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I'm not fully sure of how to go about conveying the meaning of sentences like "I should be going to bed now" or "He should be speaking decent English". I think part of my problem may stem from the fact that I'm not even sure what you would call the "be [infinitive verb] + ing" part in English.

Let's take my second example: "He should be speaking decent English"

I imagine that one could possibly translate this as "Er soll gut Englisch sprechen", without any trace of "be speaking", but I feel this is losing some information. In English, the two phrases "He should speak good English" and "He should be speaking good English" are not exactly equal.

The former is implying that he probably speaks good English, where as the latter is implying that he is expected to speak good English.

Is there a compact way of translating this into German, or is it necessary to change the sentences to be more explicit in meaning?

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    Ich würde ja gerne antworten, aber ich sollte jetzt wirklich ins Bett gehen …
    – Wrzlprmft ♦
    Commented Apr 30, 2014 at 0:52
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    Well that was quick. It's really so simple?
    – Astrum
    Commented Apr 30, 2014 at 1:00
  • Well I'd say you should be asking more questions. They are good questions ;)
    – Vogel612
    Commented Apr 30, 2014 at 7:12
  • @Astrum: It’s not wrong. But most of all, it’s a meta joke (at least for people in my time zone), as I was answering this at 3 o’clock and when I really should be going to bed.
    – Wrzlprmft ♦
    Commented Apr 30, 2014 at 13:10

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The problem is that ...

Er soll gut Englisch sprechen

... can mean two things in German: 1) He speaks good English (they say) and 2) He should be speaking good English (he's been in the country for a few years, after all).

This is really not all that different from the English "He's supposed to speak good English", though, is it?

Is there a compact way of translating this into German, or is it necessary to change the sentences to be more explicit in meaning?

Yes, I think you'd have to reword slightly to remove any ambiguities. A few examples: 

Eigentlich sollte er gut Englisch sprechen (but for some reason he does not)
Ich nehme an, dass er gut Englisch spricht (but I don't know for sure)
Angeblich spricht er gut Englisch (or so I've heard)
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In present it's the same:

Jetzt sollte er gut Englisch sprechen.

But in past you do differentiate both meanings. And you do so by choosing if you want the modal verb as auxiliary or if you use haben as auxiliary:

  • The objective use (objektiver Gebrauch):

    Petra hat sehr gut Englisch sprechen sollen. (d.h. sie war verpflichtet, z.B IELTS abzulegen)

  • The subjective use (subjektiver Gebrauch):

    Petra soll sehr gut Englisch gesprochen haben (weil ich jetzt sehe, sie hat die Prüfung mit unglaublich gutem Ergebnis bestanden)

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