How can I gain self-esteem a little faster?

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I have helpers of mine that come to my house 4 times a week. We usually do things outside the house (gym, mall, that sort of stuff). I am working on my self-esteem and social skills. My conversation skill needs a lot more work than I actually realized. I was told to be engaging to others in conversation, but I have a hard time processing or thinking of what exactly I need to say. Do you know how to engage others at the beginning of a conversation?

I think my social skills need more work done than I realized before. Another thing has to do with the fact I am a little nervous about these guys hanging around me with others. This can affect it too. And since we are taking it slowly, how can I speed up the process of gaining more self-esteem a bit?

Asking questions gives people an opportunity to tell you more about themselves and gives you things to comment on, too, but too many and people might feel like they're being interviewed.

You can sometimes guess what people might want to talk about by things like their age. Young adults are likely to enjoy video games and may be attending college. Little kids are more likely to enjoy talking about their toys or what they do with school friends. Those can be good conversation starters.

get a long list of positive traits. check of all the ones you exhibit even sometimes. go over the list every morning. i can give you a couple to start you off. you're reading this, so you're literate. you're taking steps to improve yourself.

Set goals. Accomplish them. A sense of competency supports self-esteem.

I don't think it is possible to speed up the process.

I'll second everyone's advice. Also it's ironically important that you just don't worry about it, you have to have a relaxed attitude about it to have a good self esteem.

On another note, I'm curious who these "helpers" are. So are these people professionals or just friends?