That’s always hard. It really depends on the person you are talking to, and finessing it takes a lifetime of experience. That’s why the Talmud – I forget which passage – says that the forties are the decade where you gain understanding and the fifties the decade where you give good advice. But that aside, I can only offer a little general advice.
Open your heart. Really listen. Try to drop down to the level of what the mystics[*] call “The Hidden Conversation” the things they’re trying to say outside of the actual words. It’s not easy, but even making the effort works. Try not to project what you think they’re saying onto it, but – don’t know how to say this – shut off the chattering part of your brain and be quiet inside so you can hear what their soul is saying, not just their lips.
Don’t try to force someone to talk when he or she doesn’t want to. People who are already in pain recognize this and react poorly to it. Be sympathetic. Let them talk when they want to. In other words, comfort and invite rather than trying to force or manipulate, especially when the grief is fresh. Sometimes they’ll say they don’t want to talk, and they might not at that moment. But if you take what they say seriously and allow the warm and loving side of your soul to come through it will encourage them to talk when they are ready.
You are obviously a kind and compassionate person. That’s why you want to help people feel better. One of the hardest things to learn is that sometimes you can’t help all you would like. You can only help as much as you are able.
[*]Yes, I have non-Jewish friends including Sufis, Buddhists and former Catholic monks. They all use the same term “Hidden Conversation” that I learned from a very wise rabbi. It must reflect some common thread of understanding of the human soul.