>>> thus, if you’ve been criticized (for example) for offering solutions rather than listening, >guilty

This is not necessarily a question of "guilty". There are two major directions a conversation can go - "sympathy" or "solution". If your partner wants one, and you give the other, you operate under wrong premises due to an unstated assumption. On both sides.

(If your "guilty" was a request for sympathy, I'm currently failing majorly. :)

You could do worse than ask people what they want out of a conversation when you start the conversation.

This is crucial. I've found that when I talk especially with people who reside more on the emotional side of the spectrum (I myself seem to be more on the logical side of the spectrum), I need to really clarify before the conversation gets too deep that I'm good at expressing solutions, but I'm not so good at expressing sympathy/empathy. I'm good at having sympathy (not always empathy), but I'm not good at expressing it.

People who contact me frequently to talk about something have come to understand this, and they just trust that I am being sympathetic, even if I am not showing all the signs. But for people who are not used to talking with me, they can sometimes find me unsettling and get upset at me. If someone could explain to me how to appear sincerely sympathetic in a way that makes sense to me, I'd love it. But nobody's ever been able to do that in a way that doesn't make me feel like I'd be pretending, which is awkward and weird, because it's not like I'm not sincerely sympathetic in my heart of hearts.

I'm also not naturally good at it, and the best I've come up with is that it's basically letting them know (in a way that is natural for you) that you believe that a world in which they have this problem is worse than a world in which they don't have this problem.

In fact just switching my default response to someone presenting a problem to: "that sucks" showed a marked improvement in interpersonal relationships for me.

What was your previous default response?

Watch how other people do it and fake it 'til you make it.

It helps to remember that you aren't lying in this; the feeling is real, only the performance is (temporarily) synthetic, and you're doing it to help your interlocutor feel safe and comfortable in the conversation, which in turn makes it more likely you will be able to help them. It will feel fake for a while, and you'll need to keenly observe reactions to know when you've got it dialed in. Eventually it becomes second nature and the feeling of fakeness goes away.

  If someone could explain to me how to appear
  sincerely sympathetic in a way that makes
  sense to me, I'd love it.

I'd go with the direct approach and not bother with appearances. It's consistent, easy to remember, and emotionally honest. For example:

  I'm an analytical person and am genuinely interested in
  what you have to say.  If you'd like to hear possible
  solutions I can think of, then they would be with the
  intent of trying to help.  If not, I'm here to listen.

"Emotionally honest" is a copout. What you mean is that it's easy for you and keeps you squarely centered in your comfort zone, while the person you supposedly think you're going to help has to do all the scary work of leaving her own.

I don't see how being emotionally honest qualifies as a cop-out. The GP's statement was about appearing to be sincerely sympathetic. What I recommended was to be true to themself and offered an example of how that could be stated in a constructive manner.

Perhaps the example I provided was not appealing to you, which is entirely understandable.

The GP's comment also included this crucial statement, which you might have overlooked:

> I'm good at having sympathy (not always empathy), but I'm not good at expressing it.

He wants to be better at expressing the sympathy he feels. That's why I said that, even though it feels fake at first, stick with it and model yourself after what you see other people do, and over time it will become quite natural. This is the same process by which humans learn almost all social behavior; it's just relatively rare to do it as an adult, when consciousness and introspection are fully formed and the concept of sincerity discovered.

The problem with the example you provided is not that it didn't appeal to me; I can understand where you're coming from with it, and I appreciate its sincerity. The problem I have is that that statement is not fit for purpose. In almost any case, it's not a tool which will work.

When I participate in this kind of conversation, I do so expressly because it's an opportunity to help someone. In order to accomplish that goal, it is necessary that my interlocutor be comfortable enough to open up and share the kind of information I need to fulfill the role I've chosen for myself in that context. In order for that to occur, I need to meet that person where he is. As I said, I understand and appreciate the nature of your proposed statement - but I also understand that most people are not like us, and not the sort of person with whom a such a bald statement ("Message: I care") is going to resonate.

So it's going to be very rare that a statement like that will serve the purpose I require of it, which in turn means that, if I use it, I will fail at something into which I've decided it is worth investing considerable time and effort toward succeeding.

My initial analysis suggested that, in order to make it possible for people to be comfortable enough with me that I might have a meaningful probability of being able to help them by any means, it would be necessary to develop a great deal of social fluency. So I did that. Then I went looking for ways in which I could deploy it to the benefit of others, and I found them. I'm still nowhere near as good at that as I intend eventually to become, but retrospective analysis suggests that even the moderate degree of skill I've developed in that regard has enabled me to produce a net positive emotional impact on the people around me - perhaps marginal for the most part, but demonstrable nonetheless, and showing a distinct if modest upward trend.

But I've put a lot of work into it, too, and it is not quite accurate to say that I'm the same person I was when I started. You might want to put some thought into whether that's something you feel is worth your while.

I hope you'll decide that it is. I've chosen to make a vocation of creating for other people, for a little while, a world to live in in which, sometimes, someone just cares. If you decide to do the same, it increases the chance that someday someone will do that for me. And there are days when I could really use it.

Leading with sympathy in personal relationships is usually a good idea. If you express sympathy when they want solution, they will often start thinking of solutions aloud, or flat out ask for your opinion. If you suggest solution when they just wanted sympathy, they will often respond with disappointment, anger, or defensiveness.

Perhaps just as often people don't know or understand what they want.

One thing that helps for expressing sympathy is using words or metaphors that describe the the person's emotions, like "that sounds scary" or "you sound angry"

Another thing is to describe what seems to be the heart of the problem, like "you want to trust him, but you aren't sure it's a good idea."

Also, once the person feels like they have expressed themselves and been well-heard, that may be all they want. But other times they then move on to a solution, either on their own or are interested in your ideas.

I too am guilty of every characteristic of bad listening. It's turning out to be a hard thing to work on.

Recognizing that is probably step one in getting better at it.