Risk aversion has been the focus of a few HN discussions recently: http://www.google.com/search?q=site:news.ycombinator.com+rejection+therapy http://www.google.

Risk aversion has been the focus of a few HN discussions recently: http://www.google.com/search?q=site:news.ycombinator.com+rejection+therapy http://www.google.com/search?q=site:news.ycombinator.com+rej... This book also immediately came to mind (there are lots of great free summaries online): http://www.amazon.com/How-Win-Friends-Influence-People/dp/0671723650 http://www.amazon.com/How-Win-Friends-Influence-People/dp/06... It's probably nothing you haven't heard before, but as they say, common sense is often not common practice. I think, in the end, you will only improve and gain confidence with practice. Some specific tactics that might help: - Ask leading questions rather than directly stating your point. - Before a meeting, create a mental image of yourself having successful exchanges with the other attendees. - Work hard to be better informed/prepared than others in the meeting.