Ο προϊστάμενος επέμεινε να στείλουμε την αναφορά σήμερα, παρόλο που είχαμε ήδη κάνει υπερωρία.

Ο προϊστάμενος means the supervisor, the manager, or the person in charge.

A few useful notes:

• προϊστάμενος is masculine singular here.
• It is often used for someone who is above others in a workplace hierarchy.
• Depending on context, English might translate it as supervisor, boss, department head, or manager.

So in this sentence, it refers to the person who had authority to insist.

Ο is the masculine singular definite article, meaning the.

It appears because προϊστάμενος is the subject of the sentence:

• Ο προϊστάμενος = the supervisor

In Greek, nouns normally take an article much more often than in English, especially when you mean a specific person or thing.

The two dots are a diaeresis. They show that the vowels are pronounced separately.

So προϊστάμενος is pronounced roughly as:

• pro-i-STA-me-nos

not as if οι were the normal Greek vowel combination pronounced ee.

Without the diaeresis, a learner might try to read it as one sound, which would be wrong here.

Επέμεινε is the aorist of επιμένω and means insisted.

The aorist is used because the sentence presents the insistence as a single completed event in the past. In other words, the speaker is not focusing on the duration of the insisting, but on the fact that it happened.

So:

• επέμεινε = he/she insisted

If Greek used the imperfect instead, it would suggest more ongoing or repeated insistence in the past.

After verbs like insist, Greek commonly uses να plus a verb form, where English often uses that + a clause or an infinitive-like structure.

Here:

• επέμεινε να στείλουμε... = he insisted that we send...

This is a very common Greek pattern:

• verb of wanting / demanding / insisting + να
  • subjunctive

So να is introducing the action that the supervisor insisted on.

Στείλουμε is the aorist subjunctive of στέλνω, while στέλνουμε is the present indicative or present subjunctive form in other contexts.

After να, Greek often chooses between:

• present subjunctive for ongoing, repeated, or habitual action
• aorist subjunctive for a single complete action

Here the idea is to send the report once, as a complete task. That is why Greek uses:

• να στείλουμε την αναφορά = that we send the report / to send the report

If you used να στέλνουμε, it would sound more like to be sending or to send regularly, which does not fit this context.

The ending -ουμε shows first person plural, so the subject is we.

Greek often leaves the subject pronoun unstated because the verb ending already tells you who the subject is.

So:

• στείλω = I send
• στείλεις = you send
• στείλει = he/she/it sends
• στείλουμε = we send
• στείλετε = you plural send
• στείλουν = they send

Here, there is no need to say εμείς unless the speaker wants extra emphasis.

Την αναφορά is the direct object of στείλουμε.

• αναφορά = report
• την = the feminine singular accusative article

Because αναφορά is feminine singular, and because it is the thing being sent, Greek uses the accusative:

• nominative: η αναφορά
• accusative: την αναφορά

This is one of the most important article patterns in Greek to learn.

Παρόλο που means although, even though, or despite the fact that.

It introduces a concessive clause: something is true, even though another fact might have suggested the opposite.

In this sentence:

• παρόλο που είχαμε ήδη κάνει υπερωρία
• even though we had already worked overtime

After παρόλο που, Greek normally uses a regular finite verb, not an infinitive. Here the verb is είχαμε κάνει.

Είχαμε ήδη κάνει is the pluperfect or past perfect:

• είχαμε = we had
• κάνει = done
• ήδη = already

So together:

• είχαμε ήδη κάνει = we had already done

In this sentence, κάνω υπερωρία means work overtime, so the whole phrase means:

• we had already worked overtime

This tense shows that the overtime happened before the supervisor insisted.

Because κάνω υπερωρία is a very common fixed expression meaning to work overtime or to do overtime.

Greek often omits the article in set expressions like this, especially when talking about an activity in a general sense.

So:

• κάνω υπερωρία = I work overtime
• κάναμε υπερωρία = we worked overtime

You may also hear related forms such as υπερωρίες in plural when talking about multiple overtime hours or shifts, but here the singular without an article is perfectly natural.

Σήμερα means today, and here it modifies στείλουμε:

• να στείλουμε την αναφορά σήμερα
• to send the report today

Yes, Greek word order is fairly flexible. You could also say:

• να στείλουμε σήμερα την αναφορά

Both are correct. The difference is usually about emphasis or rhythm, not basic meaning.

Greek often moves words around more freely than English, but the case endings and verb forms keep the meaning clear.