The specific nature of medium-sized business requires an understanding of its nature and criteria for distinguishing these entities from other companies. One of the problems of the slow development of small and medium-sized businesses in transitive economies is the lack of coherence between the business development programs implemented by local authorities and the real needs of business entities. This result was confirmed on the basis of a survey of small and medium-sized businesses (150 respondents) on the example of one of the local communities of Ukraine. It is proved that the low efficiency of entrepreneurship development programs is due to the methodological flaw that persists in the formation of strategies of community development at different levels. Building the analysis of existing problems and the choice of community development priorities on the methodological principles of environmental analysis, including SWOT analysis, further adjusting strategies using dynamic strategic analysis and balancing of the territorial community project portfolio are not carried out, as a result of which programmatic indicators of goals achievement are usually not achieved.?This is based on the example of an analysis of five topical development strategies that have been developed using a common methodology, each of which supports entrepreneurship as one of the priority operational goals. In order to increase the efficiency of local business development with the support of the authorities, it is proposed to combine the methodology of strategic community development management and the methodological principles of project management. To this end, criteria and an algorithm for making decisions on adjusting the community development strategy and keeping it up to date are developed, which are based on the results of the environmental assessment. Approaches to strategic management of “weak signals” (I. Ansoff) to the specificity of strategic planning in territorial communities are adapted and developed.