In this paper 'facilitated modelling' is exercised as an intervention tool for supporting the 'structuring' phase of strategic decision making in an application that approaches modelling a choice/investment challenge in the Greek publishing sector as a multicriteria decision problem. The set of possible publishing products as well as a consistent family of evaluation criteria reflecting company strategy are identified. Further enhancing the methodology under study is the development of quantitative indices for all criteria, so that they can be modelled as measurable criteria based on macroeconomic environment, opportunities, existing and forecast market data and trends, executives' views, public's estimations derived from surveys, and third parties' data banks. For illustrative purposes an indicative application is presented through which the value of all criteria for a candidate publishing product is estimated.