It's true that in small claims you often don't need one to represent you in the actual proceeding - and many lawyers, especially fairly "big" ones, would have no interest. However, retaining one to advise you on how to navigate the process, how to phrase your arguments, how to communicate with the opposing party, etc., is probably valuable even if they aren't running the case for you directly.

In most (maybe all?) small claims courts you are forbidden to have a lawyer present. Companies generally send an administrative assistant or something similar. You are welcome to retain an attorney before and after the hearing, but they can not be present during.

In Massachusetts, you may have an attorney in small claims court. [1] I think most states allow it, but it isn't super common to actually do.

[1] http://www.mass.gov/ago/consumer-resources/consumer-assistan...

Not in California, fwiw. (Mention only because many people here are in CA, although I know the op is in MA).

My company had a fairly expensive lawyer on retainer when we had a $3-4k bill go un-paid and was forced to start a small claims proceeding in order to get paid. Since we had never been through something like that we asked him for help, and he did help us quite a bit, because it became quite a hassle.

I assume that he assumed it would just be a couple letters drafted and they would cough up, but they really dug in their heels and used the dialog between the lawyers to extend hassle, and it took a bit more than a few letters. We didn't settle until the day before the court date.

Needless to say the $500/hour bill for his services pretty much nullified the settlement, and when the process concluded he politely informed us that this was a little below his scope as our retained lawyer and to gladly not bother him again with things quite so trivial and time consuming.

>>he politely informed us that this was a little below his scope as our retained lawyer and to gladly not bother him again with things quite so trivial and time consuming.

Frankly, at $500/hour, I would politely tell him that I will bother him with whatever I need, he's not doing me a favour.

Courts do have their own small-claims advice service (for free too, I think) which serves the same purpose.

> However, retaining one to advise you on how to navigate the process, how to phrase your arguments, how to communicate with the opposing party, etc.

How, exactly does one "retain" a lawyer?

Is that a formal, monthly-fee kind of thing, for the ability to call them up for questions and advice?

Or is it more like an informal, having done business in the past, maybe for a larger lawsuit, getting to be friendly, and knowing a guy who knows a guy, sort of thing?

Retain means pay monthly.

Are you sure about that? My understanding is it simply means you pay a certain amount up front.

That money is held by the firm and Billings are placed against it until time to top it off again.

I wonder if an attorney would have taken this case pro bono for the opportunity to represent a case against a big name company such as Uber.

Yes, but probably not for $4k-worth stolen laptop case. You can't make your name as a lawyer getting compensation for a single stolen laptop. If that were a $400m nationwide class-action lawsuit, that'd be different matter.