Initiative is a funny word. Initiative is something that requires great discernment and discretion at times, but spontaneity and boldness at others. Initiative always requires a divergence from a current path, or at least a parallel to the one you are on. Initiative has one more paradox, it can be simple or complicated. It can be good or bad. No one is right every time to take the initiative. However, no one will always be right to never take the initiative.
In Christ, initiative is part of our life. You cannot sit back on your hackles and just let things happen. Many think that is what you do with faith, wait for God to do everything. Some think that you have to initiate faith, that God expects you to do all the work. Both are wrong. God expects the Christian to know the lessons in the scriptures well enough to use them in discerning when initiative is appropriate. There are times for witness in discretion (John 3:1-21), there are times for spontaneous witness (Acts 8:27-37), and times for bold unapologetic witness (Acts 7).
Whatever the circumstance, witness is the sole responsibility of the believer exercised directly to the world. One might argue that testimony is a Christian responsibility. True, but shining the light of Christ (Matthew 5:16) is passive. Others observe you and respond. Proactive engagement testifies Him to the unbeliever. This is where Jesus expects us to take the initiative and it does not always require the unbeliever’s inquiry.
In John 4:35-38 Jesus teaches His disciples this very lesson. They did not want to witness to the Samaritans, they simply got the food and returned. Jesus shares with them that they should take every opportunity to witness to whomever is placed in their path. Others prepare the way, our part is often simply to say, “Jesus loves you and died on the cross for you.” Keep witness simple. Take the initiative.