Few conversation tips in general, for face-to-face, IM, etc.
(in general, I don't like IM, so these are more from my face-to-face experiences). I'm by no means an expert, but here goes:
1. First, learn to start the conversation. Ask a question (it can be almost anything, but avoid very personal subjects [e.g. relationships, sex, etc.], unless the conversation/relationship has progressed to that point) or better yet, state something about yourself or your surrounding & ask the other person if their the same, different, in a similar situation, etc.
Can't find a topic? Look around you... what are you drinking, eating, what are you listening to, what's the weather like, etc... It doesn't matter if it's interesting to you or not, it's just an ice breaker, the conversation can lead to something interesting, but you have to start somewhere.
2. Avoid yes/no or single-word questions/answers when possible (remember, if you getting single-word responses it can be your fault as well. Assume the other person sucks at this more than you do). If you do get one-word answers, follow-up on the answer:
e.g. If someone says, yes, they like coffee, follow up with: what type of coffee? where do they like to go to buy coffee? do they link starbucks or dunkin donuts? do they like the new free wi-fi at starbucks? ... the last question here is particularly good b/c it takes the conversation in a new direction - business, wi-fi, technology, internet, etc.
3. You must inject information about yourself (even at times when your not directly asked for the information). Don't be afraid to state your own opinions, ideas, etc. and try to include a few bits of details.
e.g. Let's say someone replied that they like starbucks coffee, you can reply that you love starbucks as well and that you especially love their frappachinos... you can, of course, then ask what they think about the frappachinos?
4. Don't be afraid to disagree, but do so politely unless it's someone you can be brash with. Don't forget to state why you disagree.
e.g. You don't like starbucks' coffee. You say: I don't really like starbucks' coffee, I prefer seattle's best, it has a richer flavor... again, this can naturally lead to a question: have they tried seattle's best?
If it looks like things will turn into a flame war, just say: let's agree to disagree... but do not cave to the other person just b/c the situation gets tense.
5. Don't abruptly change the topic unless it's necessary (note: it will be necessary at times). You don't want things to feel like a Q&A session, a conversation should be an organic back and forth.
6. Don't talk about technical or nerdy stuff unless it's with someone who'll understand it. Probe first with a general question (e.g. do you know javascript?), steer way if the answer if no or it'll be a very one-sided conversation.
7. Silence is fine. Relax... don't panic!... Just look for another topic or some additional details about the current topic. oh, if this is face-to-face, you can stare away for a while, but don't pull out your phone (rude, makes the other personal feel ignored) or look down (same as with the phone, but also makes you look less confident).
8. Practice! It does get easier. One your close with someone, you can also be more brash and don't worry about some of the "rules" I mentioned above: you can pull out your phone to browse the web, you can lecture them on tech stuff, etc.
