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The heartbeat of discipleship is found in principle as one surveys all the New Testament one anothers (examples include encourage one another; pray for one another, teach one another; serve one another; bear with one another; confess your sins to one another; regard one another, etc). The model and mandate for discipleship are found in biblical texts like 2 Timothy 2:2 and Titus 2:1-5.
Common challenges to formal and informal life on life discipleship include:
A) Busyness
B) Laziness
C) Confusion as to what to say/do
D) Not understanding the proper motivations behind intentional relationships.
E) A shortage of older Titus 2 men and women (who are willing and able to disciple others)
F) The proliferation of dual income households (which can contribute to excess busyness and/or to misplaced priorities (note Titus 2:4-5).
G) Complacency
H) Finding and making time for life on life discipleship especially during certain seasons of life (eg. Godly and spiritually mature mothers with young children can feel overwhelmed).
Practical wisdom principles on how to encourage a disciple-making culture in the life of your church:
1) Disciple leaders (2 Tim. 2:2), who in turn will disciple others, who in turn will disciple others.
In some ways discipleship is as much caught as it is taught (1 Cor. 11:1). I am grateful for faithful men who modeled biblical discipleship and who invested in me; (my father, Jerry Wragg, Carey Hardy, Rick Holland, Joe Flatt, Kevin Hall, etc). God wants every believer to pour themselves into someone who is less mature then they are for the sake of mutual edification. Every believer should try and have a Paul figure in their life, as well as a Timothy, (a son or daughter in the faith).
2) Convey to those you serve and to those you are trying to reach that you have their best (spiritual) interests in mind.
3) We must always be about the fundamental questions.
No one ever graduates from the ABC's of the faith. Pastors, seasoned saints, and lay leaders need to be asked basic questions, such as: How's your time in the Word been? What has God been convicting you of lately? How's your prayer life? Are you taking advantage of the evangelism opportunities in your life?
4) Older women tend to be more open and transparent than older men.
We need to learn how to draw people out and teach them how to articulate for themselves their growing biblical convictions.
5) Sanctification and discipleship requires time and effort. In other words, their are no shortcuts (1 Tim. 4:7-8; Phil. 2:12-13).
“Making disciples takes time. It cannot be done through a series of lectures and a training seminar in the church alone nor can it be done by reading a book. It cannot be rushed. One of the dominant characteristics of our modern culture is our ability and desire to mass-produce. We mass-produce everything – cars, appliances, furniture, pots and pans, and household gadgets… It is so easy to take this “mass-produced mentality” and apply it to disciple-making. It cannot be done. Disciples are made, but not mass-produced. Each one is molded and fashioned individually by the Spirit of God.
How long it takes is a matter of conjecture and varies from person to person, depending to a large degree on where they are when they begin the training process. But one thing is certain; it does take time. The Lord Jesus began with 12 monotheistic, God-fearing men, who came from reasonably good homes. He devoted Himself full time to their training and development. He was a Master at the art of training, and yet it took Him three full years. We can hardly hope to do it in less.” From Disciples Made Not Born, p. 111 – Walter A. Henrichsen; HT: Tanner Ripley.
6) Teach people how to be intentional in the informal contexts of life and ministry.
7) In one sense, by investing in people relationally you "earn" the right to speak truth into their life (see Paul's example in 2 Cor. 6:11-13; 1 Thess. 2:7-8)
In order to move conversations beyond the ho-hum (weather, sports, hobbies, etc) we need to love people and meet them where they are. The goal is to build more personal relationships so that we will have sturdy platforms as we "speak the truth in love" (see Eph. 4:11-16; Prov. 27:17).
8) When believers experience the joy of being used as instruments in the Redeemer's Hands it will become contagious.
9) Actively seek to address the common challenges listed above.
Topical Bible studies on time management, the roles and goals of a godly man and a godly woman, true fellowship, the N.T. one anothers, biblical priorities, how to build Titus 2 relationships, etc can be invaluable helps as you seek to foster organic discipleship in the life of Christ's church.