I have two main issues
First, I find myself to be a lousy conversationalist. At work I'm a bit of a bore, so I tend not to be the most solicited (which I don't really care since I'm an introvert to begin with). Although I realize this is actually detrimental to my career. Some are actually really skilled and always seem to have an entertaining story to tell. It's like they spend the ride to work thinking of stories to tell for the whole day, it's maddening. And when someone finishes telling me an anecdote, most of the time I just have no idea what to say other than "cool", a grin, and a nod. Should I just make a list of cool stories to tell in MS Word and memorize them or something?!
My other problem is quite simply my introversion. I actually don't care much for conversation. I could go most of the day without talking to anyone, so long as I'm being productive and keeping my mind occupied. I often find myself phasing out when someone is talking to me quite simply because I just don't care. My mind is always busy thinking of something else anyway. So tell me, what are the odds of getting laid with that kind of attitude? Nil, right? So is that something I can change easily to the point of always wanting to be around people? Are there any success stories out there?
Another question: am I a lousy conversationalist because of my introversion, or am I introverted because I'm a lousy conversationalist?
Here's an update almost 1.5 years later for anyone who's curious.
First, I've found the answer to my question above: I am/was a lousy conversationalist because of my introversion, not vice versa. I don't care for what many people have to say, probably because they bore the fuck out of me and I'd rather focus on stuff life spreadsheets and financial news. Going on about your vacation for five minutes? Get out of my face. Telling me about your weekend? Fuck off, and no I will not tell you shit about my weekend because I probably didn't do anything exciting like jump off a plane. Trying to discreetly tell me a racist joke at the office? Now I'm all ears. So I've come to embrace my introversion.
Second, given the above, and given that one of the primary motivations was to improve my relations with colleagues but that since then my career is both flying and less important than before, I feel less pressure to improve conversation skills. Also, good conversation skills are not the only element to improving relationships with colleagues: there's being attentive to their needs and keeping a positive attitude. Even with good relationships with colleagues, there are other important aspects to get ahead within your organization: delivering quality work and more than your colleague/client/boss expected ahead of time, being prepared ahead of a meeting, being authoritative/confident, and being knowledgeable about your subject matter. Even without having stellar conversation skills, or being an introvert, if do the above you can quickly advance.
Third, I DID join Toastmasters, but didn't put much effort and quickly dropped out. I found that many (but not all) people in the club were kind of losers of society, for a lack of a better description. No one that I could truly associate with to learn more. In fact, I would rather look up to the several different managers in my organization to truly learn public speaking skills and general social skills. Mind you, there were some definitely competent public speakers in my club.
Fourth, despite my lack of effort to improve my conversation skills, I found that they weren't the most important asset with regards to girls. One key asset that can quickly be forgotten and mixed with conversation skills is confidence, composure, and leadership. A girl can control 90% of the conversation, but for the 10% you speak, you better make it high-value material to send the signal that you're a boss.
Fifth, despite my introversion, I found that your environment and surroundings can quickly transform you into an incredible extrovert and a good conversationalist. Last year I went away with my family to a resort down south. I believe the combination of my sister acting as a pivot, my intoxication, and not having to worry about work transformed me into one of the most social beings. I began interacting with anyone and everyone. I got laid, and after returning home she flew out to visit me twice (I gave her the axe after she began annoying me).
So there you have it. While overall I'd say I've improved my conversation skills marginally, I don't think conversation skills are the most important aspect of my life at this point. Onto other projects.