To that end (..the culture around us..) it is worth saying out loud. It is ill-productive, bordering on arrogant, to think there is a one-size fits all approach to telling people about Jesus. Christ, Himself, was systematic as He approached people. He truly met people where they were; and through us, desires to continue to meet people where they are. Christ was "bold", but not always "brash". Likewise, our lack of pointed-ness does not necessarily indicate a lack of boldness. Then again, there are times that a "tough-love" approach is appropriate. The Holy Spirit, indwelling Believers, is our guide.
The woman at the wel, as told ofl in John 4 is a wonderful example. Jesus didn't beat around the bush, but He did "identify" with this woman's need. Not only her "needs", but as well ...her belief. Jesus calculated various aspects of this woman; her culture, her belief, her own sin (keep reading), etc. You and I don't have the luxury of omniscience, or all-knowing-ness. We may have to be a little more "intentional" in our approach. Regardless... we need to model the "Jesus approach" to telling His good news. A few things noteworthy of this "chance" meeting with the woman at the well....
Jesus could have simply indicated that He is the way, the truth, and the life... ...but He recognized the need to build trust with the woman. He realized the profoundness of relating to her culture, her belief, and her own needs. It has been said that people do not care how much you know ..until they know how much you care. We should strive for the compassion, and the passion, of Jesus. The result of winning the trust of the Samaritan woman was that... "many Samaritans from that town believed in him because of the woman's testimony."
Winning people to Christ is not a notch we mark on a self-righteous belt. Many of us are planters, some are harvesters. The Lord says, Himself, in following passages that fields are white for harvest. The laborers truly are "few". Whether your personal role is that of seed-planter or harvester... it is of the utmost importance that we be intentional, sensitive, comprehensive, compassionate, passionate, and loving ..with a right motivation.. to the world we endeavor to reach with the good news of Jesus Christ.