This research compiles from the scientific literature, the benefits of telework and the difficulties evidenced for its adoption. The objective is to investigate, in a regional context, among companies' managers from Manizales-Colombia, which are the barriers for its implementation and the possible associations with administrative regulations. For this purpose, a questionnaire was applied to 252 managers, and for the processing of data, Multiple Correspondence Analysis was used. Results show that neither investment costs nor technological constraints emerge as major barriers; they are those related to unfamiliarity with the subject, and management problems. Highly differentiated profiles among managers from companies adopting telework and those that do not do it. Also, patterns of association between their willingness to adopt teleworking and certain administrative positions are observed. Among these are distrust of nontraditional organizational schemes, reluctance to change the way of working and to use of new digital tools.