•Middle management strategies are decisive when transforming healthcare services.•Learning-oriented leadership and adaptive management emphasizes involvement and facilitate workplace learning.•Employees and managers need help to make sense of the complexities in changing work practices.•Scenario planning and backcasting are tools for sensemaking in complex organizations. eHealth is considered a solution to current challenges in healthcare. However, its use is not very well developed, and its potential has been little exploited. There are many reasons for the limited diffusion of eHealth. Knowledge, opportunities for training and collaborative activities are examples of factors that influence diffusion. Managerial responsibility is decisive in transforming healthcare. This paper aims at exploring middle management strategies that can facilitate workplace learning when introducing eHealth and new ways of providing healthcare. Introduction of eHealth will imply new and innovative working processes, where both employees and managers need to be aware that their work will change fundamentally, from routine work to work that involves learning, skills development and continuous changes in work practice. This study takes a qualitative approach by analysing data collected through focus group interviews. The findings indicate a necessity for a shift towards learning-oriented leadership and adaptive management that emphasizes employee involvement and opportunities for learning. Helping employees make sense of the complexities associated with continuously changing work practices is another identified middle management strategy. Scenario planning and backcasting stand out as suitable tools for sensemaking in complex organizations and as techniques that can promote workplace learning.