Sometimes there are scenarios where I am in communication with a business contact for a while that eventually leads to a work opportunity to apply for. This has happened a number of times to me, and in each instance I wonder...
....if a cover letter is appropriate or if it will be perceived as overly-formal.
To me it seems jarring to go from casual conversation into an email complete with a cover letter. For one, I've already been introduced to the contact, but also, they are possibly (not always) already familiar with my goals and skills.
In some of these instances I have asked while the application was the subject of the conversation, which I highly recommend. From there it can go either way. But what if you forget and don't want to contact again in order to ask?
I should add that my idea of a cover letter is a PDF as an attachment, as opposed to just an email. I don't think everyone does that, and it may be part of my perception of it being overly-formal.
In my current instance, it seems like my email should include some professional speak and some marketing of myself, but trying not to over do it.
The current instance is also a contract, non-permanent opportunity, which may be another consideration.
So if I don't provide a cover letter, will I seem like I'm falling short of expectations. And if I do provide one, will I seem like I'm trying too hard?
I know this question is similar to a more general question about whether or not a cover letter is generally necessary (in formal applications). I know it's a common question among those new to job applications. I already know that in regards to formal applications, a cover letter is always recommended. In this instance I am talking only about casual conversation that leads to an application. Because it's never felt quite right to plop a cover letter on someone I've already be introduced to.
Edit: I have specified why this question is not a duplicate, and I think the reasoning is very clear.