The objective for your disciple is to live his life as Jesus did. John writes, “This is how we know we are in him: whoever claims to live in him must live as Jesus did.” (1 John 2:5-6) Part of your role is to observe your disciple in different scenarios in order to commend him when he is living as Jesus would and to exhort him when he is not, as demonstrated for us by Jesus with his men. He formed his team and observed them in many situations over three years, including how the disciples related to one another. Sometimes they did well and other times they did not but in each case Jesus was there in the moment both to commend and to correct.
It is not sufficient to obtain information about your disciple just from him. Even the most honest of people has blind spots, fears, and assumptions, which will limit and skew the information he will give you. Incomplete information will result in you giving him bad counsel and so it is important for you to observe your disciple in various scenarios over a long period of time to ensure that you have an accurate picture of him. This essential component of observation necessitates for you to live in close proximity to your disciple to provide the opportunities for you to see him in different settings.
This is one reason why I believe that the home is the optimal place to make disciples. The family setting provides ample opportunities for the parents to observe the behavior of each child in many situations and so they are able to give accurate and therefore effective encouragement, correction, and instruction. At home the children can both observe the parents living out the values of the kingdom of God and also experience those values as the parents serve and love them.