Recent and ongoing societal changes have brought about a need to foster multiple-use forestry and to strengthen customer orientation in family forestry outreach. The study assesses how forest management planning in family forest holdings could be developed to tackle these challenges. The approach introduces a new way of evaluating the effectiveness of information- and communication-based policy instruments. Here, the cultural-historical activity theory is applied in studying the interwoven practices of present-day planning and the associated advisory services targeted at landowners. The data, comprising semi-structured in-depth interviews with 19 professional planners, were qualitatively examined, and a forest management planning activity model was constructed with the emphasis placed on the inherent contradictions of planning work. As the main contradiction, the forest and the forest owner compete as objects. The aims of making the forest productive and advising the landowners towards an increased activeness motivate forest management planning but the planners feel that they lack the opportunity to respond to the needs of the landowner. A wood-production-emphasizing interpretation of the benefits to the national economy frustrates the policy goal of genuinely promoting the goals of multiple-use forestry. The conclusion drawn is that the actors engaged in forest management planning can reveal the needs for change by discussing their opinions and practical innovations. This can be done with the aid of facilitation by e.g. researchers oriented to developmental work study.