"When I have had to break bad news I never know whether I .." or "I never knew whether I ..."?

Question

From "Do No Harm" by Henry Marsh:

'Well, it's very difficult,' I said in a gentler tone. 'That's why I was asking you.' When I have had to break bad news I never know whether I have done it well or not. The patients aren’t going to ring me up afterward and say, ‘Mr. Marsh, I really liked the way you told me that I was going to die,’ or ‘Mr. Marsh, you were crap.’ You can only hope that you haven’t made too much of a mess of it.

Shouldn't it be "I never knew" or "I never have known", since the instances he recalls are in the period up to the present moment (have had)?

Or maybe it should be "When I have to break bad news", to harmonize it with "I never know"?

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Additional context: this is from the book's story titled Ependymoma. The neurosurgeon shows a scan of a just-discovered incurable brain tumor to a group of students he supervises. He then asks a student to tell what he would tell this woman patient if he were her surgeon. The student fumbles for words, telling of "abnormality" and "mass effect" in the brain. The neurosurgeon mocks the use of such terminology, saying that the patient will guess the harsh truth anyway. The student stalls. Then Henry Marsh says the words in the quotation above.

Answer 1

I have just had a cup of coffee. This means that I'm not drinking coffee at the moment. But if someone asks me how I'm feeling, I might say that I've just had a coffee, because that's a description of my current state.

Now, I never smoke when I'm having a coffee. I hate the way that smoking makes my coffee taste - the coffee tastes disgusting. But after I've had a coffee, I always have a strong urge to have a cigarette. I don't want to have a cigarette when I'm smoking, but I always want to have a cigarette after I've had a coffee.

So I could phrase the situation above like this:

• When I have a coffee, I want to have a cigarette. (not good)

The problem here is that the sentence sounds like it's describing me wanting to have a cigarette while I'm drinking my coffee. I really want to describe the situation that I'm in when I've already had my coffee. I can use the present perfect to do this:

• When I have had a coffee, I always want to have a cigarette.

This sentence is better, because it says that when I am in an I've had a cigarette situation, I want to have a coffee. Notice that this sentence isn't about the past. It isn't about right now. It is referring to general time. It means I always want a cigarette in I've had a coffee situations.

Now consider the speaker in the Original Poster's example. They often have to give patients bad news. If you phone them up up one day and ask them how they are, they might say I have had to give a patient bad news. They're using the present perfect here because the giving bad news action is finished, but the phrase have had to give a patient bad news tells you something about their present situation.

Now this writer regularly has to give patients bad news. After he tells them the bad news, he often thinks a lot about whether he gave the news in a bad way. Maybe he worries about this for a few hours or maybe a few days. When he thinks about it, he never knows if he gave them the news in a good way or not.

The writer does not say that he thinks about it when he has to give them the news. He thinks about it afterwards when he is in an I've recently had to give someone bad news situation. To show this the writer uses a present perfect:

• When I've had to break bad news ...

This sentence isn't about the past, it's about every time that he is in a situation where he has just given someone bad news - now, in the past and in the future. What happens when he is thinking about whether he broke the news well or badly? He says:

... I never know whether I have done it well or not.

Here he uses the present simple to indicate it is always how he feels in this post-breaking bad news situation.

Conclusion

The anchor time, the time the author is speaking about, is the time after he has had to break the bad news. He doesn't use a present simple to describe this, because the breaking bad news always happens just before this time. He uses the present simple for the second clause because it describes the mental state he always has during this anchor time, the post-breaking bad news situation.

In my opinion, the writer could make the sentence clearer by changing a few words. They could use whenever instead of when. This would help us understand that this might be a recurring situation. Secondly, the writer could use the word recently or just. This would reinforce that the present perfect is being used to show the anteriority (earlier-ness) of the breaking news event:

Whenever I've just had to break bad news to someone, I never know whether I've done it well or not.

Answer 2

The sentence may sound unusual to many, but I believe that it's perfectly grammatical, and actually quite appropriate to the occasion:

When I have had to break bad news I never know whether I have done it well or not.

Let's think of it this way:

[ I never know ] [ whether I have done it well or not ] [ when(ever) I have had to break bad news ].

• I never know = the main clause
• whether I have done it well or not = the main idea
• when(ever) I have had to break bad news = the condition

(Perhaps many will feel more comfortable with the paraphrase above.)

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The context suggests that this is not a one-time thing (because of The patients in the next sentence). So, this When has the meaning of whenever (= every time this happens/has happened).

I believe that the use of the perfect aspect is more appropriate here because it's his reflection upon the past events when (read "after") each instance of such events has happened, and he projects his thought into the future. (In other words, this condition still holds true and it's unlikely to change in the foreseen future.)

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This kind of sentence, though not very common, is not too rare to find on the web. For example,

I know that whenever another person has chosen to know me and be with me for only my sake, I have tasted the future; I have tasted the reality of resurrection.
-- Relationships Unfiltered: Help for Youth Workers, Volunteers, and Parents on Creating Authentic Relationships By Andrew Root, p. 92

“... Whenever he has been choragus, you know, his choir has always won.”
-- Delphi Complete Works of Xenophon (Illustrated), p. 857

Answer 3

The author is using the present tense since he is saying that during the moment that he needed to tell bad news, he does not know if he is doing it well. It is also reflected by the present perfect have done.

I never know whether I have done it well or not

There are three time periods portrayed in this example (in reverse sequential order)

knowing the outcome (most recent or continuing)
whether a good job was done or not
breaking the bad news (furthest in past, but repetitive)

Since breaking bad news may be repetitive (whenever) in the future, the speaker might say

When I have to break bad news I never know if I have done it well or not

In your example, the speaker is relating his experiences.

To refer to repetition in the past

When I have had to break bad news I never knew if I had done it well or not

If the speaker were to contrast that he used to not know how to break bad news, but now he does know a better way to do it, he might say

When I had to break bad news I had not known whether I had done it well or not.
But then I learned how to do that better...

All these forms, including your original example, are understandable to mean:
the speaker was concerned with giving bad news as gently as possible but was not sure how the bad news was received