Che cosa intende con questa parola?

Yes. Che cosa and cosa can both mean what.

• Che cosa intende con questa parola?
• Cosa intende con questa parola?

Both are natural. Che cosa is a little fuller and can sound slightly more careful or formal, while cosa is often more direct and common in everyday speech.

You may also hear:

• Che intende con questa parola?

That is possible too, though che cosa is often clearer for learners.

Intende is the third person singular form of the verb intendere in the present indicative.

So it can mean:

• he means
• she means
• it means
• you mean in a formal sense (Lei)

In this sentence, context usually tells you which one is intended. Very often, this sentence is used as a formal question meaning:

• What do you mean by this word?

Because Italian uses Lei as the polite/formal word for you, and Lei takes third-person singular verb forms.

So:

• Tu intendi = informal singular you mean
• Lei intende = formal singular you mean

That is why Che cosa intende con questa parola? is a polite or formal way to ask the question.

If you were speaking informally to one person, you would usually say:

• Che cosa intendi con questa parola?

With intendere, Italian commonly uses con to express by in the sense of what someone means by something.

So:

• intendere con una parola
• intendere con un’espressione

This is the normal pattern.

English says mean by, but Italian says intendere con in this type of sentence. So con is the preposition you should expect here.

Questa parola is a noun phrase made of:

• questa = this (feminine singular demonstrative adjective)
• parola = word (feminine singular noun)

They agree in gender and number:

• questa parola = this word
• queste parole = these words

Because parola is feminine singular, the demonstrative must also be feminine singular: questa.

This is a normal Italian question structure. Italian often does not need to invert the subject and verb the way English sometimes does.

The sentence is basically:

• Che cosa = what
• intende = do you mean / does he mean
• con questa parola = by this word

Italian can form questions just with intonation and context, without changing the basic order very much.

You could sometimes hear slight variations, such as:

• Con questa parola, che cosa intende?

This version gives more emphasis to con questa parola, but the original sentence is the most straightforward neutral form.

It is generally formal or polite, because of intende used with formal Lei.

A more informal version to one person would be:

• Che cosa intendi con questa parola?

To more than one person formally or informally, you might say:

• Che cosa intendete con questa parola?

So the level of formality depends mainly on the verb form.

Sometimes yes, but the meaning is not always exactly the same.

• Che cosa vuol dire questa parola? usually means What does this word mean?
• Che cosa intende con questa parola? usually means What do you mean by this word?

So vuol dire often asks about the dictionary meaning of the word itself, while intendere con asks about the speaker’s intended meaning or use of that word.

That difference is important.

Yes. Grammatically, intende could also mean:

• he means
• she means

For example, in reported speech or discussion:

• Che cosa intende con questa parola l’autore?
  = What does the author mean by this word?

Without extra context, the sentence alone is ambiguous. In real conversation, though, the situation usually makes it clear whether it means you or he/she.

Here are the most useful versions:

• Informal singular: Che cosa intendi con questa parola?
• Formal singular: Che cosa intende con questa parola?
• Plural: Che cosa intendete con questa parola?

So the main thing that changes is the verb:

• intendi = you mean (informal, one person)
• intende = you mean (formal, one person)
• intendete = you mean (more than one person)

Yes, it is fairly common, especially in formal, written, or careful speech.

Common meanings include:

• to mean
• to intend
• to understand in a certain sense

Examples:

• Cosa intendi dire? = What do you mean?
• Non intendo offenderti. = I do not intend to offend you.
• La parola va intesa così. = The word should be understood this way.

In your sentence, intendere has the meaning of to mean or to have in mind.