was using X products in their network, how would I know for sure whether there were backdoors in them?

As for whether the foreground question itself is rhetorical or not, David Wallace is correct that there's no way to tell. It's entirely situational and pragmatic, not grammatical.

Answer 3

Subjunctive admin role, determinate organisational user of Product X, asserting the low possibility of knowing, projecting the subjunctive knowledge of the presence of back-doors:

If I were an admin responsible for the security of the network of an organisation that uses Product X on their network, how would I know for sure if there could be back-doors in them?

Subjunctive admin role, indeterminate organisational user of Product X, asserting the low possibility of knowing, projecting the subjunctive knowledge of the presence of back-doors:

If I were an admin responsible for the security of the network of an organisation that were to use Product X on their network, how would I know for sure if there could be back-doors in them?

Comments

• 1: try not to use "who" on an organisation. Use "that", "which".
• 2: practice of proximity - of who/which/that (relative pronouns) to "organisation" - rearrange the phrase to network of the organisation.
• 3: "whether" is redundant colloquialism.

Even after smoothing out crinkles, the logic of the sentence is still ill-phrased because it is akin to asking, "If I were a man attracted to women, how would I know the desires of a woman". It is has a sense of disconnectedness.

The better way to phrase it would be,

Even if I were an admin responsible for the security of the network of an organisation that uses Product X on their network, would I know for sure the presence of back-doors in them?

Alternatively, in a different mood:

Even if I were an admin responsible for the security of the network of an organisation that were to use Product X on their network, would I know for sure the presence of back-doors in them?

i.e.

If I were a man attracted to women, would I even know the desires of women?