Last week I was hired by a client specifically to work with her on strengthening her interviewing skills. She had been seeking to leave her current place of work for almost a year, and had reached the interview stage a number of times, but was consistently losing out when it came to job offers. She knew deep down that she was doing a sub-optimal job of “selling” herself and confessed that “I was brought up in a family where I got the message that people who bragged about themselves were low class and basically untrustworthy, so I’ve never been comfortable talking about myself.”

Whether in an interview or often in a networking situation, it’s vitally important to be able to convincingly articulate your strengths and accomplishments. But it’s also vitally important that this be done in a way that feels natural, at least to a significant degree. Merely stating your assets without an accompanying sense of conviction will not be convincing; people are surprisingly good at sensing insecurity or insincerity.

So, if this is an issue for you, how should you tackle it? First, try self-examination. Rather than simply accepting the fact that you aren’t good at promoting yourself, be a detective. Where does this reluctance come from? Is it familial-based (as was the case for the client described above)? Is it related to your gender? Women, at least until recently, have been subtly discouraged from being boastful, as it is seen to be somewhat “unladylike”. Is it discomfort with your speaking voice or your mastery of vocabulary? Did you suffer some traumatic incident as a child (e.g. forgetting a line in a school play) the impact of which you are still carrying?

Second, practice articulating your strengths in an anecdote-based manner. What I mean by this is, rather than simply stating a strength, for example “I’m an excellent team player,” tell a little story about the strength. A couple of simple, illustrative examples:

“As early as age 8, when I first went to summer camp, I loved working for my team in Color War and learned how to contribute without stepping on other teamates’ toes.” Or “Right after I started my first job there was a major crisis and my department had to meet a really unreasonable deadline. I didn’t wait to be asked, but volunteered to do whatever was necessary, establishing my reputation as a great team player.”

Not only will situating your strengths in anecdotes make it more comfortable for you to espouse them, but they will leave a far more lasting impression than simply stating them.

Back to self-examination; unfortunately most people can’t really step outside themselves and do the kind of objective analysis that would identify the problematic issues. That’s why working with a trained professional, ideally with a good deal of psychological expertise, makes sense. Friends and family may have useful insights into your issue, but are unlikely to be able or willing to express them in ways that are as actionable for you as would be ideal.

Obviously, to the degree you can identify the source of your discomfort you can begin to employ counteracting measures, for example signing up for, and attending, Toastmaster sessions (Toastmasters International is a USA headquartered nonprofit educational organization that operates clubs worldwide for the purpose of helping members improve their communication, public speaking, and leadership skills). But probably the most valuable tool in improving your self-promotion is role playing with an accomplished coach who can help you determine how to best state and anecdotally illustrate your accomplishments, so that you have a greater level of comfort in expressing them. Practice makes perfect, and repeated drilling of your key “selling” points will certainly improve your performance.