Rhetoric

Oration and rhetoric were among the highest arts of ancient Greece and Rome. Then, as now, it is vital for the Renaissance Man to have the ability to influence people, emotionally or politically, through one’s communication rather than actions.

Probably the first goal would be to reflect on the types of connections you are trying to develop. While it’s good to have some ready-made facts at your disposal to create conversations, these tools only work at a superficial level of communication. People with a more intricate or deep level of connection with you will require different tools. Elocution, for example, becomes more important professionally, while word play and trivia can be more socially useful.

Many shy people believe they need to ‘say what is on’ their mind. I don’t agree with that, generally. Saying what you are thinking implies a sort of “presentism” or a bias toward the given moment, which might change quickly. Secondly, often our thoughts aren’t socially acceptable, or may be awkward and disorganized. Discretion usually reduces misunderstanding and insult. Far better to learn how to make a point or barring that allude to a point than to run roughshod over others while still being ‘shy’. The worst outcome would probably be the most probably; the listeners start disagreeing with (or retort stronger to) the shy person, who then crumbles.

Mitigated speech is becoming a bigger topic as of late. Malcolm Gladwell's new book "Outliers" is bringing light on the concept. Mitigated speech is when people weakened their point or don't make it at all. This is usually done out of respect and draws on cultural and gender mores. East Asians and women, for example, tend to say things more indirectly. This is can be nice when discussing politics or biscuits, but fails when trying to land commercial jets, as Karl E. Weick notes in (and Gladwell takes from quite liberally) "Making Sense of the Organization". It's in Google Books.

Then again, better to make a point in a respectful and weak manner than not make it at all. In my time in Japan, often conversations exist solely for the listener to figure out what the speaker is trying to say. ("The project is under budget" may mean, when said to a boss, "Can I have tomorrow off?” or “Can I have a raise?” or even “Congratulations!”)

For people who have difficulty saying anything for fear of recrimination, perhaps the best practice might be to find more subtle (read: ambiguous) ways to state an opinion and note the listener's response, and go from there.