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There seem to be some examples where dass does not seem to be needed but I don't know how to differentiate when it's required or not.

For example:

Wollen Sie ihm sagen, er sollte es mir so schnell wie möglich schicken.

or

Wollen Sie ihm sagen, dass er es mir so schnell wie möglich schicken sollte.

It doesn't seem to relate to a simple sentence structure because, for example, the sentence "will you tell him to call me?" seems simple, but requires dass.

Werden Sie ihm sagen, dass er mich anrufen soll.

Are there any rules or ways to tell?

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Covered by the answer of PMF, but here's the last sentence without dass: "Werden Sie ihm sagen, er solle mich anrufen?" –  Em1 Jan 10 at 8:39
    
@Em1 ... I doubt that very much. We can modify the example a bit and say "Werden sie ihm sagen, er sehe gut aus.". I don't think the conjunctiv is correct here. It doesn't sound that bad with "sollen" but with other verbs it starts to be out of place. I think "sollen" works because there is the same phrasing with "er möge/möchte mich anrufen" which expresses an order pretty much but that is a special case –  Emanuel Jan 10 at 10:52
    
@Emanuel Good point. I'd actually even say "er solle mich doch bitte anrufen" which covers the "möge" part. I guess the politeness is the reason that I'd like to use K1. Need to think about it further. –  Em1 Jan 10 at 11:44

2 Answers 2

Will you tell him, (that) he should call me?

The method to use here is the so called 'uneingeleiteter Nebensatz'.

Würden Sie ihm sagen, er soll mich anrufen?

In spoken German this is actually used as much as the version with 'dass'.

You cannot per se apply this to all 'dass'-expressions. Just refer to Wiki for details.

I would say: For now stick to the 'dass' and try to pick up these exceptions on the fly.

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I guess verbal speech is meant to be direct speech. Try a colon and quotation marks. However, the ~verbal speech must be rephrased. Anyway. Try K1. –  Em1 Jan 10 at 8:41
    
I think what you meant with 'verbal' or direct speech is: Würden Sie ihm sagen: "(Du/Sie) (sollst/sollen) mich anrufen."? And never forget to say "bitte" ;) –  Thorben Jan 10 at 9:18
1  
They are called "uneingeleitete Nebensätze" and they are totally grammatical (official part of German grammar as of Duden) and they are written as follows... "Er sagt, er kommt." No need for semicolon. Y –  Emanuel Jan 10 at 10:57
1  
Your example "Würden Sie ihm sagen; Er soll mich anrufen?" is still wrong. First no semi-colon but comma, second no capitalization of "Er". And I would say "... er solle mich anrufen" but I'm not sure if this correct here. It would be correct "Er sagte, dass er ... ist" -> "Er sagte, er sei ..." but can't find anything on the net what proves I'm right on this here. –  Em1 Jan 10 at 11:35
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@Em1... "Er sagte, er sei ... " this is only done in writing or by the intelligenzia ;). The general public does not use the conjunctive for that. If you want to weird out your friends at the bar say "Er sagte, er komme zu spät" –  Emanuel Jan 10 at 11:56

You can often replace the second part with indirect speech to remove the "dass", but that could change the meaning or the point of view:

Sagen Sie ihm, dass er es mir schicken soll.

Sagen Sie ihm, er solle es mir schicken.

Oder:

Medien berichteten, dass diesen Winter schon 8 Personen in Lawinen umgekommen sind.

Medien berichteten, es seien schon 8 Personen in Lawinen umgekommen.

Since the form with indirect speech sounds formal and is sometimes hard to get right (even by native speakers) the form with "dass" is more common.

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I think you should take out all the conjunctive forms. Just because we change a dass-sentence into a v2-sentence, that does not change the mode. We can modify the example a bit and say "Werden sie ihm sagen, er sehe gut aus.". I don't think the conjunctiv is correct here. It doesn't sound that bad with "sollen" but with other verbs it starts to be out of place. –  Emanuel Jan 10 at 10:54

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