I’m squarely in the middle of the pack of the Internet. I’m not famous and never will be, but I’ve been around a fair bit and have worked in a number of places, so there are many social networking connections to manage.

After conventions and performances, I sometimes see a spike in friend requests or connection requests from strangers with no context. And this makes me sad, because I’m not going to accept a request without context, but I know on the other end there MIGHT be someone who is looking for a mentor or a partnership. So if you find yourself on the other end of the networking game, reaching out to other people, here are the rules I apply to myself when figuring out how to move forward. Maybe they will be of some use.

First off: Our identities are the most valuable things we have (well, aside from love and family and health and ice cream) and many of us are quite cautious about sharing those online identities with others. Even sharing a birthdate with birth year can be dangerous! Keep that in mind when extending contact to other people – on both sides of the equation.

Secondly: Are you using social networks to reach out? Is your profile picture of a cat or robot? Sorry, fail, try again. Would you accept a date from someone on a dating site without a photo? Probably not. There’s a reason face-to-face meetings diffuse tensions that crop up over email, and it’s tone and emotion. A photo of you smiling lends a good tone to your communication. A photo of your cat tells me I can’t go over to your house because I’m allergic.

And now, the etiquette of reaching out to people On The Internets:

Category 1: People You’ve Never Met
If you’ve never actually shaken hands with someone or been introduced by name, you have to assume that the other party is going to be skeptical.

DO: Use Twitter or email.
Twitter is low-intrusion and gives you a chance to look for an “in” in their conversation. Remember that Twitter won’t let you direct-message someone who isn’t following you, so whatever you say will be public!

If you’re emailing, be short and to the point but show that you’re interested in their perspective and not just selling something. It’s not the same as a cover letter when applying for the job. And try and be actionable. Ask a specific question, not a general “any advice?” or something that puts the burden on the receiver.

DON’T: Use Facebook for networking with strangers.
Avoid friending folks you don’t know on Facebook. If you must, make sure you put in a note about why you’re friending them – did you read an article they wrote? Saw them at a con? As a rule my Facebook is a private space, and I won’t let strangers in unless there’s a very compelling reason. You may have 1,300 friends and that’s great, but many folks prefer to keep their Facebook lists small.

CAUTION: Be thoughtful when using LinkedIn for cold-call style networking.
I’ll reject requests from folks I’ve never worked with unless, again, it comes with some sort of introduction and explanation as to why the person is reaching out. It’s not that I don’t want to meet new people, but LinkedIn implies a level of familiarity and implicit recommendation of your colleagues that one must monitor. However, you can use LinkedIn’s “introductions” feature to try and request an introduction through references if you’re a 2nd or 3rd degree connection of someone you’re interested in meeting – that’d be far more likely to end in success.

Category 2: People You’ve Met Once Or Twice
This is the trickiest part. You have to put yourself in their shoes – do you think they’d remember meeting you? Did you exchange some sort of promise to follow up in communication? Did you talk about becoming Facebook friends? Did you leave a business card? (Always carry business cards!)

If you’re pretty sure they’d remember you, then I’d recommend starting with LinkedIn (for professional networking) or Twitter (for personal networking.) Always add a note – in LinkedIn, along the lines of “Hello [X], I really enjoyed meeting you the other day at [Y event] and hope our paths will cross again. Can we keep in touch via LinkedIn?” Make sure you mention where you met, and even what you discussed if you had a conversation. Facebook is OK if you talked about Facebook or you know you have mutual friends; otherwise I’d recommend starting elsewhere.

Email is fine too, and recommended if you discussed something *specific* (like many times when I meet folks from related nonprofits.) Plus email contact tends to get you both on the address book radar, so it’s more beneficial down the line.

If you’re not sure they’d remember you, then go up to Category 1 above.

Category 3: People You Actually Know
The only time you don’t need a note is for someone you’ve met many times either in a social or professional setting (like a former coworker from another company.) In those cases you can get away with a quick invite – as long as your profile photos aren’t of your cat or a robot or something.

But especially on Facebook, consider whether the person you’re friending may someday be your boss or vice-versa. Professional relationships are always best started on LinkedIn.

Remember – just because you’re not sending an email doesn’t mean your recipient doesn’t need or want context. ALWAYS ADD A NOTE. It takes you a few seconds and helps tremendously. After all, it’s all about their decision to click “Accept” or “Decline” – the worst they can do is click “Decline”, but if you’re going to this trouble you probably want to maximize your chances of getting the “Accept”.

And if you DON’T get a response… try not to take it personally. We’re all busy people and any number of things may be behind the silence. Pick up and move on. As for trying again, on Twitter that’s pretty harmless, but in email, Facebook, or Linkedin, I consider it the same as most companies consider hiring. Give it 4-6 months and try again. That’s enough time for situations to change.

But most importantly… don’t treat it as a game. Your goal is not to have the biggest list of contacts. Everyone you meet is an opportunity and can be very exciting, but the real value comes in cultivating meaningful relationships with friends and co-workers over time. Make sure you’re not neglecting the bird in your hand for the many birds Tweeting in the bush.