לא משנה מתי תשלחי לי את הטיוטה, אני אקרא אותה הערב.

In this sentence, לא משנה means it doesn’t matter or regardless.

Literally, משנה comes from the verb לשנות / להיות משנה in the sense of to make a difference / to matter. So לא משנה מתי... is literally something like it doesn’t matter when...

This is a very common Hebrew expression:

• לא משנה מי = no matter who
• לא משנה איפה = no matter where
• לא משנה מתי = no matter when

So the beginning of the sentence, לא משנה מתי תשלחי לי את הטיוטה, means No matter when you send me the draft.

Yes, מתי normally means when? as a question word.

But after לא משנה, Hebrew often uses question words in a way that matches English no matter + question word:

• לא משנה מתי = no matter when
• לא משנה איך = no matter how
• לא משנה למה = no matter why

So even though מתי is usually interrogative, here it is part of a fixed pattern.

תשלחי is the future tense, second person singular feminine form of לשלוח (to send).

So it means:

• you will send — when speaking to one female

Hebrew marks gender in the you forms, unlike English.

Relevant forms:

• תשלחי = you (feminine singular) will send
• תשלח = you (masculine singular) will send
• תשלחו = you (plural) will send

So this sentence is being said to a woman.
If you were speaking to a man, it would be:

לא משנה מתי תשלח לי את הטיוטה, אני אקרא אותה הערב.

In Hebrew, when you talk about something that will happen in the future, you normally use the future tense, even after words like when.

So:

• מתי תשלחי = when you send / when will you send

In English, after no matter when, we often use the present:

• No matter when you send it...

But Hebrew keeps the verb in the future because the action is still future from the speaker’s point of view.

That is completely normal Hebrew:

• כשתגיעי, נדבר = when you arrive, we’ll talk
• אם תכתבי לי, אענה = if you write to me, I’ll answer

לי means to me or for me.

It is made of:

• ל־ = to
• ־י = me

So:

• תשלחי לי = you will send to me
• more naturally in English: send me

Hebrew often uses this kind of preposition + pronoun suffix:

• לו = to him
• לה = to her
• לנו = to us
• להם = to them

את here is the direct object marker. It has no equivalent word in English.

Hebrew uses את before a definite direct object, such as:

• a noun with ה־ (the)
• a proper name
• a pronoun

So:

• תשלחי טיוטה = you will send a draft
• תשלחי את הטיוטה = you will send the draft

Because הטיוטה means the draft, it is definite, so את is required.

Important: this את is not the word you. It is a completely different word.

הטיוטה means the draft.
The ה־ at the beginning is the definite article the.

So:

• טיוטה = a draft
• הטיוטה = the draft

Using the draft suggests that both speaker and listener already know which draft is being discussed.

In Hebrew, the future tense is usually expressed by the verb form itself, without needing a separate word like English will.

So:

• אקרא = I will read

You can include אני for emphasis or clarity:

• אני אקרא = I will read

But the future meaning is carried by אקרא, not by אני.

This is very normal in Hebrew:

• אכתוב = I will write
• אבוא = I will come
• אשלח = I will send

In your sentence, אני is included, probably for clarity or emphasis:

• אני אקרא אותה הערב = I will read it this evening

אותה means her / it for a feminine singular direct object.

Since טיוטה is a feminine noun, the pronoun referring back to it must also be feminine:

• טיוטה = feminine
• אותה = it (referring to a feminine noun)

Hebrew object pronouns reflect gender:

• אותו = him / it (masculine singular)
• אותה = her / it (feminine singular)
• אותם / אותן = them

So:

• אני אקרא אותה = I will read it
  where it = the draft

English uses one word, it, for both masculine and feminine objects, but Hebrew does not.

Hebrew, like English, often uses a pronoun to avoid repetition.

So instead of saying:

• אני אקרא את הטיוטה הערב

the speaker says:

• אני אקרא אותה הערב = I’ll read it this evening

Both are grammatical. Using אותה just sounds more natural when the noun has already been mentioned.

Here הערב means this evening / tonight.

Literally, it is the evening, but in actual usage it often works like a time expression:

• אני אקרא אותה הערב = I’ll read it tonight / this evening

Hebrew often uses הבוקר, הצהריים, הערב, הלילה as adverbial time expressions:

• הבוקר = this morning
• הערב = this evening / tonight
• הלילה = tonight / at night

So although it literally contains the, the natural English translation is usually tonight or this evening, not the evening.

The sentence is:

לא משנה מתי תשלחי לי את הטיוטה, אני אקרא אותה הערב.

A natural breakdown is:

• לא משנה = it doesn’t matter
• מתי תשלחי לי את הטיוטה = when you send me the draft
• אני אקרא אותה הערב = I will read it this evening

So the structure is roughly:

No matter when + subordinate clause, main clause

Hebrew word order is fairly flexible, but this order is very natural and common.

You would change the verb that agrees with you.

To a man:

• לא משנה מתי תשלח לי את הטיוטה, אני אקרא אותה הערב.

To a group:

• לא משנה מתי תשלחו לי את הטיוטה, אני אקרא אותה הערב.

Only the you will send form changes:

• תשלחי = you (feminine singular)
• תשלח = you (masculine singular)
• תשלחו = you (plural)

The rest of the sentence can stay the same.