In an earlier post I pointed out that though we might think from our college experience that functional skills are key to success, that's false. It's those six relational skills that make possible nearly all business expertise--from managing up or building a network to taking advantage of entrepreneurial opportunities resolving interpersonal conflicts--or just learning new technology.
The capacity to initiate conversations with individuals who do not know you is an inevitable requirement in the business setting. Of course, not everyone has a strong, charismatic personality that includes the necessary people skills. Still, all of those initiating skills are quite learnable.
The place to begin is with the assumption that people around you want to get to know you and want to lend a hand when you need it. Upper Midwestern humility is a good characteristic, but it will hamper all kinds of opportunities if you keep thinking, "I don't want to be presumptuous and assume that someone wants to get to know me."
If you're still uncomfortable, become a really good noticer. Watch how other people introduce themselves. Pay attention to what works best and what doesn't. All of us humans learn by mimicking, so plagiarize the language you hear until you're comfortable with it. Try it on in a secure setting, outside of work, at the mall, the garage or the grocery.
The largest warehouse grocery in our community has a highly diverse customer base, so I take advantage of opportunities there to get to know the immigrant community and practice my initiating skills. Here's my secret: the best place in a large grocery is the produce section where people are pawing the vegetables and fruit and taking their time. I'm curious about the Muslims, Indians, Ghanians and Southeast Asians that I see there, so I engage them in a conversation. I've never been turned down for a conversation, even by Muslim women in hijab. As soon as you gain one level of comfort, move on to still others. Keep moving out of your comfort zone as you gain skill.
I lay out both the protocols and scripts for initiating relationships in still another post on the specific communication skills. It's really basic/basic, and you'll want to move on as quickly as you have some comfort with it. However, it's a tried and tested model that clients all over the nation have found successful. By the way, all kinds of people including senior officers at major corporations are very uncomfortable initiating conversations. About ten years ago the CFO at a Fortune 50 corporation hired me for maximum fee to help him learn to do one thing: initiate conversations at a cocktail party. His job required conversational skills that he'd previously avoided. If you're uncomfortable learning initiating skills, you're certainly not the only one.
Talk first, and don't wait for others to intiate the conversation. At work it's important to learn to initiate conversations with peers and bosses you'll be dealing with. Don't get in the traditional habit of waiting for your manager to initiate conversations. And get to know senior managers in other parts of your firm, and ask to learn about their side of the business.
Learn to lean on people without thinking of it as a burden. It's actually a chance to build bridges and relationships. Clearly, the people who are most successful in business have concluded that asking for help gives the people you ask an opportunity to share their "goodies." There are few people who don't want to advise. They genuinely appreciate the opportunity to help, especially if you have some great initiating questions.