The Scoutmaster conference is the principle contact with between Scout and Scoutmaster:
Why does the Scoutmaster engage in this one-on-one review? The relationship between a Scout and his Scoutmaster is important for the troop’s health and for the Scout’s success. The Scoutmaster must watch the troop’s dynamics to see who is showing leadership, who is holding back, who is shy, who is working with the younger boys, who is skilled in outdoor activities, etc. Further, the Scoutmaster must watch the individual Scout to determine whether he is advancing, whether he is having fun, and whether he seems eager or uneasy.
Training emphasizes that this is not an opportunity for re-testing a Scout’s skills; the greatest single misdirection experienced in many Troops. Once a Scoutmaster is disabused of the misconception that he or she should be testing a Scout during the conference they can move on to more important business:
A Scoutmaster conference is simply a chance to talk to a Scout about how he is doing, how he feels about the troop and his role in it, how he is advancing, and how he is striving to live up to Scouting’s ideals.Most importantly, the Scoutmaster conference should be a way of encouraging the individual Scout. The Scoutmaster conference is the most personal method in Scouting to assess the needs and desires of a Scout, to encourage and support him, to learn of his fears and hopes, to help him to see himself in the greater context of Scouting, and to encourage his personal growth, both in skills and in living up to the ideals of Scouting.
Quotes are from this brief yet comprehensive training module on the BSA website.
I attempt to ask questions that provide the opportunity for the Scout to contrast his likes and dislikes;
Is there a subject you dislike or struggle with?
Altering the subject of these questions allows the Scoutmaster to get a fairly good idea of a Scouts progress and experience in his Patrol, Troop, camping experiences etc.
Many younger Scouts are typically a little more cowed and taciturn at Scoutmaster Conferences. Most do not have regular informal conversations with adults outside their family. I often find younger Scouts looking for the ‘right’ answer as if they believe I am trying to trip them up. It often takes two or three conferences before they understand there aren’t any ‘right’ answers. I have found that if I begin the conference by asking about subjects outside of Scouting they are more likely to open up.
Conferences last as long as needed but never beyond five or ten minutes. Many may be quite brief indeed. I often find my briefest conferences are those for higher ranks, especially Eagle. Scouts completing these ranks are in leadership positions and have usually been with the Troop for several years so we have had a number of conversations before sitting down to a conference.