1

I was with some colleagues and an English native today. We talked about the work we still have to do, and he mentioned kind of "tracking the outstanding items".
I was taught at school that "outstanding" means something like "extraordinary", so I asked him and he explained that both ("extraordinary" as well as "something to be done") is correct and commonly used.

This seemed acceptable, but I'm in doubt about how one can distinguish what is meant. Imagine sentences like these:
"Let's talk about your outstanding work"
-> Can I expect to be complimented or should I better be afraid?

"He's keen on delivering outstanding work products"
-> Is he just keen on getting work done, or is he keen on doing the very best one can do?

Or would the perfect English speaker never use the above constructions?
Or are they just wrong?
Would the perfect English speaker have an eye on the context and possibly decide to better use a different word than "outstanding"?

2

As your friend explained, 'outstanding' can have either of those meanings, depending on context. As such, their meaning usually relies entirely on the situation in which they are said - the sentence itself, without the surrounding facts, won't tell you much.

I suppose the hypothetical 'perfect' English speaker would avoid such words, but most of us just grab for whichever word is closest, relying on the context of the sentence to convey the meaning. In your first example, whether you should be happy or afraid depends entirely on the tone of the person speaking (and whether you're late in delivering any work!).

2

In one meaning of outstanding you could say it is describing things that stand out compared to other things.

As I read your examples, this is the meaning I get from them. This is sense 2 in the definition linked below.

When you use the phrase:

tracking the outstanding items

outstanding has a different meaning. Here outstanding means things that have not been completed or settled. See this definition outstanding sense 3.

I will finish the outstanding tasks next week.

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