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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.

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    Does this answer your question?: Is a cover letter really necessary? – DarkCygnus Aug 5 at 1:52
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    I also found this one: Should I include a cover letter? – DarkCygnus Aug 5 at 1:52
  • if any of those addresses your question (which I think it does), please tell me so I can mark this as dupe. If not, tell us why your situation is different – DarkCygnus Aug 5 at 1:54
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    Thanks. If any I am sure those will also be a good read to you :) – DarkCygnus Aug 5 at 2:29
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    If we're talking about an email, the body of the email itself is the "cover letter". No need for separate attachment unless they specifically ask for it. If you suspect they want one, it doesn't hurt to put the same email body content in a "cover-letter" attachment but formatted like a real letter. Whatever form you choose for your cover letter, the same rules about cogency and correctness apply. – teego1967 Aug 5 at 10:09
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My personal opinion is that unless you are securing the position purely through your personal connection (i.e a friend, ex co-worker who has HIRING POWER) it would never be a bad idea to include a cover letter.

Including a personalized, professional cover letter shows that you are seriously interested in the position. Also, the person you have been talking to may not have direct hiring power. In that case they will have to discuss your hire with a superior and chances are the superior doesn't know you well so they might want to look at your cover letter.

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I'd include a cover letter regardless - your application is likely to be reviewed by more people than your contact, and the cover letter is your introduction to them, not just your contact.

However, if you're already on such good terms with your contact, you can always ask them what their expectation is.

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Even if all they do is rip it off and look at the resume, it's a good idea to have a cover letter. The letter states intent, what you're looking for, why them, etc. It can give context to someone who is looking at your resume for the first time, but hasn't been in contact with you.

Signal V. Noise talks about the cover letter being one of the most important tools at Basecamp, and is always key to their decision making process for who gets past that first gate.

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I will do a casual/funny cover letter when I am being referred.

When I was applying for jobs, a former co-worker referred me to her company. I was going to get an interview either way, but it was also going to be my first impression on several people.

For example, if they want knowledge of git, I will do something like:

I am hoping you git cherry-pick m4tth3wg41s3r over to [company].

Or if they want someone who can build scalable software, I might write:

• Don’t have nested for loops?

It reinforces that I actually do have skills while seeming less dry and keeping the conversation and the interaction as a whole quite casual.

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