Social isolation is an important determinant of elderly people’s health and well-being. Modern technologies could be a powerful ally in combating social isolation. However, instead of replacing human relationships they should help build them within a person’s most natural social circles. This paper presents a framework for development of a technological coaching solution that can safeguard or even boost the everyday social life of the elderly. The modus operandi of this system spans from unobtrusive data collection through data processing and situation assessment of social behaviour, to selection and rendering of the most appropriate coaching actions to the elderly person including through members of their social circles. The assessment and decision-making process also integrates three important groups of external factors which influence the solution. These are: (i) personal profiles of the elderly and those members of the social circles who participate in the coaching process; (ii) objective external environment and (iii) the quality of the coaching actions. The latter is a crucial element of the system’s learning abilities.