True remorse requires sincerity.

There is a good thought in that, however; when people are nice, are they doing it because they are sincere or because it is in their own self-interest?

I think, naturally, it depends. Should one apologize, then, even if it is insincere? What do you think, Adam?

See: http://acrowdedspace.com/its-all-about-team-but-ever-wonder-why-no-vcs

"3) When I lie. Listen, this is what many VCs do.  Perhaps it's more like leaving out some details than outright lying.  Or if they don’t want to lie, they just don’t respond.   If you're out pitching VCs and you feel like you keep getting rejection reasons that don't really make sense to you -- the harsh reality is that it's likely a team issue.  "We need to see more traction" is the ultimate easy-out, because you can't argue with it.  I've had people followup with "how much traction do you need to see."  And this question is an easy dodge as well -- "I can't really give you a hard number, it's more about proving unit economics that could scale."  I feel bad about giving bogus reasons, but the alternatives aren't great either."

For what it's worth, I think josh is an absolutely classy individual. We can only but interpret his words.

Sincerity is definitely important. The problem is, sincerity is something you feel on the inside that may or may not be seen on the outside.

People who are not very good with emotions may not understand why their feelings are not being effectively conveyed so I like to focus on the apology-receiver's perspective (analogous to the end-user.)

David, I believe it's a bad idea to apologize if you don't mean it.

But the article Eric shared suggests that it's better to apologize, even if you don't mean it, than to let the apology-receiver continue to feel hurt and/or angry.

I think that the differentiator is what you are apologizing for and how you word it. Never start an apology with words like "I'm sorry you..." It's a backhanded accusation. Apologies are powerful and meaningful only when you take ownership of your part in the hurt/anger/confusion. So, instead of saying something like, "I'm sorry you feel that way" you could instead say, "I'm sorry that what I say/feel/think causes conflict/makes it difficult for us to agree/is something that causes you pain". The key to moving on isn't apologizing when you don't mean it, it's acknowledging that if there are 2 or more people involved in an exchange, there are 2 or more people that have contributed to the outcome of that exchange. I think most people aren't actually apologizing when they say they are sorry. They are putting thinly veiled excuses for their own behavior out there which just increases hurt/anger/anxiety/confusion. Or, they are just being lazy.

Well said, Christine.

Empathy is important to understanding why the other person is angry or hurt.

Being specific in an apology will likely make it better.

I always figure a good apology should include detail about what you're going to do to make sure it doesn't happen again -- if only to add backbone to your points about sincerity and explanation.