Are you a closer?
My other friend is the total opposite. He can have really great fun, 'enchanting' conversations with people but never seems to bring anyone home. He gets stuck in his own head too much, overthinks things, he doesn't have the ferocity or the intent to actually get shit done.
Here's the thing, both of my friends are salespeople and their personalities and biases are largely the same when you compare them career wise too. My friend which gets laid a lot is always opening and closing deals, while my less persuasive friend always has shit he leaves in the pipeline for weeks and even months.
Being a closer is different to being a salesperson, to draw a contrast a closer may not be as silver tongued or as eloquent as a professionally trained sales stud but he is focused on completing what he starts, so he does it.
A salesperson can have all the conceptual and people skills, but there needs to be a certain energy behind what you say and do, people want and need to feel it. They want to feel your animalism and desire for the sale, I think sometimes these more laid back guys could do with being just a tiny bit aggressive, not too much, but enough to make people take your offer more seriously.
From what I've observed from my passive friend is that he almost feels guilty for wanting something, like he doesn't feel he deserves it and instead resigns himself to hypocritical self-deceit; he wants it, but he feels judged for his desire so he won't fully commit to a decision.
I would say that this isn't too far from what most people experience that's holding them back, you'd think that people would be happy living a life completely of your own choosing, but most are miserable, and it's because people are so darn hypocritical when it comes to simply taking what we want, whether it's taking a girl home or asking for the order.
The biggest difference is the mindset and largely by how much you doubt yourself, how goal oriented you are and what your bias for action is. Everything else you can be taught, but these core foundational qualities can only be developed from within yourself. It's not really something you can intellectualize usefully, but rather it is something that you live by every day that being a closer eventually becomes part of who you are rather than what you are trying to be.
I love sales because every great salesperson I've met has always been an amazing person as well. I'm talking about long term success here which is only built on solid reputations of trust and honesty and all that other boyscout stuff.
There's always a certain 'thing' about every good salesperson I've met which can only come from a mutual recognition, you can just sense these things about people if they are going to be a killer salesperson or not and it's normally true.
Being a closer is about making a decision to close with no excuses.
People don't like simple answers, I know. But that's really all there is to it, less is more afterall.